I get that itch and a second one: I want to make changes when the business is working.

That second itch has two main causes, an addiction to chaos and an aversion to boredom. Left unaddressed, both of these tendencies become forms of self-sabotage. They have hurt my business, and my livelihood and family by association.

I think of these two tendencies as crusty knots in my psychology that I need to unravel and understand so that they no longer come between me and two things that most entrepreneurs want—deeply meaningful work and long-term financial stability.

I can pinpoint the exact moment that I first recognized my addiction to chaos. I was reading Dan Martell’s book Buy Back Your Time, and I came to this passage:

“Entrepreneurs can also become so accustomed to stressful and unknown environments that they become downright addicted to chaos.

Chaos can feel so normal that calm can actually feel strange. Entrepreneurs have been so trained in dealing with stress, like making difficult decisions based on incomplete information and last-minute changes, that they’re always looking for the next problem, even if it doesn’t exist. Without a fire to put out, they can grow inwardly anxious.” (51)

“Oof” is the involuntary sound you make when some bully punches you in the stomach. That’s also the sound my poor, unprepared mind made when Martell’s observation hit it.

I claimed to want peace, but my business ventures stretching back to 2009 told a different story of self-inflicted stress and disorder. I had a tendency to fix things that weren’t broken, stop doing what worked, and generally not leave well enough alone, as we say in the South.

I probed for threats, problems, and weaknesses and believed that this is what a responsible entrepreneur does. When he founded Virgin Atlantic, didn’t Richard Branson buy an airliner he could return within two years and say something like “protect your downsides”?

We get in trouble when we take good advice out of context, and if you had asked me, I would have defended my chronic overthinking and frenetic learning as being “strategic.”

I wasn’t being shrewd or strategic as much as I was looking for the miracle business cure, the crucial insight, tactic, or relationship, that would cause my problems to vanish.

The assumption that the answer to my woes was out there, not right here, caused me to discount what I already had in favor of more, new, and extra. Surely, the odds would tip in my favor. (Pro Tip: You don’t need the odds if you wear out the fundamentals.)

This way of thinking, driven by an addiction to chaos, caused my priorities to shift constantly. Too many projects competed for my attention, and no matter how smart or capable an entrepreneur may be, we don’t get very far if we try to go twelve directions at once.

A fraction of focus means a fraction of progress. This is math. Or science. Or Oprah.

The lack of meaningful progress fed my anxiety. “I’ve been working so hard, and yet I have so little to show for it.”

Don’t get me wrong. I had modest successes along the way. A silly mustache-themed photo booth app grew into a $250,000 side hustle and a tiny exit. A conversation at a farmer’s market led to a tech startup. My co-founder and I did the incubator, accelerator, and fundraising rodeo. I parlayed the startup experience into growth strategy and consulting. I’ve helped one of my consulting clients, an e-commerce company, build a brand and grow it past $2 million.

My wise wife reminds me of these accomplishments even when my ambition dismisses them as false summits.

If I listened to her more, then I would have overcome my addiction to chaos sooner. I wouldn’t see so many instances of the cycle repeating: get some traction, second-guess my path, change my mind about what I should be building or doing, start over without cutting existing commitments, take on too much, and make excruciatingly slow progress.

When my self-inflicted, anxious chaos didn’t bite me, my boredom did.

The irony is that small businesses start to feel boring when they start to work:

• You charge a profitable price.

• You deliver the desired outcome.

• You figure out how to get new leads.

Even working businesses still have problems because every business does, but its revenue model and core value proposition are no longer a Rubik’s Cube. Or rather, they are one that you can solve with your eyes closed.

I’ve gotten to that place of predictability a handful of times, and then that second itch would show up. Like a petulant Roman emperor, I would yawn, give a lazy wave, and say, “Next. I want to be entertained.”

Perhaps I’m too much a product of my elder Millennial generation because I believed that my work should entertain me. I was supposed to follow my passion. If you love what you do, you’ll never work a day in your life, right?

I had the freedom to bend the trajectory of the jobs I created for myself toward the trajectory of my passion, so shouldn’t I exercise that freedom?

Yes and no.

Yes, we should try new things in the same general direction. That’s called innovation.

No, we shouldn’t expect our businesses to provide a nonstop drip of creative and intellectual stimulation. That’s not its purpose. Its purpose is to create a livelihood.

Most people use the words “work,” “livelihood,” “job,” and “career” interchangeably, and this causes confusion because sometimes entrepreneurs think we’re optimizing for one when we’re really optimizing for another.

Clear definitions for work, livelihood, job, and career become very important:

• Your work is what you accomplish in your lifetime—your life’s work.

• Your livelihood is how you make money and pay your bills.

• Your job is the specific set of roles and responsibilities you have. It may include a title.

• Your career is the jobs and roles that you’ve had.

Some people work but don’t have a job. For example, my friend and mentor Bruce is technically retired, but he still advises CEOs and young entrepreneurs and helps nonprofits when they need a fractional CFO. He would tell you, “It’s fun.” We want to keep working when the work is fulfilling. Why would we deny ourselves the pleasure even after retirement?

Some people have a livelihood but no job. They live off income from other people, savings, investments, inheritance, social security, companies that they’ve built and fired themselves from, or some combination.

To create a livelihood for my family, I started various business ventures and side hustles. Most of them created a job for me. Each job came with some roles and responsibilities I enjoyed and some I didn’t.

But a business doesn’t care what its owner finds distasteful or tedious. It doesn’t stop having problems or needs because the owner is bored. It simply keeps acting according to its nature the same as a cat.

• We ought to find work that we love because fulfilling work is one of life’s greatest gifts.

• However, our work, our livelihood, and our job usually don’t overlap perfectly—at least not for a long time.

• Some of us need to admit our discontentment with our work. In “How to Do What You Love” Paul Graham would tell you that acknowledging your discontentment puts you “a step ahead of most people, who are still in denial.”

• Some of us need to address our addiction to chaos and aversion to boredom. Otherwise, our desire to feel passionate will continue to endanger our livelihoods.

Most of my entrepreneurial endeavors have been attempts to break the relationship between time and money and free up more of my time for the work I wanted more of—namely, writing fiction, nonfiction, and poetry.

Meanwhile, my family of five did need a livelihood.

So I always felt like an artist-entrepreneur or entrepreneur-artist—which identity was foremost? I didn’t know—trying to ride two horses pulling apart. The horses were those desires I mentioned, deeply meaningful work and long-term financial stability.

Though I can’t say I’ve got it all figured out, I can say that the business that represents my livelihood doesn’t need to entertain me. I can get my entertainment elsewhere. Taking my business in a new direction is exciting, and it can cause whiplash.

Following some hand-wavy passion doesn’t feel so noble, wise, or light when I’m wondering how I’m going to cover my mortgage payment and I feel that subsurface churn of stress and anxiety.

My business was never supposed to entertain me. It was supposed to create a livelihood.

Now that I better understand my own misplaced expectation, I’m ready to accept some monotony and boredom if that means a predictable livelihood.

I can see the choice in front of me:

• I can go get a full-time job, which I still don’t want.

• Or, I can change my relationship with my own business and figure out the systems, support, and sales that remove me as the bottleneck to growth.

That is the job to be done, and doing it well will ensure that I have more time to spend on the work I find most meaningful, some of it inside the business and some of it outside.

What I’m trying to say, my entrepreneur friend, is stop scratching the second itch. Wean yourself off chaos. See the long-term opportunity in boredom.

If you don’t know me, I’m Austin L. Church, coach, author, founder, and father of three hilarious aspiring humans.

Through the Freelance Cake Community, I connect advanced freelancers with each other, resources, and advice tied to the $300K Flywheel framework. Click my profile link for more info.

Or, if you’re a solo founder, I will define your strategy, write it in plain English, and walk beside you for 90 days while you implement it. Send me a DM.

All you have to do is set your business up so that it can’t do anything without your expertise and constant attention.

To illustrate, let’s pick on a slow-learning, glutton-for-punishment entrepreneur named Austin L. Church.

Last year, my friend Nick and I bought a 100-year-old building. You know the type. It has lots of “character” and “charm,” which means that some of the original hardwoods are intact and there isn’t a level surface to be found.

I am not what Carhartt-wearing men with luxurious beards would call “handy” or “being good at fixing much of anything.” What I am good at is not pretending, so I found an electrician, plumber, HVAC technician, cleaner, handyman, locksmith, termite terminator, and retired neighbor named George willing to mow the eight-foot strip of lawn between cigarettes.

In the beginning, I had to do tedious things like bring justice to carpenter bees, buy toilet paper, and set up Hostaway, a property management software dreamed up by ex-TSA agents dismissed for inappropriate conduct.

When my to-do list did finally peter out, I had two realizations:

• I could go days at a time without thinking about the investment property. Bookings came in, five-star reviews came out, and the office tenants downstairs were prompt with rent payments.

• I had acted like a non-stupid entrepreneur for once.

The question is, why hadn’t I done the same with my core business? Why hadn’t I built a team and systems and gradually removed myself from day-to-day operations?

I couldn’t claim ignorance. Though I never took a business class, I had learned quite a bit through trial and error and by reading books like Michael Gerber’s The E-Myth Revisited and Robert Kiyosaki’s Rich Dad, Poor Dad.

Kiyosaki helped me see that, if I ever wanted to stop trading time for money, I needed cash-flowing assets to pay me. A dividend-yielding stock is an asset. An investment property is an asset. A self-operating, owner-independent company is an asset.

A job is not an asset. When I look back at my various business ventures, I see that I have created more jobs than assets.

That distinction might matter less if my main reason for starting any business venture hadn’t been to get back more of my time so that I could spend it writing. Every hour that went to a job couldn’t go to the craft of fiction, nonfiction, or poetry.

That building we bought was a reminder that I have accumulated plenty of business-building acumen and can put it to use, but I still have a tendency to forget the plot: In order for me to waste time on craft, I must think and act like an entrepreneur by setting up a business that doesn’t require my expertise and constant attention.

The only way to wean the business off of my attention is to create systems and processes and get appropriate support (that is, people to run the systems).

And if those systems and people are going to operate independently of me, they cannot depend on my expertise.

Are you still tracking with me?

Good, because this is precisely where freelancers and consultants run headlong into a wall and bloody their teeth.

Why? Because we build businesses whose main product is our expertise.

The easiest and most obvious thing for me to do after I got laid off in April 2009 was to sell my writing skills.

Over time I also gained expertise in project management, marketing, brand development, and strategy, and so I sold those capabilities, too.

And what happens when every project requires my skills, my capabilities, my taste, my decisions?

In an expertise business the expert inevitably becomes the bottleneck. This is as true for a writer as it is for a management consultant or my HVAC guy.

If the HVAC guy builds a team and systems that slowly but surely remove him from day-to-day operations and turn his job into a cash-flowing asset, who is the better entrepreneur, him or the brilliant management consultant?

With the investment property, I had no electrical, HVAC, plumbing, construction or cleaning expertise to rely on, and as long as I had honest experts to call, my lack of expertise became an advantage.

Let me repeat that: My lack of expertise became an advantage.

Once I got operations sorted out, my role was to set priorities, make decisions, and pay for stuff. I acted like a CEO in that respect. CEOs drive vision and strategy, solve big problems, and oversee resource allocation.

Meanwhile, in my expertise-based business, which consists of strategy consulting, one-on-one business coaching, and the Freelance Cake Community, most of the customers, problems, projects, and tasks require my expertise. I still have to touch most everything.

My expertise puts me at a disadvantage. I am the expert and the bottleneck.

I’m not ready to kill the expertise-based business, and I want to spend more time writing. This isn’t a conundrum as much as it is a design constraint and opportunity.

The only way for me to keep growing the business without growing its dependence on me is to only grow the 80% of the core offer that is easier to delegate because it is easier to teach or codify as process.

I’ll keep growing what is scalable, and that means that I must figure out what to do about the remaining 20%. Maybe that last slice of the core offer is what I’m really good at. Maybe it’s where I as the expert really shine. Maybe it is what truly differentiates the offer.

Okay, this is a solvable offer design problem. What can I substitute that will make the offer less dependent on Austin’s taste, experience, or expertise while making it even more valuable to customers?

What they want more than access to my cupboard of goodies is positive outcomes. Am I smart enough to figure out how to give them cookies without having to be the one to bake every batch? I think I am.

I also think I am ready to suffer less, and I’m going to do that by turning a job into a company that can scale without my constant attention. To do that, I’ll codify 80% of my expertise as systems and process, hire more support, and redesign my offers so that I have replaced the 20% of my expertise that can’t be easily taught.

It’s that or keep working a job in an owner-dependent, expertise-impaired business. The choice is mine and yours.

If you don’t know me, I’m Austin L. Church, an author, founder, business coach, and father of three hilarious aspiring humans.

Through the Freelance Cake Community, I connect advanced freelancers with each other, resources, and advice tied to the $300K Flywheel framework. You can get more info here.

Or, if you’re a solo founder, I will define your strategy, write it in plain English, and walk beside you for 90 days while you implement it. Message me here or through my website.‍

Keep reading if you want to steal my ideas or conclude that yours are better. You can’t lose.

1. I finished my new offer, the Growth Partnership.

Check out the deck here, and reply to this email if you think you may need this.

This Growth Partnership is exciting to me for two reasons:

1. It represents the culmination and compression of what I’ve been doing since early 2016 when I first started selling strategy. The Growth Partnership isn’t really a new offer so much as me putting on my big boy strategy pants.

2. I tripled my price. I called the previous version of this offer a “1-Day Growth Sprint” and charged $7,425. I always overdelivered. I know a guy who wrote a book called Free Money and decided to take his advice by charging a price commensurate to the value I create.

What is kinda new about this offer is the messaging and certain pieces of the scope—for example, writing the strategy doc in plain English and walking alongside founders for 90 days.

I’ve written before how most founders aren’t shopping for strategy, even if they need it. I’ve also written about what strategy is and why writing it out in one- and two-syllable words makes it more effective.

And I’ve known that most founders need someone to walk alongside them as they begin implementing a new strategy. I’ve done a little of that with consulting clients. Marrying an initial strategy diagnostic and sprint with coaching during the implementation phase is something I should have done years ago.

In case you’re wondering, here’s how AI came into play:

• I used Viktor (AI coworker that lives in Slack) to sharpen my thinking. My prompt was 1) explaining that I want to sell larger $30K and $50K strategy projects, 2) dropping in links to the work I’d already done on my offer, positioning, and deck, and 3) asking for an actionable plan for getting from where I am to where I want to be (i.e., another $30K strategy project closed).

• The messaging and copy that Viktor and later Claude gave me was hopelessly derivative, terse, and gimmicky. It also whiffed faintly of bro. Like, who told Claude that good copy consists of 90% sentence fragments? And just please stop with questions like this: “Got your attention yet?”. I edited all of the copy myself multiple times.

• I had to edit the scope and fulfillment processes because, surprise, Viktor and Claude have never actually delivered a consulting engagement. Things that sound good in theory don’t work when you need to convince a warm-blooded human to give you their sweat-soaked money.

• Claude did save me time when I created the deck itself. I created fantastically juvenile slides with my copy in Canva, dropped in the identity guidelines for the Austin L. Church brand into Claude, and got a 90% not terrible result in the first pass. ChatGPT’s version was worse this time. That’s a first.

This is perhaps the most important insight I can share: AI can help you increase clarity, but it can’t supply conviction.

The main reason I’m excited about this new-ish offer is because I believe strongly that what I can do is exactly what founders who are eyeballs deep in complexity need. I can’t wait to do this engagement five, ten, twenty times and see more transformations.

That conviction and excitement enables me to share the deck with a straight face and state my fee without wetting my pants.

So if you haven’t pushed your new offer out yet, ask yourself, “How strongly do I believe in the transformation?” Or, the inverse: “Why aren’t I more excited about this?”

With or without help from AI, you’ll struggle to sell something you don’t believe in—sales is a transfer of belief, after all—and you’ll move very quickly once you reached the right level of conviction.

Just watch how quickly I can move toward smoked brisket or Funfetti cake, and you’ll see what I mean. Conviction.

Creating a signature offer you believe in is harder without a step-by-step process.

If you don’t already have one, then reply to this email. I’ll share the playbook I give to my $10K coaching clients.

2. I designed an “AI semester.”

I was feeling behind with AI, and I was also thinking about a coaching client and a friend:

• My client used Claude Cowork to remove dozens of hours from his workflow and give his clients better results. He quadrupled his monthly recurring revenue in less than six months.

• My friend started by telling me all of the wild things AI was doing and automating for him, but when I asked about his revenue, he told me it was down.

AI is like fire. Put it in an open field and it does more harm than good. Put it into a combustion engine, and it provides propulsion.

Knowing that I can’t afford to be unfocused and play with fire right now, I designed an AI semester with a syllabus, curricula, projects, and assignments.

Clarity on what I want to accomplish has helped me separate signal from noise as I saved certain posts, videos, and other resources and purposefully ignored others.

One of my self-assigned projects was creating a comprehensive content archive or vault, and though getting to the finish line took effort, it was still laughably easy compared to what would have been required in the pre-AI era.

Here were my steps:

1. I watched this video from Nate Herk based on Andrej Karpathy’s idea.

2. I copied and pasted Karpathy’s idea into Claude Code and said in effect: “I want to do this.”

3. I downloaded Obsidian for free and followed Claude’s instructions to get it connected.

4. I started exporting and downloading archives going back to early 2009: WordPress posts, Webflow posts, Medium posts, Kit newsletters, LinkedIn posts, Ulysses .md files (a writing app I used), my book, several guides, podcast episode transcripts, video transcripts, really anything I could think of that I might want in a searchable archive.

5. Claude automatically converted all of those files so that every new markdown file (.md) has parallel structure, and more importantly, all of them have the right meta data—everything from the date the piece was created to the original title to themes and keywords.

6. When I ran into issues, such as LinkedIn not exporting the full archive, Claude helped me troubleshoot.

7. When Claude ran into issues, such as not having the right Python script for unzipping and converting and archiving, it did its own troubleshooting.

The end result was 2,985 unique pieces of content spread across eleven platforms.

Again, creating this vault took effort, but it wasn’t hard in the way that figuring it all out on my own would have been hard. And it would be hard to overstate how valuable this is to me.

I recall several occasions when I was 80% finished with writing about a topic, and when I returned to it later and used keywords to search for the draft in GDocs, I found something else I’d already written on the same topic.

Sometimes, the older piece was shorter, sharper, and better. I had clearly put a lot of effort into it way back when. Realizing that I had spent hours creating a net-new and worse piece on the same topic left me feeling sick to my stomach.

I would peg my lack of strategic content repurposing as the single biggest bottleneck in my marketing, especially for the Freelance Cake Community, and therefore the single biggest obstacle to the growth of the business.

I was finally able to build the vault that will serve as the foundation for future content repurposing.

On that foundation I have stacked other building blocks:

• A rich, vivid ICP based on specific details, patterns, and problems from a couple hundred Freelance Cake Community and one-on-one coaching applications

• A content strategy based on those recurring problems

• A library of post types based on what is working right now on LinkedIn

• A content roadmap that marries the content strategy and post type library

So I now have a way to know what I should write next and why (strategy) and when (roadmap) and how (post types) and whether I already have a strong piece of content on the topic that I can repurpose (Obsidian vault).

I’m finally leveraging some of the efficiencies of AI without running the risk of publishing AI slop, which would be counterproductive in every respect.

Excuse me, what took me so long? What have I been doing with my life?

This content vault was only the first project in my AI semester. I’m both excited and focused. Imagine that.

3. I’m building a marketing habit app with Studio.

Through lies, bribes, and blackmail, I got the opportunity to build a Coaching App with Studio.com. Just kidding. I was invited through a community I’m a part of, Creator Science Lab.

Some of you are familiar with my course, Morning Marketing Habit which is pretty good at what it’s designed to do.

But this new Coaching App doesn’t teach you about marketing in the abstract. Instead, the experience is built around one daily practice, a focused 20- to 30-minute lead-generation effort that I call the “Daily Apple.”

The Daily Apple is personalized each day based on your niche, chosen strategies, relevant channels, strengths, and current stage. You do specific, targeted actions every day, log what happened, and receive coaching feedback grounded in my methodology.

In the first 30 days, you choose up to two lead-generation strategies in addition to the core strategy, the 3 R’s. You also generate your first warm leads.

Over the following 60 days, you continue to implement your chosen strategies, develop a Morning Marketing Habit, and fill your pipeline with warm leads.

So you go on a structured, 90-day journey to build your pipeline in real time, and the app makes your progress visible.

Eventually, the Morning Marketing Habit becomes automatic.

The app launches next month, and one thing that has dramatically cut down on the time required to create it is… drumroll… my content vault in Obsidian.

I dropped my App Blueprint, a 27-page document, into Claude Code, and then I asked it to create a list of everything in the vault that was relevant. Then, it bundled up all of those .md files into an archive I can drop into Studio’s app builder.

I mean, c’mon! That would have taken me hours and hours.

The reason I chose to build this Coaching App is because it enables me to do at scale something that used to be impossible: personalized, one-on-one coaching focused on building a consistent lead generation system suited to your strengths so that you become less dependent on referrals and get off the feast-or-famine rollercoaster.

At the risk of sounding ridiculous, I’ll admit that I may use the app myself.

That’s it for now, and I suppose that’s quite a lot.

If you’re so inclined, email me at helloataustinlchurchdotcom and tell me what you’re working on and what you need help with.

My goal with this series is to start conversations with these founders or catch the attention of others who realize they’re leaving money on the table and that I can help.

Anna Reich’s public letter to Jay Clouse provided half the inspiration for this one, and my belly provided the other half. Or rather, Meat Church BBQ did. Since I discovered Matt Pittman’s YouTube channel and started doing what he recommends, people have told me that my barbecue is the best that they’ve ever had. I smile and thank them while knowing that barbecue isn’t all that difficult if you follow the right recipes. I use Matt’s.

(Sidenote to all readers: Everything that follows I pulled from publicly available sources. I didn’t do anything weird, stalker-ish, or sneaky. Instead, I used the puzzle pieces to come up with a plausible picture.)

Dear Matt,

I’ll start with a story about the time I got mistaken for you.

My wife and I were going to Austria to celebrate our fifteenth wedding anniversary, and I needed to renew my passport. So I drove from Knoxville to the passport agency in downtown Atlanta, and around 11:00am I got a text saying that my new passport was ready for pickup.

I happened to be wearing my favorite hat, a navy Meat Church BBQ snapback, and as I was leaving, a security guard glanced at it and asked me, “Is that your channel?”

He thought I was Matt Pittman!

“No, I’m just a fan,” I said, and we talked barbecue for a couple of minutes.

That experience is what barbecue is all about for me. Slowing down for a moment (or a whole Saturday), noticing people, bringing levity and a smile, salt and light. The effort doesn’t cost much, but it means a lot.

Maybe that’s why I like your approach. From what I can gather, barbecue goes deeper than recipes and techniques for you. Barbecue requires us to slow down, be patient, and pay attention. Barbecue is the doorway to hospitality, friendship, and deeper connection.

People are even hungrier for that connection right now than they are for smoked meats and killer sides, but let me get to the meat (had to) of this letter.

I believe some tiny insights and corresponding tweaks to Meat Church’s growth strategy could add $500K to $1 million to your topline over the next 12 to 18 months. Here is what’s on tap:

• Status Quo → You’ve built something extraordinary.

• Current Strategy → Lifestyle Media Company

• Meat Church Cookbook → You have better opportunities.

• Opportunity → Thousands more customers like me

  • Quick detour → Pursuit Spirits Video

• Email List → Getting more ARR out of it

• Shoot me a message here or text me

Let’s get to it.

Status Quo

Meat Church has publicly reported eight-figure revenue with a team that’s stayed deliberately small (~10 employees). Dang. Most companies the size of yours have a team 5 to 10 times larger.

From the operational standpoint, you’ve built something extraordinary: a founder-led brand with significant distribution leverage (1.17m subscribers on YouTube alone, plus Insta, FB, and TikTok), an easy-to-understand, consumable product (rubs, apparel), and strong channel partners (Ace Hardware, Buc’ees, etc).

In early 2026, you diversified beyond your products and brand partnerships (Traeger, Yeti, Cowboys, et al) to equity stakes in (Pursuit Spirits, EIGHT Elite).

Let me read between the lines and summarize the current growth strategy.

What Your Current Strategy Appears to Be

The most coherent version of your 2026 strategy based on my research goes like this:

Meat Church is becoming a lifestyle media company that can cover the range of your audience’s interests, including Texas, BBQ, being outdoors, hunting, fishing, bourbon, beer, and football. The podcast launched and expanded the content platform that raises awareness for the core barbecue brand and adjacent categories, strengthens sponsorships and partnerships, and drives revenue.

This is the MrBeast model (media company with satellite brands and products) filtered through your interests and rooted in Waxahachie.

At a high level, Meat Church is all about what I’ll call “the slow-cooked life.”

Meanwhile, a couple of paragraphs from your 2023 Phi Delta Theta interview caught my attention:

“When asked where he sees Meat Church in five years, Matt acknowledges that it is difficult to be strategic because the company has grown and changed so much. They enjoy being small and nimble, and Matt likes to be the face of the brand; he loves cooking and teaching. He wants to continue inspiring people to cook and make memories around food. He’ll be doing this through his YouTube channel, in-person cooking classes, recipe development, and writing a cookbook. You will also find him tailgating in the Cowboys’ parking lot with his Phi Delt chapter brothers, creating memories with slow-cooked food grilled over a fire.” (bold mine)

There aren’t any in-person cooking classes in the calendar, and I’ll talk about the cookbook idea in a moment.

I had my plane tickets booked for the 2026 Block Party, which you canceled because your kids sports were keeping you too busy to host. I totally get it. Family comes first. Each of my three kids had a different extracurricular this spring (theatre, soccer, baseball), and it was… a lot.

Is what you said in the interview still true? Are you finding it difficult to be strategic in 2026?

If so, that wouldn’t surprise me. All of the biggest names and brands in the BBQ space have a slightly different business model and strategy. I’ve analyzed most of them, including Malcolm Reed (HowToBBQRight), BBQ Pit Boys, Susie Bulloch (Hey Grill Hey), Jeremy Yoder, (Mad Scientist BBQ), Chuds BBQ, Aaron Franklin, Smokin’ Joe’s Pit BBQ, and Meathead (AmazingRibs.com).

There are so many tempting ideas and opportunities, and even a “good” idea can prove to be a distraction, from the strategic standpoint.

For example, how about that Meat Church cookbook?

It’s an obvious move. Franklin Barbecue’s cookbook sold 200,000+ copies. Rodney Scott’s cookbook sold between 30,000 and 50,000. Susie Bulloch just published her cookbook, Backyard BBQ Hero, back in April.

Meat Church has more reach than any of them. This is achievable for someone in your position, and you can certainly find a worse opportunity. Here’s some rough math based on my research:

• A mid-tier food influencer cookbook earns an advance of $75,000 to $150,000.

• If royalties are around $3 per copy at a $35 cover price, then you would need to sell 50,000 copies to earn out your $150,000 advance.

• The timetable is 18 to 24 months from contract to shelf, with significant time required for recipe testing, writing, and photo shoots.

However, unless you just want to put a book out into the world, which was true for me with both my children’s book Grabbling and my business nonfiction book Free Money, you do have better opportunities.

By “better” I mean ones with more financial upside, with more strategic alignment with what you’re already doing, and with less overall effort required on your part.

For example, how about a “How Flavor Happens” series?

Long before I discovered Meat Church BBQ, I read Meathead’s article, “The Science of Rubs.” What is your take on how barbecue takes on flavor and why Meat Church rubs work so well?

How does flavor even happen with barbecue?

The title “Science of Rubs” or “Science of Flavor” would be off brand, but I have a hunch people would like to hear you explain how flavor happens, specifically why certain rubs compliment certain meats, woods, and preparations; how to build a spice profile and layers of flavor; and what actually happens with smoke, fat, moisture, and bark formation over time.

A 10-part series could drive 500,000 to 1,000,000 cumulative views in year one. Ad revenue, sponsorship revenue, and product sales from the series could push its long-term value into multiple six figures. Thousands more customers like me will lose count of how many bottles they have gone through.

Behold Exhibit A, the Meat Church section of the Church household’s spice cabinet.

Before we move on, let me make a quick detour to your video focused on Pursuit Spirits.

I enjoyed it because I love bourbon and occasionally watch bourbon-related videos. Matt Pittman plus a Pursuit barrel pick, what’s not to love?

Apparently, I was of the minority opinion.

That Pursuit video has gotten 28K views in 5 months. Despite the Pursuit Spirits investment offering a genuine storytelling opportunity, it has one third of the views of your latest video (”I made Pulled Pork tastes like Whole Hog BBQ!”) which has gotten 76K views in 5 days. It comes nowhere close to the lowest of your top 100 videos (~333K). Your top video has 5.2 million views.

Currently, lifestyle/entrepreneur framing doesn’t do well with your audience. Your top-performing videos focus on recipes and techniques.

If I had to guess, you made the Pursuit video because you’re an investor, yes, but more importantly because picking a barrel with friends is fun so why not? You’re to that point where you can and should do things just because they’re fun. Life’s short.

That said, I’ve spent the last several weeks studying your business, and if I may be so bold, I believe I see some ways for you to tighten the overall growth strategy and the YouTube content strategy and drive significant revenue around the core product line.

You’ve got a $20M business and a dozen directions it could grow. That’s one of the most exciting and dangerous places for a founder to be.

There’s no time like the present for growth by subtraction with the help of a 1-page strategy written in plain English:

• What can you remove?

• How can you do less but better?

• What is one thing that, if you were to do it, would make everything else easier or unnecessary?

For example, what if we start with your email list?

I’m a subscriber. The emails are good at what they do: announce a new video, promotion, or product drop. I read some of the emails and occasionally click through.

But I can’t help but think that your email list—conservatively, over 100,000+ subscribers for an eight-figure product business with huge social reach—can get you more leverage:

• Your top ten YouTube videos have over 20 million combined views, and every single one teaches a technique: brisket, ribs, pulled pork, turkey.

• You’ve got more than a content library though; you’ve got curriculum.

• Aaron Franklin’s Masterclass got mixed reviews. You can do better.

• You’ve already got an audience and pent-up demand.

Why do I believe that there is pent-up demand?

Your in-person barbecue classes usually sell out fast, and people travel from all over to attend. For example, your half-day barbecue class with Malcolm Reed drew students from sixteen states, Canada, and Italy.

Your community is clearly action-oriented and instruction-hungry, and they run the gamut of weekend grill warriors to burgeoning pitmasters. You already got tons of social proof in the form of hundreds of comments on your videos like, “You made my little girl’s first birthday a hit. I totally followed your steps.”

You could likely do six figures with a single launch of an inexpensive $99 course based on a handful of your most popular videos (”Brisket on a Pellet Grill,” 5.2 million views; “How to Trim a Brisket,” 1.9 million; “Texas Style Brisket,” 1.1 million). 100,000 subscribers × 1% purchase rate × $99 = $99,000. Maybe Traeger would cross-promote it?

That launch would be just the beginning. It’s a no-brainer to upsell course customers on the bundle of rubs and other products used in the course. And after the initial launch you could create an evergreen funnel, complete with YouTube promotion and organic discovery.

200 purchases per month at $99 is $237,000 per year without you having to do much beyond the initial content creation. Compare those numbers to a cookbook or brand partnership that requires you to lend your audience, or even an equity stake.

2026 may be the exception, but it seems like life is full and busy for you right now. Some strategic recalibration may be in order. I believe in growth by subtraction, and think what I outlined is worth a closer look because it requires no new partnerships, employees, or platforms.

And if courses eventually die as futurist folks are so fond of predicting, then you’ll be well positioned for other strategic ways of repackaging what already exists.

In short, I think you can get more burnt ends from your brisket, and I’d genuinely enjoy a conversation about that if you’re interested.

Shoot me a message here or email me at helloataustinlchurchdotcom.

Meanwhile, I’ll still watch your videos, buy your rubs, and confuse people when I wear that navy snapback and tell them that, yes, my name is Austin Church, but, no, Meat Church BBQ is not my channel.

Cheers to a slow-cooked life you’re not mad at,

Austin L. Church

Austin L. Church is a growth strategist and advisor who works with lifestyle-focused founders doing over $1 million in revenue. His framework, the 7 Levers for Growth, is built around a simple idea: sustainable growth comes from strategic subtraction, not addition and complexity.

They can’t help but ask this question because they are in their thirties, forties, or fifties with a colorful collage of gigs, projects, and ventures, and they still don’t know what they want to be when they grow up.

When they see friends and acquaintances who have had several jobs recognizable as a career, they aren’t envious, per se, but they can’t help but make comparison.

Despite ample evidence that they’re good at a variety of things, they wonder if maybe there’s a problem. Maybe there’s a wire loose. Maybe they need to be fixed.

I think of this as the plight of the platypus, and I’ll explain it further before I point out three traps and give you six tools for moving forward with confidence. You’re fine the way you are, and you can have more satisfaction in your work and joy in your life.

But you have to move like a platypus, not like a Golden Retriever.

The Plight of the Platypus

Some of us are multi-faceted, multi-passionate, and multi-potentialite. As multis, we’ve got a diverse set of skills and capabilities that don’t ordinarily go together. Some of our parts even seem mismatched, like a platypus with its duck bill, waterproof fur, and beaver-like tail.

That versatility is a gift, but it complicates our work and careers. Our education doesn’t prepare us to navigate a hyper-specialized workforce with no obvious place for us. No wonder so many of us end up self-employed.

Still, I’ve found myself wishing that I could find The Thing. Wouldn’t life be simpler if I was happy spending most of my time on logistics, nursing, or fixing cars?

If I found The Thing, then it could be the lantern that pushed back the darkness of my uncertainty. It would fix my allergy to doing just one thing.

Surely platypus with a lantern wouldn’t be plagued by second guessing the path he was on or get tossed around by whatever emotion was blowing, from confusion and frustration to sadness and grief to tiredness and near-resignation. He could silence that voice saying, “Something is wrong with you,” and throw himself fully into The Thing. He could experience real, lasting momentum. His career path would feel less like trudging uphill in dense fog and more like coasting downhill on a bicycle.

As a platypus, I want two things: a mind quiet and confident on the subjects of work and career and the momentum that would come with clear commitment to a single direction.

And as a platypus, I’ve been left with more questions than answers:

• Why do certain former colleagues, siblings, and friends with well-blazed career paths get promotions, titles, and raises when they don’t seem especially brilliant, no offense?

• Why can’t we, the platypuses, be more like them, the Golden Retrievers, and be happy doing one or two things for decades?

• Why can’t we just decide and commit already?

If I’m honest, I want focus and variety, and I have carried these two competing desires like an arrowhead in my heart. Evidence of what being unfocused has cost me deepens the cut.

Other platypuses find their way to me after they stumble across an essay or podcast episode and realize that I’ve spent some time thinking about the plight of the platypus, which fundamentally is about having a wealth of skills, opportunities, and possible paths in a world that rewards specialization.

Our optionality is paralyzing, and I would like to offer some reassurance then some advice.

Nothing is wrong with you.

Here is what I have to say to the platypuses reading this: Nothing is wrong with you.

Maybe you do need to change some things about yourself, but being a platypus isn’t one of them. God put a disco ball of potential inside of you that shines many directions at once. God loves how you are made, and you can rest secure in that fundamental belovedness.

What is equally true is that being a platypus who is pretty good at a variety of things means that you need a different way of thinking about your work and career and your relationship to them.

You don’t need to know what you want to be when you grow up, but now that you are grown up, you do need to know how to keep reinventing yourself, as needed, without slipping into the old pattern of self-doubt, quitting things too soon, or not quitting them soon enough.

A platypus can get caught in traps that a Golden Retriever easily avoids, so you need to be aware of them. You also need a different set of tools to find your way forward.

I’ll explain three of the most common traps before I share six tools that have been helpful to me.

Trap #1 - The Fallacy of Certainty

The first trap is what I call the “fallacy of certainty.”

On any given day, we don’t know what will happen to us, good or bad. We have no choice but to get dressed and get on with the day. We know that roughly half of marriages end in divorce, including those where both partners felt very certain on their wedding days. We still exchange vows.

We order a salad at lunch, knowing that it’s good for our waistlines and cholesterol. Meanwhile, any healthy choice can be rendered irrelevant in an instant by a car wreck.

We’re used to acting without certainty in big and small decisions, so why is it that when we’re trying to decide what to try next, work wise, or where to take our businesses, we suddenly dig in our heels and act as though we must wait to be sure?

In my case, one of the reasons is because money is on the line and I have three kids. When the stakes seem high, I tell myself that I need more research, information, advice, clarity, expertise, credentials, repetitions, and confidence before I can proceed. I try to reach Certainty through its secretaries, Preparation and Control.

Subconsciously, I fall into the fallacy of certainty. I act as though certainty will save me from dead ends and wasted time, from costly mistakes and embarrassment.

Ironically, while I wait for this wizard on the white horse to deliver me, I dither. My delays seem reasonable, strategic even, because I can point to times when more preparation would have yielded better results. If you have ever botched a speech because you didn’t rehearse enough, then you know what I’m talking about.

But entering that wide territory where our work and our heart intersect isn’t like rehearsing a speech or anything else where we already know how to get better results. And Certainty with a capital C is an unreliable wizard. Certainty rarely shows, and even then, the wizard doesn’t deliver the safety, confidence, or bags of money as promised.

And our sense of readiness before we act is rarely an accurate indication of how rewarding a pivot, transition, or foray will be after six or twelve months.

Have you ever been surprised by your enjoyment of a certain project or type of work that you would have dismissed out of hand had you not stumbled into it?

Or have you landed a project with a big brand or a cool client in a market you wanted to break into only to watch your enthusiasm swirl down the drain as the people or circumstances made it decidedly uncool? I have.

We cannot know how everything will turn out, so we do the only thing we can, which is make a judgment call and scrape together enough courage to take one step, and then another.

Confidence in the path comes not from waiting and thinking more about the act but through acting. Each new step brings fresh feedback and intelligence. Each step brings a richer understanding of our recent hesitancy and our real desires.

You and I already know this from experience. I didn’t have to know if my wife was the one. I only had to know if I wanted to spend more time with her. A series of 60% sure steps culminated in our marriage.

It’s worth mentioning here that there’s a difference between knowledge and knowing. No matter how many books we read or experts we consult, we must still act to know something for ourselves. And through acting, however tiny and trembling the step forward may be, we prove to ourselves that certainty is not necessary for our action, growth, or satisfaction.

No wizard is coming, and that’s okay because, like Elsa in Frozen 2, you are the one you’ve been waiting for. And like Elsa’s sister Anna, you change the plight of the platypus if you do the next right thing and the one after that.

Trap #2 - People Pleasing

The second trap for my platypus friends is people pleasing.

I’m a recovering people pleaser myself, and I recently interviewed two other mid-career creatives with the same tendency. In their cases, an unexpected pregnancy and a lawsuit revealed what had long been true—a compulsive desire to keep other people happy was the root cause of problems in their businesses and lives.

Many of us start service businesses because we have the required skills, we want to serve, and we’re good at it. The trouble starts when we can’t separate being liked by clients and collaborators from truly serving them. Managing their current feelings about us consumes our attention, to the detriment of the project and the health of the relationship long term.

There’s just no pleasing some people, and some of the people I have displeased were immature, unreasonable people who said unfair things, because that’s what they do.

Yet, when my sense of self-worth was tangled up with their approval and good opinion of me, I believed them. Their poor opinion of me—or even the anticipation of it!—shook my belief in my abilities, value, and long-term prospects.

The anger came later when I emerged from the toxic cloud, saw a more complete picture of the situation, and recognized that the other party had misrepresented it in a way that served them.

Why hadn’t I seen what was happening?

I tried to make it so that everyone would speak well of me, and that fool’s errand lowered my self-respect, lengthened my recovery time, and delayed my progress. Jesus himself said, “Woe to you, when all people speak well of you” (Luke 6:26 ESV).

People pleasing starts out as a snack machine that spits out rewards and snacks. Who doesn’t love praise and a bag of Doritos?

It turns into a trap because it gives us a distorted view of ourselves, our service to other people, events, and the part we played in them.

Ironically, people pleasing poisons relationships. The better you are at it, the more energy you put into it. The more energy you put into it, the further you get from the real prizes of a deep belief in your belovedness apart from your performance, results, or people’s opinion of you and intimate knowledge of your will, desires, and dreams.

I have found the inverse to people pleasing to be helpful. When I am living well, I will inevitably displease some people, and my willingness to be disliked gives me a clear and continuous advantage in my work and business. Yesmen are a dime a dozen, but nomen—nofolk?—are rare and valuable as friends and advisors.

Not everyone is going to love or even like us. Once we embrace the discomfort of that, we find it easier to know what we really want.

Trap #3 - Comparison

The third trap for multipotentialites wanting to reinvent themselves is a more familiar one that I mentioned at the beginning, comparison.

My friend Lauren comes to mind here because she is, in many respects, my platypus opposite, the Golden Retriever. Lauren and I were two of the “smart kids” in high school and study buddies. Lauren always wanted to be a veterinarian. I had no clue what I wanted to be. I knew I liked writing and making people laugh. I was protective of my time. Therefore, my career path was… [inconclusive].

Fast forward twenty-five years from our graduation, and Lauren owns a successful vet practice in an affluent neighborhood. My parents take their horrible cat Ellie there, and I have no doubt they pay a pretty penny to medicate Ellie who pulls out her own fur and pees in their foyer.

My work isn’t intelligible the way “vet practice” is. My many fascinations have commonalities and coherency, but compared to Lauren’s, my career looks like I got lost at a county fair: freelance writer to lean agency founder to iOS developer to tech startup cofounder to children’s book author to branding and marketing studio co-owner to online course creator to business coach to strategist to business nonfiction author to retreat facilitator to paid speaker to online community leader. I tell jokes and am great at parties. Hire me now.

I haven’t been idle obviously, but if I were to set my trophy case of modest entrepreneurial successes alongside Lauren’s vet practice, income, 401k, health insurance, house, pool, car, weekly massage, fancy groceries, and vacations, then I might start to think something is wrong with me.

While assuming that Lauren’s life is smooth and luxurious as Wagyu butter, I might minimize or forget what I have accomplished.

I might look back at young Austin, bursting with potential, and mistakenly believe that I am wasting his one wild and precious life.

Comparison bleaches the bright colors of joy from our work and pursuits, and that loss is even sadder when you consider that you don’t really know the true contents, challenges, and compromises of the other people’s lives. Maybe Lauren is tired of being a vet. Maybe she feels suffocated by her schedule. Maybe she’d give both pinky toes and one nostril to spend hours each week writing on her back porch the way I do.

Comparison is writing fiction. We allow a fiction to cause us to believe that we missed our chance, that we are lost, and that it is too late to go a different direction.

The stories of many entrepreneurs, artists, and luminaries who didn’t start the thing that would make them famous until later in life testify that we aren’t as far behind as we think. Maybe we’re right on time.

If you want to pivot, you can.

Just remember that the pivot that sticks will be the one that honors and works with who you are and the ways you prefer to show up in the world. Remember also that, even if you get it right, you may want to pivot again.

Speaking of pivots, let’s talk about tradeoffs and tools. You can’t keep all your pet projects and ventures and have extraordinary success with one of them and work reasonable hours and love your life. You have to pick your tradeoffs.

These six tools have enabled me to gain clarity and test new directions without putting pressure on myself to go all in.

1. The Magic Word

2. Timeboxing (i.e., Expiration Dates or Semesters)

3. Experiment Framing

4. Career Portfolio

5. Groundhog Day

6. Clean Values

Tool #1 - The Magic Word

The subconscious belief among platypuses is that there is The Thing that they ought to be pursuing. This belief causes suffering even if it doesn’t cause physical pain.

We’re so itchy with the prospect of finding The Thing that we worry about missing it, like a ship leaving a dock, and we will drop what we’re doing as soon as a possibly better option pulls into the harbor.

We bounce from one thing to the next thing hoping to find The Thing, and if we don’t curb this impulse, then we end up with a curiosity cabinet full of half-finished passion projects, half-launched business ideas, and assorted ceramic frogs painted in the avant garde style of Half-Committed.

This hummingbird impulse causes regret. Anything we do halfway doesn’t bring the satisfaction of a wholehearted commitment. More on commitments at the end.

Plus, the underlying restlessness prevents us from fully appreciating the good things and good work we do have.

What helped me focus and have fewer regrets was admitting to myself that The Thing might not exist. A better bet was making a wholehearted commitment to the next thing for a period of time.

“Next” is the magic word that helps us pick one good option and ignore the many others—if only for a little while. “Next” points our own changeable hearts in a single direction that we can easily explain to ourselves. “Next” shrinks the mystery of the future to a concrete stepping stone.

I used the magic word before I started my online community in November 2024. About two years prior, I told a friend, “I have no desire to manage a community.” I meant it, then time passed. A cohort of group coaching clients asked me to keep the cohort going. They described what they wanted. That sounded suspiciously like a community to me.

“I’ll try it for six months,” I said, “but I’m not making any promises after that.”

Eighteen months later, the community is still growing.

Do I still sometimes wish that I had a plan for my life that was more like a blueprint for a castle than a curvy line of stepping stones? Yes. And wouldn’t it be nice to see the next twenty or thirty stepping stones all at once instead of just one or two? Yes. But that’s just not how my life has unfolded or how my wayfinding has worked.

I have needed the magic word, and if you need it too, then answer these four questions as honestly as you can:

• What do I want next?

• Or, what would I regret not trying?

• What is the next concrete stepping stone?

• What would wholehearted commitment look like?

You can pick the next thing without knowing what you want forever.

Tool #2 - Timeboxing (i.e., Expiration Dates or Semesters)

Many of us aren’t ready to go all in on a six-month commitment, let alone three years. As the time horizon stretches out, our anxiety goes up.

I find it easier to pick the next thing if I give the commitment an expiration date, and thinking in terms of a semester, or three months, has helped me release any hidden pressure to turn the next thing into The Thing.

I can tolerate nearly anything for ninety days, so it’s okay if I end up disliking the next thing.

Ninety days also gives me enough time to learn and accomplish something measurable. College courses count as credit hours toward degrees.

And if we stick with the next thing long enough, we gain what Cal Newport, the author of So Good They Can’t Ignore You, calls “career capital.” Commitments with expiration dates give us new skills, experience, and competencies, which in turn bring new clarity, direction, career capital, and opportunities.

Here are some of my commitments that became capital:

• Commitment: Investing in Mike Pacchione’s Speech Club, a group coaching program for public speaking

• → Capital: Knowing how to put together a memorable speech and more confidence and comfort as I deliver it in a way I’m proud of afterward

• Commitment: Optimizing my friend Mark’s Etsy shop

• → Capital: Getting paid to see if this is a direction I want to pursue with consulting or even a lean agency

• Commitment: Publishing every weekday on LinkedIn for several years*

• → Capital: Becoming a better writer and building an audience

• *Worth noting is that I kept extending this commitment.

• Commitment: Creating and delivering a group coaching program, Business Redesign

• → Capital: Testing this business model which also forced me to better define the outcome and create the playbooks that made it possible

• Commitment: Investing in Krista Miller’s Launch with a Summit Accelerator, a group coaching program for hosting virtual summits

• → Testing a virtual summit as a marketing vehicle for audience growth and profitable launches and grossing over $42,000

Did any of these things become The Thing? No. But public speaking, Etsy optimization, writing, group coaching, and virtual summits are all things I can do confidently now.

I could write a much longer essay about how each of these commitments has expanded the surface area of good things that can happen. I’ll share one specific example: The same year that I did Mike’s Speech Club, a single speaking engagement netted me five figures, a trip to Australia with my wife, and several new friendships and collaborations.

I’m not sure that speaking is The Thing, but I sure am glad I didn’t wait for more certainty before committing to improve at it.

Take out your journal and ask yourself three questions with all the honesty you can muster:

• Can you think of anything you’d like to do but haven’t started because you left the commitment big and open-ended?

• Or can you think of something that interests you and would be valuable to learn even if you don’t end up doing it all the time?

• What might a semester of that look like? What is one measurable outcome you could reasonably see by the end? For example, the outcome of that Speech Club program that I joined was giving a 30-minute talk I was proud of.

Platypuses don’t have to know where we’ll end up before we make commitments. Even our temporary commitments can have permanent value.

Tool #3 - Experiment Framing

Experiment framing is nothing new. Anne-Laure Le Cunff explored the idea at length in her book, Tiny Experiments, and if you read Benjamin Franklin’s Autobiography, you’ll find that America’s favorite polymath was running experiments to improve his virtues, habits, and routines as far back as 1700s.

Experiment framing for the next thing I want to try has helped me in three ways:

• Limited time horizon

• Sampling

• Better “data”

The word “experiment” implies a limited time horizon, and as I mentioned, I find it easier to make a wholehearted commitment if I give it an expiration date.

Being a chronically fascinated person, I know that I may change my mind later. The impermanence of experiments sends a message to my weird brain: “Relax. The stakes are low. You don’t have to know if you want this forever. You just need to finish the experiment.”

I keep returning to that idea of high and low stakes and betting because my mind constantly tries to convince me that the stakes are higher than they are.

I feel this pressure, as though I must know, I must have certainty, I must commit indefinitely.

None of that pressure or mental rubbish is real, and experiment framing helps me to push it all aside, knowing that the goal of an experiment is to sample this new thing, not find The Thing.

Sampling is important for me because past experience has shown me that I misjudge how much I will like or dislike something. I expected to like leading the Freelance Cake Community less than I have. I expected to enjoy being a fractional CMO more than I did. I can speculate, but I simply cannot know what something is really like until I try it.

My coaching clients and community members fall into the same trap as they agonize over whether to try a new type of work, offer, or niche. With all of the anxiety they bring to a change that is still theoretical, you would think someone was forcing them to get Mickey Mouse face tattoo in fifteen minutes.

I reassure them that, unlike the tattoo, most decisions are easily reversible, and that, before they reach any sweeping conclusions, they should use experiment framing as they try the new thing once and see if they like it:

• If you think you’d like to be a fiction editor, don’t think about the next decade. Instead, convince one novelist to pay you to edit her latest manuscript. See if you like it enough to edit a second novel.

• If you think you’d like to pivot your content writing business to coaching, don’t start a coaching business. Craft a one-page coaching offer in a GDoc and put it in front of ten people. Coach one paying client for three months, then reassess.

• If you think you want a big email list, don’t launch a newsletter. Commit instead to writing one email. Text, email, or message one hundred people who already know, like, and trust you—or at least you think they do—and ask if you can send them a piece you wrote that you think they’ll enjoy. Send the first newsletter. Repeat eleven more times. Then, reassess.

You may discover that you hate editing fiction, coaching, or sending a regular newsletter.

Part of you knows you may change your mind later about the new thing, and that is the part of you that digs in your heels and creates resistance before you have even started.

So if you want to get stuck less often, pretend The Thing and the certainty wizard on the white horse don’t exist and let your curiosity lead you into framing the next experiment.

Then, you let your enjoyment tell you whether to recommit after the first experiment.

It’s worth mentioning that you can sample new things in a way that doesn’t make you smarter or give you career capital.

That’s how experiment framing differs from a loosey-goosey approach to trying a new thing. Scientists design experiments. They form a hypothesis. They identify variables in advance. They pick a control. They run the experiment and measure the results. They compare the results to what they expected to happen, what they expected to learn.

Scientists bring a sharp intention and deliberate acts of observation to what otherwise might be a whim, gut feeling, or intuition.

It’s fine to use your intuition to get you moving as long as you recognize the problem that Daniel Kahneman, the late Nobel Prize-winning behavioral economist, points out:

“The problem with our intuitions, one of the many problems with our intuitions, is they come too fast. We form impressions very, very quickly, and then we tend to confirm them.” (source)

When we’re walking into the unknown, Kahneman recommends “disciplined intuition”—that is, a structured, disciplined approach to evaluating the pieces of a problem or possibility one at a time, poking at your assumptions and impressions, and extracting the maximum amount of insight.

We have better judgment and make better decisions after any experiment if we’ve done that.

So take out your journal and frame your next experiment:

• What is my hypothesis? What do I expect to happen? What do I expect to learn?

• What do I think this experiment will give me that I don’t already have?

• What story do I want to be able to tell afterward?

• How will I know if this experiment is successful?

• What question am I trying to answer?

Instead of the next thing happening to you, you happen to it, and because you proactively decide what you will measure and what data you must collect, you have more true intelligence and data at the end of any experiment. You have more clarity and confidence about the next experiment you will perform. You imposed discipline on your intuition.

Tool #4 - Career Portfolio

Most of us won’t have a career path like a single train on a rail spanning fifty years. The very idea of doing the same work for fifty years may sound horrifying and claustrophobic, even if it works for Golden Retrievers.

If platypuses don’t have a career path, what do we have? A career portfolio.

You build your portfolio by using the magic word to decide what you want to do next and running experiments with expiration dates.

One of my former coaching clients, Rachel Bicha, thought she might like creating and sending a monthly print newsletter. She chose to “pick the smallest possible idea to try first” and “keep expectations light.” She got started without having to carry a heavy psychic load. (source)

Now a year has passed, and the newsletter has become a regular project that has won a place in Rachel’s career portfolio. She can point to twelve one-of-a-kind newsletters, and feel a sense of pride. That stack of newsletters also gives her authority when she talks to a potential client about their direct mail piece or print project.

Many platypuses like Rachel don’t have a straightforward resume to show for their work experience. They have a portfolio rich with projects, ventures, and accomplishments. They have proof of their commitments and stories to tell.

It may be harder to explain at times, but it opens more options and opportunities for you.

To the right future collaborators, your career portfolio will be more interesting, attractive, and persuasive than a traditional resume.

Here are some of the projects in my career portfolio:

• Graduating with my Master’s degree in Literature with a focus in creative writing and publishing my poems in literary journals

• Developing and eventually selling a portfolio of 30+ iOS and Android apps (Bright Newt)

• Completing a Nanowrimo challenge (writing 50,000+ words of a novel in a month)

• Cofounding a business training library of high-quality videos for freelancers (Kicktastic)

• Cofounding, raising money for, and attempting to scale a tech startup (Closeup.fm)

• Creating and teaching a travel hacking workshop

• Writing a guide on improving your credit in 30 days

• Hosting 9 retreats for entrepreneurs (SPACE Retreat)

• Speaking at TEDx, Pecha Kucha, and various conferences

• Creating and selling physical time management cards (FoFi)

• Hosting a virtual summit (Fix Your Pricing Masterclass for Freelancers)

• Co-founding a branding and marketing studio (Balernum)

• Productizing a one-on-one business coaching engagement for freelancers

• Creating and launching a business-focused course for freelancers (Freelance Cake)

• Creating various other programs, products, and smaller courses for freelancers (e.g., Morning Marketing Habit)

• Leading a private, paid community for advanced freelancers (Freelance Cake Community)

• Starting and growing a weekly email newsletter (Freelance Cake)

• Launching a podcast (Freelance Cake)

• Publishing a children’s picture book (Grabbling)

• Publishing a pricing and money mindset guide for freelancers (Free Money)

I finished each of these commitments in a meaningful way, and now I can point to a career portfolio and say to myself, if no one else, “Here’s what I’ve been doing with my life.”

Here are some questions to help you build your career portfolio:

• What passion project is worth finishing even if it never makes you money?

• What skills and competencies will be more valuable in the future?

• What commitment will help you develop one of them?

• What will you finish now to minimize regret later?

You may not know The Thing, but you can finish a bunch of different things. Through finishing you can learn how to do many things. You can be proud of what you have accomplished in your life and work, even if your career isn’t as easy to understand as running a veterinary practice or climbing the ranks in a corporation.

Tool #5 - Groundhog Day

Like the human race at large, platypuses want to get what we want, but what we want changes.

On any given day, it can be hard for us to define “success” and articulate what we are optimizing for. Control over our calendars? Autonomy over our work and livelihood? Higher income? Delight in the creative process? Intimate relationships? Health?

I’ll take one of each. Thank you.

Goals dance around our heads like butterflies, and that kaleidoscope only adds to the fundamental distraction and second-guessing problem. Goal fatigue is real.

So I’ll offer an alternative to that least helpful of words, success, and to goals that may be difficult to catch and quantify. Your good day repeated. Your Groundhog Day.

You generally know what your good day contains and feels like, right?

As Atomic Habits author James Clear noted, a good day repeated can become a metric for how well you’re doing with your work and life:

“I do think there can be a simple philosophy that you can carry around. Just have one good day. Just have one good day, then repeat it.” (source)

Human beings invented philosophy to help us understand what a good life is, and because we’re brilliant at overcomplicating things—which explains the existence of baseball and U.S. tax law—I want to get annoyingly specific about what a good day and good life is, using some first principles thinking:

• A life consists of days.

• Therefore, a good life is a collection of good days.

• Different individuals prefer to spend their days, or about sixteen waking hours, in different ways, so the definition of a good day varies from person to person.

• Some uses of sixteen hours we enjoy, and they make our lives qualitatively better.

• Other uses of our time we enjoy, but they make our lives qualitatively worse. We ignore these negative effects for any number of reasons, from a sense of duty to apathy to addiction to confusion to fear.

• Other uses of our time we don’t enjoy, but they make our lives qualitatively better. We ignore these positive effects for any number of reasons, from laziness to forgetfulness to poor planning to ignorance.

So if we want good days, then we must deliberately spend our time on things we enjoy that benefit us and things we don’t enjoy that benefit us while we reduce the time we spend on things that we enjoy but that make our lives qualitatively worse. When we put together enough good days, we end up with a good life.

That last paragraph may read like a bowl of oatmeal, but how often do we nurse dissatisfaction with our lives while also failing to change the makeup of their basic building blocks, our days?

You’ve surely heard the parable about the American executive who tries to persuade his Mexican fishing guide to build a fleet and business empire in order to get the simple life that the guide already had, one spent fishing, playing music, and enjoying his family.

There’s a near-universal temptation, at least in the Western hemisphere, to fall into this trap. We climb the ladder only to end up where we started.

We work hard to create a sense of abundance, security, and significance that was always available to us if only we paused to glance around. Do I really want a new car or do I want to invite old friends over for barbecue and stay up late talking?

Consider my several “bad” months of revenue in 2024 and 2025 when I still managed to pay my family’s bills. While we barely broke even, I spent less time on billable work and more time writing.

If a good day repeated had been my primary metric, then I would have seen those months of lower earning as remarkably good. Apart from bank accounts or other vanity metrics, I know I’m succeeding (or whatever) if I’m stringing together more and more days that do not include nonstop meetings, big egos, corporate politicking, and bureaucratic red tape; and days that do include various spiritual practices like prayer and reading scripture, exercise, eating healthy foods, reading, writing about what fascinates me, unhurried time with my family, and coffee with a friend. I already know what my Groundhog Day contains.

I am referring to the classic 1993 Bill Murray movie “Groundhog Day.” Murray plays Phil Connors, an arrogant, self-centered TV weatherman who keeps waking up on February 2 in Punxsutawney and repeating the same unpleasant day until he decides to use the loop to improve himself and help others.

When you have no other clarity to speak of, your Groundhog Day will guide you:

• What does the container of a good day hold for you?

• If money were no object, how would you spend your time? How would you spend your freedom? Take some time and describe what a satisfying day looks like for you.

• Will the path, pivot, or transition that you’re considering give you more days spent on those pleasures, people, pursuits, and beneficial discomforts and challenges?

• Will it take you there directly or is it roundabout?

As you think about where to go next with your work, optimize for days, not dollars.

Tool #6 - Clean Values

The word “values” is similar to the word “success.” We use it so much that it has lost its meaning. Rather than reach for a dictionary, I’ll make up my own definition: Values are the invisible principles and preferences that make us pick one option over another.

If predictability, safety, and comfort matter a great deal to Sally, then she will take on a big, high-paying project she doesn’t find all that interesting for a company she doesn’t believe in. Her values sent her that direction.

Sade may take on a smaller project with an apparel brand. It doesn’t pay as well, but she cares about sustainability, equity, and doing design work she’s proud to share. Different values, different direction.

Values are like fuel that we burn. If your fuel is dirty, then you will experience less peace and contentment. No matter what you achieve in your life, you will enjoy it less.

Entrepreneur and investor Brent Beshore was the first person I heard talk about “dirty fuel”:

“The world loves my false self. The world loves that fear-driven self. I can get an extraordinarily incredible amount done. A friend of mine calls it clean fuel versus dirty fuel. It’s very difficult to see. The car looks like the car from the outside. Very difficult to understand. Is it clean fuel or dirty fuel that’s operating the car? And I mean, that car can go fast. It can take a lot of people with it if I’m on dirty fuel. And in some ways dirty fuel is a more potent fuel in the short term for me. I get more stuff done quicker, and even sometimes with higher excellence, out of dirty fuel than I do with clean fuel. That fear is a heck of a motivator.”

Beshore goes on to point out the problems with dirty fuel:

“The problem is that it’s [dirty fuel] got all kinds of contaminants in it and you eventually torch yourself, and the car breaks down and you go off the rails and blow yourself up—whatever analogy you want to use. So getting back to the original question, What’s changed? I think that more and more, I’m trying to operate on clean fuel. I’m trying to be self-unconcerned. I’m trying to become an elder.” (source)

My fuel has often been dirty. My wife would tell you that I have trouble sitting still—that is, not working—and if you asked me why I struggled to slow down, ignore my to-do list, and relax, I would have concocted a bogus answer about how my work and hobbies overlap.

The full truth was that my relationship with work was complicated and that I hadn’t taken the time to pull it apart and understand the ingredients in my fuel.

On the one hand, I worked because I wanted to do good. I wanted a better, more equitable world. I wanted to give people a hand up because I have suffered less and had more advantages than many.

I liked seeing my effort become concrete results. One of my early hospitality clients increased bookings 198% year over year. Another client, a prosthodontist, told me that his patients and colleagues loved the copywriting I had done. I liked knowing that my work had a positive impact on others.

I worked because I wanted better for myself and my family. I want my kids to have plenty of opportunities: You want dance lessons? Go for it, darling. I worked because I wanted more beauty and poignance in my life, more bedazzled moments.

On the other hand, I worked because I was afraid of what would happen if I didn’t.

I worked because I experienced betrayal, rejection, and profound loneliness in middle school, and without knowing it, I made a compact to achieve and achieve until no one could deny my worth, make me feel ashamed, or push me to the outside. Achievements would prove that I deserved love, respect, and belonging—a seat at the Cool Kids Table.

What was the result? I always had to be achieving something.

Work was camouflage and armor and anxiety made manifest. I worked to meet external measures of success not because they mattered deeply to me but because I was afraid of what people might think or say if they found out that I had quite ordinary problems.

I worked because my bank balances embarrassed me and because my family’s finances felt fragile. What would happen if we came up short too many months? I white-knuckled my calendar and to-do list to convince myself that I had more control over my life than I really did and burned out hard in 2015 and 2016.

Work was a hiding place and distraction from deeper questions. I often felt powerless to do something about the bigger problems in the world, and I couldn’t do much improve my wife’s health. People have always told me that I had great potential. Did my life reflect that potential, or had I wasted it? I didn’t love myself fully. I didn’t accept myself.

What was the result? I worked more than I wanted to, more than was good for me, in an attempt to silence the voice in my head saying, “You aren’t doing enough. You aren’t enough.”

Work was salvation. I worried that things would always be this way, that I would always feel like I was one bank deposit away from obvious failure, ridicule, and rejection. My life felt messy and chaotic, but here was one thing I could point at and believe I was doing well. “The rest of the house is a disaster, but the kitchen is clean.”

What was the result? I became too efficient, which meant not spending time on other things that nourish me. Fly fishing. Friendship. Poetry. Playing with my kids. Rest.

I worked too much to temper my disappointment in my compromises, my frailty, my limits, my smallness, my humanness.

Inside of me were two boys, one boy looking at the sky and dreaming and another with his innocence crushed like a flower under reality’s heel. Part of my journey has been welcoming both of those boys into my center, fully accepting how they helped me get to where I am, and soothing them the way I would my own children, “It’s okay to rest. You are cherished. Like the birds of the air, your needs will be taken care of. Trust God.”

If the main ingredient in dirty fuel is fear, then clean fuel must contain fear’s opposite, love. Love drives out fear. USC philosophy professor and theologian Dallas Willard put it this way:

“Love focuses on the promotion of what is good, and if you love a particular thing, then you focus on the particular good of that thing.” (source)

Love is clean fuel, a clean value, and when I’m feeling stuck, confused, or discouraged, I now know to ask, “What do I love?” I’ll ask myself yet again. “What is good for that person or thing? What am I capable of today?”

Here are other clean values that drive me: curiosity, enthusiasm, kindness even in the face of anger or spite, generosity, making beautiful things, relationships over incremental profits, joy as a posture and practice, and full presence in the vein of Jim Eliot: “Wherever you are, be all the way there.”

I doubt that our values will ever been completely clean. Moving toward love, curiosity, kindness, and joy will be a lifelong journey.

The sooner we examine our deepest motivations in our work, the sooner we know what type of fuel we burn most often—and the sooner we begin to separate our identity and sense of significance from anything we do or don’t accomplish.

This is how we have more peace, and this is how we redeem work.

So what drives you? And what type of fuel do you want in your tank?

These questions can help you find your way forward:

• What non-negotiables or guiding principles determine how you show up in the world and do business? What will you never do?

• What can you not imagine not still being true 10 years from now?

• What are you not willing to compromise on even if it means losing in the short term in business?

• What would go on the motivational poster on your wall, even if it seems cheesy to other people?

• What do you love for its own sake? Is my work promoting what I love?

• Beyond making money to pay bills, why do you work? What makes good work “good” in your mind?

• When you aren’t working toward a specific goal, what musts, oughts, and shoulds influence decisions and actions? What loves are etched in your bones?

• Which criteria and conditions in your business will leave you with the least regrets? What is required for you to do business with a clear conscience?

• What are you not willing to sacrifice under any condition? For example, I want to be the dad who’s around so much that his kids complain about it to their friends. And I want to keep my marriage. And I want to protect the basic dignity of people I meet and do business with.

Our work and our businesses have a way of tying us up into knots and putting our heads on backwards. Ambition doesn’t heal inner wounds any more than money buys intimacy. Occasionally, we need our values to straighten us out and point us in the right direction.

Closing Thoughts (or, make clear commitments)

I’ve got some bad news: You may never know what you want to do with your life, and you still have to live it.

I’ve also got some good news: You may never know what you want to do with your life, and you can still live a beautiful life.

Uncertainty makes us feel fragile, and yet uncertainty traces the beauty of the human condition. We do not know and cannot know what will happen, tonight, tomorrow, or ten months from now, and this is true for platypuses and for Golden Retrievers, no matter how certain they may be about the path they’re on.

One bad knock on the head, and all of a sudden, you can’t do the work that defined your identity and fed your certainty.

Certainty is the racket we’re all participating in to varying degrees, and there’s nothing inherently wrong about wanting to feel more certain. Getting more intel and hardening it to insight is what wise people do. Wisdom is experience distilled to truth and made shareable.

However, we’ve got to choose and act even when we don’t feel wise, and that leads me to the remedy for uncertainty, which is commitment. Jim Dethmer, founder of The Conscious Leadership Group, talks about how we’re always 100% committed:

“Everyone is already fully committed. You can’t get more committed. Telling yourself or others to get more committed is a waste of time. The key is not more commitment, it’s clear commitment.”

Clear commitment means you don’t have one metaphorical foot out the door. Clear commitment means you’re all in for a certain amount of time.

In a way, the other six tools are the conditions for clear commitment. Use the magic word, next, to pick your next pivot or change in focus or direction, without knowing what you want forever. Timebox the choice with an expiration date. A single semester is fine to start with.

Use experiment framing to bring sharp intention and deliberate acts of observation to what otherwise might be a rather vague detour.

Think about how the results of the experiment can fit into your career portfolio and help you have more of the kind of day you want to repeat, your Groundhog Day.

And reconnect with your clean values so that the fuel that drives you isn’t contaminating your work and life but producing the good you intended.

If you remove any of those conditions, it’s much harder to make a clear commitment.

And if you’re confident that a new commitment meets those conditions, then your mind can relax into it, and you won’t be plagued by the self-doubt and second-guessing that grows up around unclear commitments.

You’re already 100% committed to the path you’re on, so if you want to take your work or your business a new direction, then take the time now to renegotiate the commitments you already have. Free up some attention and give it to your next experiment.

Above all, we must be honest with ourselves. We all know people who don’t do much of anything, and they try to convince themselves and us that caution and good sense are driving them. The truth is, they’re afraid—afraid to make mistakes, afraid to be ridiculed and rejected, afraid to find out they are wrong in their thoughts and choices, afraid to discover that the very people they criticized had the right of it, afraid of the grief caused by time wasted not on failures but on a purely theoretical pursuit of wisdom, growth, and excellence.

I still find fear in my fuel. You will too. The trick of growth is naming it faster and doing the next thing scared.

There is no courage without fear. There is no progress without mistakes. There is no change without pain. There is no certainty, only a more or less convincing illusion of it. There is only acting despite the fear.

The only choice that life’s mystery leaves us is believing. We act on faith, or we don’t act at all.

I recall a series of meetings in 2018 wherein the resident “strategist,” easily the least helpful person in the room, tossed out ideas like hand grenades. When the real work began later, he performed his famous disappearing act.

It only takes one bad apple, as the saying goes, and strategy is similar to used cars or timeshares in that what people actually get may not resemble what they thought they were buying.

Now that I am a strategist myself, I sometimes assume a role last occupied by someone who provided next to no practical value. The CEO or founder who hired me might still be bullish on “strategy,” but the rest of the team needs convincing.

Like a good puppy or teacher, a good strategy can change your life, so one of the first things I do to restore faith is provide clear working definitions of “strategy” and “strategist.” I’ll share them here.

What is strategy?

I define strategy as the path to superior results.

Former PepsiCo CEO Indra Nooyi provided the raw material for this definition. Running a $200 billion global company taught her a thing or two about good and bad strategy. Here is the relevant excerpt from the interview I listened to:

“And that’s the challenge with strategy. You’ve almost got to have a 360-degree view of the environment, of competition, of the markets, of customer revolution, everything else. And then you’re crafting a path to say, ‘This is how we should proceed. This is why it’s going to be better for us than it is today. And incidentally, if the world around us changes, we’re going to zag a little bit, but we’re still going to focus on getting to a better place.’” (bold mine).

I take the idea of a “better place” or superior results one step further by tacking on an important idea from Michael Porter’s classic 1996 Harvard Business Review article, “What Is Strategy?”: “The essence of strategy is choosing what not to do.”

Strategy is the path to superior results, and to walk that path, you must consciously ignore other paths. That principle of growth by subtraction became the foundation of my approach to strategy. Or perhaps it’s more accurate to say that the principle is the fulcrum and strategy is the lever. Together, they give you better results with less effort.

Once I understood growth by subtraction, I realized that I had already brushed up against the principle in a hundred observations and a thousand conversations. In every domain, from investing and athletics to agriculture and spirituality, growth by subtraction appears. An apparel company grows faster after the CEO decides to focus exclusively on socks and not diversify to other garments. A Michelin star chef sends a message with the pre fixe menu: ”This isn’t Cheesecake Factory. We offer fewer dishes, and we execute them much better.”

When I was a boy working with my grandmother in her garden, she instructed me to pinch off the suckers that grew between the bigger branches and stems. Why? Fewer suckers meant bigger tomatoes later.

Businesses sprout their share of suckers. They intercept resources that could have gone to a single strategy more likely to produce superior results or a step change in growth.

The trouble is, in business, some suckers are diversions, distractions, and dead ends, and some of them are pretty good options. It’s not until you compare the possible paths to one another and hold them up against your goals that you see lesser paths for what they are.

Founders and CEOs can lead this process or do this comparison on their own, but there are a couple of reasons they face several challenges:

• Visionary gift. A CEO’s expansive vision, which is required to see many forks and offshoots, can get in the way when it’s time to pick a single path and walk resolutely down it.

• Complexity. Companies and strategies grow organically over time, and complexity starts to seem necessary and realistic, even if complexity doesn’t scale.

• Sunk cost bias. The more time and resources that you invest in certain underperforming products or tactics, the harder pruning them becomes.

• Blind spots. When it’s your company, you’re under the curse of familiarity, and no matter how hard you try, you can’t attain true objectivity and see what you’ve been missing.

• Agreeable team members. It’s hard for full-time employees whose livelihoods are on the line to say to their opinionated CEOs, “That looks like a shiny object to me.”

Some leaders overcome these challenges on their own, and some bring in an unafraid outsider with the expertise and outside insights needed to identify the suckers, pinch them off, and run the new strategy. Even a good strategy can’t produce superior results if the team drifts from their commitment to it.

What do good strategists do?

If strategy is the path to superior results, and one that must be consciously chosen again and again, then a strategist is a person who finds the path to superior results and reminds the team what they’re not doing.

To be more specific, a strategist has four main responsibilities:

1. Define “superior results”—and get everyone to agree on that.

2. Take inventory of possibilities and pathways.

3. Pick the one that seems best—and get everyone to agree on it.

4. Communicate the strategy in plain English.

It’s shockingly easy to optimize for the wrong things in any business. Several examples come to mind. One of my clients ran a promotion that attracted the cost-conscious customers they didn’t want. Another client prioritized growth over profitability, and rising customer acquisition costs (CAC) combined with frequent discounting and debt service created a serious cashflow problem.

“Superior results” means “better” or “different” as often as “more”—better profits, different customers, better products, different marketing channels. “Superior results” can mean higher revenue, but it can also mean a shorter, easier sales cycle or a single channel partner driving hundreds of sales.

So one of my first tasks is to get everyone to slow down long enough to decide what success looks like really. We have a name for growth for its own sake, ”cancer.” Is more-more-more the goal? Or do we need to sharpen the team’s understanding of how we’re defining and measuring desirable change?

Here are five examples of superior results that emerged during my client engagements:

• Food company: “Get to $500,000 by December 2026”

• Pet supplement company: “Get revenue to $15,000 per month”

• SaaS company: “Build brand awareness and drive signups by forming strategic partnerships”

• Franchise company: “Use a live monthly webinar to build trust before leads come to disclosure calls”

• First-aid company: “Create a differentiated brand and launch a better-for-you product then court Walgreens as our preferred retailer”

What never ceases to amaze me is that the strategy best suited for those results often isn’t novel. Though I like to ask, “What else could we do?” and entertain new possibilities and pathways, I know better than to assume that a radically innovative strategy will be the winner.

The winner is often hidden in plain view, like a wheelbarrow in an overgrown garden. You know you have a wheelbarrow, but you don’t remember it until a neighbor asks to borrow it. Oh yeah. You could have been using it this whole time.

The strategist defines the goals and facilitates conversation around possible pathways, and then the strategist eliminates lesser pathways and creates consensus around the one best suited for the goals.

But let me be very clear on one point: Good strategy assumes confidence, not certainty, and a strategist helps you pick a strategy on that basis. Every twist, turn, and tactic of the chosen path will not be clear before you start walking on it.

The right strategy is one part feasible and one part uncomfortable. You will know the what and the why, but you won’t know all of the how. The right strategy forces you to recognize that you don’t know everything or everyone you need to know. You don’t have everything you need.

The right strategy challenges the status quo. It requires both you and your team to change.

Strategists are therefore agents of change, and consensus building is the unsung competency that good strategists have. A good strategy does nothing unless it gets implemented, and implementation requires people, their buy-in or belief at a high level, their optimism at the ground level, their willingness to abandon the old strategy, and their willingness to embrace the changes that the new strategy entails.

Assuming you give her the leeway, a strategist can help executive leaders smooth ruffled feathers, even with her presence alone. Her presence says, “This isn’t another one of our visionary founder’s harebrained schemes. This is a legitimate strategy with real thinking and rigor behind it, and real implications for the company. We will all benefit if I get on board and do my part.”

A strategy written in plain English goes a long way toward building consensus. People can’t get excited about the strategy if they are confused. They can’t remember the strategy if the handful of people who understand it best needed eighty slides to communicate it to everyone else.

In his book No Bullsh*t Strategy Alex M.H. Smith writes about this PowerPoint problem. When we don’t understand the strategy well enough, we think we must expound upon it with pretty designs, diagrams, and sundry declarations. Smith says, in effect, “Please don’t.” The better test for whether you understand the strategy is communicating it in plain English.

My clients have gotten better results with their strategies when the strategy “deliverable” was a document unremarkable in every way, except in its clarity. I prefer a one-page GDoc or Word doc with the rationale explained in a few short paragraphs and the strategy itself summarized in one or two sentences, ideally composed of one- and two-syllable words.

Plain, concise English does a few things for you. It’s easy to understand for folks inside and outside your company. There’s no corporatespeak or embellishment that obscures what’s being said. Half the battle with the new strategy is keeping it from becoming as complicated and confusing as the old one. The brevity leaves less room for misinterpretation and ensures that fewer people try to duck their responsibility, claiming that they didn’t know what they were supposed to do.

Plain English has one final benefit worth mentioning. It leaves strategists and executives with no place to hide. If we don’t understand the strategy well enough to state it in plain English, then we can’t blame the people responsible for implementing it for not implementing it.

If the strategist gives you a page that your nine-year-old nephew or ninety-year-old grandma can grasp, then she did her job.

So in summary, good strategists help their clients define superior results. Then, they pick the most promising pathway. Then, they get everyone to agree on it. Then, they communicate the strategy succinctly in plain English. Then, they stick around to help the team maintain their commitment to it. Or not. Their ongoing presence and support depends on your budget.

When you’re ready to grow by subtraction using a 1-page strategy written in plain English, email me at hello[at]austinlchurch[dot]com.

Now, founders want to buy what comes from good strategy. They want more clarity, commitment, or momentum. They want a qualitative change in their companies or even their relationship to their companies. Or, they want more leads, sales, or revenue—a quantitative change. Or, they want their team to agree on which direction everyone is going, to take a more disciplined approach to marketing, or to waste less effort going in the wrong direction.

The list of wants varies, and most of them are plump, ripe fruits hanging from strategy’s branches. If I stopped the founder of a DTC outdoor or food brand and pointed out this connection between the strategy tree and its fruits, they would say, “Of course.” You don’t stay a founder for long if you don’t believe strategy is important.

Still, most founders aren’t shopping for strategy most of the time. They’re focused on their problems. Strategy is just the means for the transformation, and because it is so fundamental, it can be surprisingly easy to forget and ignore.

So my awkward job is helping a very intelligent, perceptive, hard-working, ambitious, and committed group of people called founders to remember that they may be working harder than necessary and that a different strategy can help them get what they want faster.

Even after I convince a founder of this fundamental truth, I run into a second problem: Every founder already has a strategy.

Founders will keep a strategy that isn’t serving them for several reasons. Maybe it worked in the past and helped get the company to where it is, so replacing it feels risky. Or it may have been around so long that it is effectively invisible.

Or maybe the strategy is attractive because everyone already knows about it, and that familiarity means that the founder doesn’t have to push the boulder up the hill through education, inspiration, cajoling, and ultimatums. Keeping the strategy they already have is easier!

Another non-shocking reason founders keep doing the same thing and getting the same results is because they stay in reactive mode and don’t pause long enough to admit, “This isn’t working.”

Growth and speed aren’t always the goal, but most of the time, you know you’ve got the wrong strategy or a non-strategy if you aren’t getting the results you want, whether qualitative or quantitative.

Strategy is the path to superior results, and I end up talking to founders because they don’t have a clear trajectory or feel the excitement of being swept up and carried to a more prosperous place.

Instead, they feel a vague sense of unease or dissatisfaction. The distance between where they are and where they want to be is what pushes them to look for answers and make changes, often before they have fully expressed what they’re searching for. Again, they’re not rolling out of bed in the morning and proclaiming, “I need a different strategy!”

My role during the discovery phase is helping them fill in the brackets and blanks:

They want [fill in the blank] to be more “successful” than it is—[but what exactly does that mean?]—and though they’re grateful for what they have, they want more [well, this needs to be more sharply defined] without [because there are certainly some tradeoffs they’re unwilling to make].

Even if the incumbent strategy is pretty good, a dissatisfied founder will have trouble adhering to it because of the third problem: complexity.

Left unchecked and unpruned, every company drifts into complexity over time, and the longer an organization has been around, the harder it becomes to locate the good, clear, coherent strategy that once existed inside the riot of organic growth, abandoned ideas, and dead branches.

Over time, the strategy becomes an orchard with a hodgepodge of okay trees instead of a single beautiful specimen heavy with fruit.

Ironically, complexity can be hard to let go of because it seems more honest than simplicity. Have you ever heard about a company with a straightforward, easy-to-understand strategy and found yourself skeptical? Have you ever thought, “Surely it can’t be that simple”? I have.

We drift into complexity by default, and we believe we’re right to do it. Complexity seems more in line with the way the world works, and therefore it seems more effective. Though it is mentally taxing and it accelerates burnout, we tell ourselves that this is the price leaders pay. But is it?

My experience, study, and consulting practice prove the opposite. In every domain of life, from investing to athletics to agriculture to spirituality, a focused and ongoing commitment to a single, easy-to-explain strategy with 10x potential is more likely to produce exciting growth or a step change than an orchard of strategies, each of which has 2x potential at best.

To put it a slightly different way, we grow faster by subtraction than by addition.

If we cut ten priorities to three, we find it easier to focus. If we abandon three 2x strategies in favor of one 10x strategy, we know where to put our time. If we put a finger on the lead domino, the one thing that can start a chain reaction and make everything else easier, then we don’t have to grind so hard.

What never ceases to amaze me is how quickly founders can find the 10x strategy. When I asked the founder of a first-aid startup what the lead domino was, she told me without missing a beat that it was getting her flagship product, Nit Happens, into Walgreens. The product, which I helped her name, is now in 6,000 Walgreens stores across the United States, including Knoxville where I live.

If she had divided her focus by courting five or ten retailers instead of a single one, would she have achieved this remarkable feat in less than a year? Not likely.

Founders understand intuitively that there are better and worse pathways, and if we can reach an agreement that strategy is the means of transformation, whether they’re shopping for it or not, and if we can trim down or kick out the incumbent strategy, and if we can have the courage to prune complexity and locate the 10x strategy, then remarkable growth no longer looks distant and out of reach.

Strategy is summarizing that long, clunky sentence that I just wrote as “Let’s do much less much better.”

Remarkable growth begins to look inevitable—not because of any one person’s brilliance but because of the collective belief, focus, and commitment over time.

Strategy connects your belief to your focus, and commitment is simply focus repeated across months.

If you’ve read this far, and you found yourself disagreeing vehemently, get in touch.

I would welcome your rebuttal. Or, if you saw the shape of your situation in what I have written, then email me at hello at austinlchurch dot com. Let’s have a conversation about how we can get you what you want faster.

I am not one of those people. I’m less inclined to see the upside of companionship than the plain fact of a mess. As I step in urine, I don’t see the collateral damage of pure love. I see my mental to-do list growing.

Let me be clear though, I’m not not a dog lover. I like other people’s dogs the way some uncles like their siblings’ kids. You enjoy all of the cuteness with none of the responsibility. When they’re less fun, you can hand them back.

As a dog uncle, I can supply ear and chin scratches of the right vigor and duration. I can throw a frisbee or stick at an appropriate height to an adequately challenging distance. I can not overreact when an overeager canine once-removed (or whatever) jumps up on me, leaves muddy paw prints on my clean shirt, or shellacks my pants, shoes, seat, cup, book, or hands with the slobber of raw enthusiasm.

Really, it’s okay, except for my hands. Freddy’s, Noodle’s, or Taffy’s slobber will feel like a burn until I can find a sink and wash it off. I’m not a germaphobe in any other area of life, so I can’t explain why this little squirrel of neurosis took up residence in my attic. When I was growing up, my family had two good dogs, Buddy and Button, and my two sisters have always had dogs. I never got bullied by a neighborhood pit bull or had my heart broken by a beautiful French bulldog. I have no visible scars or dog trauma that I can remember.

Even so, I find it difficult not to feel a cauliflower head of germs on my hands until I put them under a faucet and, as irony would have it, probably don’t wash them long enough to make much disinfecting difference.

My distaste for being licked by someone else’s best friend doesn’t make much sense, and given everything I have just shared, neither did my decision to get our family’s first dog. I say “my decision” because on our way to dinner and Swan Lake on February 7, 2026, my wife said, “I’ll let you decide.”

I answered immediately, “We’re getting a dog.”

I then relayed another conversation I had that revealed the bones of the decision. The conversation wasn’t with my daughter who was about to turn thirteen and asked for a dog because she knew we wouldn’t buy her an iPhone. The conversation was with God.

I asked two questions that I have reached for again and again ever since reading a book called Living Fearless by Jamie Winship, a former police officer in D.C. and CIA operative in the Middle East.

In the one place in my house I have eighty percent certainty of privacy, the bathroom, I asked the first question: “What do you want me to know?”

“you want your daughter to have a dog,” whispered God’s still, small voice.

“What else?” I asked because that didn’t seem particularly helpful.

“you don’t want a dog.”

That’s true, I thought. We seem to be at an impasse.

I asked God the second question: “What do you want me to do?”

“you have to decide if you want her to have what she wants more than you want to have what you want.”

Suddenly, there they were, the naked bones of the decision, plain as if they were sitting on the cold tile. What I want versus what my daughter wants. The continued convenience of a dog-free, lick-free home versus my daughter’s delight.

Some notes on my daughter would be apropos. She was a nightmare in restaurants for her first eighteen months. She was a runner and turned my nerves into a ball of lightning anytime we were in public. My spirited girl has always been independent and tough. She rarely cries, and yet the instant she sees a dog, she exclaims, “Puppy!” and forgets all of her careful, one-eyebrow-lifted coolness and melts into praise and affection.

We have two cats, Poppy and Minnie, and at least once a day, my daughter fetches me to show me what one of them is doing. It finally hit me: The cats are a proxy for our relationship, the neutral middle of cuteness, animal Switzerland.

Perhaps ten total seconds had passed in the bathroom before I reached a decision, and the weight fell from my shoulders. I’ve always found not knowing what to do to be more painful than doing the thing itself. Once I knew I shouldn’t be in a relationship with Lauren, I told her within minutes. Once I made up my mind to tell a client how I screwed up, I called Dustin immediately. Once I have clarity around what is right, I can do what is hard. The puppy was a choice between my logic or my daughter’s heart.

Whenever she has mentioned getting a dog, her top choice was always an Australian Shepherd. She liked the miniature ones. She liked a “wiggle butt,” meaning their tails were docked. She liked the blue merle coloring best. She liked ice blue eyes or two different colors.

For once, I knew what she wanted.

I stood there in the bathroom for a minute more, my mind not chasing its own tail for once, thank you God, knowing that I will fail my daughter a thousand times more, in ways big and small, and I already feel her growing up and slipping away into personhood and distance, geographic or otherwise—but here was one tangible way I can be her hero simply by shoving my own reasonable preferences aside for whatever the lifespan of a miniature Aussie is. Fifteen years? Consider it done.

“We’re getting a dog,” I told my wife.

She turned to look at me, her face so like our daughter’s and the smile there made my little death to self worth it all over again.

I am not and never will be a “Dog Dad.” Our puppy’s sire is Rip. His dam is Lola. They didn’t consult with me or require any biological input.

However, I do aspire to be my daughter’s hero. It sounds cliché, and she’s enough like me that if you asked her if she admired me she’d have to recover from her eye roll before she could count off ten ways I had fallen below her standards that day.

Even so, I want my presence and undivided attention to be ordinary, trite, and boring. I’m going to fail her, but I want to fail her close by so that I can see her unforced smile those rare times I manage to get it right.

A puppy is a way to expand the neutral territory and give us more places to meet, so dam it and sire it, we’re getting a puppy. I don’t want it, but that doesn’t matter much. It doesn’t matter much if my daughter adores me. I adore her. I’ll clean up the messes. I’ll be the one with the wagging tail.

When we’re kids, we’re told by well-meaning adults that we ought to finish what we start. Supposedly, this builds character. Kids aren’t sure what character is, but giving in to a mother or father with stronger will is easier than fighting them, especially when parents can bestow or withhold ice cream.

And once kids become adults themselves, they know not to take what their own kids say too seriously because half the time kids forget what they said they disliked once they’re in the middle of it. After adults force kids to do what laziness, insecurity, or fear of embarrassment would otherwise make them avoid, kids see for themselves that the spelling bee, orange chicken, or Little League baseball season wasn’t so bad.

I was ready to quit Tee Ball after a couple of games, but my parents made me finish the season. That parent-imposed perseverance probably did fill some vacant nook in my character cabinet. Perseverance is useful later in life.

And once we’re grown, perseverance comes with an opportunity cost. The “I’m not a quitter” mindset has driven me to finish things that consumed lots of time, attention, and resources. If I had quit those things sooner, I could have diverted resources elsewhere and seen a higher return of enjoyment, money, or opportunities.

What management expert Peter Drucker said about stupid efficiency also applies to stupid perseverance:

“There’s nothing so useless as doing efficiently that which should not be done at all.”

Quitting can be more valuable as gumption. Quitting can be a sign of maturity and wisdom, not of a character defect.

So if no one will give you an award for exploring the last inches of a dead end, how do you recognize dead ends earlier? How do you know when you’ve seen and learned enough to quit?

I will share four ways to know when to quit.

Quit when you don’t enjoy it.

The first way to know when to quit is to assess your own enjoyment, with one important caveat called the law. I don’t enjoy filing my taxes, but I keep doing it because I don’t want to go to jail. A whole category of required but unpleasant obligations exists. Here I’m not referring to that category but to a second bucket of unnecessary and unpleasant things that we can quit at any time.

Why we don’t empty that second bucket more often is complicated, and it’s worth taking a few moments to examine the reasons.

Being a good friend, partner, parent, citizen, and member of a faith community means that we accumulate commitments. We voluntarily tangle ourselves in many strings of roles, meetings, favors, social norms, peer pressures, and other time sucks that seem like a good idea at the time.

One such idea I had was to serve on a nonprofit board. The executive director was a friend, and I believed in the Christian ministry that she led. So far, so good. As the months passed, I came to dread the meetings. Sweet, well-intentioned people discussed the same issues ad nauseam, and each time we reconvened, nothing had happened. For someone with my bias toward action, the meetings were drowning in honey.

As funny as it sounds, my wife had to remind me that I could resign, and when I told my friend that’s what I wanted to do, she was confused and said, “It’s only one meeting a month.” True, and my willingness to have the awkward conversation and snip the string of that small obligation produced an outsized amount of joy and relief.

If you want more simplicity and joy in your life, be willing to quit more commitments that you’ve come to resent or dislike, for whatever reason—even if quitting requires an awkward conversations.

Quitting what you dislike automatically makes more room for what you do like. Duh.

Quit when it hurts your health.

The second way to know when to quit is to be honest about your health by asking questions with that framing:

• Does this hurt my relationships or body?

• Does this make me feel heavy, gray, and pessimistic?

• Does this make it harder to enjoy the simple, good things I already have?

I’m not suggesting that we oversimplify health in its various dimensions, including physical, mental, sexual, emotional, relational, social, financial, and spiritual. I’m also not suggesting that we ignore the reality of chemical imbalances, disease, substance abuse, and addiction or pretend that it’s easy to quit things that harm us.

Rather, I’m suggesting that “health,” despite being a broad and multi-faceted concept, provides a simple, intuitive measuring stick for our less complicated attachments and choices:

• Does this make me healthier?

• Is this additive or subtractive?

• Does it get me more than it costs me?

The Apple News app wasn’t reliably giving me the news, but it did reliably make me feel lousy. When I recognized that fact, I couldn’t help but think of Dr. Phil’s question: “How’s that working for you?” Um, not well. That app hurts my health.

On the other hand, regular exercise makes my life less comfortable while also making me feel better, not worse. The same goes for being a part of my church when I’d rather sleep in on Sundays and saving money when we could have spent it. I don’t always enjoy frugality, but it contributes to my health.

On balance, we need more difficult things that add to our health and fewer easy things that subtract from it.

A simple exercise will help you decide what is additive and subtractive:

1. Take inventory. Write down every obligation and commitment, running meeting and regular appointment. List every role, responsibility, and demand on your time and attention. List every habit without judging it good or bad just yet.

2. Ask, “Does this add to health? If I were to keep doing it for months and years, will it enhance my ability to get and keep what I want most?”

3. If the answer is no, then ask, “Am I okay with that?”

4. If the answer is no, then ask, “What is my new commitment?”

Health as a metric or magnifying glass may reveal you that you are too quick and free with your yeses and have a near-pathological tendency to refill your calendar as soon as you’ve cleared it. No may need to be your default answer for six months.

You may see that your current habits will keep producing your current results, and that you can’t reasonably expect different results until you form new ones. James Clear’s Atomic Habits is a bestseller for a reason.

You may see that you need better rules, such as no alcohol on weeknights, no iPhones in the bedroom, and no inbox before 11:00am.

Though I can’t tell you exactly what or how to quit, I can tell you when to quit. Quit when there’s no denying that whatever it is costs you more than it gains you.

You’ll be more satisfied with your life if you replace old, automatic commitments with new ones that improve one or more dimension of your health. The inverse is also true—if you don’t quit the things that hurt your health, you’ll be less satisfied with your life.

You will know it’s time to quit when you tell yourself you can’t. Fear hides open doors.

Quit when you want it less.

The third way to know when to quit is to get clear on what you want more, and you gain clarity by exposing the tradeoffs you’ve been making.

I’ll share an example from my marriage. For years my wife and I didn’t keep a budget or categorize our monthly expenses. All of our spending was rolled into one multicolored ball of Play-Dough, and without any real visibility into where the money was going, all we could say at the end of the month was “Geez, we need to get our spending under control!”

That realization didn’t do much except start arguments, and we didn’t experience meaningful change (and fewer fights) until we started categorizing certain transactions as utilities, entertainment, or dining out.

Categorizing expenses showed us where our money was going, and then the cause-and-effect connections and tradeoffs became painfully obvious. We dined out more often than we could afford because we didn’t make a meal plan and go grocery shopping. If we kept spending money on burritos and sushi, then our credit card balance would keep growing. If we racked up more debt, then we wouldn’t be buying a house anytime soon.

What I learned is that it’s much easier to make a meal plan and cook a cheap spaghetti dinner at home when I can say between bites, “I want to buy a house.”

Discipline is easier when you make the tradeoffs as obvious and jarring as potholes.

Discipline is easier if you clarify what you want more—house more than burrito, exercise-fueled health more than a self-indulgent diet, good sleep more than whiskey, wholesome simplicity more than chaotic excitement.

Discipline can be intermittent too. Sometimes the tradeoff is worth it. When I ate at Uchi in Austin, Texas, I spent too much on Bluefin Chutoro, Tasmanian Ocean Trout, and Hama Chili. My aim isn’t perfect performance but conscious compromise.

Quit when that allows you to produce more.

The fourth way to know when to quit is to take an honest look at how you’re spending your time and make the changes required to spend more time on what you care about most.

We collect claims on our time and attention because we aren’t clear on what we want and because we mistakenly believe that more irons in the fire equals more lottery tickets. You just never know, right?

Paul Graham’s advice in “How to Do What You Love” strikes me as the better bet: “Always produce.”

Instead of trying to find success or fulfillment through a mishmash of commitments, zero in on the thing you think you want and produce more in that area.

Is the thing being a novelist? Write one thousand words a day. Being a musician? Write two songs a week. Full-time nonprofit work? Mentor one kid on Saturdays. Always produce.

If you aren’t sure what your one thing is, then ask questions that will help you come at it sideways:

• What would you start doing more of if you assumed that your big break was never going to come?

• What would you start doing right away if you knew the timing was always going to be terrible?

• If you didn’t need money, how would you spend your time?

If you still don’t have a clue about what to produce, then read Anne-Laure Le Cunff’s book Tiny Experiments. Running experiments is one way to produce more.

Producing more takes you from wishful thinking to reality. You thought you wanted more short stories, songs, or at-risk kids in your life, but now that you are producing more, do you like your life more?

A measurable commitment to what we think we want brings clarity—and strips us of our fantasies. Only after you’ve produced for six or twelve or twenty-four months will you know if you need to quit that too.

Don’t quit until you’ve answered yes to these three questions.

Some people quit before they make a clear commitment to producing or before they finish that commitment. They can’t really say that they sampled the thing, and thus they don’t have a true process of elimination. These serial quitters just walk away when the thing gets hard.

To avoid becoming a serial quitter—meaning, to avoid quitting too early—you ask yourself, “Am I proud of my progress or the milestone I’ve reached?”

You don’t quit until you can quit with your head held high.

You also ask, “Is quitting right now fair?”

You don’t quit until you believe that you have left other people and the situation or shared goal in better shape than you found them. You don’t screw people because screwing people will screw you eventually.

Finally, you ask, “Have I gained more intelligence?”

By “intelligence” I mean insight into what you like, what you’re good at, what reliably causes joy and flow, and what you ought to try next or avoid.

If we slow down to consider what question we’re trying to answer or what we’re trying to learn about ourselves, then it becomes obvious when it’s time to move on—or when it’s time to renegotiate the commitment so that we can gain new intelligence.

Knowing when to quit comes down to discovering what is most important to you, being brave enough to pursue that, and accepting yourself.

I think spotty judgment belongs right up there with those big business killers, and I’ll explain how I reached that conclusion.

In this case “judgment” means how we look past words and circumstances and make calls about other people’s character, intentions, and motivations.

When we’re young, we’re bound to hear some adult say, “Actions speak louder than words.” And being young, we’re prone to ignore that bit of homespun wisdom because it came from boring old people.

Later, even after a cheating ex breaks your heart and ruins the summer—should have seen that coming—or a self-centered business partner chooses the easy way over the high road—again—we realize that it’s not what people say but what they do that matters. The old people know something after all.

Forensic accountant Anthony Scilipoti, who predicted the Enron scandal and various other historic implosions, goes so far as to say,

“Business is judgment. People run companies; they don’t run themselves.”

I think he’s right. Our long-term results in business and life often hinge on our ability to see people as they really are and respond accordingly.

Oprah Winfrey would agree. I can’t remember exactly how I stumbled across the clip from 1997, but it presents an unusual scene for brilliant business advice: pajamas and a big brass bed. Oprah and Maya Angelou lounge side by side and discuss something the author had taught her years earlier:

“When people show you who they are, believe them the first time.”

About that lesson from Angelou, Oprah said, “Of all the lessons I’ve learned in my entire life, this may be at the very, very, very top of the list.” Considering the many famous and brilliant people she interviewed and hundreds of ideas and principles she must have heard, her show was the highest-rated talk show in American television history, and her many successes as a businesswoman, serious entrepreneurs ought to give the lesson serious attention.

The lesson is easy to understand and difficult to implement.

Or maybe it’s more accurate to say that acting on what people reveal about themselves can be very costly in the short-term.

One of my favorite stories illustrating this difficulty came from Bernie Marcus. After he and Arthur Blank got fired from Handy Dan, they were trying to raise $2 million to start what would become Home Depot. An investment banker named Ken Langone got them a meeting with Ross Perot. Everything went well until Perot and Bernie started discussing Bernie’s Cadillac.

“My people don’t drive Cadillacs,” Perot said. “My guys at EDS drive Chevrolets.”

Bernie explained to Perot that buying the Cadillac he already had leased would be cheaper than buying a new Chevrolet, and furthermore, he was a big man who needed a big car.

Perot wouldn’t budge: “My people don’t drive Cadillacs.”

Bernie and Ken stepped outside for a moment to talk, and Bernie foretold his own future: “If this guy is going to be bothered by what kind of car I’m driving, how much aggravation are we going to have when we have to make really big decisions?”

When people show you who they are, believe them the first time.

Bernie and Arthur walked away from the deal with no backup plan.

One of my old mentors, Ray, once shared the same lesson in slightly different packaging: “People show you who they are. They keep showing you who they are. You should let them.”

Ray’s exact words lodged in my mind like a fishhook, and I can’t help but wonder why. I don’t aspire to build an empire like Oprah or Bernie. I like writing and making barbecue more than I like courting the Ross Perots of the world.

I think the reason is this: Even lifestyle entrepreneurs like me get burned, and we need a way to navigate new relationships and opportunities, collaborations and deals, obstacles and impasses—without repeating past mistakes in judgment.

How do I give new people the benefit of the doubt without becoming an easy target? How do I differentiate between “bad actor” and “decent person who made a mistake on me”? How do I exercise good judgment without expecting a bogeyman around every corner?

Parsing all that data would be overwhelming even if I didn’t have presets and blind spots. I grew up in a relatively healthy, stable, and safe family, and I tend to be an open, honest, generous, and trusting person. I brought naïveté with me into business and soon discovered that everyone wasn’t trustworthy.

I could regale you with stories about folks who said the right things to win my trust so that they could take advantage of my talent, mind, and network without reciprocating. It’s the oldest story in the business book: The client, mentor, or partner who offers to take the promising youngster under his wing and teach him everything he knows in exchange for [insert exciting but vague and ultimately empty promises here].

Getting duped isn’t fun, but neither is being jaded. The whole apparatus of self-protection and especially the heavy armor of skepticism and suspicion is mentally and emotionally taxing. The entrepreneurs who wear it daily enjoy the journey less and burn out faster than those who don’t, and ironically, the people who trust the least come off as least trustworthy.

I’ve met certain individuals who had been burned a lot, and in our interactions I felt as though I were being subjected to a battery of covert character and reliability tests without my consent. While they remained closed off, controlling, and unpredictable for reasons known only to them, they expected me to be transparent and impeccably reliable to win a spot on a list of vetted allies. Rather than submit to that double standard and continue through an exhausting trial of proving myself, I simply opted out. Naw, I’m good. I have other options.

So what’s an entrepreneur to do if neither naïveté nor jadedness is best?

My friend Jerry gave me a clue. Jerry has endured a great deal of pain and betrayal, and he’s one of the most joyful, light-filled people I’ve ever met. He once told me that he keeps choosing trust because skeptical people get burned about as often as trusting people and trusting people get to go through life seeing the best in people. Over time, the math evens out. We benefit more by assuming positive intent than by assuming ill intent.

Okay, but what does that look like at a conference when I’m meeting new people? How can a startup founder embrace this actions speak idea when in a room of potential investors? How does a freelancer approach an exciting collaboration, one that could grow into a full partnership, with both optimism and realism?

A Russian history scholar named Suzanne Massie answers with these three words: “Trust, but verify.” Massie taught President Ronald Reagan the original Russian proverb, and Reagan relied on it during nuclear disarmament discussions with the Soviet Union.

In my own business meanderings I’ve found it helpful to make the proverb more concrete and actionable by turning into a rule, practice, and response:

1. Rule. Lead with trust;

2. Practice. Watch what people do;

3. Response. Match their access with their actions.

Let me double-click on the rule for a moment.

Though Peter D. Kaufman is one of the more successful businessmen of our era, he has flown mostly under the radar. He doesn’t have a Wikipedia page, and unless you knew to look for “The Multidisciplinary Approach to Thinking,” a speech that he originally gave to some college students in 2018, you probably wouldn’t stumble across it.

In the speech Kaufman touches on “mirrored reciprocation.” In essence, we get what we give, and according to Kaufman, we get better results 98% of the time if we lead with trust: “You want to go positive. You want to go first.” And, “You have to be constant [in doing that].”

I also like the “opening bid” framing that Stanford business professor Bill Lazier used:

“You need to decide on your opening bid when you are establishing a relationship with someone when you’re interacting with the world. Is your opening bid to assume trust, to assume that someone is trustworthy, and to grant them the full benefits of that? That’s your opening bid and that trust can be lost, but the bid is trust. Or is your winning bid to not trust, but the trust can be earned? So many aspects of your life will be affected by which fork you take.”

I can look back on specific situations where my opening bid of trust, followed by close scrutiny of a person’s actions and a matched response, enabled me to sidestep misery.

Back during my startup days, a music industry veteran told my co-founder and me that he could help us scale Closeup.fm much faster. I’ll call this guy William, and we had enough mutual contacts to believe he might be able to deliver on that promise.

The relationship progressed, and eventually William asked us to make him interim CEO. He said he’d need that title and clout to set everything into motion.

When I passed this idea by our investors and advisors, they were unanimous in their advice: This is a bad idea. Interim CEOs communicate instability to investors, and this guy is untested. Offer to make him the Head of Business Development instead. He can still get the same equity without the title, but the equity will vest on a schedule with certain milestones. In effect, date before you get married.

When I went back to William, laid out the plan, and explained that the CEO title wasn’t on the table, he was furious. He cursed at me. He told me that our advisors were “idiots” and that he was the only one who could get us in the right rooms.

“Yes!” I thought. “This is the man I want leading Closeup into our exciting next chapter.”

Just kidding. After that call I knew that we didn’t want William involved in our company in any capacity.

Several days later, he sent me a copy of Venture Deals with a note inside about how he was disappointed about my lack of appreciation for value received. Yeah, because being bullied on the phone was so enriching. Please.

I appreciated the manipulative gift because it put an exclamation mark after our decision to have no further dealings with William.

As I close, it’s important for you to know that I haven’t always stuck to the rule, practice, and response I shared. This is my reminder as much for myself as you: Lead with trust. Watch what people do because actions speak louder than words. Believe people the first time, and match their access with their actions.

Even as I write those words, part of me wants to roll my eyes like my teenage self when my father told me anything of importance. “Ugh. Thanks, Dad. I know that already.”

But do I value thinking? How much time do I make for it?

Judging by the number of authors, leaders, and luminaries who have called out a lack of thinking across two millennia, the lack is more common than its opposite. More on that in a moment.

Human beings are impressive in part because of our ability to categorize and automate various decisions—that is, to think less about them. Much of our lives follows predetermined patterns, from how we make breakfast to the route we drive to the office, and that autopilot isn’t all bad when you consider how time- and resource-intensive rethinking every decision every time would be.

Sticking to patterns can have benefits.

By always ordering the same thing at my favorite restaurant, I waste no time re-reading the menu and give my full attention to the person I’m eating with while also ensuring that I will enjoy what I eat. A triple win.

Most of life consists of situations where the consequences of not thinking and making worse decisions are negligible. I don’t risk or suffer much when I make a snap decision to order the daily special, and the meatloaf ends up being bland and dry.

The trouble is, we’re always forming habits, and those habits work against us in the ten or twenty percent of situations where not thinking can truly hurt us.

Business and entrepreneurship is one of those high-stakes domains. Forensic accountant and investor Anthony Scilipoti once said in an interview, “Business is judgment. People run companies; they don’t run themselves.”

Bad judgment pops up all over the place like a rash of mushrooms. An email written and sent in anger can derail a longstanding and fruitful partnership. A pricing mistake that with some foresight could have been avoided can destroy the quarter’s profit. An ill-considered marketing campaign can create a publicity nightmare that eventually kills the company.

No entrepreneur needs to be reminded of the consequences of bad judgment or value of good judgment. We overthink decisions and second-guess ourselves precisely because we know the stakes.

So why don’t more of us put thinking time in our calendars?

Why don’t we schedule good judgment?

Our pace of life and the very fabric of society, at least in the West, fights this type of intentionality. Duties, distractions, and details encroach on every side, like acid eating the edges of a paper.

But before you and I try to blame Modern Life or Culture or some other vague capital-letter Enemy, we ought to do some reading and then take some responsibility.

You see, a lack of it isn’t a modern problem.

A Roman Emperor and philosopher you may have heard of, Marcus Aurelius, wrote down this reminder for himself in Meditations sometime between 161–180 AD:

“You must reclaim your mind from distractions.”

Um, excuse me, Marcus, do you realize how good you had it in a pre-industrial-digital-Internet-mobile-social-AI age?

Daniel Defoe was a merchant before he was a writer, and in The Complete English Tradesman, published in 1726, Defoe doesn’t mince words:

“The want of thinking is the ruin of many a tradesman.”

In the 1920s Thomas Edison went so far as to post this reminder on signs around his laboratories:

“There is no expedient to which a man will not go to avoid the real labour of thinking.”

Edison’s friend, Harvey S. Firestone, who founded Firestone Rubber and Tire Company, wrote this on the first page of his 1926 business memoir, Men and Rubber:

“For the most difficult thing in business is first getting yourself to thinking and then getting others to thinking. I say this is difficult because, in the natural course of business, an infinite number of details come up every day, and it is very easy indeed to keep so busy with these details that no time is left over for hard, quiet thought—for thinking through from the beginning to the end.”

Aurelius had too many distractions, and Firestone had too many details. Has the thinking problem improved over the last century?

In Michael Eisner’s 2010 book Working Together (2010), Warren Buffett says, in effect, “No, it hasn’t”:

“I insist on a lot of time being spent, almost every day, to just sit and think. That is very uncommon in American business.”

Admittedly, this brief survey of “evidence” from (mostly) dead white men presents a lopsided view of the not enough thinking problem, but still, I hope that these three points hit home:

1. It’s important to recognize high-stakes situations for what they are.

2. It’s harder to do that and to make good decisions if you don’t improve your judgment through dedicated thinking sessions.

3. Entrepreneurs who force themselves to do more thinking have a distinct advantage over those who don’t.

I say “force” because, if achieving the focus, attention, and self-possession required for clear thinking was difficult two thousand years ago, then you and I have our work cut out for us.

Here’s how entrepreneurs can fix their thinking problem:

1. Shoehorn thinking time into otherwise packed calendars.

2. Do more thinking on the go.

My favorite example of scheduled thinking time is Sara Blakely’s “fake commute.”‍

“I’ve identified where my best thinking happens, and it’s in the car,” she said. “I live really close to Spanx, so I’ve created what my friends call my ‘fake commute.’ I get up an hour early before I’m supposed to go to Spanx and I drive around aimlessly in Atlanta with my commute so that I can have my thoughts come to me” (bold mine).

Do any reading at all, and you’ll discover that the most successful entrepreneurs of any generation made a habit of deliberate thinking.

They planned for it and protected it though it isn’t easy or convenient and can feel indulgent, counterproductive, and wasteful.

Thinking is important. If it’s important, you’ll plan for it and put it in your calendar. What gets scheduled gets done.

As for more thinking on the go, when I started looking for the space, I found it.

Recently, as I waited in the checkout line at the grocery store, I reached for my phone in my back pocket. I froze mid-grab as a thought occurred to me. I could spend the five-minute bubble of time thinking instead of checking my inbox or social notifications.

At first my mind pinballed among questions. What’s on my mind? What has been bothering me? What do I need to think about?

I soon arrived at a real concern fizzing with anxiety: bookkeeping. I loathe it, and yet I’d formed a new LLC with a partner and wanted to do right by him, which meant keeping accurate, up-to-date books.

The solution arrived in seconds. Hire someone. Duh. But hire how and where?

Again, the answer came quickly. Hire in the Philippines. That had worked well for my full-time assistant and podcast editor.

The full plan unfurled in my mind like a hot air balloon, and before I had even gotten home, I had used the voice memo app on my phone to draft the job description.

Good for me, but let’s not skate past the point of the story. My progress didn’t require a cold plunge, offsite planning retreat, or solitude-rich walk in the woods. It came from five minutes’ worth of deliberate thinking in a busy, loud, crowded place.

Though certain environments make thinking harder, the act matters more than its setting.

Thinking is available to everyone. We can think anytime, anywhere, for free, without help, permission, or special equipment.

Thinking shouldn’t be an advantage, yet it is. The relatively few folks who make a habit of it have a predictable way to have (or receive) more great ideas, to improve their judgment and make better decisions, and to get extraordinary results, whether in a material sense with better-than-the-market returns or in a harder to quantify sense like not entering what would have been a miserable partnership.

I’ll end with practical ways I squeeze in more deliberate thinking:

• Questions. Keeping and updating a Journaling Questions document in Notion where I can always go to find thought-provoking questions. Better questions lead to better insights.

• Journaling. I journal most days, if only for a few minutes. I start by practicing gratitude, and then I often ask myself, “What’s on my mind?” Julia Cameron’s Morning Pages exercise from The Artist’s Way is worth a look.

• Weekly Planning. I use Hyatt Co.’s Full Focus Planner and plan out my weeks on Sunday afternoons. The planner has built-in reflection questions.

• Monthly Retrospectives. I’ll be spending an hour or so at the beginning of each month reflecting on the last month. I use the same template each time.

• Quarterly Planning. I reflect on the last quarter at the beginning of each new one.

• Annual Planning. I take myself through a Year in Review and a Year in Preview exercise each December.

• Miscellaneous Habits for Making Space.

  • Making a point to not turn the radio, music, or a podcast on in the car and driving in silence.

  • Not reaching for my phone in the interludes between activities and simply thinking instead. See the grocery store example above.

  • Runs. As much as I love listening to podcasts, I’ll also take out my AirPods and think.

  • Walks. When I’m wrestling with head trash, a creative conundrum, or an opportunity or gnarly business situation that requires judgment, I’ll walk around my neighborhood.

  • Prayer and meditation. Obviously.

  • Solitude. In Digital Minimalism Cal Newport draws on a helpful definition of solitude from Lead Yourself First by Russell Hittinger and Kethledge Erwin: “a subjective state in which your mind is free from input from other minds.” So, I purposefully cut out otherwise good inputs so I can think on my own.

She grew up on a small farm in Fayetteville, Tennessee, and always had a vegetable garden. Because Martha (aka, Grandmother) was basically my favorite person in the world, I would follow her out to the garden. I might get put to work, but that was okay because work resembles fun when it happens alongside a kind, lit-up, and laughing person like Grandmother.

One job I could do was pinch off suckers. No garden in the South was complete without tomato plants, and Grandmother showed me how new sprouts would appear in the crooks of the bigger, more established vines and stems. She called these sprouts “suckers” and said we needed to pinch them off. Grandmother explained that, when left alone, suckers would keep growing and take up water and nutrients that should go to the tips of the vines and stems. There, they could become flowers and then tomatoes.

To an inquisitive kid like me, pruning tomato plants seemed backwards. How do you get more tomatoes when you have less, er, plant? I certainly hadn’t learned addition by subtraction in math class.

Grandmother always provided the proof later though: mounds of beautiful tomatoes, more than enough to share with her daughter’s family and the neighbors.

Pinch off suckers, get higher yields. Growth by subtraction. Right you are, Grandmother.

It’s funny how such childhood lessons have to be dressed up and reintroduced later in life. I remembered that homegrown lesson from Grandmother only after I became an entrepreneur and started seeing growth by subtraction everywhere. Consider these three instances:

• In Adagia, first published in 1500, the Dutch priest, Desiderius Erasmus, gave us this adage in Latin: Duos insequens lepores, neutrum capit. “Chasing two hares, he catches neither.” Or, to state the inverse, pick one objective, not two, and you’re more likely to succeed.

• After being appointed Braun’s Director of Design in 1961, the German designer, Dieter Rams, began developing and articulating the company’s design philosophy in his “Ten Principles for Good Design.” At their heart was a single idea: Weniger, aber besser. Less, but better. Eliminate to improve.

• In 2023, the Canadian marketer, Katelyn Bourgoin, posted an X thread about her business growth, which started with this tweet: “My little one-person business made $127,305 in January / How? Subtraction.” Grow by subtraction.

Taken together, these three examples start to sound like a joke: “A Dutch priest, German designer, and Canadian marketer walk into a bar.” Separated by five hundred years and differences in culture, language, geography, worldview, and occupation, they all arrive at the same realization as my gardening grandmother. Strategic subtraction produces superior results.

That same counterintuitive discovery awaits the ambitious entrepreneur, the curious scientist, the passionate artist, the analytical engineer, and even the smart-but-kinda-lazy student.

One of the more famous stories about growth by subtraction unfolded after Steve Jobs returned to Apple in July 1997. At the time Apple had roughly 350 active products and projects. Jobs described the product strategy as a “mess” at Macworld in August 1997, and over the ensuing months, he and Jony Ive developed the now-famous 2x2 product matrix (Consumer vs. Professional, Desktop vs. Portable) and cut 97% of the lineup. By the middle of 1998, Apple had only 10 products.

Apple’s numbers speak to the difference that strategic subtraction made. In 1997 the company had $7.1 billion in revenue in the 1997 fiscal year and lost $1.04 billion—the worst performance in company history. However, in 1998 Apple had an eye-popping turnaround, with $309 million in profit. Revenue rebounded to $6.1 billion in 1999, and profits kept climbing.

As impressive as Apple’s turnaround is in hindsight, it contains a sobering truth about growth by subtraction and many of the other long ideas I plan to share. Long ideas can help you “avoid common ways of failing,” as Charlie Munger would say, but they aren’t easy to implement. They won’t make you popular. They raise eyebrows. As Howard Marks observes in his book, The Most Important Thing, extraordinary results in business require deviating from what’s considered normal: “The problem is that extraordinary performance comes only from correct nonconsensual forecasts, but nonconsensual forecasts are hard to make, hard to make correctly and hard to act on.”

Deviation confuses or even angers some people, many of them your former admirers and fans. People will think you’re crazy for months or years unless and until your point of view, strategy, and actions prove to be correct.

The point is, we can agree with growth by subtraction from a philosophical standpoint, but we still have to muster the courage to turn principle into pruning shears.

It’s worth noting, too, that pinching suckers off tomatoes is easier than pinching sucker off companies. Apple had sunk billions into developing product lines that became so much trash on the cutting room floor. Revenue went down before it went back up.

So prepare to be misunderstood as you find the courage to consolidate your focus and grow by subtraction.

I leave you for now with this two-part question:

• What is my best opportunity right now?

• And what will I courageously cut so that I can funnel more resources into that opportunity?

Though I can’t remember when I first starting thinking about long ideas as a category, my bottomless appetite for books and decades’ worth of underlines, highlights, and chicken scratch in the margins all point to a fascination with ideas that reappear across time. My notes contain phrases like “Reminds me of…” and “This is like what so-and-so said about such and such.” Without realizing it, I was collecting echoes.

Long ideas bounce around the canyons of time and human thought. They’re not old, as in worn-out and obsolete. They’re not new, as in novel or never seen before. Once or twice a generation, they recirculate after a scholar, artist, priest, entrepreneur, den leader, or average jane gets struck by one like a mental meteor and bends down metaphorically to examine it.

Take, for example, the Golden Rule. All major world religions have some expression of “Treat others the way you want to be treated.” The principle goes back as far back as human civilization. Yet, an author may still pen a book on the beauty and necessity of fairness and see it sell a million copies. Two esteemed professors may conduct research showing that 90% of participants dislike it when newcomers cut in line and conclude that most people live by and expect a basic ethic of fairness. A celebrated CEO gets paid $25,000 to delivers a keynote entitled “Fairness Is Better Business” and receives a standing ovation.

Long ideas are old ideas under new management.

Unfortunately, not all of them are benign. Wouldn’t it be nice if fascism died already, and many other -isms, too? The same defects in our psychology that cause one group of people to forget one long idea (say, frugality with its well-documented benefits) also make another group susceptible to a long idea that works as well for the common good as hydrochloric acid works for cleaning cotton.

The book of Ecclesiastes says, “There’s nothing new under the sun.” The more I read and observe, the more I believe in the truth of that.

However, that’s not to say that every long idea has the same stickiness in every era. Their acceptance or popularity varies. My maternal great-grandmother, Pearl, grew up during the Great Depression. No one had to teach Pearl about frugality. It was part of her air and soil. She once gave me a ragged book of tiny gray ration stamps that she’d saved during World War II. She reused aluminum foil long after that was strictly necessary. Frugality dissolved into and become inseparable from her environment, her thinking, and her behavior.

But what happened to frugality over the generations succeeding Pearl’s? It not longer seems necessary. Its ordinariness fades. Credit cards become a thing. Frugality loses its appeal until the zeitgeist shifts yet again. The cycle repeats when money pundits like Dave Ramsey unearth and popularize the long idea.

Nietzsche wrote about “eternal recurrence,” but that possibility of a cosmic version of Groundhog Day doesn’t interest me as much as the certainty that long ideas represent tools for better living and better results, no matter which era you happen to be born in. Long ideas give the people who use them a distinct, fair, and repeatable advantage.

One of the easiest ways to find a long idea is to think of a common failure and ask oneself, “What’s the opposite of common failures?” The famous investor and Warren Buffett’s business partner, Charlie Munger, was fond of saying, “Avoid common ways of failing.” He might as well have said, “The opposite of every common failure is an advantage.”

Of course, human beings acting the way we do, some long ideas you can only embrace like a life preserver after you’ve swallowed sufficient saltwater.

Long ideas have value precisely because they enable us to bypass future near-drownings, disappointments, and dead ends. They can’t save us from all our bad ideas, but they can leave room for fewer of them. Collecting long ideas is like eating salad first.

Like wise habits and honest friends, long ideas have only as much value as we give them space in our lives.

In a 1675 letter to Robert Hooke, Sir Isaac Newton wrote, "If I have seen further it is by standing on the shoulders of Giants." I’d like to see further by standing on a stack of long ideas. They haven’t disappeared yet, which means they’re more likely to keep existing. So says the Lindy Effect, a key concept in Nassim Taleb’s 2012 book, Antifragile: Things That Gain from Disorder.

If this idea of long ideas (and the anti-fragility they offer) intrigues you, then stick around. Subscribe here to get my collection of long ideas for entrepreneurs. Each newsletter contains a single idea, polished and delivered with as much brevity as I had time for. The idea ends with a single question designed to plant the idea in your business where it can grow, yield fruit, and leave less room for weeds. I hope the long ideas benefit you as much as they have me.