Most solopreneurs focus obsessively on making money. Very few know what to do with it once they have it.

In this workshop, my wife, Jennifer Welsh, walks through the exact financial systems we use behind the scenes to run a multi-million dollar business without stress, chaos, or surprises.

This is not theory. It is the real playbook built from years of mistakes, missed expectations, and hard-earned lessons.

We covered:

• The most common financial mistakes solopreneurs make (and how to fix them)

• Why co-mingling personal and business money creates long-term problems

• How to set up the right foundation with a CPA, bookkeeper, and clean accounts

• The simple system we use to set aside taxes every single week

• Why unexpected tax bills happen and how to make sure they never happen again

• How to pay yourself consistently instead of riding the feast or famine cycle

• The importance of building an emergency fund for your business

• The weekly “money meeting” system that keeps you organized in 30 minutes

Jennifer also shares how small, simple habits can replace stress with clarity and give you total control over your finances.

If you’re making money but feel disorganized, uncertain, or anxious about it, this workshop will change that.

Below, please find the presentation, a coupon for Jennifer’s free 2-hour course called Money School, and a copy of our weekly money meeting worksheet!

Get Money School for FREE. Coupon code: Unsub

Get our FREE Weekly Money Meeting Worksheet here.

Jenn Finance Presentation April 22

504KB ∙ PDF file

Download

Download

Subscribe now

The other day, I grabbed my phone, opened X, and started scrolling my feed looking for something interesting to read.

But after about 5 minutes of scrolling, there wasn’t a single piece of content that grabbed me. Then I logged into LinkedIn, checked that feed, and found it be about the same.

This is a pretty common outcome nowadays. Most of my social feeds are filled with culture wars I’m not interested in, over-exaggerated takes on the future of AI, proclamations that everyone is doomed, or some promise to cure my sleeping/fitness/health/nutritional problems in less than 5 minutes.

I very rarely find anything inspiring, motivating, or remotely interesting anymore.

I know that scrolling isn’t a great habit anyway, but I used to enjoy it. I used to spend a lot of time reading content, understanding how people got attention through words, and trying my best to mimic that on platforms like LinkedIn as I learned to write.

Once I finally had my own signature style, I felt less intimidated by (what was then) Twitter, and I finally decided to start writing there, as well, in 2021. I had a great experience meeting new people and learning a lot about marketing and business.

Five years ago, that’s what these platforms gave me. I’d go down a rabbit hole on some topic, learn more than I could ever imagine, and it would change the way I worked, lived, or thought about something.

Now I scroll, and everything is the same. AI-generated videos with no point. Political extremism without nuance or context. Race-baiting. Articles promising you can reset your entire life in 30 minutes. Carousel posts that say absolutely nothing but look incredible. And 99.9% of the comments written by bots.

There are more posts than ever, and I can point to maybe a handful that are even mildly impactful.

I yelled something like, “All of this content is terrible now!” to Jennifer the other day, and she just said, “So, stop scrolling.”

Fair point. But I don’t think the answer is to just look away.

A few weeks ago, I clicked open a newsletter from a guy I’ve been subscribed to for the last three or so years. Someone whose writing I really look forward to reading every week that it hits my inbox. This week was totally different. I read the entire piece and struggled to find his old voice. The one that sucked me in so hard when I first read his stuff. The ideas in his most recent issue were fine, the structure was clean, and the overall takeaway was…ordinary. But that voice, the thing that made me subscribe in the first place, felt like it had gone missing.

I scrolled back on his page and checked a few of the older issues to make sure I wasn’t just imagining it. I wasn’t. And listen, I don’t know for sure that he’s using AI, I don’t really care, and I’m not the AI police. But I know what their writing used to sound like, and I know what it sounds like now. And that left me feeling bummed out.

The entire surface of the internet is filling up with content that technically “exists” but doesn’t really say much.

And the scary part is that I think this trend is in its infancy.

I think real, actual creativity is going to move underground.

I think about creativity in a similar fashion to how I think about food. Fast food took over decades ago because it’s cheap, easy, and efficient. So, up until recently, most people have eaten mostly processed, factory-made stuff every day without even giving it a second thought.

But that doesn’t mean that real food has died or gone away. It just stopped competing as hard for shelf space at big box chains like Walmart.

Instead, it went elsewhere. It moved to farmers’ markets, community-supported agriculture farms, and intimate private dinners with foodies who didn’t want to eat microwaved hamburgers or plastic chemical substitutes.

The people who actually care about food stopped expecting to find it the way they used to, en masse, and started having to be intentional about where to seek it out.

I think something similar is going to happen with writing, music, art, and other creative outlets. The people who make real, creative stuff are going to look at this boring landscape of AI slop and decide they don’t feel like competing. I mean, why would you? Why spend days creating an original piece of art just to watch it get buried under millions of posts, generated in 10 seconds, that perform better because an algorithm can’t tell the difference?

So they’ll go somewhere else. They’ll start and join paid communities and private memberships. They’ll create small collectives, both online and offline. These will become the places where you find new music that a human actually wrote and performed. Writing that someone actually sat with, thought about, and edited meticulously.

The price of admission will be taste rather than money.

I recognize this piece makes me sound like an old curmudgeon, but I often wonder where I’ll fit in here.

LinkedIn and X are how most people found me and started reading my content. They’re the foundation of my entire business, but now I watch them fill with mess, and I’m not sure what that means for me.

Part of me also wonders if the underground will even accept folks like me. I grew my audience using the same algorithmic machinery that I’m now criticizing. I absolutely spent time optimizing headlines, studying what performed, and playing “the game.” The fact that I did it with real ideas and writing doesn’t necessarily change the fact that I built my house on the same land that’s now being flooded.

I think my future is with people who have raised their hand and said, “I want to hear from you.” It’s with the 215,000+ people who read my essays every week because they enjoy what I’m writing about. Not because an algorithm decided it was trendy enough that week to show them. I want those people to see my best writing, enjoy it, and come back for ME. That’s my only goal nowadays.

I want to read stuff from real people who are sitting down, thinking deeply about something, and writing it in their own words for people who care enough to read it. I think that’s rare.

And what’s rare is about to become what’s valuable.

I don’t know. Maybe I’m totally wrong.

Maybe the timeline is a lot farther in the future than I think. Or maybe the platforms clean things up faster than I expect, and everything goes back to “normal.” Or maybe everyone is an AI writer in the future, and I’m just behind the times.

But I don’t think so.

I think the real creatives are already moving. They’re already going “underground.” And they’ll continue to find each other in small, quiet, private spaces.

So my question for you this week is this:

Where are you finding the best original creative art online nowadays? Stuff written or created by real humans?

Click the button below and tell me. I read every response.

Leave a comment

If you enjoyed this read, the best compliment I could receive would be if you restacked this for your readers. Thank you so much for a bit of your valuable time today.

Share

Most offers fail for one simple reason.

They try to solve too many problems for too many people.

In this workshop, I break down the framework I use to design offers that actually sell. Not gimmicks. Not hacks. Just the fundamentals that separate profitable businesses from those that struggle to get traction.

We covered:

• The four biggest mistakes that cause most offers to fail.

• Why vague problems and broad audiences kill conversions.

• The difference between selling knowledge and selling outcomes.

• How to define a transformation that people can clearly visualize.

• The credibility test every buyer runs before purchasing.

• Why simple frameworks outperform complicated programs.

• How early wins inside your offer create momentum and word of mouth.

• The exact formula to pressure test your offer before you launch it.

We also walked through real examples from creators and founders who built highly profitable offers by getting these fundamentals right.

If you’re trying to monetize your audience, launch your first product, or refine an existing offer that isn’t converting the way you hoped, this session will help you diagnose what is missing.

Cheers,

Justin

How To Build Your First Profitable Offer

840KB ∙ PDF file

Download

Download

Subscribe now

A few days ago, I was scrolling on X and came across a Tweet* showing how many famous self-help authors supposedly led miserable lives.

The guy who wrote “How to Save Your Marriage” shot his wife. Dale Carnegie, the legend behind “How to Win Friends and Influence People,” died alone. And parenting expert Dr. Benjamin Spock’s own sons tried to put him in a nursing home.

The tweet ended with this simple takeaway:

“They sell answers to life. They were just as lost as everyone else. Maybe even more.”

I wasn’t surprised to find this post had gone viral. People love nothing more than the idea that experts, influencers, and wealthy people are all secretly frauds. It makes everyone feel better about not having their own life figured out.

But the more I gave the post some thought, the more I felt that the author’s conclusion wasn’t correct.

I think the more accurate version is a bit simpler and a whole lot less satisfying:

Knowing how something works and being able to do it yourself are two completely different skill sets. They always have been and likely always will be.

I’ve seen this both personally and in practice.

I’ve spent the last seven years writing about how to build a business that supports your life instead of consuming it. I talk about freedom and flexibility, taking long lunches with my wife, mid-day walks, traveling, and more. We do all of that stuff, and I built my business specifically so that we can.

But I’d be lying if I said I always live exactly the way I encourage others to live.

There are weeks where writing two newsletters, forty or fifty pieces of social content, managing a membership community, and a partnership all take their toll. And at the end of the week, I look up and realize I’ve been staring at my laptop for five days.

Jennifer has been there, working alongside me, in the same house day after day, and somehow we’ve barely talked to one another. It doesn’t happen often, but when it does, it’s a reminder that living my values is a lifelong journey, not something you get perfect every week.

For example, last Tuesday was supposed to be an open day on my calendar for us to explore the town we’re currently living in. I had no calls, no immediate deadlines, and not much work to finish that day. That’s the whole point of how I set up my schedule.

But by noon, my schedule had been captured by some unexpected problems. A partner reached out and wanted to have an urgent meeting. Jennifer found a few problems in my newsletter that needed to be immediately corrected, and one of the pages on my website broke, so customers were having a hard time finding my product.

Jennifer asked if I wanted to grab lunch, and I said, “Give me thirty minutes.” Thirty minutes turned into two hours, and I can’t even remember if I closed my laptop.

But I know exactly how my week should look when I’m getting it right.

Open Tuesdays. No meetings. Protect the life you built. And I believe every word of what I write. But sometimes, a busy week shows up unexpectedly, and I do exactly what I tell 1.5M+ people not to do.

I don’t think that makes me a fraud at all. I think it makes me a person who’s better at seeing the pattern than executing it perfectly every time.

And I also think that’s true for most people who teach, write, or share what they’ve learned. It’s true for my friend who’s a fitness coach and knows exactly how to train, but skips his own workouts when life gets stressful. It’s true for the financial advisor I know who understands the poison of credit card debt more than anyone, and still carries it himself. It’s true for my old therapist, who could spot issues in her clients’ marriages, but couldn’t see them in her own.

I don’t consider any of these people hypocrites or frauds. They’re people who simply understand something intellectually and struggle with it practically. Knowing and doing have never been the same thing.

The gap exists because most advice is general, and life is very specific. When I write and encourage readers to “protect your time,” I mean that. But then a specific opportunity shows up that’s exciting or urgent, or a deadline gets tight, or a day stops feeling open because a bunch of new problems coincidentally land on my plate at once. And when that happens, the advice I wrote doesn’t feel like it applies to me anymore. Even though I’m the one who wrote it!

That’s part of the trap. You start to believe you’re exempt from your own lessons because you understand them so well. At that point, understanding tries to become a substitute for action, even when it isn’t. And nobody calls you on it because from the outside, it looks like you’ve got it all figured out.

I love it when Jennifer calls me on it. I’ve found that’s one of the biggest benefits of working with your spouse a few feet away at home. She doesn’t care what I wrote about last Saturday, if I’m not living it right now.

So, I don’t really agree with that tweet. The people writing those books might have been lost in a specific part of their personal lives, but I don’t think they became “go-to experts” without having massive success helping other people. Nearly all of them understand exactly what “good” looks like in their field. They just couldn’t do it consistently. And, I think if we’re all being honest, neither can most of us.

When I read books from experts, I don’t spend the majority of my time being skeptical about the usefulness of their advice. I simply keep showing up and trying to follow it, especially on the weeks when it’s hard. And I definitely try to follow the advice that I give, since I’m the one who’s writing it.

I don’t always get it right, but it will forever be a work in progress.

So here’s what I’m wondering this week:

What’s a piece of advice you fully believe in but still struggle to follow consistently?

Click the button below and tell me. I read every response.

Leave a comment

If you enjoyed this read, the best compliment I could receive would be if you restacked this for your readers. Thank you so much for a bit of your valuable time today.

Share

*Note: A few of the “facts” in the Tweet can be verified, while others appear to be false. Dale Carnegie did NOT die alone. Turns out I didn’t do enough diligence. I think this is both ironic and speaks to the topic quite well. Lesson learned!

Subscribe now

A few years ago, Jennifer and I were relaxing inside a little wine bar in Lisbon, enjoying a glass of wine together on a sunny late afternoon.

It was a cool little spot called Senhor Uva, opened by a couple from Canada who moved to Portugal in 2019 with the idea of building a community around natural wine.

And it went well.

They created the kind of life you imagine when you daydream about leaving it all behind and starting over somewhere beautiful, affordable, and slower.

While I was sipping on a glass of rosé wine, I watched one of the owners, Marc, head out the front door to grab a case of wine from some other business down the street. And in the one hundred feet or so it took him to walk there, four different people stopped him.

They weren’t customers. They seemed to be neighbors who clearly knew him. From inside the window, I watched him navigate what looked like light and easy conversations. I’d imagine they were asking how he was doing or chatting about something that happened in the community. He wasn’t rushing at all. He was just there, being part of the neighborhood, and part of a place that wasn’t even his home country.

I sat there watching Marc, wine in hand, and felt something I didn’t expect.

Jealousy.

I wasn’t necessarily jealous of Lisbon or the wine bar or the sunny weather we were lucky enough to be blessed with that day. I was jealous of the fact that Marc and his partner Stephanie built something small enough that it let him enjoy his day in that way. That the people around him knew his name and stopped him on the street and wanted to chat. That his work and his community were interwoven.

I mentioned my observation to Jennifer on our stroll home that evening. About how rare that felt nowadays. About how we keep meeting people like this and walking away with the same strange feeling of jealousy.

Back where I live in New York, there’s a guy named Page who used to be the executive chef at Google in Los Angeles. He left that world and moved back to the Hudson Valley to open a little breakfast and lunch spot in Stone Ridge called Hash. It’s relatively small. It’s local. It serves really good, healthy food to people who live nearby. It’s a place where I meet my friends once a week, or stop by for an egg white wrap after I work out at the local gym.

When I talk to him about the community restaurant he’s built, he lights up. Not because the business is some $10M+ enterprise or because he’s got a crazy big expansion plan. He lights up because he loves running it. Because he’s part of something in his community that didn’t exist before he built it.

I think about the sushi chef Jennifer and I met in Sonoma a few weeks ago. A guy from Venezuela who walked into fifteen restaurants in Los Angeles looking for work, got rejected by fourteen of them, and eventually apprenticed under the one chef who gave him a shot. Now he runs a twelve-seat omakase bar in wine country, and he’s one of the happiest (and proudest) people I’ve talked to in a long time.

These people aren’t building massive empires. They’re building what I call “corners.” A little spot in the world that’s unapologetically theirs. Something small enough to care about deeply, and connected enough to actually feel like it matters.

Jennifer and I talk about businesses like these more than I’d like to admit. I’m obsessed with second mountain, small, community-driven places that meet a need and act as a gathering spot.

A bed and breakfast. A small wine bar. Something that would make us a real part of the community we live in, instead of just people who live there and work from home. We talk about it the way people talk about dreams they’re not sure they’re allowed to have.

And then we go back to our laptops and keep building the thing we’re already building.

There’s absolutely nothing wrong with what we’ve built. I love my work. I love writing. I love the people who read what I write, and I love that Jennifer and I get to do this together. I love the fact that I get hundreds of positive emails from people saying I’ve made an impact on their lives. But there’s something about the way Marc walked down that street in Lisbon that sticks in my mind because it makes me feel envy.

He wasn’t optimizing for scale. He wasn’t trying to reach more people or grow his audience or hit some milestone that would make him feel like he’d finally made it. He was just getting a case of wine and saying hi to his neighbors.

I think most of us know that community and connection matter more than revenue or followers or any of the metrics we track or brag about.

We know that the people who seem happiest aren’t usually the ones with the biggest businesses. They’re the ones who built something small enough to actually be present for.

But we often don’t choose it. Or at least, I haven’t, yet.

Part of me wonders if it’s because I don’t actually believe it. Like maybe I think I’m the exception, the one who can scale and still feel connected. Who can build something big without losing all of the small things that make it feel small, private, and intimate.

And part of me wonders if I’m just addicted to the game. The numbers going up, the audience growing, and the feeling of momentum. That stuff is hard to walk away from, even when you know it’s not the thing that actually makes you the happiest.

I don’t have an answer to all of this stuff I’m wondering about. I’m not going to pretend I’ve figured it out, because I haven’t yet. But writing it down, sharing it with folks, and hearing their stories has a way of helping me learn more.

I keep meeting people who chose the “corner” instead of trying to build an empire. And every time I do, I walk away feeling like they know something I don’t.

Or maybe they know something I know too, and I’m just not ready to act on it yet.

So here’s what I’m wondering this week:

Who’s a person in your life that built a “corner” business that makes you think, “Wow. That person knows how to live.”

What did they build, and why did it make you feel that way?

Reply and tell me. I read every response.

Thanks for reading, and I appreciate your time.

Who’s a person in your life that built a “corner” business that makes you think, “Wow. That person knows how to live.” What did they build, and why did it make you feel that way?

Leave a comment

If you enjoyed this read, the best compliment I could receive would be if you shared it.

Share

If you’ve felt like LinkedIn “doesn’t work” the way it used to, you’re not crazy. Richard van der Blom broke down exactly what’s changed inside the algorithm, why reach is down, and what actually drives visibility in 2026 .

Richard has analyzed millions of posts over the last five years through his annual LinkedIn Algorithm Report. In this workshop, he unpacked what’s real, what’s myth, and what you need to adjust right now.

We covered:

• What “360 Brew” actually means and how LinkedIn now builds interest clusters instead of prioritizing your network

• Why deep topic clarity matters more than hashtags

• Why reach has dropped up to 60 percent for many creators, and why that is not necessarily a bad thing

• The shift from dwell time to consumption rate and why long carousels now underperform

• Why AI copy-paste posts are being flagged and how credibility scoring works

• The truth about external links and why hiding them in comments no longer works

• Why saves and reposts now matter more than likes

• How a single thoughtful comment can outperform a six-hour post

He also explained why engagement strategy might now matter more than content strategy.

Richard’s LinkedIn Algorithm Report is something I buy each time it comes out, so if you’re interested in it, you can find it here. IMO, well worth the research he puts in.

Cheers,
Justin

Unsubscribe Linkedin Masterclass Feb 2026 V1

3.53MB ∙ PDF file

Download

Download

Subscribe now

If you’ve ever spent time with smart people, they’ll convince you that they’re right about everything. That, in most cases, they make great decisions based on available logic. The smarter they are, the better decisions they make.

Doesn’t seem like a big stretch, right?

But recently, I’ve taken stock of some very smart friends who have made seemingly disastrous choices in their personal lives, relationships, or businesses.

And I started to wonder...does intelligence often work against good judgment?

The more I look around, the more this seems to play out.

Friends who stayed in toxic relationships that, to concerned outsiders, seemed so obviously bad. Or invested in sketchy deals covered in red flags. Or made huge career moves based on their ego instead of evidence.

If you give these folks an IQ test, they’ll score like geniuses.

So why does this happen?

I think people believe their intelligence in one arena translates seamlessly to another. That their brain power gives them immunity from stupid mistakes.

The engineer who thinks he’s an expert on nutrition.
The surgeon who believes she’s a world-class investor.
The finance exec who’s sure he understands politics better than anyone.

So when they see a clear red flag, they think, “I’m smart enough to handle this.”

But it’s not just intelligence translating from one domain to another.

Smart people also love to overcomplicate the simple. They’ll create these elaborate justifications for a bad choice because “this is obviously a bad idea” feels like they’re missing something. There must be something more intricate or complicated at play.

But most good decisions are boring and obvious.

And if I flip this whole argument, I often see the opposite. The people I know who consistently make the best life decisions aren’t necessarily the highest-IQ friends in my circle.

They’re people of above-average intelligence who have strong instincts, who listen to their gut, and who don’t feel the need to “outsmart” the situation.

They see a red flag and say things like, “That’s obviously a scam.” They don’t need some big, elaborate analysis. And they don’t go down a path of “well, if I factor in these seven variables...” They just say no, and the deal is done.

Smart people can’t (or simply don’t) do that as often. If they walk away from something without fully understanding it, that feels like intellectual failure to them.

So they stay, analyze, and build some mental framework that explains why this terrible situation might actually be fine.

And they’re convincing. Not just to themselves, but to everyone around them. They’ll explain their bad decision so articulately that you start to doubt your own instincts. You go in thinking “this is clearly wrong,” and leave thinking “maybe I’m the one missing something.” I know that’s happened to me more often than I’d like to admit.

And that’s the real trap. Intelligence doesn’t just help smart people fool themselves. It helps them fool everyone else, too. Which means fewer people challenge them, they get corrected less, and the bad decisions pile up.

It pays to remember that sometimes the obvious answer is the right one. Even for smart people.

Especially for smart people.

Have you seen this same thing in your experience? When have you watched a highly intelligent person make a terrible decision that was painfully obvious to others?

Leave a comment

If you enjoyed this read, the best compliment I could receive would be if you shared it.

Share

Subscribe now

Back in 2024, I wrote something that struck a nerve on X.

This is my sixth most popular post of all time, and I started thinking about why it resonates so deeply.

I think it’s because most of us feel it. We’re constantly being pulled in so many directions, with so much noise, and it’s 24/7/365. And a lot of us are struggling to unglue from the distractions. To feel calm again.

For a long time, I thought the way to get back to this feeling was through addition. If I could make enough money, invest in the right stocks, and set up the right business systems, then I’d finally feel calm again. I’d have space to think. I’d arrive somewhere that felt peaceful.

But it turns out that’s not true. The more I added, the further the goalposts moved. The further those moved, the more I had to make. The more I made, the more I spent, and around and around the circle goes.

At some point, without really planning it, I started moving in the opposite direction.

Jennifer and I don’t buy much stuff anymore.

I get new clothes maybe once a year, if that. I own mostly black sweatshirts at this point, which makes getting dressed every day really easy. We drive a 2022 Subaru, which we bought in cash a while back, because we knew it would last, and we didn’t want to think about cars, leases, and interest rates. We don’t have many subscriptions piling up. And we don’t upgrade our phones or laptops until they actually stop working.

None of this is because we can’t afford things. It’s because we started noticing what stuff actually costs. The attention. Not the price. Everything you own takes up a little bit of space in your brain. Every subscription you start is a small decision you have to manage each month. Every new device costs thousands of dollars that you have to earn to cover the expense.

Most of this stuff accumulates quietly, and then one day you realize that almost none of it has made your life better.

So we stopped adding and started removing. And the less we own, the lighter life feels.

Now, I ask a different question when I’m trying to decide whether to spend money on something.

Instead of “Can I afford this?” I ask, “Does this add time, energy, or life?”

Most purchases don’t. A new phone doesn’t give me any time back. A newer car wouldn’t give me more energy or life. Most subscriptions don’t do much for my business or give me more time back.

But some purchases do. A housekeeper means we’re not spending weekends cleaning. Healthy food means we actually feel good instead of just full. Travel that’s designed for rest instead of cramming in a million sights means we come back feeling fulfilled instead of exhausted.

The price tag isn’t the point. The question is whether it frees up space or takes it.

I have a friend named Steve who’s figured this out better than nearly anyone I know.

He runs a coaching practice, and he’s good enough at what he does that he could easily take on more clients, build out more programs, hire people, and scale the whole thing up. The playbook is obvious and available to him, and he could likely double or triple his revenue.

But he doesn’t. He keeps his practice small on purpose. He spends his time in Upstate New York, biking, playing with his kids, and staying mostly offline. When I talk to him, he’s calm in a way that most people I know aren’t. He’s certainly not checked out or detached. He’s content. Like he’s not running toward something or away from something. He’s just there. And happy.

Here’s the part of that tweet I find the most interesting:

“…in a world designed to prevent all four.”

Remember that the new default is that the world is total and utter chaos.

Your phone is built to interrupt you. Social media is built to addict you. The news exists to make you worried. Even the way most businesses work is designed to add complexity, not remove it.

Everything around you is pulling in the direction of more noise, more urgency, and more stuff competing for your attention.

Which means calm isn’t something you find. It’s something you’ve got to fight for. And the fight isn’t about adding the right things.

It’s about removing the wrong ones.

I’m curious what you’ve removed that made your life noticeably better. Or what you know you should remove but haven’t been able to let go of yet.

Reply and tell me. I read every response.

I appreciate your time.

What is something you’ve removed that made your life noticeably better? Or what’s something you know you should remove but haven’t been able to let go of yet?

Leave a comment

If you enjoyed this read, the best compliment I could receive would be if you shared it.

Share

Subscribe now

A few years ago, I said yes to something I should have said no to.

A company I admire asked me to speak at their event, unpaid, and it required me to travel even though I was behind in my work.

But I said yes because I didn’t want to disappoint them.

Over the next six weeks leading up to the event, I felt angry each time I thought about it. I wasn’t mad at the company for asking me. I was mad at myself for saying yes when I clearly should have said no.

The talk went really well, and I met a lot of great people at the event. But I came home totally exhausted and even further behind on everything. I knew I had to get better at protecting my time and energy.

The problem is that most entrepreneurs are terrible at saying no.

Not because they don’t want to. They just don’t know how to say no without feeling like they’re letting someone down.

So they do one of three things:

They ghost. The request hits their inbox, they feel uncomfortable, and just never respond. The ask sits in their inbox for weeks until it becomes too awkward to reply at all. So the relationship is damaged, and they end up feeling guilty about it.

They over-explain. They write an encyclopedia-length response about how busy they are, how much they wish they could help, and how terrible they feel about declining. The person on the other end reads all that and wonders why you’re giving them all your life’s details.

Or they say yes when they really mean no. They accept things they don’t want to do because saying no feels hard. Then they resent the commitment, half-ass the execution, and damage the relationship anyway.

None of these work. And I know because I’ve tried all three of them.

A good no should do four things.

1. It should be fast.

2. It should be warm.

3. It should be clear.

4. It should leave the door open (if you mean it).

Fast means you respond quickly when someone asks. I’ve found that the longer you wait, the weirder it gets for everyone. A response in 24 hours feels respectful, but waiting three weeks feels like you were stalling.

Warm means you remember to acknowledge the ask and thank them for thinking of you. Most people skip this and jump straight to sending a rejection. It’s important to recognize that someone paid you a compliment by asking for your time.

Clear means you don’t hedge. You don’t say “maybe” when you mean “no,” and you don’t say “let me think about it” when you mean “no.” Being unclear is not kind. It just delays the disappointment and wastes everyone’s time.

And, lastly, leaving the door open means you give them a path later, but only if you truly mean it. The thing you can’t do today might be the thing you’d love to do in three months. But if not, don’t leave the door open at all.

Here’s the template I use now (feel free to steal it):

Hi [Name],

Thanks for thinking of me for your [ask]. I really appreciate it, and I normally love doing stuff like this.

Unfortunately, I’m at capacity right now, and I’m not booking anything new at the moment. I hope you won’t take this personally. I field a lot of requests, and I have to say no in order to make progress on my projects.

Please feel free to reach out again in 90 days or so, and I might be in a better position to accept.

Again, thanks for thinking of me, and best of luck with the [ask].

Cheers,
Justin

Seven simple sentences that take less than fifteen seconds to customize and send. I used to do it myself, and now my VA does it on my behalf. Easy either way.

I’ve used this template probably 500+ times in the last two years. And not once has someone responded poorly. In fact, most people write back and say something like, “I totally respect that and figured you might be busy.”

We forget that the person asking expects you might say no. That’s a potential outcome, and they’re not going to hate you for it. If they do, that’s a “them” problem, not a “you” problem.

What damages relationships is ghosting, being wishy-washy, or saying yes and then backing out because you should have said no.

A clean no, delivered quickly and warmly, builds trust. It tells the other person that when you do say yes, you’re in 100%.

I still hate saying no. No matter how many times I get asked to do things, it never feels good to disappoint someone.

But I know that protecting my time isn’t selfish. It’s the only way I can show up fully for the things I actually commit to.

So here’s what I’m wondering this week: What’s something you’ve been meaning to say no to but haven’t yet? And what’s stopping you from doing it right now?

Leave a comment and tell me. I read every response.

I appreciate your time.

P.S. This past Monday, I launched something new called The Expert OS.

It’s a free 30-day program where I help you take your expertise, package it into your first offer, and earn your first $1,000 in business revenue. No spending months on stuff that doesn’t matter. You bring the knowledge, and I give you the system, templates, and technology.

Saying no to other people’s requests is important. But it only matters if you’re saying yes to something of your own. If you’ve been sitting on expertise that could be a business, this is the system that will help you get there.

Start The Expert OS

Note: This was built in partnership with Kajabi, so email support@kajabi.com with any issues.

What’s something you’ve been meaning to say no to but haven’t yet? And what’s stopping you from doing it right now?

Leave a comment

If you enjoyed this read, the best compliment I could receive would be if you shared it.

Share

Most people think “community” is a business model. Jordan Godby explains why that belief is exactly why most communities fail.

Jordan has helped build and launch 100+ paid communities, including my own. In this workshop, he broke down what actually makes a community profitable, sustainable, and worth the effort without burning out the founder.

This session was not about platforms or software. It was about strategy.

We covered:

• The four real community business models and why picking the wrong one guarantees frustration

• Why free communities almost always backfire and attract the wrong members

• How to validate a community idea before building anything or writing a single line of copy

• Why selling first and building second dramatically increases your odds of success

• The difference between connection-driven and outcome-driven communities

• How to price a community so it stays motivating for you and valuable for members

• Why specificity beats scale and how niche communities quietly outperform big ones

• How to turn cohorts into long-term recurring revenue through alumni communities

Jordan also walked through how we launched the Creator MBA community in record time by validating demand first and designing around outcomes instead of features

If you have ever thought about starting a community, tried one and shut it down, or felt unsure whether the ROI was worth the time, this workshop will save you months of guessing.

If you want to learn more about Jordan, you can do so here:

https://growthcommunity.co/

Cheers,

Justin

Subscribe now

Paul Millerd’s new hardcover edition of The Pathless Path unexpectedly arrived on my front steps a few days ago.

As I opened up the package, the first thing that hit me was how absolutely beautiful the book is. It’s more like a piece of art. It’s the kind of thing you want to pick up just to feel the weight of it in your hands.

I texted Paul and immediately let him know my thoughts:

I opened the book and happened to randomly land on page 45, the beginning of Chapter 3, called “Work, Work, Work.”

Within about ten minutes, I remembered exactly why Paul’s book keeps pulling me back when so many other business books end up unread on my shelf.

Most business books tell you what to do. The Pathless Path gives you permission to stop doing what you thought you had to do.

And that difference is exactly why it’s been so impactful to me.

I first read Paul’s book back in January of 2024, after closing out a year where I hit an all-time revenue high of multiple seven figures in my business.

I should have felt like I was winning, but instead I felt this intense pressure, the weight of my own expectations, and a nagging sense that I was supposed to want more and push even faster.

To fulfill those feelings, I began exploring the possibility of signing a book deal. I got into deep talks with a well-known non-fiction publisher, and off to the races we went.

As the pace of the conversation quickened, I thought: this is the exact kind of thing that’s supposed to be the next logical step for someone like me.

But every time I sat down to think about actually writing it, I felt sick. I’d open my laptop, stare at a blank page, and my mind would start spinning. Not because I didn’t want to write the book. Because I knew what would happen if I did.

I’d cross over into complete pressure cooker territory. The book would need to sell, and I’d need to promote it. I’d need to build a business model around it. I’d have to do the PR circuit, the book signings, and the bookstore tours. And suddenly, my simple, low-cost, frictionless, 100% organic business would be turned into a bigger and more complex machine.

The problem was, I felt like if I said no, I’d be considered a failure. Like I was giving up on something I was supposed to want. Like I would be disappointing my family, all of whom are big readers, and were thrilled to hear I was even considering it.

I’d actually been wrestling with this tension for months. In July 2023, I attempted to express the feeling in a quasi-diary entry article titled, “When is enough, enough?” which questioned whether constant growth was even the point. And the book deal felt like exactly the kind of growth-for-growth’s-sake move I’d written about avoiding. But knowing something is wrong for you and having permission to actually say no are two different things.

That’s when I picked up Paul’s book. And it gave me permission to say no.

I’ve started saying no to a lot of other things as well.

I decided to forego the traditional playbook that online educators like me use. I didn’t hire a team or build complex funnels or even run ads. I didn’t follow any of the playbooks that people with businesses my size are supposed to follow. Instead, I kept my products low-cost and the buying experience frictionless. I kept growing organically, making content, and experimenting rather than following best practices.

And it worked. My audience grew to over 1.5 million, my newsletter reached 175,000 subscribers with a 61% open rate, and I continued doubling my revenue.

But more importantly, I got to keep my business small (just my wife and me) and work on something we actually enjoy doing.

As I skimmed further along in the book, I hit a line that really stuck out to me:

We are convinced that the only way forward is the path we’ve been on or what we’ve seen people like us do.

After reading that, I realized something. I’d been working to do the opposite of what “people like me” do, following Paul’s advice without even noticing.

Over a year after reading Paul’s book, I launched this Substack. I have no expectation of revenue, and I’m not interested in talking about business strategy and tactics.

I launched it because I wanted to write shorter, more personal essays that feed my creative spirit. I want to write about things that light me up, no matter what the topic.

The newsletter you’re reading right now is what redirected ambition looks like. It took me over a year to get here, but Paul’s book planted the seed.

I never signed the book deal. I didn’t hire a team. I didn’t build any funnels or ever run ads. I probably never will.

And I ended up with more revenue, more freedom, and more creative energy than I would have had if I’d followed the script that “people like me” were following.

Paul and I talked about a lot of this stuff on his podcast last year. If you want to hear more about how I’m trying to embrace creativity, we dig into it around the 32-minute mark:

If you’re wrestling with what you’re “supposed” to want in your business, go read The Pathless Path. The new hardcover edition is stunning, and more importantly, it might give you permission to stop following someone else’s script and start writing your own.

I’ll leave you with this question: What script are you still following that you don’t actually believe in anymore?

Leave a comment and tell me. I read every response and try my best to reply to as many as possible.

I appreciate your time.

Tell me: What script are you still following that you don’t actually believe in anymore?

Leave a comment

If you enjoyed this read, the best compliment I could receive would be if you shared it.

Share

Subscribe now

Every day, I block off noon to 3 p.m. for deep work.

Three hours with no meetings, no calls, no distractions. And most days, I finish everything I need to do in about two hours, which means I have an hour of empty time just sitting there on my calendar.

You’d think I’d enjoy that. But instead, I feel this pull. This urge to grab tomorrow’s tasks and drag them into today.

The logic sounds reasonable in my head: if I can pull Tuesday’s work into Monday, and Wednesday’s into Tuesday, then I’ll create this glorious five-day weekend stretching out in front of me. Wednesday, Thursday, Friday, Saturday, Sunday. Pure open time with nothing hanging over me.

But here’s what actually happens: I never stop pulling. I finish today’s work, pull in tomorrow’s. Finish that, pull in the next day’s. The open time I’m chasing never actually comes because I keep dragging the future into the present and filling it before I get there.

I’ve done this for years. I’m working on it, and I’ve gotten significantly better. Most Fridays now, I don’t work at all. But recently, something happened that made me realize this isn’t really about productivity or time management or discipline.

It’s about something deeper that I’ve never fully examined.

Last week, I got the flu. And for maybe the second or third time since Jennifer and I got together 14 years ago, I took a nap in the middle of the day. I was just completely exhausted, so I lay down and slept for two hours and fifteen minutes.

When I woke up, she told me two things that have been rattling around in my head ever since.

First, she said it was the first time she could remember in a decade that I had taken a nap. A decade. I’ve gone an entire decade without sleeping in the middle of the day, and I never really noticed until she pointed it out.

Second, she said she didn’t know whether to wake me up. She knew I needed the sleep, but she also knew I’d probably be irritated with myself for “wasting” part of the day. Because apparently I talk about that a lot.

I had to really sit with that for a second. I was sick. I had the flu. My body desperately needed rest. And my wife had to genuinely debate whether letting me sleep would make me angry at myself.

That’s when I started to realize something might be off about how I relate to rest and productivity and my own sense of worth.

I’ve been thinking about this constantly since it happened. Not just the nap thing, but all of it. The pulling work forward. The inability to sit with open time. The low-grade guilt I feel whenever I’m not producing something.

And I’ve started paying attention to what happens in my mind and body when I try to do nothing.

I feel antsy. Unsettled. I look at open time and freeze. What do I do with this? How should I spend it? What’s the right choice? And when I freeze like that, when the openness becomes overwhelming, I retreat back to what’s comfortable. And what’s comfortable is generally work.

Work has rules. Work has a finish line. Work gives me that small hit of completion that my brain has learned to crave. Doing nothing has no finish line, and I think that’s what terrifies me about it.

I keep coming back to the same memory. July 11th, 1995. The day I turned 14, my father dropped me off at the McDonald’s in Chesterland, Ohio, and told me it was time to get a job. I’ve worked nearly every day since. By 16, I was a manager at Burger King, wearing a shirt and tie, managing men and women three and four times my age. I remember how proud my parents were of that.

By 19, I snuck into a career fair for Ohio State graduates while I was still a sophomore and somehow landed two job offers from companies that thought I was about to graduate. I had to go back and tell them I still had two years left. One of them hired me anyway when I finally graduated.

Achievement was what got me praised. Output was what made people proud of me. Being useful was what made me feel like I mattered. And I learned those lessons early.

But there’s another piece to this that I don’t talk about much.

I was overweight as a kid. Uncool. Picked on constantly in middle school and into my freshman and sophomore years of high school. I got beaten up a lot. There was one kid, Mike, who waited for me outside of math class and punched me in the stomach every single day in front of all the other kids.

When I got older and learned to stand up for myself, I started looking for ways to feel secure and important and worthy of respect. Some kids had athletic ability. Some had social status or good looks or whatever else made you cool in high school. I had achievement.

So I leaned into it. Hard. It became more than just a strategy for getting ahead. It became a chip on my shoulder, a way to prove that I mattered, a way to make sure nobody could ever make me feel small again.

And somewhere along the way, I think I started believing that I’m only okay if I’m being useful.

Jennifer is different from me in this way, and I notice it all the time.

She’s content naturally. She looks around at our life, at our three dogs, our house, and our financial security, and she just feels grateful. That’s her default state. She doesn’t have to do anything to feel okay. She is just okay.

My default state has always been restless. Searching for the next thing that will finally make me feel like I’ve done enough. I’m 44 years old. I’ve built a business I’m proud of. I have zero debt and more financial security than I ever imagined I’d have. And for most of my adult life, I’ve still felt like I had to keep producing to deserve any of it.

But something has started to shift.

I used to think I had a productivity problem. That I needed better boundaries, or better systems, or more discipline around rest. But once I realized it was never really about productivity, and was actually about permission, things started to change.

I never gave myself permission to just exist without producing something. I never believed I was allowed to rest without earning it first. I combined my output with my “okay-ness” so completely that I didn’t know where one ended and the other began.

Now that I can see it, I can work on it. And I have been.

Last year, Jennifer and I went on what we thought would be a short hike at Minnewaska State Park. We got a little lost and ended up being gone for about six and a half hours, just wandering around, finding new paths and waterfalls and rock formations, with no real plan or destination.

It didn’t feel like a waste. It felt like one of the best days I’d had in years. I didn’t produce anything. I didn’t check anything off. I just existed out there in the woods with Jennifer, and I felt completely okay.

That was the first time I realized the voice in my head might be wrong.

Since then, I’ve been collecting more moments like that. I’ve gotten better at noticing when the pull to be productive is actually just discomfort with being still. I’ve started letting empty hours stay empty instead of filling them with tomorrow’s work. Most Fridays, I do absolutely nothing, and I don’t feel guilty about it anymore.

But just yesterday, I caught myself doing it again. I finished my work by 1 p.m. and had two completely open hours. And within five minutes, I was pulling Thursday’s tasks into Wednesday. The old pattern was running on autopilot. But I stopped myself this time, closed my laptop, and went out for coffee. But the urge was there, just as strong as ever.

I’m not going to tell you the voice is gone, because it isn’t. I still catch myself pulling work forward. I still feel that twinge when I sit still for too long. But the voice is a lot quieter now. And when it speaks up, I recognize it for what it is: an old belief that helped me survive when I was younger but doesn’t serve me anymore.

I’m learning that I don’t have to earn my okay-ness. I can just have it.

Jennifer’s known this her whole life. It took me about 44 years to start figuring it out. But I’m getting there.

And if you’re someone who’s spent your whole life believing that your worth comes from your output, I want you to know that you can unlearn it too. It’s not easy, and it doesn’t happen overnight, but it starts with noticing.

Once you see the pattern, you can interrupt it. And once you interrupt it enough times, it starts to lose its grip on you.

So here’s what I’m wondering this week.

When you’re not being useful to anyone, when you’re not producing or achieving or checking something off a list, when you’re just sitting there existing without having earned it first, do you feel like you’re allowed to be there?

And if the answer is no, what would it take to change that?

Leave a comment and tell me. I read every response.

I appreciate your time.

When you’re not being useful to anyone, when you’re just sitting there existing without having earned it first, do you feel like you’re allowed to be there?

Leave a comment

If you enjoyed this read, the very best compliment I could receive would be for you to share it.

Share

Subscribe now

For the last three years, I’ve gone back and forth about writing my first book.

Not a self-published book or an eBook. A traditional book. The hardback kind you see on Amazon or at Barnes & Noble with the glossy cover and my name printed on the spine.

I picture myself on podcasts talking about the book or doing the morning show circuit. The feeling of walking into a bookstore and seeing my book on the shelf. I think about how proud my mom would be. So damn proud.

Every time I imagine it, I feel this pull. Like, “Yeah, I should definitely do that. That’s the right next step.”

But over three years, I’ve done almost nothing to move it forward. I’ve talked to some agents and bestselling authors. But I’ve never written a proposal. Not even an outline.

A few weeks ago, I finally asked myself: Am I putting this decision off because I’m not ready? Or because I don’t actually want to do it?

To be honest, I genuinely don’t know yet.

About three years ago, I talked to a very successful creator who was in the process of writing his very first book (he’s since become a New York Times bestselling author).

He said something that I haven’t been able to shake since our conversation:

“Writing a book is the most stressed out I’ve ever been in my entire life for a full two years.”

Writing a book is a monster decision. A two-year minimum commitment. You hire an agent, pitch publishers, and wait for responses. If you get a deal, your publisher becomes your quasi-boss. Your editor shapes the direction, and you have deadlines you cannot move.

I haven’t had a boss in six years. The idea of giving that up for two years? I don’t know if I want to.

A few months ago, I went to an author’s dinner in New York. I was one of fourteen people invited, and it was filled with some of the biggest names in non-fiction. I was the only person there who hadn’t written a book.

When one of the authors asked what stage I was at, I fumbled for an answer about not feeling like a person who could write a book. How I’m just some guy who writes a short newsletter every week, and not a real writer like everyone else there.

I felt ridiculous when I left.

All my friends have written books. I can name ten people who’ve dealt with the stress, the deadlines, and the loss of control. They still managed to publish and move on.

And I’m still sitting here three years later, thinking about it.

The decision itself is getting heavier.

Three years ago, “Should I write a book?” was a light question I was kicking around. Now it’s this big thing I tend to avoid. When my friends publish their books, I feel this weird mix of pride and guilt.

The longer I defer it, the harder it gets. It’s no longer just a decision I haven’t made, but proof that I’m actually stuck.

And as I’ve danced around the idea, I’ve realized that I literally have no space to even act on it. I’m trying to figure this problem out while living the exact same life that’s kept me stuck for three years. I’ve got the same routines, same systems, and everything is optimized for consistency.

You can’t make a good decision about something big when there’s no space to make it.

A few weeks ago, Jennifer and I were sitting on the couch talking about how nothing big was really changing in our lives. We’re busy, sure. But we’re busy with the same things. The same work, the same schedule, the same conversations.

I said something like, “I don’t think I can figure out this book thing from here. I need to be somewhere else for a while.”

So we made a decision. What if we spent the next 3-6 months living up and down the California coast? Different time zone, different scenery, different surroundings. We’d meet new people, start new conversations, and shake up our stagnant routine.

Not because we need a vacation. But because I need space to figure out what I actually want instead of what I think I should want.

Maybe after a few months in California, the answer to the book problem becomes obvious. Maybe I realize I’m ready to commit to the two-year grind. Or maybe I realize I don’t want to do it at all, and I can finally let the idea go without feeling guilty about it.

Either way, I’d love to come to answer. And I hope that giving myself some actual room to feel it instead of just thinking about it is exactly what I need.

If you keep deferring a decision for years while sitting in the same environment, doing the same work, and having the same conversations, you’ll likely never come to an answer. You’ll just stay stuck.

But if you actually create space, if you change something significant, if you give yourself room to test what you want instead of just sitting around and analyzing it, the answer might actually show up.

I still don’t know if I’m going to write a book.

But I’m done trying to figure it out while staying exactly where I am.

If you’ve been deferring a decision for so long that you can’t remember when you first started thinking about it, the problem might not be that you don’t know the answer.

It might be that you’re trying to find it while everything stays the same.

You can’t think your way to the “a-ha moment” on something this big. You have to create the conditions where the answer might actually reveal itself to you.

So here’s my question for you:

What decision have you been stuck on for months or years? And what would actually have to change in your life for you to finally know what you want?

Reply and tell me. I read every response.

That’s all for this week.

I appreciate your time.

What decision have you been deferring for so long that you can’t even remember when you first started thinking about it?

Leave a comment

If you enjoyed this read, the very best compliment I could receive would be for you to share it.

Share

Subscribe now

Back in December of 2021, I was at my parents’ house in Cleveland, Ohio, because my mom was going to be having hip surgery.

At that point in time, I’d been writing on Twitter for about two months and had grown a small following of maybe 10,000 people. As I was having coffee in their kitchen, I wrote a short thread sharing eighteen creators I thought were doing interesting work online at the time. Without realizing it, I included only two women and sixteen men. It wasn’t meant to be malicious or intentional. It was simply an oversight on my part. The kind of mistake you make when you’re new to a platform, you’re rushing around, and you’re not thinking about how everything you post will be scrutinized.

I posted it around 8 a.m. and then went about my day, getting my Mom prepped for surgery, coming home, making dinner, and eventually helping my Mom get back into the house.

At 10 p.m. that night, my father screamed from the living room downstairs and woke me out of deep sleep. My mom had crashed after taking some sort of medication post-surgery. She was slumped over at the table, completely unresponsive. I jumped out of bed, ran downstairs, called 911, and followed that call up with one to my mom’s best friend, who’s a nurse. I was frantic. The paramedics showed up, revived her with Narcan, and rushed her to the ER. My father and I followed in the car behind them, more shaken up than either of us had likely ever been.

I sat in the ER waiting room for what felt like hours, not knowing if my mom was going to be okay. My hands were shaking, and I couldn’t sit still. So I did what I always do when I’m anxious and need a distraction.

I opened Twitter.

The thread I’d posted that morning had gotten some serious traction. Over 2,800 reactions. But when I noticed one particular retweet, my stomach dropped.

A University Professor from Harvard had taken offense to my oversight and retweeted it to their audience. Underneath her post, hundreds of people were calling me every name you can imagine. Sexist. Misogynist. Piece of shit. People were screenshotting it, quote-tweeting it, telling others how I was “part of the problem.”

And I was sitting there in an emergency room, terrified about my mother, watching strangers tear me apart for a mistake I didn’t realize I had even made.

The truth is that I’m a big boy, and I can certainly handle criticism. It was less the criticism and more just the timing. Frantic, panicking, and dealing with a genuine family emergency, while the internet mob had their way without any insight as to who I am as a person. They just saw a thread that fit a pattern they were angry about, and I became the latest target.

I wasn’t a person to them. I was a brand that, in that moment, needed to be destroyed.

That was my first real introduction to what it actually means to be a “big” creator.

Like any mistake in the 24/7 online world, it passes pretty quickly. I thought about defending myself, but I realized it would just add fuel to the fire. So I blocked the person, went to sleep, and basically never thought about it again.

So over the next few years, I kept growing. I built my Saturday Solopreneur newsletter to 175,000 subscribers, my LinkedIn following to over 800,000, and my Twitter (now X) following to 555,000. I’ve helped thousands of people start and grow their own businesses and built a more successful business for myself than I ever thought I would by simply writing on the internet.

But the bigger I’ve grown, the more I’ve started to understand what happened on that ER waiting room day.

When you’re big online, you cease to be a person. You’re a thing people project onto. A brand they expect to behave a certain way. And a target when you don’t.

And there’s this really interesting thing that happens as you hit certain growth milestones. You plateau and start maintaining.

Every week, I send an email to 175,000 people. And every week, a percentage of them unsubscribe. When your list is that big, the math gets pretty brutal. Losing one percent of 175,000 subscribers is 1,750 people, and that’s a pretty common number to hit “unsubscribe” when I send out an email. Which means I need to gain 1,750 new subscribers every single week just to stay at the same number I was the week before.

I could run ads to replace them or push even harder on social media. I could trade subscribers with other big accounts. I could create more content, find new platforms, and probably hustle my way back to growth.

But that’s a never-ending game of muscle and horsepower. More effort, more content, more strategy, just to avoid going backward.

And honestly? I don’t really want to play that game anymore.

Because I’ve realized that “big” doesn’t actually mean growing, it means running as fast as you can just to stay in the same place.

There’s something else I lost by getting big that I didn’t expect to lose.

When you have 175,000 people reading your work every week, you can’t really experiment as much anymore. You can’t just change your mind about what you want to write. You can’t be vulnerable in ways that might make people uncomfortable or confused about what they signed up for.

You’re expected to stay in your lane and deliver on the promises you made when people subscribed. To be the expert who has it all figured out and can teach them how to figure it out too.

The piece I wrote a few weeks ago about trying to finish my life instead of experiencing it? I couldn’t have written that for the Saturday Solopreneur. It’s too personal. Too raw. Too much admitting that I don’t have everything figured out.

Most creators I know would never admit to struggling with the exact things they’re supposed to be teaching people how to overcome. Admitting failure or personal struggles can be suicidal for your business and your income. People don’t want to learn from someone who’s still figuring it out. They want the expert with the answers!

But I’m not interested in being inauthentic just to protect my subscriber count.

At 175,000 subscribers, I have to be “expert Justin.” The guy with the playbook. The guy who’s built the business and figured out the systems can teach you exactly how to do what he did.

And that version of me isn’t entirely false. For the most part, I’ve figured out social media, marketing, business building, networking, and more. But it’s also not the whole truth either.

The truth is that I’m still figuring a lot of things out. And the bigger my audience got, the less I felt “allowed” to admit that.

So I started Unsubscribe here on Substack.

It’s small in comparison to my other newsletter. It’s currently around 28,500 subscribers. I don’t promote it very often. There are no aggressive growth tactics. I’ll be turning off paid subscriptions soon because I don’t want the pressure of monetizing it.

And I can write whatever I want here.

I can be vulnerable without worrying about whether it’s going to cost me business. I can admit when I’m struggling with something. I can write about things that have nothing to do with solopreneurship, business strategy, or how to grow your newsletter.

I can change my mind about what interests me. I can experiment with topics I’ve never written about before. And I can be the version of myself that’s still figuring things out instead of having to pretend I’ve already figured it all out.

Could I figure out how to monetize this again someday? Most likely. But I feel absolutely zero pressure to do that or grow it or turn it into anything other than what it is right now. A place where I can write and think and be honest without worrying about the consequences.

That freedom is worth more to me than the growth ever was.

I think a lot about what happened in that ER waiting room four years ago.

At the time, I thought the lesson was about being more careful. About how I had to think through every post, anticipate how people might react, and protect myself from getting torn apart again.

But the real lesson is actually quite different.

The bigger your audience gets, the less you can actually be yourself. At 175,000 subscribers and 1.5M followers, I’m a brand. People have expectations about what I will write and how I will write it, and what kind of person I am supposed to be for them.

Here, with a lot fewer subscribers, I get to be a person. I can write things that surprise people or challenge their expectations or just honestly reflect where I am right now instead of where I’m supposed to be.

And I’m realizing that being a person is where I’m having the most fun.

I spent years building systems to grow an audience. I know exactly how to do it. I have the playbook. I can teach other people how to do it. I could apply everything I’ve learned to Unsubscribe and grow it to 50,000 or 100,000 subscribers in the next 12 months if I wanted to.

But I don’t.

Because eventually it will come with the maintenance just to be stagnant. The pressure to stay in my lane and never deviate. The inability to be vulnerable or experimental or honest about the parts of myself that don’t fit the brand people expect.

I’m choosing to stay small here because small gives me the freedom to be whatever writer I want to be on a weekly basis. To talk about whatever pops into my head when it’s time to sit down at the keyboard.

So here’s what I’m wondering this week.

What are you chasing right now that might actually make your life worse once you get there? What goal are you working toward that might cost you the exact thing you’re hoping it will give you?

And if you’ve already gotten there, if you’ve already built the thing everyone told you to build, are you allowed to choose something different?

Leave a comment and tell me. I read every response.

I appreciate your time.

What are you chasing right now that might actually make your life worse once you get there?

Leave a comment

If you enjoyed this read, the very best compliment I could receive would be for you to share it.

Share

Subscribe now

A few months ago, I was looking back through my calendar, trying to figure out when Jennifer and I had been on a specific vacation.

I scrolled back through four months. Then six. And when I finally found the vacation, I couldn’t help but notice the thousands upon thousands of completed tasks on my calendar. Meetings checked off. Workouts logged. Content written and published. Newsletters sent.

There was so much stuff that I’d done. The problem was that I couldn’t remember much of it.

I mean, I knew it happened. The calendar obviously proved it. But when I tried to recall specific experiences from those thousands of tasks, I came up with way fewer than I should have. Conversations that stuck with me? Workouts where I actually felt something? Meals I actually tasted? Not many.

It was mostly just a blur of completed checkboxes.

The sad reality is that I’ve often treated my life like a task list. And for the past sixteen years, I’ve been rushing through it as fast as possible.

I’m 44 now. Success in my career (and eventually entrepreneurship) started at age 28 when I moved to New York City.

That was sixteen years ago. And from the outside, it looks like I’ve done a lot. I’ve helped build two billion-dollar healthcare companies, launched a successful business with Jennifer, grown a newsletter to 175,000 subscribers, created courses, and made more money than I ever thought I would.

I’ve also lived in New York, San Francisco, Los Angeles, Boston, Nashville, and many other really amazing places.

But the scary part is that I can barely remember much of it because I was so focused on completing the next thing that I never fully experienced the thing I was doing.

I was always three tasks ahead in my mind. Finishing coffee so I could get to the workout. Finishing the workout so I could get to content. Finishing content so I could get to the newsletter. Finishing the newsletter so I could get to dinner. Finishing dinner so I could go to bed, wake up, and do it all over again.

Somewhere along the way, I stopped experiencing my life and started completing it.

And those sixteen years went by in what feels like sixteen months.

The scary part isn’t that I’ve been doing this. It’s that I might keep doing it for the next sixteen years.

I could wake up at 60 and look back at my entire adult life and realize that a big chunk of it was a series of tasks I completed. That I had fewer experiences than I’d like to remember and fewer moments where I was fully present.

That’s the most depressing thought I’ve had in a long time.

Because what’s the point of building a successful business, writing a newsletter people love, or making good money if you’re not actually there for much of it?

You’re just completing your way through your one life.

I’m not going to tell you I’ve fixed this. I haven’t. And I don’t know that you can really fully fix it anyway.

But about a year ago, I started noticing when I was trying to complete things instead of experiencing them.

I started with small things. Leaving my phone in the other room during coffee. Actually tasting my food instead of eating to finish. Taking walks without listening to podcasts.

But the bigger shift has been in how I think about my work.

I started this Substack because I wanted to write for the sake of being creative. Not to hit a word count or check off a task or grow to a certain number of subscribers. I just want to write and see what comes out.

I’ve also been trying to stay off social media more. Not because I need a break, but because scrolling social media is just another way to distract myself from being present.

And with Jennifer, I’ve been working really hard to be fully there when we’re together. Not thinking about the next thing or checking my phone. Just being with her when we’re walking the dogs, watching TV, or having dinner.

Some days I can do it. And some days I still catch myself rushing to the finish line.

I’m not going to lie and say my life is suddenly different overnight. It’s not.

I still try to complete things constantly. I still find myself mentally three tasks ahead. I still look at my calendar and see a blur of checkboxes. That’s because I’m a do’er. A taskmaster at heart, and always have been.

But now I notice when I’m doing it. And some days, I stop myself.

Last week, Jennifer and I were watching a show (The Beast In Me — highly recommend), and I realized I was fully there. I wasn’t thinking about work or mentally planning tomorrow in my head. I was just fully immersed in the show, watching and talking about it with her. And when one of the episodes ended, she said, “That was really nice.” And I realized that she must have noticed that I was present and engaged for an entire hour.

A few weeks ago, I was writing this newsletter issue, and I wasn’t trying to finish. I was just writing because I was enjoying the creative moment and the pleasure of the topic. Three hours passed without me checking the clock once.

I’ve been in LA the past week, so yesterday I was fortunate enough to walk in the beautiful weather. And I did it without my phone. I just walked around, noticed beautiful things, and felt engaged. Not because anything particularly interesting happened, but because I was actually immersed in my surroundings.

These are small wins for someone actively trying to be more present. And that’s the whole point.

If you’re like me and you’ve treated your life like a task list, it’s going to blow by as a series of checkboxes. There will have been significantly fewer moments where you were fully present. And in their place will be things you completed so you could move on to the next thing.

And one day you’re going to look back at your calendar and realize you don’t remember as much of it as you should.

That’s the thought that scares me. And if I’m being honest, it’s probably the thought that scares you, too.

So here’s what I want you to do. Look back at your calendar from the past three months. Scroll through all those completed tasks. And ask yourself:

How many of those can you actually remember?

If the answer is “not as many as I’d like,” then maybe it’s time to stop completing your life and start experiencing it.

Leave a comment and tell me. I read every response.

I appreciate your time.

Do you struggle with this problem at all? Leave a comment and tell me.

Leave a comment

If you enjoyed this read, the very best compliment I could receive would be for you to share it.

Share

Subscribe now

I was scrolling through old photos on my phone last week, looking for a very specific picture my mom asked me to find, when I stumbled upon a totally different photo. One that caused me to stop and stare at it for a moment.

It was my wife Jennifer and I at a beer festival in Brooklyn back in 2012. We’re standing there with these huge smiles. Like 10/10 smiles. The kind you absolutely can’t fake.

Behind us, you can see the crowd and the tents and hundreds of other people having a great time, but we look especially locked in on whatever moment we’re in.

I stared at that photo for a little bit, and then I did what I always do when I come across some piece of nostalgia. I kept scrolling, looking for more. More photos from that year. Our tiny apartment on Waverly Avenue in Clinton Hill. Jennifer and I at some random bar. A friend’s dinner at my buddy Matt’s place in Williamsburg.

And all I could think was…I want to go back to that moment in time.

Yesterday was a Monday, and I felt like shit, to be honest.

Not sick. Just tired and uninspired. I found myself unconsciously scrolling through social media and consuming all the negativity that comes with it. How terrible the economy is, how the stock market’s going to crash, and more fear-mongering about everything.

And I caught myself doing something I’ve started to notice lately.

When the present feels heavy, I look to escape.

I started reminiscing. “Remember when everything was so much easier? So much lighter? When we didn’t have to worry about quarterly taxes and business decisions and could just walk down to Putnam’s, see our favorite bartender Nikki, and grab a beer? Damn, I miss that.”

Then Jennifer walked in, and I made the mistake of saying it out loud.

“Sometimes I just miss how simple things used to be. Back when we lived in Brooklyn. Remember?”

She looked at me like I was insane. “Why? Our lives are SO much better now.”

And she’s right. They are. In 2012, I was making $80K a year, stuck in an office building from 9 a.m. to 6 p.m., cold calling medical practices all day. We were living in a 600-square-foot apartment with $55,000 in credit card debt. The floor literally buckled in the middle of the living room, and the ceiling dripped when it rained. We were living our lives paycheck to paycheck.

Now I’m 44, and I run a successful business I’m proud of. I get to help thousands of entrepreneurs every year. We live in a house we love with zero debt and actual financial security. We built something together out of nothing.

After Jennifer shut down my trip down memory lane, my brain immediately jumped to the other place it sometimes goes. The future.

“Well, maybe when business slows down a bit, I’ll finally relax. Maybe when I learn to let go of control a little, I’ll have time to work on that book. Maybe when things ease up, I’ll feel different.”

And that’s when I realized what I’ve been working on understanding about myself.

I’m not always as present as I want to be.

It’s not constant. But I’ve started noticing a pattern. When something feels uncomfortable or heavy in the present, part of my brain wants to be somewhere else.

Sometimes I’ll be dealing with something stressful in the business, and I catch my brain jumping to “remember when you didn’t have to deal with this?” Or I’ll be looking at financials, and suddenly I’m thinking about that beer festival photo. Or something feels heavy and my mind immediately goes to “maybe when things slow down...”

I’m realizing I sometimes vacillate between two places: the past and the future.

When the present feels hard, I retreat into memory. Remembering when I was younger, fitter, had fewer obligations. When I didn’t carry this weight around. When ignorance was bliss.

And when that doesn’t work, I jump to the fantasy future, imagining a time when there will be less stress, less worry, more freedom. When I’ll finally have time to do all the things I want. That magical someday.

What I’m working on understanding is: What’s the cost of doing this?

It’s not that I’ll feel bad sometimes. The real cost is that I’m missing parts of my actual life while they’re happening.

I think this type of behavior is a coping mechanism. The brain’s way of avoiding sitting with the uncomfortable parts of right now.

Getting older. Having to provide for my family. The stress of running a business that’s dependent on attention and relevance. Never feeling like I’m reaching my creative apex or finding time to do all the creative things I want to do.

Those things are real. They’re heavy. And sometimes they’re uncomfortable to sit with.

So occasionally, instead of sitting with them, I escape. Either backward into a time when I didn’t have those problems, or forward into a fantasy where I won’t have them anymore.

But I’m realizing that neither of those places exists.

The past I sometimes romanticize? It had its own weight. In 2012, I was stressed about money daily. I was grinding at a hardcore job, had a lot of debt, and no clear path forward. But I don’t remember those parts when I look at old photos through rose-tinted glasses.

And the future I sometimes fantasize about? I doubt it will arrive the way I imagine. Because when I get there, there will be new stresses, new problems, and new reasons my brain might want to escape into memory or fantasy.

The only place that actually exists is right now. And I don’t want to miss it.

After Jennifer called me out about my trip down memory lane, I sat there for a while, just feeling it.

And then I decided to do something about it.

I picked up my phone and texted my friend Michael. “Dinner Monday night at Foxfire? Need to get out.” He responded in ten minutes. Done.

Then I started searching online for things happening this month here locally in the Hudson Valley. I found a murder mystery dinner in Rosendale and grabbed two tickets. I didn’t even ask Jennifer first. I just bought them because if I thought about it too long, I knew I’d talk myself out of it.

Then I texted a few old high school and college buddies about planning a trip next year. Not someday. Not when things calm down. A specific weekend with a specific location.

All in all, the whole thing took half an hour. And when I was done, I felt different. Not because I’d fixed anything or solved my time-traveling problem. But because, for half an hour, I was actually here in the moment. Working to make the present better instead of wishing it were different.

I’m trying to get better at noticing when my brain wants to escape. And when I catch it happening, I’m working on pulling myself back. I’ll ask myself, what’s actually good about right now? What can I do with this present moment instead of wishing it were different?

It’s not perfect. I still catch myself doing it. But I’m definitely getting better at recognizing the pattern.

I think a lot of people fall into this trap. We escape into memory when the present feels heavy. We escape into fantasy when memory doesn’t help.

And we call it nostalgia or ambition or reflection or planning. It doesn’t matter what we call it. We’re just avoiding being here and now.

But the past had its problems, too, and the future will have its own new set of problems. The only place we can actually live is here and now. And if we’re somewhere else in our heads, we’re missing it.

So here’s what I’m wondering this week: Do you ever catch yourself doing this? When the present feels hard, where does your brain escape to?

Leave a comment and tell me. I read every response.

I appreciate your time.

When the present feels hard, where does your brain escape to?

Leave a comment

If you enjoyed this read, the very best compliment I could receive would be for you to share it.

Share

Most people wait for courage to arrive before they take action. Jenny Wood teaches you to act first and let your courage catch up.

Jenny is a former Google executive turned New York Times bestselling author of Wild Courage: Go after what you want and get it.

In this workshop, she shares how to communicate with conviction, push past fear, and win more customers through bold, clear, and shameless self-promotion.

We covered:

• Why fear (not lack of skill or talent) is the biggest barrier to success

• The three traits that drive growth: reckless, brutal, and shameless

• How to use the Rule of Three + One to make confident recommendations

• The “Tame the Octopus” method for speaking clearly and avoiding rambling pitches

• The “Pull It and Bullet” framework for writing sharper, more persuasive emails

• How to reframe fear and self-doubt using the Truths and Tales exercise

• The mindset shift behind “wooing with you” to make your audience the hero

• How one word, yet, can completely change your self-belief

Jenny also shared the unforgettable story of her grandmother, Lila, an 88-year-old bridesmaid and fearless negotiator whose mantra, “No is just an opening offer,” captures the essence of wild courage.

If you’ve ever hesitated to raise your rates, pitch your dream client, or ask for what you want, this session will show you exactly how to do it anyway.

Cheers,
Justin

Subscribe now

Nearly everyone I know on social media is obsessed with numbers.

How many followers and subscribers do I have? What are my impressions like? Is engagement up or down? The digital scoreboard is one major marker of success nowadays.

Behind the scenes, there’s a much different story. I know entrepreneurs who’ve built massive followings but can’t seem to make any real money. Not only do they struggle to monetize, but even worse, they feel completely disconnected from the people they’re supposed to be serving.

Isn’t connection and community the big idea?

The allure of a big audience can be extremely intoxicating. It feels like validation. Like you’ve finally “made it.”

But reach isn’t the same as impact.

If you really dig deep into the online entrepreneurs who have built sustainable businesses, I suspect you’ll find something very different. It’s not about their audience size. It’s about their connection depth. They don’t have the biggest audiences; they have the most engaged ones.

This isn’t necessarily about small versus big. I know folks with big, engaged audiences. It’s more about superficial versus meaningful.

Width creates awareness, while depth creates transformation. And transformation is what people pay for.

We’ve all heard some version of the idea that “when you focus on reaching everyone, you often end up reaching no one.” It’s true. Your message becomes diluted, and you avoid saying anything too specific because you might alienate someone.

But that’s a recipe for losing your personality. Those specific opinions (often polarizing, edgy, or unique) are exactly what creates impact for the people who choose to read what you’re writing.

I know this because I’ve been on both sides of this equation. I’ve flip-flopped between bigger numbers and more eyeballs and writing simply because I had something incredibly impactful to share. My business reached a high point when I found the intersection of what I love to write about and what makes a massive impact on my readers.

So, instead of asking “How can I reach more people?” start asking “How can I matter more to the people I already reach?”

Send more meaningful emails to your existing subscribers instead of obsessing over growing your list. Have deeper conversations with current customers instead of chasing new ones. Create more impactful content for your community rather than optimizing for whatever silly change the algorithm has made that week.

When you go deep instead of wide, something really interesting happens. The people you serve become evangelists. They spread the word because you’ve created something that genuinely matters to them. Something that changed them.

You’ll be surprised to find out that’s how most real growth happens anyway. It’s not through clever marketing tactics. It’s from people who are impacted, sharing something with a friend or family member who will feel its impact as well.

The scoreboard lies.

Impact is the metric that matters.

Go deeper, not wider.

What’s your take on today’s article? Did it land? Miss the mark? Change your perspective?

Leave a comment

If you enjoyed this read, the best compliment I could receive would be if you shared it.

Share

Consider becoming a paid member if you’d like to attend our upcoming events or view our previous workshops from creators, entrepreneurs, CEOs, New York Times Bestselling Authors, makers, and more. You’ll also gain access to live bi-weekly Q&As and invitations to our members-only networking events worldwide.

Subscribe now

Subscribe now

It’s become wildly popular to tell people how grateful they should be.

If you tell someone that you feel stuck in your career, they’ll tell you that millions of people would kill for your job. If you admit your marriage feels empty, a friend might tell you to appreciate what you have. If you confess that your life feels small, randoms on the internet will convince you to start a gratitude journal.

Be grateful, focus on the good, and remember to count all of your blessings.

And if you’re still unhappy after all that gratitude? Well, that’s a you problem.

Unfortunately, I feel like gratitude is often weaponized against people who want more from their lives.

Gratitude is a feeling, not an obligation. It’s not a performance you’re supposed to put on to prove you’re not selfish or entitled or broken.

But, still, we perform.

We write in our journals every morning. We list three things with our partners before bed. We post about our blessings on social media and perform gratitude like it’s a personality trait that makes us better than everyone else.

But gratitude can become a cage.

When you’re told to be grateful for a job that’s killing you, gratitude keeps you trapped. When you’re reminded to appreciate a relationship that makes you lonely, gratitude prevents you from walking away. When people tell you to focus on what you have instead of what you want, gratitude becomes the reason you never change anything.

I spent the last two years of my corporate life writing gratitude lists every morning, even as my life was falling apart around me.

Grateful for the money, the title, and the respect that came with the position. I wrote down three things every single morning for over 700 days in a row.

And then I’d go to work and feel absolutely nothing. Just an overwhelming emptiness that no amount of journaling could fix.

Gratitude wasn’t making me happier. It was just making it easier to ignore that I was objectively unhappy.

Real gratitude doesn’t come from forcing yourself to appreciate things that make you miserable. It comes from contrast. From finally walking away from something that wasn’t working and running toward something that does.

I’m grateful now. Genuinely grateful for my life and work.

But I wasn’t when I was working 70-hour weeks. I was completely dissatisfied. And no amount of gratitude journaling was going to fix that. I needed to be dissatisfied enough to actually do something about it.

The people who are most grateful for their lives are often the ones who were willing to be completely, honestly ungrateful first.

They finally stopped pretending everything was fine and actually did something about it.

The same people who tell you to be grateful for your life and work are often the ones who’ve never actually taken a real risk. The folks preaching gratitude for your “comfortable situation” are usually the ones most afraid of change.

They need you to stay grateful because your dissatisfaction threatens their choices.

Maybe it’s time to stop performing for them.

And give yourself permission to be a bit ungrateful.

Today’s topic was an odd thought that occurred to me the other day. How did it land? Do you agree, disagree, or is there something I missed?

Leave a comment

If you enjoyed this read, the best compliment I could receive would be if you shared it.

Share

Join our private network of 950+ entrepreneurs who have access to the following upcoming events and previous workshops from 6 and 7-figure entrepreneurs, CEOs, multiple New York Times Bestselling Authors, creators, makers, and more. You’ll also gain access to live bi-weekly Q&As and invitations to members-only networking events worldwide.

Subscribe now

Most entrepreneurs overcomplicate business. Tim Stoddart built several seven-figure companies by keeping it painfully simple.

In this session, he shares The Machine Method. His framework for building a business that runs without you, one step at a time. Tim’s journey from carpenter to recovering addict to multi-business founder is proof that success comes from process, not genius.

We covered:

• The six “departments” every business needs and why three matter most at the start

• How to build your first $100K by mastering marketing, offers, and sales

• Why you should build an audience before building a product

• How to turn your skills into a high-ticket service that funds everything else

• The transition from service → program → product (and why that order works)

• Why vulnerability and simplicity are secret growth multipliers

• How to use a CRM from day one to turn relationships into revenue

• What Tim learned after selling his company and walking around a Denver lake for 40 days

If you want a repeatable playbook for building a calm, cash-flowing business, this one’s worth your full attention.

Cheers,

Justin