September 16, 2025

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Let’s play entrepreneurship bingo. 

I’ll list activities. If you do them, you check it off.

Close to a bingo?

If so, this one’s for you.

I totally get why and how this kind of thing happens. It happens because you care. But caring doesn't make it sustainable.

It’s the entrepreneurial equivalent of deciding to sprint “the rest” of the race, without knowing how much distance you have left.

Whether you feel it or not yet, you’re on the road to burnout.

In this newsletter:

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Weekly Insight

In 2017, Justin Jackson was living the entrepreneurial dream. Sort of.

He was running consulting gigs, selling online courses through MegaMaker, blogging, podcasting, and juggling multiple side projects. From the outside, it looked like he was crushing it.

On the inside, he was crumbling.

Some weeks, Jackson could barely manage 5 hours of work. Depression hit him so hard that the always-on lifestyle he'd built to drive his success was now threatening to end it entirely.

That's when he realized something sobering: when you crash as a solopreneur, there's no one there to keep things going.

Instead of doubling down on the grind, Jackson put himself first. He decided he needed boundaries more than he needed hustle.

Some entrepreneurs, like Marie Poulin, lean on systems.

Others, like Jackson, lean on people.

First, he found a co-founder. Jon Buda became the person he could lean on “when times get tough.” AKA, most of the time when you’re an entrepreneur.

Together, they started Transistor.fm in early 2018 with two explicit goals: 

To achieve number 2, without sacrificing number 1, they designed for what Jackson calls “margin.”

Of course, this just sounds like what every (reasonable) person wants.

The key, however, is how it’s put into practice.

Jackson and Buda turned down big clients when servicing them meant sacrificing product quality or their sanity. 

They hired slowly, and only when absolutely necessary. 

They stayed bootstrapped, maintaining complete control over their values and business ethos.

When hearing about people that do this, my old brain would automatically assume they’re content staying small.

Yet Transistor now hosts 30,000+ podcasts, serves 7,500+ paying customers, and generates around $375k monthly.

Jackson put it perfectly: “It is possible to make money, enjoy your life, and be around your kids.”

You just have to be intentional with your boundaries.

​​📚 Related Reading

Intent to Action

Saying yes to everything feels like it should be the path to success. And, to be fair, there’s definitely something to be said about increasing the surface area of opportunity.

But you don’t get there by blindly saying yes. Try that, and all you’ll get is burnt out.

Instead, try it from the other side: come up with a “Hell No” list.

Come up with 3 types of clients, projects, or opportunities you'll automatically reject, even if they pay well. Not because you're “too good” for them, but because they don’t serve you.

Think about it: 

Write those down. Be specific.

Maybe it's clients who expect you to be available 24/7. Or projects with impossible timelines. Or people who nickel-and-dime every invoice.

Once you have your list, put it somewhere you'll actually see it. I keep mine saved on a note in my phone. Sounds silly, but when a “great opportunity” comes up that hits one of my criteria, I don't have to debate it internally. I just whip out my phone, look at it, and It's already decided.

The next time something comes up that triggers your list, practice saying: “Thanks for thinking of me, but this isn't a good fit right now.”

No long explanations or apologies. Just a clean no.

Here's the thing: every yes to the wrong opportunity is a no to the right one. And when you stop saying yes to everything, you create space for the work that moves your business forward, and brings you closer to your dream life.

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