This week’s episode is about decision-making and how to know what’s actually worth it when you work for yourself.

We recorded this right after speaking at a conference in Jamaica where we walked through some of our own real-life crossroads as business owners with a group of entrepreneurs. The talk resonated so deeply, the only feedback we got was: “Can you just put this all on one page?”

This is our answer to that.

We’re talking about those high-stakes, low-certainty moments every entrepreneur, side hustler, or freelancer has to face eventually like what to sell, when to say yes, how to price your work, when to hire help, whether to spend or play it safe. And, maybe most importantly, how to move when the pressure’s on and the money feels tight (or even when it’s flowing).

We get into:

Why emotional decisions are so expensive
What Annie Duke’s poker strategy has to do with entrepreneurship
The $500 mistake we made early on that cost us double
How to protect yourself from thinking too small without blowing your budget
And the biggest difference between people who survive in business and people who burn out early

Whether you’re self-employed, freelancing, or bootstrapping something new, your decision-making process should match the size of what you’re trying to build. If you’ve ever felt like your goals were too big or your fears were too loud… this one’s for you.

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