Chronically Automated - Episode #21 Why “Burning It Down” Might Be the Smartest Move You’ve Ever Made

This episode might be one of my favorite conversations yet, because we dive headfirst into something every entrepreneur has dealt with: building something amazing, only to want to burn it all down three months later. Sound familiar? Yeah. You’re not alone. I’ve done it. Anthony’s done it. You’ve probably done it too. But here’s the thing, I don’t think that’s sabotage. I think that’s evolution.

I kick things off with a hilarious (and strangely relevant) story about my youngest son becoming the number one ranked professional air hockey player in Wisconsin. Yup. That’s a thing. And while it started off as just a funny mom moment, it quickly turned into a metaphor for entrepreneurship: you can turn anything into a money-making opportunity if you love it enough. But... it might not pay the bills. Passion projects are beautiful, but not everything we love will feed us, and that’s okay. You still need them. They’re fuel.

Then, Anthony and I get into the nitty gritty of what it really means to "burn it all down." The truth is, sometimes starting over is not sabotage. It’s a pivot. It’s iteration. It’s reinvention. If you’re like me, and you need stimulation and momentum to stay motivated, blowing things up might not be destruction. It might be clarity in motion.

We also get real about timelines. How long do you let something sit before you decide it’s not working? 30 days? 90 days? A year? And what if the thing that feels like a failure was just ahead of its time? I share my experience with “Neighborbee,” and how shutting it down wasn’t a failure, it just wasn’t the right time or built the right way. But the idea? Still fire. Still necessary. Still coming back.

This is the episode for you if you’ve ever second-guessed blowing up your business, questioned your need to change direction, or felt like maybe your pattern of reinvention was just self-sabotage. Spoiler: it’s probably not.

We talk dopamine, creative energy, how some of us need newness to stay engaged, and why the messiness of entrepreneurship is where the real magic lives.

If you’ve ever felt like you were the only one who kept wanting to throw the match on your own worK, you’re going to feel very seen in this one.