When I Chased Money, It Ran. When I Chased My Craft, Everything Changed.

Nov 16, 2025

There was a five-year stretch of my life that felt like I was drowning in presentation decks and investment calls. My creative instincts were shelved, my energy drained into pitch decks and investor meetings, and my home life was unraveling in ways that were way too big to ignore. I wasn’t building anything—I was surviving. Barely.

The Chase That Broke Me

Here’s the reality: when you're desperate for money as a creative and that's the thing you're chasing—money runs the other way. You start second-guessing yourself. You jump lanes, trying to be someone you’re not. You shelf your best ideas and start contorting yourself into whatever shape you think will unlock funding. It doesn’t work.

What happens next? You start to look desperate. You lose the small wins that fuel your momentum. No dopamine hits. Just a string of dry, soul-sucking days. People feel that. Even if you think you’re hiding it. It repels the exact opportunities you're trying to attract.

That was me. I thought I was being strategic. In reality, I was just drifting further from the stuff that made me valuable in the first place.

The Cost of Shelving Your Creativity

My last startup became a cautionary tale. I tried to play the traditional CEO game—raise capital, push the product, manage the optics. All while burying the parts of me that had built everything up to that point. The creativity. The curiosity. The spark.

Meanwhile, the financial pressure was relentless. My home life was a disaster—my kids were going through some truly awful stuff. And me? I was fried. Depressed. Burnt out. I wasn’t leading—I was barely showing up. My face showed it too: those deep frown lines that basically moved in full-time between my eyebrows.

Enter the Sherpa: Kirk Westwood

At one of my lowest points, my old business partner Jeff connected me with a guy named Kirk Westwood. Kirk’s like a work/life sherpa—a guy who shows up when you’re lost in the fog and hands you a flashlight.

We did a session together, and it landed like a gut punch. He looked at me and just saw it. The stress. The burnout. The internal tug-of-war. He told me straight up:

"Your left brain’s gasping for air, and your right brain’s trying to take the wheel just to keep you alive."

Yep. Nailed it.

Rewiring My Voice, My Circle, and My Mindset

Kirk and Jeff didn’t just point me in a direction—they helped me change how I talk to myself and the world. I stopped undermining my ideas. I cut the self-deprecating humor that had become a weird safety blanket. I started leading with what lights me up, not what I thought would sound safe or smart or fundable.

Post-COVID, I had a narrow social circle—and like a lot of people, I stopped doing external meetings and kind of defaulted to being a homebody. But I had to force myself to start getting out again. To connect. To re-engage with people and energy that actually lit something up in me. That shift wasn’t automatic, but it made a massive difference.

The Advice That Realigned Everything

Kirk left me with this piece of advice that still rings in my ears:

"Focus on what you love to do, what you’re great at—and the right opportunities will come find you."

And he was right. Once I started doing that—getting back into creative flow, trusting my gut, chasing ideas that felt like me—the shift was real. The spark came back. The energy. The right people started showing up. Not overnight. But consistently.

It’s Still Work—But It’s the Right Kind

Let’s be real—it still takes work to stay out of that rut. It’s easy to fall back into the old habits. It takes discipline, effort, and daily intention to keep choosing the path that aligns with your creative core.

But here’s the thing: it’s the right kind of work. The kind that actually gives you energy instead of draining it. The mojo’s coming back. The wins are stacking. And I’m showing up as me again—not the exhausted, filtered version built for someone else's expectations.

So if you’re a creative founder who's stuck, here’s my unsolicited advice:

Step back. Reset your voice. Reconnect with what makes you special. Let go of the chase. The opportunities will come—but only when you're finally showing up as yourself.

More From This ADHD Circus Tent

If this story made you nod, laugh, or aggressively point at your screen like “yes, that’s me”—you might like a few of these other brain-scrambled adventures from the creative trenches. Same flavor, same chaos, maybe even a duck metaphor or two.

Late-Night Hustle, Morning Regret:
The Hidden Cost of Working Like a Firestarter
The ND Team That Saved My Agency Bacon Again and Again