“Everything you’ve ever let go of has claw marks on it.”
David Foster Wallace
I still open spreadsheets like they’re haunted.
Every cell looks calm, but I know that’s how they get you.
It usually starts with a cheerful Google Sheet—too many colors, too many tabs. I open it telling myself I’m looking for insight, but mostly I’m just looking for reassurance. That the math and I are still on the same team.
Most days, we are. But it’s a fragile truce.
I’m not bad at math in the general sense. I can split a dinner bill, I can estimate a tip. I’ve just never been emotionally stable enough for marketing math. Because marketing math doesn’t want to be solved—it wants to be interpreted. It’s like jazz, but with decimals.
And every so often, I find myself staring at the numbers like they’re hiding something from me. And maybe they are.
The math was never the math
It’s never really the numbers that get to me. The math isn’t out to get me—it’s just sitting there, minding its own business, being math. The problem is me. Because every time I don’t instantly understand something, a little voice in my head stands up and says, “You should’ve mastered this by now.”
That voice sounds suspiciously like the version of me who used to be the master of everything—the guy who designed half the product, sketched the other half, wrote the copy, ran the demos, worked the booth, and yes, even designed the booth. If something needed polish, clarity, or whatever final touch would make it look like we totally meant to do it that way, it somehow ended up on my desk.
And that made sense in that season of life. We were a small team trying to build something that mattered, and everyone wore more hats than any one person should. When you’re building something from scratch, “I’ll just do it” feels like both leadership and love. You’re not thinking about scalability or job descriptions—you’re just trying to get through Friday without the wheels coming off.
But that wiring doesn’t carry over neatly into a company big enough that I’m not in every room anymore. Suddenly, there’s a structure—teams, roles, reporting lines— and you can’t just swoop in and fix something because you feel like it. What used to look like commitment starts to look like control. And if you’re not careful, the habits that once built the company start quietly holding it back.
Old wiring, new world
Right now, I’m in this weird in-between place—trying to lead at a higher level while still fighting the urge to jump in and do the work myself. And if I’m being honest, I still do it. A lot.
I tell myself it’s helping. I tweak the copy, rebuild the slide, dig into the funnel metrics because I “want to understand them better.” On paper, it looks like commitment. But most days, it’s really just insecurity dressed up as effort.
Because every time I step in, I get that same old rush—that little hit of “See? I can still do this”. It feels good. It works. Until it doesn’t. Because the truth is, I have incredible people around me. They’re smarter than me in all the right ways. They know the math, the models, the machinery.
And still, some part of me feels like I need to master it all—not to control it, but to earn my seat at the table. To prove that I belong in every conversation.
That’s the trap.
It’s not that I don’t trust my team—I do. I’m just still learning to trust that my worth holds up when I’m not the one doing.
I can feel that tension in real time: between letting go and wanting to be the hero, between empowering others and quietly keeping the cape within reach.
It’s an exhausting place to live—half in leadership, half in logistics. And I know it can’t last forever. Something has to give: the pace, the habit, or me.
Unlearning myself
Lately, I’ve been trying to sit with the discomfort instead of outrun it. To let the math be math, the team be brilliant, and myself be… unfinished. It’s harder than it sounds. There’s something deeply uncomfortable about realizing that your greatest strength—the ability to “figure it all out”—might be the very thing you need to stop doing.
But I’m starting to see that leadership isn’t a promotion from doing the work. It’s a completely different kind of work. It’s choosing clarity over control, and trust over certainty. It’s letting people find their own rhythm, even when your hands itch to take the wheel.
And sometimes, it’s just sitting quietly while someone walks you through the numbers, reminding yourself that mastery isn’t the goal anymore—multiplication is.
I don’t have it figured out yet. Most days, I still feel that pull to prove. But on the good days—the ones where I actually lead instead of perform—it feels like breathing again. Like maybe the point isn’t to be the hero after all.
Maybe it’s to build a world where you don’t have to be.
