You've probably heard that Reid Hoffman quote: "If you're not embarrassed by the first version of your product, you've launched too late."
It's a good line. Smart. Punchy. Easy to repeat in pitch decks and dev standups. But here's the thing they don't tell you: it's one thing to say it, and it's another to live it.
Because shipping is terrifying. Still. Even now.
And I've been building things—apps, startups, tools, teams—for over 20 years.
The Lie of Experience
When I was younger, I assumed this fear would go away. That someday, after enough launches, the muscle would just be trained. I'd ship with swagger. No nerves. No second-guessing. Just smooth execution like an old jazz drummer laying down a groove.
But it's the same every time. I build something. I get 80% done. Then I start reworking the UI. Doubting the copy. Imagining edge cases no one will ever run into but that suddenly feel critical to solve before I release anything.
So I stall. I tweak. I get "really close" to done.
Then I loop. Rinse and repeat.
The Problem Isn't Readiness—It's Resistance
I used to think I was just a perfectionist. That I cared deeply about the product and didn't want to ship something that didn't reflect my taste.
But the truth is: it's not about taste. It's fear.
Fear of judgment. Fear of indifference. Fear of nobody caring—or worse, caring just enough to rip it apart.
There's a piece by Ira Glass called "The Gap" that explains this perfectly. He says that when you're starting out, you have good taste, but your skills haven't caught up yet. So everything you make feels like a letdown. That gap is painful. But the only way to close it is to make a lot of stuff and ship it—even when it sucks.
Thing is, nobody tells you that "the gap" doesn't completely go away.
Even now, I still feel like I'm underachieving compared to my taste. I know what good looks like. I just never feel like I hit it. And the closer I get, the more unbearable it feels to ship something that's just shy of great.
ADHD Makes It Worse
Layer in ADHD and it becomes even messier.
The ADHD brain doesn't reward consistency. It rewards novelty. It's not built for finishing. It's built for starting.
So I'll get this huge hit of dopamine when I start building a new app, or drafting some launch copy. I'll spend 2 weeks grinding like a maniac. Then—once the novelty fades—I'm left with the boring stuff. Polish. Copy tweaks. Analytics. Testing the password reset flow.
All the things that matter.
But my brain's already moved on to the next idea. So I stall. Not because I don't care. But because the dopamine's gone, and I can't find a reason to push through the resistance.
Shipping requires discomfort. ADHD runs from discomfort.
It's a bad combo.
Taste vs. Talent
Here's the other kicker. I'm actually good at what I do.
I've launched companies. Scaled apps. Hired and led teams. I can design, build, write, lead, and ship. People respect me. Clients trust me.
But that almost makes it worse. Because now I feel like I have more to lose.
There's this invisible expectation that if you're experienced, everything you release should be tight. Smooth. Polished. A reflection of your pedigree.
But that's not how creativity—or product dev—works.
You don't get to skip the ugly version just because you're senior now. You still have to ship version 1. And version 1 is usually a mess.
This Time, I Shipped Anyway
I just launched something last week.
It's an iPhone app. Social meets trivia meets in-person community. It's called Quii (pronounced "key"). And yeah, it's probably buggy. The onboarding flow isn't perfect. Some of the copy feels clunky. I already have a list of things I wish I'd done differently. It even shipped with a Trivia card-type that wasn't ready to be released, clearly.
It's fine. It's not perfect. But I shipped it.
Because if I didn't, I never would.
I would've rewritten the landing page 14 more times. Refactored the codebase. Spent another week picking font pairs.
And then someone else would've shipped something similar, and I'd be stuck with that quiet, familiar regret: "Yeah, I built something kind of like that once. Never launched it though."
The Takeaway
So yeah, shipping still scares me. But I've stopped waiting for the fear to go away.
I just ship scared now.
Because the fear doesn't mean I'm not ready. It just means I care. And I'd rather be someone who ships nervous than someone who builds perfect ghosts.
PS: If you've ever stalled on a launch, I'd love to hear about it. Drop a reply or shoot me a message. Let's normalize the mess.
And if you want to see what I shipped—bugs, weird UI and all—you can check it out here. Feedback welcome.
