Do It Anyways

Three words that built every startup, survived every failure, and got me through every 2AM decision

You’ve been waiting for the right time.

The right time to start that side project. To have that hard conversation with your manager. To finally take the leap on the idea you’ve been sketching in your notes app for months. You’re waiting for the calendar to clear, the savings to hit a number, the kids to get a little older, the market to stabilize.

Here’s the truth: the right time doesn’t exist. It never has. And every week you spend waiting is a week someone less qualified, less prepared, and less talented than you is out there building the thing you keep postponing.

The only people who build anything meaningful are the ones who start before they’re ready.

Do it anyways. Three words. That’s the entire operating system.

The Engineer’s Trap

You know why this hits engineers harder than anyone? We’re trained to optimize. We design systems for reliability. We refactor before shipping. We wait for the right architecture, the right stack, the right abstraction.

That instinct is brilliant for code. It’s devastating for life.

Because life doesn’t have a staging environment. There’s no dry run for starting a company, no rollback for the years you spent thinking about it instead of doing it. The optimization mindset that makes you a great engineer is the same mindset that keeps you stuck in a loop of “not yet.”

You’re not being careful. You’re being comfortable. And comfortable doesn’t build anything.

What “Anyways” Actually Looks Like

2021. I had a toddler, a newborn, an Executive MBA program at Quantic, and a full-time engineering leadership role at Criteo. My co-founder called and said, “Let’s build this.”

Every logical bone in my body said wait. The timing was objectively terrible.

I did it anyways.

We bootstrapped with personal capital, hired 5 developers on day one, made every first-time founder mistake in the book. By month three we’d scaled down to 2 developers and rebuilt from scratch around what customers actually needed. In roughly 18 months, we hit a seven-figure annual run rate. Eventually acquired.

But here’s the part people don’t talk about. That wasn’t a single moment of courage. It was a decision I had to make again every single morning. Ship the feature when you’re exhausted. Take the customer call at midnight. Choose the startup over sleep, over rest, over the easy path.

Do it anyways isn’t a one-time act. It’s a repeating operating principle.

The Pattern That Keeps Showing Up

That same principle followed me everywhere.

When my current startup needed to pivot, not once, not twice, but three times in six months, from an AI journal to a home collaboration tool to an AI calendar, every pivot meant admitting the previous version wasn’t working. Every pivot felt like starting over.

I did it anyways. Each time.

The people who build things aren’t braver than you. They’re not smarter, more connected, or more ready. They just decided that feeling uncertain doesn’t get a vote.

The Cost Is Real

I’m not going to romanticize this.

The TinyWhale years were brutal. I missed moments with my kids. I skipped dinners. I asked my family to carry weight they didn’t sign up for. The sacrifice wasn’t theoretical. It was bedtimes I wasn’t there for and weekends that disappeared into Slack threads.

If someone tells you this path is painless, they’re lying to you.

But here’s what I know: the alternative is worse. Not because waiting is lazy. Because waiting while knowing you should act is its own kind of suffering. It’s slow, it’s quiet, and it accumulates. That voice in the back of your head asking what if I had just started? never goes away.

The cost of action is real. The cost of inaction is invisible, but it compounds.

This Isn’t Hustle Culture

Let me be clear: “do it anyways” is not “grind until you break.” That’s a different conversation, and a toxic one.

This is about agency. The ability to decouple action from feeling.

You will feel scared. You will feel unprepared. You will look at your calendar, your bank account, your responsibilities, and think this is not the time.

Feel all of it. Then do it anyways.

Not because feelings don’t matter. Because feelings are terrible project managers. They’ll always find a reason to delay. They’ll always flag a risk that hasn’t materialized. They’ll always recommend waiting for more data.

You don’t need more data. You need a first commit.

The Question You Already Know the Answer To

What’s the thing you’ve been telling yourself you’ll start “when the time is right”?

The startup. The side project. The conversation. The career move. The thing that lives in your notes app, your late-night browser tabs, the shower thoughts you never act on.

You already know what it is.

The timing will never be perfect. The conditions will never align. The risk will never fully disappear.

Do it anyways.