Not long ago, I found myself deep in something new — again. We’re building a people-first private equity firm, and while I know how to scale companies, build teams, and create clarity — this is a different world.

Financial modeling.

Capital structures.

Investment lingo I’ve never heard before.

Rules that seem to be passed down over drinks instead of books.

There’s no onboarding guide for this.

And just like so many other times in my life — I had that moment:

“What have I done?”

But this isn’t new for me. When I was managing failing projects with unfamiliar tech stacks, I felt the same way. When I stepped into leadership roles I didn’t feel fully “qualified” for yet — same. And every single time, the same thing happens:

I figure it out.

Step by step.

Call by call.

Mistake by mistake.

Win by win.

It never feels linear.

But momentum builds.

And confidence follows.

You Don’t Need Confidence to Start — Just Belief in Your Ability to Figure Things Out

The biggest myth about founders and leaders is that we always know what we’re doing.

Most of the time? We’re just willing to figure it out faster than most people. That willingness — that resilience — is what creates the real confidence over time.

Stuck in the “What Have I Done?” Phase?

1. Ask Better Questions

Don’t pretend you know — just ask. Most people are willing to share ideas and experiences. They enjoy being the expert (don’t we all?). It doesn’t look stupid to ask questions – it looks like curiosity.

2. Get to Know the People in the Room

Sometimes the confidence gap isn’t about knowledge — it’s about connection. Build relationships. Ask how they learned. Most will tell you.

3.  Follow the Experts

Find the people who’ve done it. Not the loudest, but the ones with real experience. Follow their content, study their frameworks, reach out when it makes sense.

4. Learn Just Enough to Take the Next Step

You don’t need to know everything. You just need enough to move forward. Clarity comes after motion — not before. I love Jim Collins’ “shoot bullet holes and then cannon balls.” Try new things on a small scale and validate your direction. Then you can move in that direction with more gusto!

5. Reflect on What You’ve Already Figured Out

Confidence builds when you look back at what you once thought was impossible… and realize you handled it. Do this regularly. It’s fuel.

If you’re sitting in the “what have I done?” phase right now, you’re not doing it wrong. You’re in the beginning of something that matters. You don’t need to be confident. You just need to be committed.

And as Marie Forleo says — “Everything is figureoutable.”

Want support while you figure out what’s next — or how to scale what you’ve started?

That’s what we do.

Let’s talk.