Confidence

A few years ago, I was on a coaching call with a young entrepreneur who wanted to start a Fractional CFO business focused on startups.

She said she wanted to pick my brain about how I built mine.

At the time, I wasn’t doing much peer-to-peer consulting, but she was early in her journey and I figured I’d have plenty to offer.

So I said yes, and we booked the session.

Most of the call went smoothly.

I listened closely to her situation and offered plenty of ideas and advice.

But then she asked a question that caught me completely off guard:

"Where do you get your confidence?"

It shook me because I didn't know how to answer.

Because, if you think about it, this is a really weird question.

Because it implies:

• That confidence is something you have to earn before you’re allowed to feel it

• That it’s not obvious what I’d have to feel confident about

• That whatever “gave me” confidence might be passed along like a toolkit

And none of those things are true.

And it's also just not a useful way to think about it in this job.

When you’re a founder, you are constantly asked to lead without guarantees.

You make high-stakes decisions with incomplete data.

You set the direction before you know how things will turn out.

You say, “this is the way” without waiting for permission.

If you think you need to deserve confidence before doing those things, you’ll hold back.

You’ll play it safe.

You’ll second-guess every move.

And the truth is, you don’t need to.

Confidence is not conditional.

It's not a badge - it's just an emotion.

One that nearly all of us feel from time to time.

You don’t have to be perfect.

You don't have to be the best.

You don’t have to have a flawless record.

You don’t need a degree from the “right” school or a certain number of years in the seat.

You are just allowed to feel confident.

At any time.

Without proof. Without polish. Without permission.

So where do I get my confidence?

I don’t always feel it. But when I do,

I get it from letting myself feel it.

From enjoying it.

And if you want to feel it more often?

Try things. Fail. Survive.

That helps too.



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