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.

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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?"

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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.

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

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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.

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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.

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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.

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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.

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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.

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And if you want to feel it more often?

Try things. Fail. Survive.

That helps too.



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