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Why do I still feel like an impostor, even when things are going well?

By Craig Leslie ·

Hayden runs a business that his clients are happy with. But he still worries that one wrong decision could show he's not good enough.

What's interesting is that he also thinks some of that same doubt helped him build the business.

So when does doubting yourself help you make better decisions, and when does it start getting in your way?

Discover

When Hayden first explored starting a data privacy business, the idea was to build software.

But after speaking to potential customers, he realised they needed something different. They needed people who could help them solve the problem, not just software.

So the business changed direction.

Looking back, Hayden thinks his habit of questioning himself actually helped.

He was worried about moving from being an employee to running a business that people would pay for. He wanted to get things right. That made him listen carefully to what customers needed rather than rush ahead with his first idea.

But there's another side to that doubt.

Even though the business has done well and clients are happy, Hayden still feels like an impostor.

He worries about small, everyday decisions. Sometimes he feels that one mistake could bring everything down, or prove he isn't good enough to do the work.

Over time, he's learnt to focus more on the decisions that really matter.

He looks back at choices he's made. What worked? What didn't? Which decisions actually made a difference?

He also talks openly about his worries with his wife, who runs the business with him. He says that trust helps them work through things together.

His doubts haven't disappeared. But he's learning how to deal with them.

Understand

There's something interesting about Hayden's experience.

Doubting yourself can lead to two very different questions.

The first is: Am I making the right decision?

That can be useful.

It can make you stop, think, listen to other people and change your mind when you need to.

That's what Hayden believes happened when he first started his business.

But there's another question.

If I make the wrong decision, does that mean I'm not good enough?

That's different.

Now you're not just worried about the decision. You're worried about what getting it wrong might say about you.

And that's what makes Hayden's experience worth thinking about.

He knows his business is doing well. But he still worries that his next mistake could prove he isn't capable.

The interesting difference isn't simply whether you doubt yourself.

It's what your doubt is making you question.

Are you questioning the decision because there's something important you need to think about?

Or are you questioning whether you're good enough to make it?

This is one way of understanding what Hayden described, not a rule that applies to everyone.

Apply

Think about a decision you're worried about making.

It could be something at work, a responsibility you've taken on or a conversation you've been putting off.

Ask yourself:

What do I actually need to know to make this decision?

Then ask:

Am I also worried about what getting it wrong would say about me?

Those are two different things.

The first question can help you work out what you need to do.

The second might help you understand why the decision feels so difficult.

You could also try something Hayden does.

Look back at decisions you've already made.

Which ones really mattered?

Which ones took up a lot of your time but didn't change much?

You don't have to feel completely confident before making a decision.

Sometimes the useful thing is simply to understand what you're worried about, and whether that worry is helping you make a better choice.

In their words

"the small daily decisions"

Hayden, at 00:10:30 in the episode

"identify the levers that are going to actually make a difference"

Hayden, at 00:12:35 in the episode

"when I made a decision on what counted, it moved forward."

Hayden, at 00:14:13 in the episode