The trap of being good at something

Why we stay in lives we've outgrown

I was made redundant last month.

This prospect often conjures panic, especially in a culture that ties what we do with who we are.

But in my case, it came with an odd sense of relief.

Not because I had a back-up plan. Or a startup idea. Or I'm secretly a Bezos.

As I wrote in a previous newsletter, deep down, I'd known for a while that I was starting to want something different.

It had been a great chapter, one that I was proud of, but somewhere along the way, I started to feel a quiet nudge that it might be time for something new.

But I stayed.

Because I was good at it. I knew the systems. I knew the lingo. I was respected, relied upon, well paid. I'd even won a few awards.

And that's where it gets tricky.

When you're good at something, you have every reason to keep doing it.

I kept telling myself the same thing many of us do: "This isn't that bad."

And I wasn't wrong. But "not that bad" isn't the same as right. Mastery alone isn’t fulfilment. Progress isn’t always growth. And just because you can do something, doesn’t mean you should.

The number one regret in Bronnie Ware's Top Five Regrets of the Dying is:

"I wish I'd had the courage to live a life true to myself, not the life others expected of me"

Most of us hear that and nod solemnly, like it's a lovely quote to put on a tote bag.

But it's not a quote. It's a warning.

A warning that often goes unheard because it's so easy to justify staying when things work just enough to keep going.

Take it from me — the guy who didn’t heroically walk away. Who needed redundancy to push him when he wasn’t quite ready to push himself.

Because we're hardwired to preserve what we've built. Even if it no longer serves us.

This is what's known as the sunk cost fallacy — the idea that you should stick with something because of how much time, effort, or identity you've already invested.

Chris Williamson, host of the Modern Wisdom podcast, puts it perfectly:

“Staying in a job you hate because you’ve worked there for ten years is like finishing a bad movie because you’ve already sat through an hour. You’re not reclaiming the investment. You’re compounding the loss.”

And it's not just about jobs.

It's about relationships. Routines. Social circles. The city you live in. The version of yourself you’ve curated to make you interesting at parties or desirable on a dance floor.

We contort ourselves into likeable, impressive, acceptable versions of who we think we're supposed to be.

And the better we are at it, the easier it is to forget we're performing at all.

I've spent years being good at things I didn't actually enjoy.

Being a “safe pair of hands” in roles I didn’t want to keep. Being the version of myself that wouldn’t rock the boat. A quieter, smilier, more polished version of me who could blend in, nod along, and keep everything nice.

You don't notice it at first, that slow erosion of self. Because it doesn't feel like a crisis.

But just like the frog in a pot of water, the trap of being good at something is that it buys you just enough success to keep you stuck.

You're not miserable. You're just fine.

And to be fair, you are fine. But you're also slowly dying of boredom, resentment, and unexpressed parts of yourself.

But hey — at least you're comfortable.

Here's the uncomfortable truth I've been sitting with:

You don't just wake up one day living a life that doesn't feel like yours.

You build it. Brick by brick.

With every "Sure, I'll come" when you wanted to stay home. Every "It's not that bad" when you knew it wasn't good enough. Every silent trade off you make to keep the peace.

I think that's what Bronnie's patients meant in their deathbed whispers.

It's not about rebellion. Or burning it all down. Or quitting your job to sell tote bags in Tulum.

It's about noticing when you're settling. Where you're staying out of habit, not alignment.

And asking yourself:

If no one was watching, would I still choose this?

If the answer is no, you don't need permission. You just need a push.

Sometimes, we have the courage to push ourselves.

And other times it might come from somewhere else. A redundancy, a break-up, an end of lease notice.

Or one person to tell you that you're not crazy for wanting more.

So let this be that.

You're not crazy. You're not selfish. And you're definitely not stuck.

You're just really good at being who the world wanted you to be.

Maybe it's time to start being who you are.