The Success Trap

Why Your Biggest Achievements Are Making You Miserable

I see it all the time in my coaching practice. A woman comes to me after hitting every milestone she set for herself. She's built the business. Landed the clients. Made the revenue. And she's absolutely miserable.

"I should be happy," she tells me. "I have everything I said I wanted. So why do I feel like this?"

Here's what I've learned after years of working with successful women: The same drive that builds extraordinary businesses can become a prison of perpetual inadequacy.

The data backs this up. Research shows that CEOs are more than twice as likely to struggle with depression as the general population. Over half of business leaders report mental health challenges. For women specifically, the numbers are even more troubling.

But here's what the statistics don't tell you: the why behind the struggle. And more importantly, what you can actually do about it.

The Moving Finish Line

Think back to when you started your business. Remember what success looked like then?

Maybe it was landing your first paying client. Or hitting £5K months. Or finally being able to pay yourself a salary.

Now you're doing all of that and more. But somewhere along the way, the finish line moved. Success became £10k pm. Then £20k pm, then £50k pm The goalpost keeps shifting, and you keep running.

This is what I call the ‘success trap’. You achieve something incredible, and instead of celebrating, you immediately redirect your focus to what's missing. What you haven't done yet. Where you're falling short.

You've trained yourself to only see the distance between where you are and where you think you should be. And that distance? It feels like failure.

Why High Achievers Struggle

The traits that make you successful are actually the same ones that make you vulnerable:

Your perfectionism drove you to build something exceptional. It also means nothing you do ever feels good enough.

Your high standards pushed you past obstacles others gave up on. They also set an impossible bar that leaves you constantly disappointed in yourself.

Your relentless drive helped you build a business from nothing. It also means you can't let yourself rest, celebrate, or feel satisfied.

Your ability to envision bigger possibilities creates innovation and growth. It also means the present moment never feels like enough.

These aren't character flaws. They're superpowers. But like any superpower, they can turn destructive when misdirected.

The Hidden Cost

When you're trapped in this cycle, the cost compounds:

You lose the ability to feel joy in your accomplishments. Every win becomes immediately meaningless because you're already focused on the next thing.

You develop chronic anxiety. There's always something you should be doing, should have done, should be doing better.

You struggle with impostor syndrome. No matter what you achieve, it never feels like proof that you're actually capable. You just got lucky. Or worked harder. Or fooled people.

You burn out. Not from working too hard, but from never letting yourself win.

And here's the cruel irony: you built this business for freedom, flexibility, and fulfillment. Instead, you've created a prison where you're both the warden and the inmate.

The Way Out

The solution isn't to lower your standards or stop striving. You didn't build what you've built by settling, and I'm not going to ask you to start now.

The shift is simpler than that. And harder.

You need to change what you measure yourself against.

Right now, you're measuring yourself against an ideal version of success that doesn't exist. It's a moving target. By definition, you can never reach it because as soon as you get close, it shifts.

Instead, measure yourself against where you started. Against who you were six months ago. A year ago. Three years ago.

Look at what you've learned. What you've overcome. What you've built. What you've become.

This isn't toxic positivity or pretending everything is perfect. It's acknowledging reality. The actual distance you've traveled, not the imaginary distance to some impossible ideal.

What This Looks Like in Practice

When a client tells me she's frustrated because she "only" hit £10K this month when her goal was £15K, I ask her: What were you making a year ago?

Usually, it was £3K. Or zero. Or she was still in a full-time job dreaming about entrepreneurship.

That £10K month isn't a failure. It's extraordinary growth. But she can't see it because she's measuring against the £15K that didn't happen instead of the £0 she started from.

Same with the woman who's beating herself up over losing a client. Yes, it stings. But can she see that two years ago, she didn't have any clients to lose? That she's built a business people actually pay for? That she's learned how to navigate difficult conversations and setbacks?

Or the entrepreneur who's stressed about not having her systems perfected. Okay. But does she remember when she had no systems at all? When she was figuring out invoicing on the fly and forgetting to follow up with leads?

The growth is real. The progress is real. But you can't see it when you're only looking forward at what's missing.

Three Practices That Change Everything:

1) End your day with three wins.

Not three things that went perfectly. Three things that represent progress. A difficult email you sent. A decision you made. A boundary you held. Train your brain to notice movement, not just outcomes.

2) When you catch yourself spiraling about what you haven't done, pause.

Ask yourself: What's the comparison I'm making right now? Am I measuring against an imaginary ideal or against my actual starting point? Then consciously choose to redirect. What have I actually accomplished? What's different now than it was before?

3) Celebrate before you pivot.

When you hit a goal, let yourself actually feel it before immediately setting the next target. Take a full breath. Acknowledge what you did. Tell someone. Do something to mark the moment. This isn't about stopping your momentum. It's about building sustainable momentum instead of running on fumes.

The Deeper Work

Here's what I know from working with many female business owners:

The external success is rarely the problem. The revenue, the growth, the achievements, those are often exactly what you set out to create.

The problem is the internal measurement system that makes it impossible to actually enjoy what you've built.

You don't need to achieve more to feel better. You need to change how you're evaluating what you've already achieved.

Because you need to remember that you're not failing or falling short and you're not behind.

You've come an extraordinary distance. You've overcome obstacles that would have stopped most people. You've built something from nothing. You've learned and grown and become someone you couldn't have imagined when you started.

But you'll never see that if you're only measuring against the impossible.

The Choice

You can keep chasing the moving finish line. You can keep measuring yourself against an ideal that will always be out of reach. You can keep believing that the next achievement will finally be the one that makes you feel successful.

Or you can choose a different metric. One that acknowledges reality. One that lets you see… really see, how far you've come.

This isn't about settling. It's about sustainable success. Success that doesn't destroy you in the pursuit of it.

Because what's the point of building the business if you can't actually feel the victory of having built it?

The finish line will always move. That's not going to change. But you can stop letting it define your worth.

Look back. See how far you've come. And let yourself feel it.

You've earned that.