What Actually Is Success, Anyway?
(And why high achievers often don’t experience theirs)
Success. It’s something we all want, right? And something that, on paper, many of my coaching clients have in spades.
I’ve had it myself. People comment on my achievements now and, honestly? I feel a bit disconnected from them most of the time. Sometimes it feels like it all happened to someone else.
I tend to downplay things – “right place, right time” – but the truth is, I’d probably dissociated so hard in my last life that I didn’t even notice I was being extraordinary.
Why? Because so much of what I achieved wasn’t really planned. I was swept away in a tide that wasn’t rooted in any strong sense of identity or purpose – constantly half-killing myself to prove I was ‘good enough’ at a load of stuff I didn’t actually care about.
The goals were often set by others: hit that target, win that client, grow here, go there. My business KPIs started to feel more and more meaningless. And before I knew it, I was busy building a business I had no interest in leading.
It was like an out-of-body experience.
But I don’t think I’m alone in this.
We all know people who’ve built impressive businesses, raised investment, led teams, sat on boards. From the outside? They’ve made it. We’ve made it.
And yet, I keep hearing the same things crop up:
“Why don’t I feel how I thought I’d feel?” “Is this really it?” “I feel stuck.” “It was luck – anyone could’ve done it.” “I’ll be happy when I have XYZ…”
And then, lo and behold, XYZ comes – and it still doesn’t feel good. Then it’s just: on to the next thing.
This isn’t about failure. It’s not even about burnout. It’s about never really stopping to define what success actually means – for you, your business, your team, and those around you.
Because how can anyone enjoy getting to a destination they never chose in the first place?
Spoiler alert – success metrics built on “shoulds” are never going to feel great.
Should Success vs. Self-Defined Success
I thought that to be successful, I should grow my business in headcount. When I “failed” at that, I was devastated. I ended up selling out in desperation because I thought I was failing.
In fact, I wasn’t.
In my early thirties, I had built a company from nothing to a multi-million-pound valuation in four years – with a headcount of two and a whopping EBITDA. My brand, reputation, client list and me were worth more than the original business plan ever imagined.
So why did I feel like I’d failed?
Because I was looking at the wrong thing. I thought my success had to look like everyone else’s: build a business, hire people, sell it.
But I didn’t need to do that. I could’ve skipped the middle step – and possibly even the last step. I was making more money than I ever had (or likely will again) and I was working in my zone of genius!
If I’d paused long enough to define success for me, I would’ve seen the value I’d created. I could’ve saved a lot of heartache – and actually been proud of what I’d built.
I didn’t do that. (Although, now I’m glad I didn’t – because right now I’m where I’m meant to be.)
So the outcome was commercially successful – but in my head, I’d failed. All because I was using the wrong measures.
A simple reframe at the start would have made all the difference.
This Is Why It Matters
This is why being deliberate about what success means for you is so important. Not just to help you achieve it – but to stop you from making yourself miserable in the process.
Success Amnesia
Some of us especially those of us with spicy brains are prone to what I call success amnesia.
The moment we hit a goal, it evaporates. We’ve already moved on. We forget to pause, reflect, or even notice we’ve done something big. The sense of progress just… disappears.
I see this all the time in founders, execs, and high-performing leaders. The pace is fast, the stakes feel high – and it’s so easy to confuse motion with meaning.
But if we never give ourselves time to reflect on why we’re doing what we’re doing – and whether it still fits – we risk chasing goals that don’t nourish us. Or worse, goals that actively drain us.
We also lose something else: the joy of acknowledging how far we’ve come.
When we don’t stop to celebrate properly celebrate the wins, we teach our brains that they don’t matter. That nothing is ever enough. That we only get to feel good when we’ve done more.
And it’s not just the big wins that count it’s the deeply personal, often invisible ones too.
For me? Making the bed deserves a mini celebration. Yes, it’s technically a basic task but my brain would find it easier to go on a 20-mile hike or do stand-up comedy than make the bed before I do something more stimulating. So when I do it first? Honestly, I deserve a medal. That’s discipline. That’s progress. That’s worth clocking.
But this isn’t just about individuals. If you’re a leader and you don’t celebrate success – your team will feel it.
If the wins aren’t acknowledged, people learn that achievement is expected, not appreciated. That nothing is ever quite good enough. That the only thing that matters is the next goal.
That kind of environment might drive performance in the short term but in the long term? It erodes motivation, confidence, and trust. People burn out. Teams disengage. Culture quietly fractures.
Recognition doesn’t have to mean confetti cannons and grand speeches. Sometimes it’s just taking a moment to pause and say:
“That thing you did – [name the thing, specifically] – it mattered because [explain the impact]. I saw the way you [acknowledge their effort or contribution]. Thank you.”
We don’t just need to define success. We need to recognise it. We need to feel it. We need to let others feel it too.
Because if we don’t, we’ll just keep sprinting past the very thing we worked so hard to achieve wondering why it still doesn’t feel good.
What Are You Solving For?
This realisation – that we’re often solving for the wrong thing – comes up again and again in coaching.
We race ahead without checking the compass. We fix things that don’t need fixing. We follow goals we never actually chose.
Sometimes the bravest thing a leader, founder or executive can do is pause and ask:
What does success mean to me, now?
Am I making space for the right things – or letting something else take over without noticing?
Am I still climbing a mountain I chose – or one that just happened to appear in front of me?
When You Don’t Even Know What You Like Anymore
This runs deep.
We’re so conditioned to aim for the next milestone – the next title, the next raise, the next version of “success” – that we lose sight of what we even want.
When I stepped away from the corporate world, I had this strange moment of realising: I didn’t even know if I liked being at home. Or going for coffee. I’d been on autopilot for so long that I’d stopped asking myself the simplest of questions.
So much of our lives get shaped by what we’re meant to do, that we stop noticing what we like – or even what we need.
That’s why I believe coaching, especially outdoors can be such a powerful reset. It doesn’t just help you re-strategise. It helps you remember who you are.
Seeing Differently
This is the work we do in coaching – particularly in nature. Not burning it all down. Not fixing anything. Just creating the space to see differently.
Because sometimes the breakthrough isn’t about pushing harder. It’s about realising you’ve been aiming at the wrong summit all along.
And sometimes your inner compass – the part of you that knows – has been whispering this for years.
If any of this resonates – whether you’re running a business, leading a team, or just quietly questioning the version of success you’ve been chasing – I’d love to chat. Coaching isn’t about telling you what success should look like. It’s about helping you define it, on your own terms.
