You Cannot Optimize Your Way to Being Enough

What if all your self-improvement is the thing keeping you stuck?

The day I landed my first corporate client, I gave myself about an hour.

I remember it because it was the same hour I had given myself many times before. A short exhale. Something like relief. And then, before the evening was over, my mind had already moved on, to the next goal, the next to-do, the next thing that promised to make the whole thing finally click.

I had lived that hour at every stage of my business. After the first client. After the first employee. Each time, the goal I had chased for months dissolved on arrival, and a new one quietly took its place.

Around it all sat a whole apparatus. The productivity books, the morning routines, the sleep tracking, the biohacks, the meditation, the next framework for the business and the next one for the self.

For ten years, I called it growth.

Only much later did I see the quieter truth. I wasn’t trying to become better because I felt free. I was trying to become better because I hoped that, somewhere on the other side of enough improvement, I would finally feel allowed to just be as I was.

The cost was not that I failed. In many ways, the opposite was true. I got better. I achieved things. I became more capable and a good deal more refined in how I understood myself and the world.

The cost was that I was never there to receive any of it.

Every achievement dissolved almost as soon as it arrived. A good result became the new baseline. A finished goal became evidence that the next one should be bigger. Even on good days there was a low hum underneath everything. Not yet. Not there. Not enough.

And slowly, almost invisibly, that logic spread everywhere. Rest became something I had to earn. Joy became something I had to justify. Beginnerhood became unbearable. Even connection was hard to fully inhabit, because some part of me was always monitoring whether I was becoming the version of myself I thought I had to be.

What makes it almost funny now is which field I poured it into.

I left the classic entrepreneur path after my first venture and walked straight into self-development as a vocation. Coaching training. Then out on my own as a coach. Then a master’s in psychology. Dozens of clients, thousands of hours, certifications, corporate workshops. Constantly improving and learning.

And let me be plain. I’m not the founder with the big exit. I had some real wins, plenty that went wrong. I’m still on the path like anyone else.

So don’t read this as a story about making it and feeling empty. When the drive comes from a feeling of lack, it doesn’t matter how successful you get. It never delivers what it seems to promise.

There’s an irony here I don’t want to hide. Today I work with people on sustainable performance. I care deeply about capacity, energy, resilience, and the inner architecture that lets someone build without quietly destroying themselves.

I haven’t stopped believing in development. But not all development is the same. There is a kind of improvement that is really a flight from the feeling of being inadequate. And there is a deeper kind that helps us understand why we had to run so hard in the first place.

I had made improving myself my actual profession. And the engine still ran on the fuel it always had.

For a long time I had the object of that engine wrong. It was never simply that I wanted to achieve more, and then more. It was closer to something else. This time, I thought, finally, I will feel good enough. Worthy. Content with where and who I am. Allowed to stop proving and start enjoying.

Those aren’t the same sentence. One is hunger. The other is a person standing at a door, waiting to be loved exactly as he is.

And it was never one field. It was all of them at once. The business had to grow. The body had to be fitter, the sleep deeper, the food cleaner. But also be social, be there for the people you love, don’t let the friendships go cold, keep the hobbies alive. Every domain became a field to be tended, and every field was always a little behind.

At the end of each year, I would sit down and take honest stock of the past twelve months. Every year the same list looked back at me. What was still missing, still unfinished, still not where it should be. The verdict never changed. Never quite satisfied, already reaching past it toward the next, bigger goal before I had let the last one land.

The list was the symptom. I read it as a to-do.

And here is the part anyone who has really tried will recognize. It helped. I wasn’t nothing. It genuinely helped. The goals, the discipline, the routines gave me real relief. I became more competent, more aware, more functional. But it was the relief of a painkiller, not a cure. Everything I did managed the symptoms, and none of it reached the dissatisfaction underneath.

And like any painkiller, it wore off. So I reached for the next dose.

Here is what I can see now that I couldn’t see then.

Every hour I spent improving myself confirmed the belief that I was not good enough. That’s why none of it worked.

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I used to picture the goal as a container I was filling. One more achievement and the level would finally rise to the line marked enough. So I poured and poured.

And the level didn’t budge.

The barrel had no bottom.

I can trace the chain back as far as I have memory. School, where the grade was only as good as your last. Football, where you win a season and the next one starts everyone back at zero. University. The first business. The first customer. The first hire. Each one was supposed to be the one that landed, and each one reset the counter the moment I reached it.

There was always a bigger achievement, and the bigger achievement was always where enough had quietly moved to.

Underneath it sat a belief I didn’t know I was holding. That as I am, I am not enough, so my worth has to be earned, performance by performance, and topped up again tomorrow.

Let me tread carefully here, because this is my own reflection, not a diagnosis I’m handing you. The only reason I trust it enough to write it down is that when I started saying it out loud, quietly, to people I trust, the thing that came back, again and again, was simple. Yeah. I know that one too.

Shame kept it buried, and alive, for far too long. That’s how shame works. It thrives on secrecy, and the moment it’s spoken out loud it begins to lose its power. Keeping it hidden never protected me. It only protected the shame.

For a while I assumed the proof I needed was external. That somewhere out there was a result big enough to settle it. It wasn’t. I know, because I kept producing results and kept not feeling them.

On paper, much of it looked like growth. The real cost ran underneath. The constant pressure to perform, the inability to let anything land, the quiet interrogation after almost everything I did. Was that enough? How can I be better? And, most of all, the slow loss of joy and play.

Let me give you a recent example, because it’s the one that finally showed me the mechanism.

I signed up for a hip hop dance class. I’d never done it before, which is the entire point of a first session. You go because you can’t do the damn thing yet.

And within minutes, I was ashamed.

Not because anyone was watching, and not because anyone judged me. The room was kind. The shame came from inside me, aimed at me, for not already being good. For wanting to move, to express something, to be a beginner at something that mattered to me and not be excellent at it on arrival.

I didn’t see it on my own. It came later, in a therapy session. I was telling the story almost as a throwaway, and my therapist reflected it straight back. The shame wasn’t something the world was doing to me. It was something I was doing to myself.

I was the one shaming myself away from my own aliveness.

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So why did more than ten years of working on myself not fix it?

Because self-improvement was the problem wearing the mask of a solution.

Or more precisely, it was the kind of self-improvement that begins with a quiet assumption. That I am not good enough yet, that something in me is missing, that I am somehow deficient and therefore have to be improved. That’s the trap. Improvement that grows out of a felt lack can only ever confirm the lack.

At first you can’t see it, because you’re inside the promise, and the promise is intoxicating. If I just try hard enough, become more successful, add a little more discipline, understand myself a little better, I can improve myself out of this. I can fix me.

And there was a sense of progress everywhere I looked, real and perceived. I became more capable and more skilled, and the people around me noticed it too. The surface kept improving, and I saw no reason to question it.

Why would I? Everyone around me seemed to be doing the same thing. We’re constantly surrounded by the story that if we only make more progress, or buy product X, we’ll feel better.

Until a meditation retreat questioned it for me.

I had practiced mindfulness for over ten years inside a Vipassana tradition built on discipline. Lead the attention through the body. Notice when the mind wanders. Bring it back, again and again. Train the mind like a muscle.

I was good at it the way I was good at everything, by gripping.

There was a Zen teacher there who, in one of his talks, named a pattern he’d seen again and again. People who stick with a practice for years, holding on to it because they’re sure that one day it will finally help them, and it never does. He said it almost in passing. Ask yourself whether what you’re learning and practicing actually brings you the relief you’re really after.

He could have been describing me. Ten years of meditation had genuinely helped me focus. It steadied my attention, it calmed the surface. But it never once reached the pain underneath. The pain that was built on exactly this, the constant trying, the endless efforting. I had simply found a quieter, more disciplined way to keep efforting.

Then the floor gave way.

Because I suddenly saw that even this, even the spiritual self-improvement, even the meditation, was the same treadmill. It had simply put on robes.

And out of that crack came the honest question I had never let myself ask. Is all this effort actually helping me, or am I just building a more beautiful facade to stand in front of the same wound?

By then I’d been at it for years. The coaching business, the training, the clients, the certifications, the workshops. All of it real, all of it growing. And I made myself answer one question without flinching. Do I feel good enough because of any of it?

No.

It had helped on many levels. On the deepest one, it hadn’t touched a thing.

The work, it turned out, was never to fix the self. It was to meet the part of me that was convinced it needed improvement.

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I want to be clear about what this is not, because the easy misreading is that ambition is the enemy. Do less. Want less. That’s not it at all. It isn’t the action. It’s the engine underneath the action. The same thing can run on two completely different motors, and only one of them costs you.

I know this from the inside.

My masters in Oxford showed me a version of ambition that didn’t feel like self-punishment. In 2022, many years after my first degree in business, I went there to study a blend of Western and Eastern psychology, and for once the result was not the center of the room. I wanted to understand. I wanted to read and think and be in the conversations and follow the questions wherever they led. A good result still mattered, but it was secondary. The experience wasn’t only valuable if it proved something about me. I wasn’t trying to extract worth from it. I was inside it.

That contrast helped me see my own coaching work more clearly. It’s a field I love, a subject that means everything to me, work I’d chosen freely and built myself. And still, much of it ran on compulsion, because underneath sat the old demand. It has to succeed. I have to prove this, to myself and to everyone. The mere thought of failing with my business frightened me.

So let me kill the comforting story. Loving the thing doesn’t protect you. Meaning doesn’t protect you. You can be doing exactly the work you would choose and still be running the wrong engine.

So how do you tell which one you’re on? The only reliable instrument is internal.

Compulsion has a feel. I must. A narrowing. Everything goes binary. Good or bad, right or wrong, pass or fail. The critic gets loud, the body tightens, and the path disappears behind the outcome.

Fullness has a feel too. I want to. An opening. Aliveness, and contact with what you actually feel. Curiosity. A kind of lightness. The critic goes quiet, the body softens, and the sheer joy of doing becomes the purpose. You don't become the game, you're just playing it.

I didn’t arrive at this distinction in a flash. It came slowly, through my training in complex trauma. Complex trauma isn’t one dramatic event. It’s the slow buildup of small, repeated moments, usually early in life, where your needs weren’t fully met by the world around you. As a child you can’t blame the people you depend on; that’s too existentially threatening. So you turn it inward and blame yourself instead. That verdict settles into the core of who you are, and every strategy of trying you build on top is just a way to feel enough. But no matter how hard you try or how much you achieve, it won’t land, not until you meet the core that believes it’s broken.

The first time I truly turned toward that part of myself, I cried. Not a sharp, situational cry, a deep, old sadness, the kind that has been waiting a long time to be felt. And it was one of the most beautiful moments.

What moved through me was release. The letting go of all the trying. For once I wasn’t trying to fix the feeling, or optimize it away, or think my way around it. I just let it be there, and let myself be there with it. And underneath the vulnerability I’d braced against my whole life, there was no catastrophe waiting. Only a tenderness I hadn’t allowed myself in years. Out of that, a deep compassion began to emerge, for myself, and even for the strategies. And slowly, the inner critic started to quiet. It had nothing left to defend. Lightness appeared. Even a little humor.

A weight came off my shoulders, and that told me everything. The other mode, the I must, had always felt forced and heavy. I’d simply never had anything to compare it to.

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So where does that leave me, honestly, today?

Not at a summit. I’m somewhere on the path, and I can only write to you from where I actually am.

I keep coming back to that Zen teacher’s question, does it actually work, and applying it without mercy.

Here’s what I’ve concluded. Pure self-optimization, in the culture we live in, does not pay into the one account I most wanted to fill. More training, better sleep scores, more supplements, more success. None of it makes me feel good enough, or okay with myself where I am. It can’t. When it’s driven by the belief that I’m not yet enough, it quietly confirms the opposite. That there is something here that has to be improved before it can be loved.

What has actually helped is something else.

Through complex trauma work I now have a clearer sense of my own survival strategies, the moves that once protected me and are now the very things creating the symptoms. I’m starting to see how they show up everywhere, across every part of my life. And instead of fighting them, I’m giving myself time to unlearn them. Slowly. Piece by piece.

It isn’t loud. It isn’t finished. There is no dashboard. But I get to be a little more myself, and it gradually feels lighter. Less pressured, less like life is a test I’m always almost failing.

What changed was not more effort. It was the turn from optimizing the feeling away to actually meeting it.

And meeting it had to become felt, not just understood. For me that meant letting in the sadness of how badly a small boy had once needed that strategy, because that was how he received love. Then a kind of compassion for him. He was doing the most intelligent thing available to him at the time.

And then the part I’d spent a lifetime forbidding. Vulnerability. The exact feeling I had ruled out, because it was the opposite of who I wanted to be. I wanted to be the best. Strong. Untouchable. Vulnerability was weakness.

It turns out it’s the door.

This is my point of view, not a doctrine. Your experience will be different, and that’s exactly as it should be. But if you’re someone who already does a great deal, who is always quietly working on yourself, trying to get better, and who has the nagging sense that none of it is making you any more content, or bringing you any closer to what you really want, then this might be for you.

This publication is going to be the journal of that turn. Not written from the far side. Written from inside it. A lot of it will be about the strategies underneath. The moves I once learned to stay safe and be loved, and how they quietly get in the way of what we actually want now. Meeting them, instead of fighting them, is where the real work lives. But that’s for another day.

Let me end where I started.

Every hour I spent improving myself confirmed the belief that I was not good enough. That’s why none of it worked.

I don’t read that sentence now as an accusation. I read it with tenderness. I was trying to help myself. That’s all the effort ever was.

And maybe that’s where the real work begins. Not in becoming someone better, but in finally turning toward the part of us that believed better was the only way to be loved.