For most of my working life I didn’t have much of a relationship with failure. Not because I’d mastered something. Because I was moving too fast for it to catch me. Fifteen years in technology and telecoms, good at what I did, promoted into leadership, sent around the world. The feedback loops were tight and favourable. If something didn’t work, there was always a next thing, and the next thing usually did.

I don’t say this with pride. I say it because I think it’s more common among capable people than we admit, and because the bill comes due eventually.

Eleven years ago I stepped away from that life. Not for a dramatic reason. For a quieter one - a sense that I’d built a career on being quick and competent at things that no longer felt like mine. What followed was a long, unglamorous period of unlearning. New training. New work. A lot of being a beginner again, in my forties, at things I cared about more than I’d cared about the old work.

And somewhere in that slowing down, the fear of failure I’d never really sat with caught up.

This is the part that doesn’t get said enough in public, so I’ll say it carefully. Going back through a working life with honest eyes is not a comfortable exercise. There are decisions I made that I can now see were wrong. Relationships I handled badly. Moments of work where my judgement was off and I carried on anyway because carrying on was what I did. These aren’t theoretical failures I’ve reframed into growth. They’re real. And when I sit with them, the inner critic has plenty of material to work with, and the body knows it before the mind does - tight chest, shallow breath, the specific heaviness of something that hasn’t been metabolised.

This is the work I’m doing now. I mention it not as confession but because I think it’s relevant to what I want to say next, which is about leaders.

The leaders I coach are, almost without exception, more generous with other people’s failures than with their own. They’ll tell a direct report that missing the mark is how we learn, and they’ll mean it. Then they’ll drive home and silently take themselves apart for a comment they made in a meeting three weeks ago that nobody else remembers.

The compassion runs outwards. It does not come back.

There are reasons for this. The role demands it - leaders are meant to absorb, not emit. The story that got them here usually involves a hard inner voice they credit with their success, and they’re reluctant to put it down. And vulnerability at altitude is genuinely more expensive than vulnerability lower down. A graduate analyst who says they’re struggling gets coached. An executive who says the same risks being quietly written off. So the feeling goes underground, where it does more damage, not less.

What I see in that underground - in the private sessions, in the long walks, in the moments where someone finally says the thing - is rarely dramatic. It’s quieter than that. It’s the brilliant operator who has stopped bringing their actual judgement because their actual judgement once cost them something. The founder who has learned to perform resilience rather than experience it. The senior leader who has become, without noticing, allergic to the stretch, the uncertain, the exposed. Careful looks like wisdom from the outside. From the inside, it’s often fear wearing a better suit.

This is what I’ve come to think the fear of failure does, when it’s left unexamined for long enough. It narrows the bandwidth of what you’re willing to attempt. It does this so gradually that you don’t notice the narrowing - you just notice that the work feels smaller, that the big conversations happen elsewhere, that you’re more tired than the workload should make you. You play smaller than you are, and you tell yourself you’re being strategic.

I’ve done this myself. It’s part of why I’m doing the current work. You cannot offer what you have to offer, at full volume, to the people who actually need it, while some part of you is still flinching from a version of failure that happened ten years ago.

There’s no technique for this, and I’m suspicious of anyone selling one. What seems to help, in my own work and in the room with clients, is less heroic than that. It’s the willingness to turn towards the feeling rather than manage it. To name the specific moment rather than the general shape of it. To let the body have its say before the mind moves in with its analysis. To notice that shame and failure, though they travel together, are not the same thing - the first says I am something that doesn’t work, the second says I did something that didn’t work, and only the second is workable.

And to accept that this is not a project with a completion date. It’s a different relationship to the material. The failures don’t stop being failures. They stop being in charge.

A note on supporting people who are in this, because leaders ask me this often. The thing someone in the grip of it almost certainly doesn’t need is your reframe. Not yet. They don’t need to be told that failure is a great teacher. They’ve read that. They need, first, to be believed. Witnessed. Given time. The most useful sentence is often the least impressive one - that sounds hard, or tell me more, or the long pause that signals you’re not in a hurry to move them somewhere more comfortable for you. The reframe, if it comes, comes from them.

Why I’m writing this

I’m in the middle of a pivot in my own work - towards organisational consultancy on one side, and on the other, towards deeper work with individuals and teams out in nature, where the usual scripts don’t hold and something more honest tends to surface. The real vulnerability, if I’m honest, isn’t in writing this piece. It’s in going to market with a new offering and not knowing how it will be received. That’s a different kind of exposure, and it’s the one I’m actually sitting with. Part of what the work has asked of me is to look at the fear that has, quietly, shaped what I’ve been willing to offer and to whom. Not the fear that stopped me doing things. I did plenty. The fear that had me doing them at a slight angle, hedged, a half-step back from what I actually wanted to say.

The point of the work, as far as I can tell, is this. To be able to step into what I have to offer, and to the people I want to offer it to, without the old fear running the negotiation. Not fearless. Just no longer governed.

If any of this lands, it’s probably because you know the feeling too.