Early Retirement - The Hardest Part of Leaving Isn't the Leap. It's the Goodbye

On stepping away from work, the people you're leaving behind, and the strange grief of ending something you chose to end.

May 2026 : 10 min read - Part of the My Personal Journey to Early Retirement series at FreeBefore65.

I've been thinking a lot about goodbyes lately. 

Not the formal ones. Not the leaving speech or the card signed by people you've barely spoken to in three years. Not the gift voucher and the awkward gathering in the meeting room where everyone checks their phone. 

I mean the real ones. The quiet ones. The ones you have - or don't quite manage to have - with the people who actually mattered. 

I finish work at the end of June. The decision was mine. I made it deliberately, over eighteen months of careful thought. The finances stack up. The plan is solid. The reasons are real and I believe in them completely. 

And I am still, in ways I didn't fully anticipate, grieving something. 

 

The people you recruited

There's a particular kind of relationship that develops when you hire someone. 

You see something in them - a quality, a potential, a fit - that others might not have spotted. You make a case for them. You fight their corner in the selection process. And then you bring them in and you invest in them. Time. Attention. The kind of patient, specific feedback that only comes from someone who is genuinely paying attention to what a person is capable of. 

I've done that over the years. More times than I can count now. And what I've discovered - only really clearly in these final weeks - is that when you invest in someone that way, a small part of your professional identity becomes woven into their story. Not in a possessive way. In a quietly proud way. 

You become, in some small measure, part of what they became. 

And leaving means stepping out of that story. Not erasing your contribution. You can't un-hire someone or un-train them or take back the confidence you helped them find. But you're no longer there. No longer copied in. No longer the person they'll come to with a difficult situation or a decision they're wrestling with. 

Someone I hired early in their career sent me a message last week. Just checking in, they said. I hope the plans are taking shape. It was warm and genuine and brief. And I read it three times. 

Because what it contained - underneath the pleasantries - was exactly the thing I didn't know how to name until I saw it. Not a request for anything. Just a person who wanted me to know they were thinking of me. That the relationship had mattered. That it wasn't nothing. 

It wasn't nothing. It was something. It was eight years of something. 

 

The projects that outlive your involvement

There's a piece of work I've been part of for several months. It started before I decided to leave and it will finish after I've gone. 

I won't see the end of it. 

This is, objectively, fine. Projects don't require their contributors to witness their completion. The work will continue. Other people will carry it forward. The outcome - if it goes well - will have been shaped in part by things I did and decisions I was part of. That's enough. That should be enough. 

And yet. 

There's something quietly painful about leaving a thing unfinished. Not failed - unfinished. Walking away from something mid-sentence. Handing it to someone else and trusting that the thread you were holding won't be dropped. 

I think what I'm feeling - and I want to try to name it precisely rather than dress it up - is not regret about leaving. It's a very specific kind of wistfulness about incompleteness. The same feeling you get at the end of a good book that ends before you feel quite ready. Not disappointment. Just a wish that there was a little more. 

 

The colleagues who became something more

Work friendships are their own specific thing. They're not the same as the friendships you make by choice, in your own time, around things you actually care about. They develop in the particular pressure of shared professional experience - the project that nearly didn't make it, the presentation that went badly, the meeting that needed surviving together. 

They're forged in context. And context, when it disappears, takes something with it. 

I know which colleagues I'll stay in touch with. I have a reasonably clear sense of which relationships will survive the transition from working together to simply knowing each other. Some will. I'm realistic that more won't - not through any failure of affection, but because the scaffolding that held the relationship up was the shared workplace, and once the scaffolding comes down, not all the structures it supported will remain standing. 

That's just the truth of it. And the truth of it is a mild sadness that I didn't expect to feel quite so specifically. 

There's are specific colleagues that matter. The ones that joined within months of me joining. Going through the same organisational upheavals, dealing with the same difficult managers, celebrating the same wins. There's a particular shorthand that develops between people who have been in the same rooms at the same difficult moments - a kind of conversational compression that means a single look across a meeting table conveys an entire paragraph. 

And then they leave. That was its own small loss, even before I'd decided to go myself. And their leaving was, I think, one of the things that made the scales tip for me. Not in a dramatic way. Just - when they went, something shifted. The thing I was holding onto began to feel less substantial. 

I've been thinking about what I want to say to the people who mattered. Not at the leaving drinks, with a glass in hand and twenty people listening. Something more honest than that. Something that acknowledges what was real without being mawkish about it. 

I haven't quite managed it yet. I keep writing things in my head and putting them down before they reach paper or screen. But I'm going to try. Because I think the alternative - the polite, vague goodbye that doesn't name anything - would feel like a failure. Like letting the relationship end on a note that doesn't reflect what it actually was. 

 

The identity that came with the job

I've written elsewhere about the identity question in early retirement - the strangeness of no longer having a professional role to answer the question "what do you do?" 

But I want to say something more specific here. About the identity that lives inside a particular job, in a particular place, with particular people. 

I was good at what I did. I want to say that plainly, without false modesty and without arrogance. I knew my field. I was trusted. When I spoke in meetings, people listened. When I made a recommendation, it was taken seriously. When something went wrong, I was the person people came to. 

That specific experience - of competence and trust inside a particular professional world - is not something you carry with you intact when you leave. You carry the underlying capability. You carry the knowledge and the experience and the judgement. But the specific social reality of being trusted in that room, with those people, in that context - that ends. It doesn't transfer. It just ends. 

And I find that - not devastating, not even particularly frightening - but real. A real ending of something real. 

I don't think I'm mourning the status. I never particularly cared about status for its own sake. I think I'm mourning the contribution. The daily, specific, tangible sense of having been useful. Of mattering to outcomes that mattered. 

Building that again - in a different form, in a different context - is part of what the next chapter is about. The volunteering. The projects. This. But I'm under no illusions that it happens automatically or immediately. It's something to build. And before you build the new thing, you have to let go of the old one. 

Which is what these final weeks feel like. A long, slow letting go. 

 

What I want to remember

I don't want to sentimentalise this. I made the right decision. I know that. The reasons were real and they remain real. 

But I want to hold onto something about the ending before it becomes the past. 

The colleague who sent me that message. The project I won't see finished. The particular shorthand of eight years with people who understood the context. The meetings that were difficult and the ones that went better than we'd hoped. The people I watched grow into versions of themselves they might not have reached without someone believing in them early. 

These things mattered. They deserve to be named, not just left behind in the rush towards whatever comes next. 

Someone wise once told me that the quality of a goodbye is proportional to the quality of what you're saying goodbye to. A hard goodbye is a compliment to the thing you're leaving. 

I'm finding this harder than I expected. 

That feels like the right thing to be finding hard. 

 

A note to anyone else in these final weeks

If you're reading this in the run-up to leaving a long career - I don't have a neat resolution to offer you. 

What I have is this. The feelings are real and they're worth feeling fully rather than rushing past them. The grief of a chosen ending is still grief. The loss of relationships that won't survive the transition is still loss. The strangeness of walking away from something you were good at, in the middle of things that aren't finished, is strange and it's allowed to be strange. 

Let it be what it is. Don't manage it into something tidier than it actually is. 

And then - when you're ready - turn around and face what's coming. 

It'll still be there. The freedom you worked for. The time you reclaimed. The mornings that are finally yours. 

Just not yet. Not quite yet. 

 

• 21 Working Days Until I Hand Back the Company Laptop - The Final Countdown
• Be Seeing You: The Prisoner, Portmeirion and Why I Finally Understand Number 6

 

Part of the My Personal Journey to Early Retirement series at FreeBefore65.

 

Tony writes about his personal journey to early retirement at freebefore65.co.uk. He is not a financial adviser. All content reflects his own experience and research.