"What Are You Going to Do When You Retire?" - The Uncomfortable Honest Answer

The question everyone asks when you retire early. And the honest answer most people are too embarrassed to give.

 

It starts before you've even left. 

Someone finds out you're retiring - a colleague, a neighbour, a distant relative at a family gathering - and the question arrives almost before the congratulations have finished. 

So what are you going to do? 

Said with warmth, usually. With genuine curiosity. Sometimes with a slight edge of challenge underneath it - a testing of whether you've thought this through properly. 

And the socially acceptable answer is ready-made. You reel off the list. The travel plans. The golf. The garden. The grandchildren. The voluntary work. The long-deferred project. The creative pursuit that work kept squeezing out. You make it sound like you've been handed a gift you know exactly what to do with. 

I've given versions of that answer. Volunteering. Home improvements. Time with family. Walking. This - the writing, the channel, the blog. 

All of those things are real. None of them constitute a plan. 

And I've been thinking about whether that's a problem. Whether the absence of a clear, structured answer to that question is something I should be worried about - or whether the question itself deserves more examination than it usually gets. 

 

What the question is really asking

Here's the thing about "what are you going to do?" 

On the surface it's asking about activities. About how the hours will be filled. About what replaces the structure and the purpose and the daily reason to get up and be somewhere. 

But underneath that - and I think this is what gives the question its particular weight - it's asking something else entirely. 

It's asking: who are you without the job? 

It's asking: will you be okay? 

It's asking: are you sure you've thought about this properly? 

And sometimes - not always, but sometimes - it's asking something the person posing it hasn't quite articulated to themselves. A version of: I couldn't do what you're doing. How can you be so certain? 

The question lands differently depending on who's asking it. A friend who genuinely cares wants to know you've got something to wake up for. A colleague who's also considering this wants to know whether the life on the other side is real. A sceptic wants evidence that the decision wasn't reckless. 

All of those are legitimate. But they're all asking something deeper than what they literally say. 

And the honest answer to the deeper question - who are you without the job, will you be okay, have you thought this through - is not a list of activities. It's something more complicated. Something that takes longer to arrive at than the pause between someone asking and you replying. 

 

The false premise buried in the question

There's an assumption embedded in "what are you going to do?" that I want to name explicitly. Because I think it's been shaping my anxiety about not having a cleaner answer. 

The assumption is that retirement is a problem of replacement. That the things work provided - structure, purpose, identity, social connection, the sense of forward movement - need to be swapped out for a comparable set of things from a different source. That the shape of your life should look roughly the same, just with different content filling the same slots. 

Go from meetings to volunteering. From projects to hobbies. From colleagues to community groups. Replace like with like. Keep the calendar full. Stay productive. Have something to show for the days. 

And maybe that works for some people. Maybe that's genuinely the right transition for many. I'm not dismissing it. 

But I wonder whether it's the only frame. Whether there's another version of this - less tidy, harder to explain at a dinner party - that involves something more fundamental than replacement. 

Something more like - stopping. Actually stopping. Not swapping the content of the days but changing the relationship with the days entirely. Allowing time to be unscheduled not because you haven't filled it yet but because the unfilled version has something in it worth attending to. 

Not emptiness. Not aimlessness. But space. The kind of space that working life makes structurally impossible. The space in which you might discover what you actually want rather than defaulting to what the shape of your previous life suggests you should want. 

The honest answer to "what are you going to do?" might be - I'm going to find out. 

 

What not knowing actually feels like

I want to be careful here not to dress up uncertainty as wisdom. Not knowing what I'm going to do isn't a spiritual position I've chosen. It's just where I am. 

I finish work at the end of June. The financial plan is solid - eighteen months of checking, scenario-planning and professional guidance have seen to that. But the life plan is considerably less defined. 

I have intentions. Volunteering that hasn't been formalised. Home projects that have been queued for years. This - the writing, the channel, the videos we're building. Time with my wife that isn't organised around a hotel stay on a Tuesday. Walks that go wherever they go with no particular agenda. 

But intentions aren't a plan. And I've made a deliberate decision - which feels slightly counter-cultural in a world that rewards having everything mapped out - not to force this into a shape before I've lived it. 

And where I am includes some discomfort. 

The discomfort of not having a clean answer when someone asks. Of the slight pause before I recite the list that gives the game away slightly. The sense that I should know by now. That someone who planned the financial exit as carefully as I did should have the next chapter as clearly mapped as the numbers. 

I've spent eighteen months planning the financial exit carefully and thoroughly. I haven't spent the same energy planning what comes next. Partly because I think some things only become clear once the space opens up. Partly because I've watched people fill their retirement with replacements for work before they've discovered what the space without work actually contains. And partly because - if I'm honest - the question of what I actually want, now that what I was obligated to do is ending, deserves more than a list assembled to satisfy someone else's curiosity. 

 

The things that are beginning to surface

Here's what I can say honestly, without overstating it or packaging it into a narrative it hasn't earned yet. 

Some things are beginning to take shape - not as a plan, but as an orientation. 

This - the writing, the blog, the videos - has a quality to it that a lot of my work never had. It's mine in a way that a senior management role can't quite be. The thinking is mine. The decisions are mine. The voice is mine. There's something in that which I haven't felt in a working context for a long time. 

The time with my wife. I'm not there yet - I'm still in the final weeks of work, still doing the Tuesday nights away. But the anticipation of just being present, properly and consistently, without the constant pull of somewhere else to be - that feels real and specific and genuinely important to me. 

The walks. I know this sounds small. But every time I've taken a proper walk with no agenda and no destination except wherever the feet go, something settles that doesn't settle any other way. I want more of that. A lot more. 

And there are things that haven't surfaced yet that I suspect will - interests I've been too busy to explore, conversations I want to have, things I want to learn. They're still below the waterline. I'm giving them the space to rise. 

That's not a polished answer to the question. But it's an honest one. 

Something is assembling itself. I just can't tell you yet exactly what it is. And I've decided - for now - that's enough. 

 

What I think the question deserves

If I could answer "what are you going to do?" honestly - fully, without the social performance of having a ready list - here's what I'd say. 

I'm going to find out what I actually want, now that what I was obligated to do is coming to an end. 

I'm going to give the space I'm creating the time it needs to show me what it contains - rather than filling it immediately with the first available replacement for the thing I'm leaving. 

I'm going to pay attention to what feels genuinely mine rather than what fits the template of what a retired person is supposed to do with their days. 

I'm going to build something - I think. Something around this channel and this writing and the conversations it's starting. But I'm going to let it build at the pace it builds rather than forcing it into a shape that satisfies the question before it's ready. 

And I'm going to be honest about how it goes - the good days and the harder ones, the things that emerge and the things that don't, the shape that gradually assembles itself or doesn't. 

The decision was right. I'm more certain of that than I am of almost anything else about this. 

But the life that follows from it is still being written. I'm at the beginning of it. And the beginning of something isn't supposed to look like the middle. 

 

A note to anyone else who doesn't have the answer ready

If you're approaching retirement - or thinking about it - and you don't have a clean response to the question either, I want to say something directly. 

That's okay. It might actually be the right place to be. 

The people who have the answer too ready - whose retirement is fully scheduled before it's begun, whose days are planned with replacements for work before they've discovered what the space without work actually feels like - I wonder sometimes whether they've given themselves permission to find out. 

Not knowing is uncomfortable. The question keeps coming and the pause before the list keeps giving you away. At some point you start to wonder whether the absence of a plan is a symptom of something you should be worried about. 

I don't think it is. 

I think it's the beginning of an honest process. The one that arrives when you stop doing what you were obliged to do and start finding out what you actually want. 

I'll be reporting back on how that process actually feels as it unfolds. The honest, unfiltered version - not the polished retrospective. Because that's what this site is for. 

The question will keep coming. I'll keep answering it as truthfully as I can. 

Even when - especially when - the truest answer is still: I'm finding out. 

 

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 and should be taken as a starting point for your own thinking, not as professional advice.