For a long time, the answer to this question seemed straightforward.
You worked until a certain age, reached your pension, and then stepped into retirement. It was a clear transition, both socially and psychologically. One phase ended, another began.
That clarity has largely gone.
Longer lives, more varied financial situations, and changing attitudes to work have blurred the boundary between working life and retirement. Some people leave early, some much later, and many move in and out of work in different ways. What was once a single moment has become a much more fluid process.
I was recently asked to contribute to a piece exploring this question, alongside two very different perspectives. One person had retired early, only to find herself unexpectedly busy, caught up in childcare, helping neighbours, and volunteering. Her days were full, but not in the way she had imagined. Another, now in her seventies, continues to work and has no intention of stopping, finding in work a sense of relevance, engagement, and vitality.
Both accounts felt familiar. Both made sense.
And yet, what struck me most was how often we approach retirement by asking the wrong question.
We tend to begin with finances. Have I saved enough? Will my pension stretch? Can I afford to stop?
These are important considerations. But they are not the most helpful starting point.
Over the years, working with people navigating later life, I’ve seen many who made what looked, on paper, like a perfectly timed decision. They reached a financial threshold, left work, and then found themselves adrift within months. Equally, I’ve seen people remain in work, not because they particularly wanted to, but because they didn’t know what else would hold their life together.
In both cases, the issue is not timing. It’s direction.
A more useful question, although a less comfortable one, is this:
What am I actually moving towards?
Retirement, at its best, is not simply about leaving work. It is about creating space for something else. That “something else” doesn’t need to be grand or fully formed, but it does need to exist in some way.
Without it, work can become either something we cling to, or something we leave behind too quickly, expecting relief or fulfilment that doesn’t quite arrive.
There are often early signs of this transition, though they are easy to ignore. A subtle shift in where your attention goes. Work becomes more familiar than energising. You find yourself more curious about what lies beyond it than about the next project or promotion. The weekend begins to feel more real than the working week.
None of these are signals to act immediately. But they are worth noticing.
There is also a more practical dimension, one that is often overlooked. The years between sixty and eighty are not a uniform stretch of time. For many people, the earlier part of this phase still holds a good deal of physical capacity: the ability to travel, to learn something new, to engage fully in activities that require energy and mobility.
Later, those capacities often change, sometimes more quickly than expected. Knees, hips, recovery time. The things we assume will always be possible begin to narrow.
I have worked with people who delayed plans they cared deeply about, assuming there would always be time. In some cases, that time quietly slipped away. Not dramatically, but gradually, almost unnoticed.
So alongside the psychological question of what you are moving towards, there is a very practical one:
What do you want to do with your body while it can still do those things?
This is not about urgency in a pressured sense. It is about awareness.
Another pattern I’ve noticed is that those who find retirement most difficult are often those whose identity has been almost entirely built around their work. When that structure is removed, there is little else to take its place. The question then is not simply when to retire, but whether a life beyond work has been given any space to develop.
In contrast, those who navigate this transition more easily have usually begun the process earlier. Not necessarily through a formal plan, but through a gradual broadening of their lives. Interests explored, relationships nurtured outside of work, small experiments with how time might be spent differently.
In this sense, retirement is less a decision and more a process. One that unfolds over time rather than arriving all at once.
So when is the right time to retire?
There is no single answer. It will depend on health, finances, personal circumstances, and temperament. But if there is a thread that runs through the many stories I’ve encountered, it is this:
The right time is rarely defined by age or by a number in a pension pot.
It is more often marked by a growing sense that work is no longer the only thing holding your life together, and that there is something, however tentative, that you are ready to move towards.
And, ideally, it is a time that still leaves you with enough energy, curiosity, and physical capacity to make the most of what comes next.
The question, then, is not just when you will stop working.
It is whether you have begun to imagine, and gently build, the life that follows.
