Career Coach Reveals the #1 Regret of Retirees: Not Taking a Break Sooner

When a senior policy adviser left government after two decades of high-level work, she assumed the hard part was behind her. She had given everything to a career that mattered: policy she cared about, colleagues she respected, a role at the centre of things. What she hadn’t anticipated was how completely that role had been carrying her sense of self.

“Unmoored” was the word she used. Not unhappy, exactly. Not ungrateful. Just adrift in a life that had lost its shape. It took her more than two years to find her footing again, and she only did so by accident, when she started writing a blog and realised that what she had truly loved about her career was never the status or the salary. It was mentoring younger colleagues, transmitting what she knew. The blog became that, quietly, from her kitchen table.

I have spent over 40 years as a career and later-life psychologist, and I have heard versions of this story more times than I can count. The structure collapses, the diary empties and people are left confronting a question they have been deferring for decades: what, actually, do I want from my life?

It is a question that a quite different generation is now being forced to ask much earlier. Recent data shows that the over-75s are the fastest-growing segment of the workforce in the United States, while on the other end of the spectrum, a growing number of people in their thirties are pursuing what has become known as FIRE: Financial Independence, Retire Early. They step back from conventional careers in their thirties or forties to live differently.

The two groups are separated by 40 years and almost everything else. But they are circling the same problem: what does a good working life actually look like, and when does living begin?

What strikes me about the younger FIRE converts is not the financial discipline, impressive as that often is, but what they discover when they stop.

Jess, in her late thirties, who I met at a retreat in Central America, had burnt herself out in a demanding corporate role, taken an extended break and spent much of it travelling in South America and training as a yoga teacher. Whether or not she pursued that path professionally, something had shifted. She had found out what replenished her, not what the job market required of her. That is a form of self-knowledge that most people only acquire in their sixties, if at all.

Chris moved abroad for six months with no particular plan, from the US to Scotland, which suggests the pull was not so much sunshine as silence. She returned to a similar role, but refreshed in a way that years of annual leave had never achieved.

Stephen, 32, freshly promoted to middle management, suddenly found himself asking the question that promotions tend to suppress: is this actually what I want? He took himself off to Australia on a working visa and came back, a year later, to a better job in the same field, but crucially, a job he had chosen rather than simply fallen into.

None of these are dramatic reinventions. None involve giving everything away to live on a narrowboat. What they have in common is a deliberate pause, a moment of stopping long enough to hear yourself think.

I know something of this from my own life. In my late thirties I was burning out, ground down by anxiety and the accumulated weight of a working life I had never quite examined. I took a year out, not for travel or adventure, but for almost nothing. I cooked. I sewed. I planned a wedding. I did not think about work for a very long time. When I came back to it, I came back differently: I wanted to work for myself, on my own terms, without the pressures that had quietly been eating me alive. That decision shaped the next 30 years.

The men and women I have spoken to who left the “bucket list” too late know this cost in a different register. So many had plans, to walk the Camino, to reach Machu Picchu, to take that long trip they had always promised themselves. These were not idle fantasies. They were real ambitions, deferred on the assumption that there would be time. And then there wasn’t, not because the years ran out, but because their health changed while those plans were still sitting in the background.

People like Susan, Debs and Rita, three women I met on a small group trip in Asia. They hadn’t known each other before the holiday, but each had come alone after losing a partner. All of them were doing the trip they had once imagined sharing.

Simon, now 68, had planned to ride his motorbike from home to India. His health made it impossible. The trip never happened.

The cultural script we are handed tells us that life is what happens after work. After the mortgage, after the school run, after the job that pays the bills. Retirement is the reward. But by the time many people reach it, they have spent so long not asking what they want that they have forgotten how to answer.

The accidental wisdom of the FIRE generation, and of anyone who has ever taken a genuine sabbatical, is not that they have escaped work altogether. It is that they have interrupted its dominance early enough to see it clearly.

The practical implication is almost disarmingly simple: at some point, you have to stop before you are forced to. Not for good, necessarily. Not even for long. But long enough to find out what is actually there when the diary is clear and the job title has been set aside.

It might be a three-month gap between roles, a negotiated sabbatical, a period of part-time work, or even a deliberate stretch of slowing down where work is no longer the centre of the week. The form matters less than the fact of stepping out of the structure long enough to see it clearly.

The people who flourish in later life are rarely those who worked hardest, or retired earliest, or accumulated the most. They are the ones who learned, at some point, what actually matters to them, and built something of that into their lives before the question became unavoidable.

The lucky ones learn it young. The rest of us can still catch up, if we are willing to pause before life forces the question on us.

Dr Denise Taylor is a chartered Psychologist and author who writes about later life and exploring meaning beyond full-time work. Her forthcoming book, ThriveSpan: Walking Gently Into What Matters Now, is published in June