Many people look forward to retirement as a reward for decades of hard work, imagining a life free from pressure, deadlines and responsibility.
Whether you are already retired, approaching it, or simply thinking about the future, this expectation is normal. Yet the reality of retirement often proves far more complex.
When work ends, it is not only a pay cheque that disappears. Work provides structure, routine, social contact and a sense of identity.
For many of us, it answers the simple question, “What do you do?” When that answer vanishes, it can leave a surprising sense of emptiness.
I experienced this myself when I retired from running schools in Cambridge. At first, retirement felt like an enormous relief. The constant demands, the responsibility for staff and students, and the pressure of daily decision‑making were suddenly gone.
For a brief period, the absence of stress felt liberating. That feeling did not last. Within a few weeks, an uncomfortable question emerged: Who was I now? Without my role, my days lacked shape and direction. The freedom I had long anticipated began to feel unsettling rather than satisfying. This loss of professional identity can quietly undermine confidence and self‑esteem.
When recognition, feedback and purpose disappear overnight, it is easy to feel diminished or invisible. These feelings are not unusual.
Many retirees struggle with restlessness, depression and a sense of isolation, particularly when social contact decreases at the same time as work ends. Without a reason to get up at a certain time or a clear sense of being needed, time drags. Yet these challenges are rarely discussed openly, which can make them feel personal rather than shared.
Like many people, I tried to deal with this by staying busy. I took up golf, believing this was what retirement was supposed to look like. For a while, it provided routine and distraction, but it soon lost its appeal. I then turned to business, developing properties in the UK and overseas, followed by running a short‑let apartment business.
These ventures were stimulating at first and gave me something to focus on, but they did not fill the deeper gap left by my former career.
I missed intellectual engagement, working with academics and being part of an educational community. Even when these projects were successful, they felt curiously empty.
Over time, I came to understand that activity alone does not create meaning. Retirement often involves a long period of trial and error, during which confidence rises and falls and motivation can be hard to sustain.
It was only later, almost by chance, that I returned to reading more widely. Reading led to writing, first books and eventually articles, including my work for the Oman Observer.
Writing provided intellectual challenge and, most importantly, a renewed sense of purpose. It gave structure to my days and a reason to stay engaged with the world. Even so, this transition did not happen quickly. It took years to discover a direction that genuinely replaced what I had lost.
In retrospect, the lesson is clear. Retirement requires preparation that goes far beyond financial planning. Psychological readiness matters just as much.
Thinking in advance about how you will find meaning, structure and identity in retirement can make a profound difference. Developing interests, being creative and imagining who you want to be can help protect self‑esteem and wellbeing. Freedom is not enough. What sustains us is purpose. Finding it after a long career may be one of the greatest challenges but it can also open new doors of opportunity.
I now realise that a fulfilling life exists beyond the pressures and routines of full‑time work and I don’t regret my decision to retire early.
Karim Easterbrook
The writer is a Former Cambridge School Principal and Author
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