Commentary: Who am I when the phone stops ringing? Lessons from my first month of retirement
After a flurry of handover meetings and farewell lunches, Jeffery Tan thought he was ready for retirement. But nothing quite prepared him for what it revealed about identity and purpose.

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SINGAPORE: Last month was my first as a retiree.
For months, I had prepared for this transition. There were succession plans to complete, farewell lunches to attend and countless conversations about what life after work might look like. I believed I was ready.
Yet the first Monday morning on Jul 6 felt both liberating and strangely unsettling.
For decades, my days were measured by meetings, deadlines and decisions. Suddenly, there was nowhere I had to be. My calendar was empty. The steady stream of emails had stopped. In fact, the work email was no more. The phone that once buzzed often with requests for approvals and urgent decisions had fallen largely silent.
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Instead of driving into the office, I went for a long walk. I jokingly posted on LinkedIn that I had found my “new office” – a park bench with a splendid view of the sea. After years of being part of the morning rush, it felt refreshing to enjoy an unstructured morning.
The silence that comes with retirement, however, can be disorienting. I found myself asking a question that I suspect many retirees confront: What happens when work no longer defines who I am?
LEARNING TO CONTRIBUTE DIFFERENTLY
The impact of retirement on one’s sense of identity is real.
For those who have spent decades building expertise, the deepest reward is often the confidence others place in their judgment. Being consulted signals that experience matters. Over time, that validation can become intertwined with self-worth, until retirement breaks that link. This may be particularly true for men of my generation, whose sense of self has long been closely tied to their careers.
But contribution does not have to disappear with retirement.
One lesson for me has been recognising that retirement is merely a change in the way we contribute. Personally, I remain involved in board work, mentoring and writing on issues I care deeply about. In doing so, I hope to offer perspectives and encourage others to think for themselves.
For others, contribution can be in the form of caregiving, community service or simply being the steady presence that younger family members rely on. These roles may be less formal, but it does not mean they are less meaningful.
PREPARING BEYOND MONEY
We spend enormous effort preparing financially for retirement, and rightly so. But we pay far less attention preparing for it psychologically or socially.
Beyond money, retirement planning should also ask whether one has built an identity beyond work: friendships outside the office, interests not tied to professional success, relationships that do not depend on hierarchy, and opportunities to invest time in others without expecting continued dependence.
In many cases, the real challenge might not be having enough to live on but having enough meaning to live with. That is why preparation should include habits, relationships and routines that can survive the loss of title and timetable. These include a greater need to learn new skills from setting up the home laptop and monitors to connecting to the printer – all of which were previously delegated to the corporate IT department. Now, as a retiree, one takes on this new role single-handedly.
Families and close friends can help ease the transition. Over the past month, some of the most meaningful moments have been video calls with my granddaughters. The phone still rings, just for different reasons. Instead of discussing board papers or complex legal issues, I find myself admiring a drawing they have proudly completed or listening to an excited story about their day.
Those conversations will never appear in an annual report. Yet they now feel like the conversations that matter most.
BEYOND THE JOB TITLE
Just days before I retired, the retirement age in Singapore was raised to 64 and the re-employment age to 69. The changes, which took effect from Jul 1, makes the focus on retirement adequacy, lifelong learning and active ageing necessary and timely.
That said, if Singapore wants longer working lives to become better later lives, it must do more to treat retirement as a stage of social and psychological redesign, not just a point of financial exit.
That means continuing to improve work flexibility, lifelong learning and re-employment options. At the same time, investments have to be made in the “after-work” infrastructure of purpose: community platforms, volunteer pathways, mentoring roles and civic spaces that value judgment, not just labour.
In this case, employers and community organisations can do more by creating mentoring and advisory roles, part-time teaching opportunities and structured volunteering pathways that draw on experience without recreating old hierarchies.
They can also design alumni networks that are more than social clubs, giving former professionals a route back into contribution without placing them back at the centre of operations.
Retirees themselves will have to navigate the transition. Some adapt quickly; others find the change unsettling even when they are financially secure. I’m not going to pretend that I have all the answers after just one month. Perhaps it will take many more months, even years. But I have already learnt this much: A successful retirement is not measured by how long one remains in demand, but by the capacity to find meaning when that demand recedes.
Jeffery Tan recently retired after four decades in the legal profession. He remains a senior accredited director of the Singapore Institute of Directors and serves as chairman of SGListcos.
Source: CNA/sk
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