I was recently at a conference in the United States, listening to Dr Joe Coughlin, the founder and director of the MIT AgeLab. He paused mid-presentation and asked the room a question that was not about interest rates or portfolio allocation. He asked this: “What will you do on Tuesday at 10:30am?”
The room went quiet.
He was not asking about a particular Tuesday. He was asking about every Tuesday after you retire. No meetings. No commute. No deadlines. Just a morning, wide open, with no structure to fill it. Most of us spend years, sometimes our entire working lives, planning our finances for retirement. Almost none of us plan our “Tuesdays”.
That gap, I believe, is the real retirement risk that few people talk about.
Singapore is ageing fast. According to Singapore’s National Population and Talent Division’s Population in Brief 2025 report, citizens aged 65 and above now make up 20.7% of our population, up from just 13.1% a decade ago. And according to the Singapore Department of Statistics, a Singaporean who reaches 65 today can expect to live a further 21 years on average. By 2050, the elderly are projected to make up a third of our total population.
What this means, practically, is that retirement is no longer a short epilogue to a working life. For many of us, it will last as long as our entire career did. And yet the way we plan for it has not caught up with this reality. We treat retirement as a destination, a number to hit, a date to reach, when it is really the beginning of a completely different kind of life, one that will pass through several distinct phases: the early years of figuring out who you are without a job title, the middle years of navigating big decisions about health and housing, the later years of managing increasing complexity, and eventually, end-of-life considerations. A wealth plan that treats all of this as a single event is planning for the wrong thing.
Dr Coughlin offered three questions he said can reveal more about your true retirement readiness than any financial projection, and I have been thinking about them ever since.
Who Will You Have Lunch With?
This is a question about community. About whether you have a life that exists independently of your workplace. According to government projections cited by Frasers Property, more than half of Singaporeans aged 60 and above have reported feeling lonely, and the number of seniors living alone is expected to rise from 77,000 this year to 92,000 by 2030. Loneliness in later life is not just emotionally painful but the research consistently links it to faster cognitive decline and poorer physical health.
When we are working, community comes built-in. Colleagues, meetings, and the daily rhythms of an office or a team give us connection without us having to engineer it. The moment we retire, all of that disappears overnight. If you have not built a community that exists outside of work such as a church, a hobby group, or close friendships that do not depend on a shared employer, then retirement can become isolating very quickly. This is something to build now, not after you retire.
How Will You Get an Ice Cream Cone?
This sounds like a strange question. It is not. It is really asking whether you have thought about independence, mobility, and access to the small pleasures that give daily life its texture. We plan carefully for major medical events. We almost never plan for the gradual loss of the ability to get around on our own, whether to the hawker centre, the clinic, or a grandchild’s school concert.
Think about where you live today. Will that home and that neighbourhood still serve you well at 80, not just at 65? If you can no longer drive yourself, do you know how your life will need to adapt? These are not morbid questions. They are practical ones. The retiree who has thought through these things will navigate that transition far more gracefully than one who has not.
Who Will Change Your Lightbulbs?
This question is about your people. Not just your spouse, who will face the same limitations you do as time passes, but your wider circle of support for the small, practical things that make independent living possible. It also surfaces something I think many Singaporeans carry quietly: the fear of being a burden to their children.
That fear deserves an honest conversation with your family but first, with yourself. Do you have a plan that does not place all the weight on one person? Have you thought about what care arrangements you might need, and how you would fund them?
During COVID, many of us got an unexpected preview of retirement. Suddenly, there was no structure, no commute, no colleagues. For some, it was a relief. For many, it was deeply disorienting. Imagine that disorientation stretched across 20 years. That is the quiet risk that no financial calculator will ever capture.
According to the Singapore Department of Statistics, Singapore’s fertility rate now stands at 0.97, among the lowest in the world. Smaller families mean thinner informal support networks. The responsibility of planning for a full and good retirement life falls increasingly on each of us individually.
The good news is that these questions have answers. But they require the same deliberate attention we give to our finances. The retiree who knows who they will have lunch with, how they will get around, and who their people are is far better prepared than the one who has a well-optimised portfolio but has never thought about their Tuesday.
Retirement is not a finish line. It is the start of something new. Plan for the life, not just the money.
The writer, Christopher Tan, is Chief Executive Officer of Providend Ltd, Southeast Asia’s first fee-only comprehensive wealth advisory firm and author of the book “Money Wisdom: Simple Truths for Financial Wellness”. He is also a Certified Ikigai Tribe Coach.
The edited version of this article was published in The Business Times on 22 May 2026.
For more related resources, check out:
1. Why Chasing a 100% Retirement Success Rate May Cost You More Than You Think
2. I’m in My 60s—Here’s the Advice I Wish I Knew in My 50s
3.The 5-Year Runway to Retirement: What Pre-Retirees Should Start Doing Now
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