On Your Own Terms · Post 5 of 6
Not what looks good. Not what’s productive. What actually does it.
Most people in their 50s can tell you exactly what they’re good at. Far fewer can tell you what they genuinely enjoy. Not what they’re supposed to enjoy. Not what looks responsible on a retirement plan. What actually lights them up.
This is not a character flaw. It is the predictable result of spending two or three decades in a life where there was no room to find out. Work filled the days. Family filled the evenings. The question of what you’d do with a completely free afternoon never needed answering — because there was never a completely free afternoon. Until now.
Why this is harder in Singapore
Singapore’s cultural script is unusually focused on productive output. Hobbies that don’t produce something — income, status, visible achievement — tend to get squeezed out early and quietly. The child who loved painting stops when exam pressure arrives. The young adult who ran for joy starts running races, then stops when the competitive drive fades. By the 50s, many people genuinely don’t know what they do for pure pleasure, because pure pleasure was never really the point.
Andrew, who retired at 53, was honest about this when reflecting on people who struggle in retirement:
“People with a lot of hobbies and passions will automatically find things to do — it will fall into place. But people who don’t have much to do… retirement may not be a good thing for them. At least not the kind where you stop everything.”
— Andrew, retired at 53
He is not being uncharitable. He is pointing to something real: the transition is much smoother for people who already have threads of genuine interest running through their life outside work. The question is what to do if those threads are thin or hard to find — and the answer is not to wait until after the leap to look for them.
You don’t have to know before you start
Some things were already there, waiting. Ben, who retired at 65, had several: sourdough baking, gardening, sewing, travel. He had been building these alongside work for years. The transition was smoother partly because the foundation was already in place.
But crochet — now one of his most absorbing hobbies — came from nowhere. He didn’t plan it. He didn’t set out to learn a new craft. He noticed his grandniece crocheting at a New Year family gathering, got curious, asked her what she was doing, and went to YouTube that evening to find out more.
“I just got hooked. I bought so much yarn, I did so many projects. I did bags, I did bouquets — you fold them and they become a proper flower arrangement at the top. I love projects. I’m quite good at it now.”
— Ben (not his real name), retired at 65
One family gathering. One question. One YouTube search. A hobby that now fills hours each week and produces things he gives to the people he loves. None of this was planned. It was discovered — by a person who had the time and the curiosity to follow a thread and see where it led.
The discovery approach: try first, decide later
You don’t need to know what brings you joy before you make the shift. You need to be curious enough to find out. Our earlier post, Stop Planning. Start Prototyping., covers the experimental approach in depth — the idea that small, low-stakes tries produce more useful data than any amount of thinking. The same logic applies here.
A few questions worth sitting with:
What did you love doing before work and family took over? Not nostalgia — a genuine question. What made time disappear when you were younger? Some of those threads are still there, just buried.
What have you always been curious about but never had time for? Not what sounds impressive — what actually pulls at you when you see someone else doing it.
What do you do in the margins of your current life — the things you squeeze into weekends or holidays — that you’d do more of if you could?
What have you noticed others doing — at a family gathering, on a trip, in a conversation — that made you think: I’d like to try that?
The last question is Ben’s. He didn’t plan to take up crochet. He just stayed curious. That quality — the willingness to be interested in what other people are doing — turns out to be one of the most useful things you can bring into this chapter.
Some things won’t wait
Not all experiences are equal when it comes to timing. Some things genuinely don’t depend on your physical condition — reading, learning languages, cooking, deepening relationships, mentoring, creative work. You can do these at 70 or 80 with the same richness as at 55.
Others are health-dependent. They require your current level of physical capacity — and the window for them is shorter than most people acknowledge.
At 45, I decided I was never going to be this young again, and signed up to learn snowboarding. The learning curve was brutal — falling and falling, bruises after every session, an injured shoulder from one particularly memorable tumble that still twinges at certain angles four months later. No regrets. Not because the injuries were worth celebrating, but because doing it at 45 was possible. Doing it at 65 would be a different calculation entirely. Better to have tried while the option was still genuinely open.
The experiences that fall into this category are personal to each person. Open-water swimming. Long-distance trekking. Learning a physically demanding sport. Travelling to places that require stamina and agility. Carrying your grandchildren on your back. Not all of these require peak fitness — but they do require a certain baseline that declines with time, however gradually.
The Die With Zero framework is useful here: Bill Perkins argues that experiences have a natural time-sensitivity that money alone can’t override. All the savings in the world won’t give you back the knees of your 50s. The question is not just “what do I want to do?” but “what do I need to do now — while I still can?”
The permission problem
Many people in this position know, somewhere, what they want. The obstacle isn’t discovery — it’s permission. Permission to want something that isn’t productive. Permission to pursue something that doesn’t generate income or social status. Permission to say “I do this because it brings me joy” — which, in Singapore’s achievement-oriented culture, can feel almost like an admission of something.
It’s worth naming directly: the things that genuinely bring joy are often quiet, personal, and not designed for an audience. Ben’s crochet flowers handed to family members. Andrew cataloguing and listening to 700 vinyl records during a slow year. CH’s board games with a rotating table of friends, the same people month after month, year after year. These things are not for generating social currency or Instagram likes. They are real, they are sustaining, and they matter — to the people doing them.
That is enough. That has always been enough. The shift to a self-directed life is, in part, the shift away from needing the world to validate what you spend your time on.
A question to sit with
If you had a completely free week — no obligations, no one to impress — and you had to fill it with things that brought you genuine joy, what would be in it?
Now ask a harder version: which of those things require your current level of health and physical capacity? Which of them, in other words, are you doing this decade — or possibly not at all?
That second list is where Post 6 begins.
Post 5 of 6 · On Your Own Terms
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