A Stranger, a Shared Table, and a Lesson in What Retirement Happiness Actually Costs

The Wife and I went out in the late morning and wandered around a nearby hippy neighbourhood. By lunchtime, we found ourselves hiding in a shopping mall to escape the tropical heat and enjoy the AC – which supposedly helped build Singapore to where it is today.

We decided on a drink at the food court, packed with the weekend lunch crowd. Since returning to Singapore, we have quickly realised that it is now easier to find a table in a food court because it is only the two of us, without the kids. But with the weekend crowd, even this small benefit did not play to our advantage today.

In the end, we asked to share a table with a solo diner. As I went to order our drinks, the Wife struck up a conversation with the gentleman we were sharing with. His name is Dave, and he is from the US. We chatted about his work – he managed manufacturing operations for a US company with a plant in this part of the world, and along the way we learnt something about welding 100mm thick steel from the trade he oversaw. Then we found out he is retired. And it sort of became an impromptu interview.

Dave worked across this part of the world – Indonesia, Malaysia, Singapore – managing manufacturing operations that made mining equipment, hence the welding of thick steel, right up to his early retirement a couple of years back. He is back to visit friends and, more importantly, to escape the summer heat back home. He does this twice a year – when it gets too hot, like now, and when it gets too cold, at year end. Dave is originally from Wisconsin but now calls the high deserts of Arizona home. The seasons give him a good excuse to fly back and reconnect with old friends.

Since retiring, Dave has been keeping busy flipping houses. As a hobby. I think it is a good idea to have a hobby that pays, and some good money at that. It is something I have on my own back burner, though more in Australia than in Singapore, since the economics is just different – if legality still allows by then. Because it is a "hobby" and not work, Dave is pretty chill about it. When he is away, work just stops altogether. He is fine to pick it up again in a month or two.

Being an engineer by training, he does some of the work himself. The more technical parts, he project manages the trades against a schedule and plan he drew up himself. He reckons each project takes about 18 months at this pace. Going forward, he thinks it will get harder to find a "cheap" property to flip, since houses have generally gone up in price, even the crappy ones. Combined with higher material costs now, most projects simply do not leave enough margin for the risk and effort.

Another activity Dave takes up is cycling. Health and fitness was not something he focused on during his working years, he said, but it is something he has been advised to prioritise now. I asked if he does any strength training – I really think this is needful as we age, and the Wife and I are looking to start in the near future – but he finds the gym too boring. Instead, he rides a hybrid bike that lets him take in his surroundings and discover new places. It has some electrical assist to give him a boost on an upslope, so he can go further. He has ridden the ever-growing Park Connectors here and highly recommends we try it.

While it seems Dave has his retirement time reasonably well filled, there are many days in between when he does nothing much at all, and wonders at the end of the day what he has "accomplished." Not in a guilty way. Some days he just enjoys a book. He does sound like a man enjoying a slower pace of life, comfortable being happy doing nothing on some days.

We did not get too "deep" to ask about his financial or investment plans, or whether he will go back to work someday. But sitting across from him, sharing a table by chance, it struck me that we did not need to. Happiness, it turns out, is not something you can only read off a balance sheet. Dave seemed settled and content in the telling of his own life, in the unhurried way he talked about a book left unfinished or a road he had not yet cycled. That his flipping "hobby" happens to produce an income probably helps – it is easier to be relaxed about money when money is quietly still coming in – but it was not the thing he measured his days by.

It is a useful correction for someone who spends a fair amount of newsletter real estate on withdrawal rates and portfolio math. The numbers matter. But they were the one subject we never got around to, and the conversation was richer for it.

As Dave finished his wanton noodles, we bade him farewell as he left for a haircut with a barber who has become a friend over the years. Only after he left did it occur to me that perhaps I should be more prepared for the next impromptu interview – not with a list of questions, but with a better sense of where the line sits. How deep is too deep, with a stranger who has generously let you into an hour of his life over lunch? I do not have a rule for that yet.

Where do you draw the line with someone you've just met – curious enough to ask, careful enough not to pry?

👉 Hit reply and share your thoughts – I’d love to hear what’s resonating with you.

☕ Sharing a table with a stranger cost us nothing but a seat, and gave us more perspective on retirement than most articles do. If these weekend reflections are worth a coffee to you, consider buying L-Plate Retiree a coffee on Ko-fi.