What I Talk About When I Talk About Walking
A walking reflection, Singapore-style. Title inspired by Murakami Haruki.
Singapore isn’t exactly known for its walkability, at least not the kind you see in big cities where people stroll breezily with coffee in hand.
Here, walking means SPF50, a hat, and a Decathlon quick-dry towel you might have to wring out halfway through your journey. It’s hot, humid, and more than a little sweaty.
And yet, I walk.
I used to cycle
Back in the pandemic years, Foolet and I clocked serious kilometres on my trusty $100 bike. We'd do weekend rides through the parks and park connectors, with Foolet strapped in snugly behind me. It was my sanity saver.
These days, with Foolittle still too young for the child seat, cycling’s on pause. So I walk. And walk. And walk some more.
From burnout to boots (on the ground)
I started because I was burnt out from startup life.
There was a stretch where I went nearly two years without taking a single day of leave. Not because I couldn’t, but because I felt guilty about it. (Naive, I know. Tsk tsk, Past Me.) Eventually, I realised that pace wasn’t sustainable, and as I began planning my transition out, I knew I needed something to look forward to. Something bold. Something absurdly specific.
Big Hairy Audacious Goals, as the business books say.
I turned to hiking, the “I need to work on my cardio” kind. When I trained for Mt Kinabalu and later Mt Fuji, it gave me an excuse to wander parts of Singapore I’d never explored before. It also meant I had no excuses as you really didn’t want to end up (too) winded trying to summit a mountain after you made _all_ the effort to get there. I still remember walking the Green Corridor more than a decade ago. It was quiet, serene, and it felt like I had the whole stretch to myself.
But then, my next job got in the way. So, after a brief 6 months, I didn’t get much time to walk again.
Despite all the greenery tucked into our little island, I felt that I never got to walk regularly in Singapore just because.
Until now, with Foolittle in tow.
Walking is a luxury
Not because it’s glamorous, but because it requires time. Walking is slow. It doesn’t promise efficiency. It doesn’t pretend to be productive. It’s the exact opposite of everything the modern world encourages.
But when you’re in the thick of parenting, that slowness is a gift. In those meandering 2–3 hour strolls, I find quiet. Not in the soundscape, there are usually trucks, birds, and small children involved, but in the rhythm of movement, of repetition, of simply going.
It's how I get my son to sleep
I walk because it puts Foolittle to sleep. Well, for 30 minutes at a stretch if I’m lucky. On a good day.
He’ll often sing to himself for a bit, then drift off while I frantically prep his feed one-handed and balance an overladen bag that feels like a badly-packed and over-packed camping trip. It’s chaotic, a little ridiculous, and yet, weirdly effective.
So I keep going.
I walk for the shrubs and shoots
I’m the kind of person who slows down to marvel at roadside plants. The ones with striped leaves. The unnamed climbers. The flowers you’ve seen a hundred times but never stopped to identify.
There’s something familiar in the steady greenness of Singapore. It’s a little wild, but tidy all at once. Obviously someone at NParks has got it all figured out, and that’s just the Singaporean way of doing things.
As a child, I was always fascinated by a particular kind of quiet rebellion, trees that pushed their roots determinedly against concrete pavements. I remember spotting them most clearly at East Coast Park, where the roots would slowly but persistently lift and crack the walkway beneath them. Over time, you’d see the paths rerouted ever so slightly, as if the planners had surrendered, just a little.
I used to wonder who had the last laugh. Because not only would the pavement buckle, but eventually the entire area might get dug up. There’s always some road to be widened, a storm drain to be dredged, and nature would get reshuffled once more.
I walk to think
This is where my brain reboots. Not at a desk, but mid-walk. That’s when the thoughts appear: ideas for writing, memories that rise to the surface, little existential questions1 I park for later. Sometimes all I think about is lunch and my grocery lists. And that’s okay too.
I also think about what I want to write in my Substack during these walks. Titles, phrases, stories I want to remember. Many of these weekly reflections begin as passing thoughts between traffic lights and playgrounds. Some get forgotten. The better ones survive long enough to be typed out during nap time.
Mostly, though, I walk to listen.
What I Listen To While I Walk
Listening to my inner voice too often for uninterrupted periods of time might trigger an existential crisis. Instead, here’s what often plays in my ears as I dodge scooters and sunburn:
Acquired – Stories of how great companies are built. From American Standard Oil to Hermès and Taylor Swift. The TSMC episode was the one that made me fall hard for long-form podcasting.
The Tim Ferriss Show – I started listening in 2016, and still dip in now and then. It covers a bit of everything, and when it lands, it really lands.
Dish and Table Manners – Food podcasts that are basically joy in audio form. Listening to people talk about meals they love? Surprisingly therapeutic.
Yah Lah BUT… – Singapore current affairs with a hefty scoop of irreverence. I appreciate how they say the things you’re thinking but might not dare to post.
Conan O’Brien Needs A Friend – Conan deserves his own tribute post. He’s always down for being ridiculous, not taking himself too seriously, always walking the line between absurdity and insight. It’s why his podcast took off during Covid, when we all needed a friend, but also needed to laugh at the madness of it all. The three amigos—Conan, Matt, and Sona—have chef’s kiss chemistry.
More tech & founder storytelling:
20VC (Harry Stebbings): Rapid-fire insights from VCs and startup founders.
The Generalist: Deep dives into individuals, companies and big ideas (we need more SG content like this).
Comfort & Growth (Crystal Lim-Lange): Thoughtful conversations on leadership and self-awareness.
Who We Are (Rachel Lim): Stories about identity, ambition and purpose, especially relevant for this season of life.
If you’ve any podcast recommendations of your own, I’m always up for expanding the queue.
Full circle, sort of
I’ll be heading off to Japan soon, where walking involves temple paths, cool breezes, and vending machine breaks. But before I trade sweat for the Japanese summer breeze and rain, I wanted to honour the humble, overheated Singapore walk.
It’s far from romantic but it’s real. And in many ways, it's brought me full circle.
From being desk-bound during my startup years to hiking up altitudes, I went from barely stepping out of the office to exploring mountains. Back then, I didn’t allow myself time. Now, walking has become something I fiercely protect, because it’s slow, and because it’s mine.
In those early months with Foolittle, I’d scramble to leave the house in the morning not just for fresh air, but so his newborn cries wouldn’t wake his still-slumbering older brother. Those quiet exits turned into long walks. Those long walks turned into a rhythm. And somewhere in between the naps, the feeds, and the podcasts, I remembered how good it felt to simply put one foot in front of the other.
& Today’s Brew
is an oldie but a goodie from Papa Palheta: a classic iced flat white made with their OG Throwback blend. Smooth and straightforward with a touch of chocolatey richness, it takes me right back to their early days at Hooper Road.
Back then, they didn’t even have a café license, you’d leave a “suggested tip” of $3.50 for your coffee (what a steal). I remember the little quirks: the old Mac sitting discreetly, the mismatched furniture, the baristas who actually talked to you about beans.
Fifteen years on, so much has changed, but that first sip still brings back the spirit of discovery that made it special.
Also includes minor existential crises, questioning of life’s bad (?) decisions such as who goes on a 13km walk with a stroller under the blazing hot morning sun?