February Reflections • Winter's Hangover

#03 | February 2025

Apr 11, 2025

Last Month, In a Thought

February refused to die.

The sky hung low and grey over Toronto, the wind biting deeper than it had all winter. This wasn't just typical February blues. This malaise cut to the bone.

The cold wasn't the enemy. It was how it shrunk everything—mind, ambitions, energy—all caving in like dirty snow banks at sidewalk edges.

February in Toronto strips life down to grayscale. This year, I finally mapped its pattern:

Mental fog turned simple decisions into calculus.
Low-grade irritability hummed beneath every interaction.
Quiet despair that stained everything it touched.

I was tired of winter.

Not just this winter, but the predictable emotional weight that descends every year. The absence of light eventually becomes the absence of optimism.

The thought hit like arctic water: I was surrendering half my life to this freeze. 5-6 months annually, sacrificed to emotional permafrost.

I didn’t want to do this anymore. Not this scheduled numbness. Not for thirty more winters. Not for ten. Maybe not even one.

I need to find another way. Another place. Another rhythm to my year.

When my energy bottoms out like this, my emotional regulation goes with it. I slip back into old patterns: needing to win every argument, fighting battles that don't matter, trying to control everything around me precisely because I can't control how I feel.

I've been working on letting go, but February showed me how quickly I can slide backward when depleted.

As the month finished wringing me out, my long-awaited escape finally arrived. The trip had been on my calendar for months: Singapore first, then Bali.

This wasn't tourism. This was reconnaissance: a calculated hunt for belonging. Singapore had been calling me at a frequency I couldn't quite explain. I needed to know:

Would my particular voltage make sense here?
Would these people recognize parts of me that lay dormant elsewhere?
Could my edges and ambitions find purchase in this soil?

Every conversation would be both casual and critical. Every connection, a data point.

(Bali would come later. But that's for next month's telling.)

So at the end of February, I dragged myself onto a plane for a brutal 21-hour flying marathon. The 12-hour time difference hits like cognitive whiplash: body stuck in yesterday while eyes see tomorrow.

After months of winter's drain, I could finally breathe again. ("Breathe" might be generous in Singapore's soup-like atmosphere.)

Singapore: A Glimpse of Effortlessness

My first morning in Singapore was brutal.

Arrived at 1:30 a.m., slept by 3, awake again at 6. FML.

So I ran. 11km along Marina Bay in the pre-dawn light, watching the skyline gradually materialize through the filthy humidity.

My heart rate variability (HRV) bottomed out to a number typically reserved for zombies in cardiac arrest, and my heart rate bounced around like someone who'd mainlined six espressos and a line of coke (to be crystal clear: as a physician, I've only observed such effects professionally).

My smartwatch was one abnormal reading away from calling an ambulance.

But something in me didn't care.

Post-run, the Mandarin Oriental's quiet efficiency collided with my physical wreckage. Staff read my micro-expressions like code. Each slight posture shift summoned attention that never intruded. They knew my name before I spoke it.

It was a hug from the universe that allowed me to exhaled fully for the first time in months.

Later that afternoon, I found myself in the hotel’s private lounge.

Floor-to-ceiling windows framed the city below. The late afternoon sun streamed in at the perfect angle, warming my skin while I sat with music in my ears, half-working, half-daydreaming.

The staff moved with almost supernatural awareness. My champagne glass never reached empty before being silently refilled. Satay skewers and appetizers materialized beside me without interrupting my flow.

I finally had to ask them to stop pouring after the third glass.

It wasn't the luxury itself that got to me. It was the complete removal of friction from existence. No decisions to make. No needs to articulate. Just... being. A kind of effortless presence that clarified something I've known for years: this quality of existence—this removal of unnecessary friction—needs to be my default state, not my escape.

The reset was necessary, but I also had real work to do.

Testing Waters

One reason I was in Singapore was the Founder’s Forum: an event for people building in the longevity space. I came to observe the landscape and connect.

Despite struggling to keep my eyes open from jet lag (one colleague joked, "Who kidnapped your family and forced you to come here?"), I met some of the people I wanted to meet.

It wasn't transformative, but it served its purpose, showing me who was building what, and get a feel for the energy.

Between ex-doctors with camera obsessions, wellness enthusiasts whose biceps could lift a small car, and quiet builders crafting the future from coffee shops, each connection added another pixel to the picture. Some building empires from laptops, others reimagining what's possible in longevity, all part of testing whether this could be one of my homes.

That evening at a restaurant called Appetite, I fell into an hour-long conversation with the restaurant manager. What started as small talk evolved into a rich exchange about food cultures across Asia: debating cities, cuisines, and reputations.

But the conversation that stuck with me most happened earlier in my trip, with Alex Loh: former water polo athlete, now coaching executives on growth mindset.

What began as a casual discussion about Singapore's business landscape shifted into something more fundamental.

On Growth, and the Art of Walking Away

"What does growth mean to you?" Alex asked.

"Growth means being able to walk away," I said, skipping the expected metrics and achievements speech.

I've spent years learning how to walk away from things. Sometimes I nail it. Often, I don't.

The hardest things to walk away from aren’t obvious disasters. They’re golden handcuffs: jobs that pay well but quietly hollow you out, relationships that look perfect but leave you numb, identities you’ve mastered but outgrown.

A decade ago, my dad sent me a Deepak Malhotra speech that I still watch each year. His message to Harvard MBAs was delightfully subversive: “Become the best quitter you know.”

What makes the handcuffs so sticky isn’t the gold. It’s the terror of becoming a beginner again. Trading mastery for mediocrity. Competence for confusion.

That voluntary demotion might be life’s most profound growth opportunity, and the one we dodge most skillfully.

Growth means learning to abandon your summits. It means climbing down from peaks you've conquered, swallowing the vertigo of the valley, and starting fresh on mountains that don't care about your previous altitude. Not because your old peak wasn't high enough, but because it stopped being yours.

People tell me I'm good at cutting my losses, that I don't fall prey to sunk costs the way others do. Maybe that's true comparatively, but it brings me no comfort. I'm still too slow. I still cling longer than my intuition says I should.

There’s that scene in The Dark Knight Rises where Bruce keeps failing to escape the pit, until he climbs without the rope. No fallback. No safety net. Only then does he make it.

Some leaps demand that. No hedges. No overthinking. Just full conviction. The older you get, the harder that becomes. You trade instinct for calculation.

I think that’s where I find myself now: hedging. Protecting my downside. But I’m beginning to see the truth: I'll keep existing in the negative space of my ambitions if I never let go of the rope.

Digital to Physical

Part of testing Singapore as home meant finally meeting people I'd known for some time online, turning pixels into people.

One evening, I met up with Kuriakin Zeng and Nat Lee, fellow writers I knew from David Perell's Write of Passage community. We claimed a corner in a taco joint and fell into one of those conversations that leaves no trace except sore face muscles and a lingering warmth.

I can't even remember what we talked about: shamans? Sketchy wellness gurus? Giant mosquitos?

My brain kept the joy but ditched the content. What remains is laughter that came from somewhere deeper than my chest, time compressing while we weren't watching.

No agenda. No pretense. Just three people trading absurdities until we forgot we were supposed to have important thoughts.

Then there was Deepti Chopra, the software engineer who built a successful SaaS business while treating it like a hobby project, now crafting something bigger between last-minute flight bookings.

The kind of person who books international travel the night before and finds hotels post-landing. She vanished to India as I landed in Singapore ("Oh, you're here? Urgent matter in... frantically opens Expedia... India!").

We finally collided in Bali. Even chaos merchants run out of continents eventually.

There were others too. Curious minds building unlikely futures, quiet architects of better systems, people whose stories deserve their own pages but will have to wait. Each conversation added another pixel to my belonging hypothesis.

Somewhere in between the reflection and the running, I also dropped by to see my Singapore tailor. It had been a year. We talked shop, caught up on life, and I finally commissioned a pair of herringbone linen pants I’d been meaning to have made for years. A small thing, but it felt like a nod to future summers and to re-emergence.

Maybe That Was Enough

Maybe this month was quieter.

Nothing shipped. No big decisions. No profound insights. No new projects launched.

And yet.

Something shifted. The fog I'd been carrying since January began to lift. I noticed old thought loops and actually stepped out of them instead of riding them to their usual conclusions.

I let certain tensions remain unresolved rather than forcing clarity where it wasn't ready to emerge.

And in the best moments, where time seemed to bend around me, I remembered what it feels like to simply exist without wanting.

Not happiness exactly, but contentment without condition. A temporary suspension of striving.

That counts too.

March looked quite different. I’ll write about that next week.

But February?

February was a long goodbye to a mood I didn’t want to carry anymore.

`Sweat Equity`

Strength went up. Running dipped. No major insights — just slow, steady work. Nothing flashy this month, but sometimes the most useful blocks are the boring ones.

Mileage: 84 km

Workouts Logged: 21/28 days active

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Yes, this is February’s issue. Yes, I know it’s April. I made a deal with myself to write one of these each month. Time keeps rolling whether you track it or not. Writing these is just my way of refusing to let a whole month vanish without a trace. Even when nothing big happens, something always shifts. And I’d rather catch it than let it rot at the bottom of my subconscious.