Two months ago, I’d been meditating for 1,891 days.
That's over five years of unbroken practice. It’s the kind of streak that looks great on my phone’s lock screen, sitting pretty next to my journaling habit.
It sounds impressive, until you realized I’d rarely sat longer than it takes to boil an egg.
So, when my cousin mentioned wanting to try 60 minutes of meditation for 60 days — my first instinct was to balk.
“I already meditate,” I said, a little defensively. “Every day.”
Anyway, we started looking at posts from people who’d done this.
Naval Ravikant, who undoubtedly started a movement about this
Reddit threads full of profound insights and spiritual breakthroughs
A lovely insight from David Kadavy, about the barbell strategy
In all, the kind of transformation stories that make you feel simultaneously inspired and inadequate.
By the end of our call, I heard myself saying: “Okay, let’s do it. Sixty minutes a day. Sixty days straight.”
(My competitive streak really needs better supervision.)
The first session was… humbling.
I set my alarm for 5:30am — the only way to carve out a full hour before the day got noisy. I wake up around 6:30am, so this was tough, and it felt like the math wasn’t working out.
20 minutes in, and my mind started its usual thing: grocery and to-do lists, and decisions I’ve been putting off came through.
30 minutes, and my back started to protest.
At 36 minutes, I opened my eyes, convinced my timer had malfunctioned.
(It hadn’t.)
Here's what five years had actually taught me: I'd been playing on easy mode.
Remember the egg boiling thing I was referencing? Most of the time, I did 10-15 minute sessions. Sometimes just 5 when I was "too busy."
Enough to check the box, maintain the streak, and feel enlightened without actually, you know, sitting with anything difficult.
I’d turned ancient practice into another productivity hack.
What I have is what I have.
This thought bubbled up, sometime in the second week.
It's embarrassingly simple. The kind of thing you'd see on a minimalist Instagram post, overlaid on a photo of succulents.
Yet, somehow profound in my mind. Like an oh, shit, that’s right moment. Maybe it landed differently in my head because I finally had to sit with it long enough to actually hear it.
Strangely, I managed to keep the practice going through the two trips to Japan and China. I found quiet corners in hotel rooms, woke up at dawn overlooking sunrises, and even a session during a flight.
Vacation-me was disciplined, proud (smug?) that I was sticking with it.
But when I returned home — to my familiar space, my regular chair, my normal life — the whole thing threatened to fall apart.
“Maybe just 45 minutes today?”
“Could I split it into two sessions?”
“Who's really counting?”
As if the different locations had provided their own kind of motivation, and now I was left with just... me, and my resistance.
On one of the days in the dreaded middle, I experienced something new: existential doubt.
Not the familiar “I don't have time" resistance I'd conquered before, by waking up early. This was different.
What was I actually doing here?
What was the point?
Was this just another way to feel superior about my morning routine?
The hour felt increasingly like theft. I could already be at the gym already. I could have written 1,000 words by now. I could be checking things off my to-do list, making tangible progress on... anything.
Instead, I was sitting. Still. Watching my mind do simultaneously nothing, and everything.
In my shorter practice, I'd never sat long enough with discomfort to reach this edge.
Fifteen minutes? That was manageable; a micro investment.
But an hour felt like a luxury I couldn't afford, even though I was the one who'd committed to this challenge to learn something, about anything at all.
But I persisted.
This isn’t a story about willpower or discipline, though — those had abandoned me somewhere around day 40.
It was sheer stubbornness. It was not wanting to admit to my cousin and myself that I'd given up. And it was about giving in to the sunk cost fallacy of having already gone through through 40-something early mornings.
Sometimes our worst traits are our best allies.
Day 61.
I sit down on my chair. But today, I set my timer for 20 minutes.
It feels strange, like that feeling you get after wearing shorts working from home, and having to put on pants to go to the office.
Part of my brain yells: This is failure! Go forward! Level up, not down!
But that’s the dopamine addict talking; the one that turned sitting still into a competitive sport.
There’s a framework I’m building called the full stack, about designing life systems that work with you, not against you. One of its core principles:
Sustainable systems beat heroic efforts.
Twenty minutes isn't the same twenty minutes it was before. The hour-long sessions rewired something. Like a musician who drills scales for hours but performs in minutes — the depth stays in the fingers.
My cousin was right to nudge me past comfortable. I was right to take the leap. And I’m right now to recalibrate.
Those stories we read promised life-altering insights. Maybe some people get those.
I didn’t. Not exactly.
But I got this: Even the rituals we sit comfortably in have more to teach, if we’re willing to stay.
Here's what I know now:
I spent 1,891 days building a streak. Somewhere along the way, the streak started building me — into someone who confused consistency with depth.
The 60-day challenge broke something open. Not in the cosmic kind of way (that I was kind of hoping for), but in the way that failure sometimes does: it showed me what I'd been avoiding.
What I have is what I have.
And what I have now is different: twenty minutes that know what sixty asked of me. A practice less about the streak, more about the sitting. Even when that means scaling back.
Day 1,954 of something.
But who’s counting?
(Still me, actually. Old habits die hard and I still love a good streak. But now the streak isn’t proof of anything — just a quiet reminder: the practice will keep practicing me.)
Other things
This week’s experiment: Very softly launched Jalyn-as-a-service (yes, it’s exactly what it sounds like) with a one-pager to circulate amongst my friends and test the concept, and it turns out — yes. People do want help untangling their finances, redesigning their exit plans, or finally figuring out what’s next.
If you’ve been half-joking about quitting your job but also secretly spreadsheeting your runway... this might be for you. Want the link? Let me know.It’s been all about politics this past week: here in Singapore, where the status quo remained hard (ruling party with ~66% vote share, but 89% of Parliament seats, ah well), and the progressive victories in Australia and Canada.
Wild to hold tension for all of that, all at once. Mostly just reminding myself that beyond my one vote in my constituency, there’s not a lot I can control. Onward and upward (hopefully)!
Until next time,
Jalyn