What success looks like
I’ve thought about it plenty — lying awake, on the commute, in the shower — but never actually put it into words. So here it is. My honest answer to the question most people never stop to ask themselves properly.
What does success actually look like for me?
A day in the life at 50
When I imagine myself at 50, my kids will be 16 and 14. Secondary school. Old enough to not need me for everything, but maybe young enough that they still want me around sometimes.
In that version of life, I’m not grinding a daily commute squeezing with people on the MRT. I’m not sitting in a corporate meeting wondering what I’m doing there. I will be at a kopitiam having my kopi and wanton mee in the morning, unhurried. Maybe I drive across to JB for a massage and a round of pickleball with my wife or golf with my friends. Maybe I take a short holiday every quarter to breathe in the air in another country. If I’m working, it’s because I’ve chosen to — consulting on something I actually know, or running something small that helps people — not because I need the money to pay the bills next month.
That’s it. That’s the image. It’s not dramatic. It will just be another morning with no anxiety about where the money’s coming from.
On work
If money genuinely wasn’t a factor, I don’t think I’d stop working entirely. But I’d never do a 9-to-5 corporate job again.
What I would want is work on my own terms. Running my own business, volunteering, something that helps people, where I’m in control of the direction and not waiting for someone above me to decide my fate.
The thing I’m most tired of isn’t the work itself. It’s not knowing where it leads. I’ve been working for 12 years and I still can’t draw a clear line from where I am today to where I want to be professionally. That uncertainty is exhausting in a way that the work itself never is. If I were a professional footballer, I’d train all day — because there’s a clear identity, a clear purpose, a clear measure of progress. Corporate life rarely gives you that.
I want to figure out how to build something that I can own. Not because I’m greedy, but because I want to be in control. Not reliant on any single employer, any single salary, any single person deciding whether I’m worth keeping around.
What “enough” actually feels like
I’ve put numbers on this before — $2.5M for functional independence, $5M for full comfort. But the number was never really the point.
Enough feels like this: I can quit my job, do nothing for a week, and not feel the anxiety creeping in. Not checking my bank balance nervously. Not calculating whether I can afford something before deciding if I want it. Just — space. Room to breathe and think without the background hum of financial pressure.
Will $2.5M get me there? Probably yes. At 5% withdrawal that’s $125,000 a year — more than enough for a comfortable life if the big expenses are under control. $5M is very comfortable. At that point, the passive income buys me genuine freedom — to go where I want, do what I want, answer to nobody.
But if I’m honest, the number isn’t what I’m really chasing. I’m chasing the feeling. The feeling that I’ve built something solid enough that life can’t be pulled out from under me by a retrenchment letter or a bad year.
What I want for my kids
This one I’ve thought about a lot.
I want to give them a headstart — but I’m deliberate about what that means. I don’t want to give them so much that they lose their sense of purpose, that they never have to work for anything, that money becomes something that happens to them rather than something they understand and manage.
What I actually want is for them to never feel the anxiety I feel about money. To reach adulthood with enough of a foundation that they can choose what they want to do with their lives — not what pays the most, not what’s safest, not what I or anyone else thinks is practical. Just what they actually want.
Reflecting on my pre-uni days, the sports science path I didn’t take — I think I made that choice partly out of financial fear to go on a safe path. I don’t want them to make decisions from that same place. That’s the headstart. A kind of freedom I didn’t fully have.
What about this site?
I don’t know if anyone will ever read this. That’s the truth.
But writing it down does something for me that thinking about it never quite does. It makes it real. It makes me accountable — to myself first, and maybe to whoever stumbles across this later. It’s part journal, part plan, part autobiography of someone who hasn’t figured it all out yet but is trying to one word at a time.
In time, someone out there will read this and recognise themselves in it. Not because I’ve achieved something impressive, but because I’m struggling with the same things they are — and they’ll feel a little less alone in that.
And in five years, I want to look back at what I’ve written here and see that the plans I made weren’t just words. That I moved closer. That the trajectory bent in the right direction, even if slowly.
That, too, is what success looks like.
- A typical morning at 50 with nowhere urgent to be and no financial anxiety
- Work that’s chosen, not compelled — preferably a business I own or through volunteering
- $2.5M–$5M in net worth — not for the number, but for the feeling it buys
- Kids who can choose their path without fear and having the headstart I didn’t fully have
- This site as proof that the plan existed, and that it worked