We Didn't Plan This – The Podcast for People Who Ditched Their Five-Year Plan
Sep 19, 2026 · 28 min · 10 segments
Faith and Isaac talk turning 30 without the milestones they expected — no house, no five-year plan, no certainty. A raw conversation about comparison, professional identity, and choosing free time…
I guess the first question we'd love to talk about, right, was what did you think turning 30 would look like when you were a kid? And how does it feel now?
Oh gosh, I think I was a very unexciting kid, you know.
I had the very traditional Singaporean dream because that was everything that was sold to us, right? Like you see everyone else around you, your parents, your aunts and uncles, your grandparents, everyone just settling down right after university and then just following the path of house, kids and then you work, work, work and then you retire.
So I thought that I would end up down the same path.
Like, you know, like my parents maybe become a specialist doctor at 30 and then I'll have a kid after that.
Everything's so meticulously planned out.
But somehow here I am at turning 29 soon and I do not have any of that figured out.
No house, no marriage or kids, nothing.
So it's a blank slate and it's scary but exciting.
Yeah, how about you?
I think when I was a kid, the age 30 didn't even exist in my realm of imagination.
To me, turning 21 was adulthood.
And that signified a few things.
Maybe a job, a degree, maybe some degree of...
I had some vague ideas of what the material trappings of that might look like.
Maybe... a house, plus minus a car, or whatever.
But basically, I think the theme to all of that was that when I was in my late 20s, which we are also unambiguously and undebatably in right now, it felt as if we would be certain or we would be 100% fixed on whatever we were doing at that point.
Obviously, at that point in time, you have no concept of how long it takes to progress in a certain career or whatever, but you still roughly think that that is an age where stability truly takes root.
And I don't know, when you thought about that, Was there a version of, you know, it sounds like you had a pretty detailed picture, time sensitive as well, that you ascribed to back in the past.
Was there any part of that that didn't come to fruition in the end or just didn't show up?
Yeah, you know, I had a five-year plan completely planned out.
When I started med school, I was like, okay, right after med school, I will train to become a psychiatrist or something.
And then after that, life will all fall into place in the perfect order, exactly as I planned it.
But then obviously, life has not turned out in such a way.
And yet I decided, oh, this path is not for me.
I guess the first question we'd love to talk about, right, was what did you think turning 30 would look like when you were a kid? And how does it feel now?
Oh gosh, I think I was a very unexciting kid, you know.
I had the very traditional Singaporean dream because that was everything that was sold to us, right? Like you see everyone else around you, your parents, your aunts and uncles, your grandparents, everyone just settling down right after university and then just following the path of house, kids and then you work, work, work and then you retire.
So I thought that I would end up down the same path.
Like, you know, like my parents maybe become a specialist doctor at 30 and then I'll have a kid after that.
Everything's so meticulously planned out.
But somehow here I am at turning 29 soon and I do not have any of that figured out.
No house, no marriage or kids, nothing.
So it's a blank slate and it's scary but exciting.
Yeah, how about you?
I think when I was a kid, the age 30 didn't even exist in my realm of imagination.
To me, turning 21 was adulthood.
And that signified a few things.
Maybe a job, a degree, maybe some degree of...
I had some vague ideas of what the material trappings of that might look like.
Maybe... a house, plus minus a car, or whatever.
But basically, I think the theme to all of that was that when I was in my late 20s, which we are also unambiguously and undebatably in right now, it felt as if we would be certain or we would be 100% fixed on whatever we were doing at that point.
Obviously, at that point in time, you have no concept of how long it takes to progress in a certain career or whatever, but you still roughly think that that is an age where stability truly takes root.
And I don't know, when you thought about that, Was there a version of, you know, it sounds like you had a pretty detailed picture, time sensitive as well, that you ascribed to back in the past.
Was there any part of that that didn't come to fruition in the end or just didn't show up?
Yeah, you know, I had a five-year plan completely planned out.
When I started med school, I was like, okay, right after med school, I will train to become a psychiatrist or something.
And then after that, life will all fall into place in the perfect order, exactly as I planned it.
But then obviously, life has not turned out in such a way.
And yet I decided, oh, this path is not for me.
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