Faith and Isaac spend this episode doing something they probably should have done years ago — actually tracing back where their paths came from. Not the polished CV version, but the real one. The one that starts with Faith wanting to be a paleontologist, and Isaac presenting a Minister of Health flip chart at kindergarten, and both of them eventually just rolling into medicine because that's what you did when you were good at school in Singapore. They talk about what it actually feels like growing up in competitive schools where being a national athlete is just table stakes, and whether any of the choices that supposedly shaped them were choices at all — or just the next obvious step in a script someone else wrote.

They also get into the bond — the part where you sign away the better part of your 20s before you're old enough to fully appreciate what that means. Isaac docu-signed his during COVID (SGD 700k on the line, very romantic). Faith sat in an MOH office with her parents behind her and signed without really thinking about the numbers. Both of them talk about what it felt like when the reality of that commitment set in, and how they navigated the stretch between "I chose this" and "why am I here" — including Faith's very short-lived but very cosy handicraft business, and the moment Isaac realised his friends were getting their first promotions while he was still meekly knocking on doors in student scrubs.

They close out asking each other the question they actually wanted answered: would you do it again? Both say yes — for complicated, pragmatic, very human reasons. This episode is for anyone who has ever followed a path and wondered, somewhere in the middle of it, whether they actually chose it, or whether it chose them.

⏳Chapters

00:00 Intro & what we're talking about today

00:40 What did we want to be as kids?

03:41 When did the pressure to "become something" kick in?

08:01 How much of our path was chosen vs. just followed?

12:25 Singapore's meritocracy — what it gets right, what it doesn't

17:37 Signing the bond (and docu-signing your future for $700k)

20:15 The emotional reality of being mid-bond and questioning everything

22:02 Chasing the "what if" — side hustles, handicraft shops & salary checks

27:10 The gratitude guilt: are we just being ungrateful strawberries?

29:29 The unpaid posting discourse & how the bar keeps moving

31:09 Parallel universe versions of us (spoiler: not always prettier)

33:04 "I'm a doctor" — how professional identity plays out in different rooms

38:25 Social currency, startup events & the 100-storey elevator pitch

40:34 Would we do it all again?

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Podcasts

We Didn't Plan This – The Podcast for People Who Ditched Their Five-Year Plan