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

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

If you've hit every milestone and still wondered “Is this it?” — this podcast is for you. We Didn't Plan This is all about raw, funny, and brutally honest conversations about purpose, identity, and what it actually takes to rewrite the script. This video podcast is hosted by Faith and Isaac — two doctor friends who wanted an excuse to have honest conversations with cool folks who've chosen a less conventional path, picked up an unexpected side quest, or just decided to build a life that actually made sense to them. New episodes fortnightly. Come hang.

Publisher

Two Singapore Doctors Navigating Careers & Side Quests – Faith Nadine Choo & Isaac Ong

Category

business · health & fitness

Language

en

Explicit

No

First episode

1 May 2026

Latest episode

17 Oct 2026

Latest episodes

11 episodes in the feed.

1. 

   17 Oct 2026

   What It’s Really Like Studying Medicine at Universiti Malaya

   Xiao Yue joins us to share her journey from wanting to pursue politics and law to studying medicine at Universiti Malaya. We talk about the reality of medical school in Malaysia, exam stress, loneliness, family, side quests and the challenge of building an identity beyond medicine. When Xiao Yue was in high school, she thought she wanted to go into politics. Then she considered law, biomedical science and eventually medicine. In this episode of We Didn't Plan This, we sit down with Xiao Yue, a second-year medical student at Universiti Malaya, to hear how she ended up choosing medicine and what she has discovered since starting medical school. We talk about everything from shadowing doctors and figuring out what kind of work actually feels meaningful, to the reality of medical school once the glossy career brochures are replaced by anatomy, physiology, exams and a rather all-consuming hospital world. But the conversation goes beyond just studying medicine. Xiao Yue opens up about feeling lonely during A-levels and medical school, finding ways to maintain friendships and family time, and her various “side quests” including running, hiking and conservation. We also get into a bigger question that I think a lot of medical students and young professionals eventually have to confront: who are you outside your degree or job? How much of your identity should come from being a doctor, and how do you build a life that still leaves room for everything else you care about? As she gets closer to clinical training and eventually housemanship, Xiao Yue is still figuring out what kind of doctor she wants to become, whether she even wants to specialise, and what she wants her life to look like beyond medicine. And perhaps the most fitting takeaway from the episode is her advice to her younger self: choosing one path doesn't mean you're locked into it forever. Sometimes you have to make a decision, see where it takes you, and trust yourself to reassess along the way. Keywords: Medical student Malaysia, Universiti Malaya medical school, Studying medicine in Malaysia, Malaysian medical student, Medical school experience, law school malaysia, Medicine vs law, Medical student life, moving to Singapore, international medical graduate

2. 

   3 Oct 2026

   Moving to Singapore as a Malaysian Doctor – What You Need to Know

   What is it really like to be a doctor in Singapore? Faith and Isaac chat with Malaysian medical student Xiao Yue (Universiti Malaya) about housemanship, 24-hour calls, workplace hierarchy, pay, work-life balance, moving to Singapore as a Malaysian doctor, and what they wish they had known before starting medicine. What is it actually like to be a doctor in Singapore? In this episode, Faith and Isaac sit down with Xiao Yue, a Malaysian medical student, for an honest conversation about life in medicine across the Causeway. We talk about the culture shock of entering the medical workforce, navigating the very specific hierarchy of house officers, medical officers, registrars and consultants, surviving 24-hour calls, and the small mistakes that every new doctor seems destined to make. We also get into the less glamorous questions: Is the pay actually worth the hours? What does work-life balance look like when you're doing multiple calls a month? Should Malaysian doctors move to Singapore? And if you do move, how do you build a life and support system from scratch? Along the way, we compare some of our experiences of working in Singapore with Xiaoyue's perspective as someone still studying medicine in Malaysia. Finally, we look back at our own first days of housemanship and ask what we would do differently if we could start all over again. Spoiler: probably less panic, slightly more coffee, and accepting that you don't actually need to arrive at the hospital at 5am. For anyone considering medicine, housemanship, or moving countries for their medical career, this episode is a candid look at what happens once the glossy medical-school brochures stop being relevant. Keywords: Singapore doctors, working as a doctor in Singapore, housemanship Singapore, Singapore healthcare system, Malaysian doctors in Singapore, doctor work-life balance, medical career Singapore, life as a doctor, junior doctor experience, Singapore vs Malaysia healthcare

3. 

   19 Sept 2026

   Escaping Singapore's Comparison Checklist: Promotion, BTO, Kids by 30?

   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 over the career ladder. We're both about to turn 30, and honestly? Neither of us feels like we have it figured out. In this episode, we get into what we each thought adulthood would look like as kids — the house, the marriage, the "settled" career — and how differently things actually turned out. Spoiler: neither of us is mad about it. We talk about the moment the five-year plan stopped making sense, what it felt like to walk away from the traditional path, and why watching friends hit milestones on LinkedIn still stirs up a weird mix of joy, envy, and relief. We also get into something we've started calling "free time maxxing" — basically our answer to burnout culture, and why we'd rather be competitive about how much joy we squeeze out of a weekend than about titles or promotions. By the end, we land somewhere unexpectedly comforting: it's not that ambition disappears, it's that we get to decide what we're actually ambitious for. If you've ever quietly panicked comparing your life to someone else's Instagram, this one's for you. Keywords: Rat race, Adulting, five-year plan, career comparison, Singapore millennials, quarter-life crisis, default path, work-life balance, professional identity, life priorities

4. 

   5 Sept 2026

   How An Interventional Pain Doctor Juggles Treating Veterans, Fitness & Family

   Part 2 with Dr. Ruan Qing Zhao — Hyrox training, VO2 max, treating chronic pain in veterans, a brutal personal back-pain story, surviving exams on 3 hours of sleep, and advice for Singaporeans weighing a career overseas. In this second part of our conversation with interventional pain specialist Dr Ruan Qing Zhao, we step outside the hospital and into everything that happens around it — the marriage that keeps him grounded, the home-cooked feasts, and the spontaneous decision to sign up for Hyrox. We geek out over VO2 max, and why it might matter more than your cholesterol panel. We also get into the harder stuff: treating veterans carrying both physical and psychological trauma, what it's like to genuinely feel a patient's pain after one very bad 24-hour stretch with his own back, and how "Dr. Google" has quietly become "Dr. GPT." Along the way, Qing Zhao doesn't hold back on what studying for exams during a six-day surgical work week actually looked like — three hours of sleep, an alarm set to wake up and read, then straight back into a 12-hour shift. We close on something we think a lot of our listeners will sit with: his advice to any Singaporean on the edge of a decision to go overseas. It's less "just do it" and more "know yourself well enough to know if this want is even real." A conversation about fitness, pain, burnout, and the cost of ambition, from someone who's actually lived it. Keywords: Hyrox training, VO2 max, interventional pain medicine, doctor fitness journey, Singapore doctor abroad, chronic pain veterans, residency exam prep, longevity biohacking, work-life balance medicine, medical career overseas

5. 

   15 Aug 2026

   A Singaporean Doctor's Path to A Harvard Anaesthesiology Residency

   A Singaporean doctor's winding, five-year fight to break into US medicine after graduating from a UK medical school. Three failed attempts, a pivot away from surgery, to a specialty almost no one back home has heard of (Interventional Pain). Part 1 of our two-part conversation with Dr Ruan Qing Zhao. Faith and Isaac sit down with Dr Qing Zhao, a Singaporean who took the well-worn "study hard, serve, come home" script and quietly rewrote it. What started as a choice between NUS and a scholarship-free gamble on UCL turned into a decade-long odyssey across the UK and US healthcare systems — three attempts at US residency, two rejections, and a five-year stretch where nothing felt certain. In this first part of the conversation, Qing Zhao gets brutally honest about the year he stopped believing surgery was for him, the phone calls with family who couldn't fully understand what he was chasing, and the week he — a self-described non-religious person — actually prayed after a dream residency spot fell through. We also get into what it's actually like inside a US general surgery residency, why he eventually pivoted to anesthesia and then into interventional pain (a field most people in Singapore have never heard of), and how he landed at Providence Veterans Affairs Medical Center hospital, wedged between Boston and New York. It's a conversation about identity, timing, and what it costs to keep betting on yourself when the answer keeps coming back "no" — right up until, eventually, it doesn't. Part 2 picks up where this leaves off, moving from career into the more personal side of his story. Keywords: Singaporean doctor overseas, medical residency US, UK junior doctor, interventional pain specialist, board certified anesthesiologist, International medical graduate, Providence Veterans Affairs Medical Center, board certified, Brown University, UCL medical school

6. 

   1 Aug 2026

   Studying Medicine in Singapore vs Studying Law in Cambridge: Unfiltered Chats

   Faith and Isaac compare their wildly different university paths — NUS Medicine vs Cambridge Law — and unpack culture shock, missed local uni experiences, and whether they'd choose the same road again. We've always wondered what it would've been like to live each other's uni lives — so in this episode, we finally sat down and asked. Faith went through NUS Medicine, the well-trodden local path with all its budget backup plans and prelim disasters; Isaac took the scenic route through Cambridge Law before circling back to medicine at Duke-NUS. Turns out we both missed out on some very different things. We get into the culture shock of formal dinners and £6 supermarket wine, the very real FOMO of never once going night cycling with university buddies, and the moments — a Moroccan desert night, a freezing bike ride blasting Jay Chou — that somehow still live rent-free in our heads years later. We also talk about how differently "success" got defined for each of us, and whether all those what-ifs actually matter in the end. It's a pretty honest look at the roads we didn't take, the ones we did, and why — most days, anyway — we've made peace with where we landed. If you've ever wondered whether the other path would've been better, this one's for you. Keywords: NUS Medicine, Cambridge Law, Singapore university life, medical school Singapore, studying abroad Singapore, university culture shock, career regrets, Singapore meritocracy, doctor career path, law school experience

7. 

   18 Jul 2026

   The Psychology of Overcommitting — Why High Achievers Are Delusional Optimists

   We Didn't Plan This started because Faith and Isaac have a lot of feelings about life not going according to plan. This episode is probably the most honest that's looked so far. The topic: optimism bias — that very human tendency to believe we'll be the exception, that this time we can handle it, that the numbers will somehow stay good if we just quietly stop taking the meds. It sounds like a psychology lecture. It isn't. It's two doctors sitting across from each other asking: on a scale of one to ten, how much of a sucker for suffering are you, really? The conversation takes a few unexpected turns. Isaac talks about the period during med school where he was simultaneously doing weekend relief teaching, one-to-one tutoring, and working as an overnight caregiver through a home care app — wiping floors at strangers' houses at 2am and heading back to hospital the next morning. Faith talks about starting her blog not out of optimism, but almost the opposite: a need to warn people what they were getting into. And then how, slowly, writing about hard things in a hopeful tone actually rewired the way she processed them. They banter about on-call stress eating (including carbonara for supper in hospital), and the witching hour between 4 and 5am where all bets are off. But the thread running through all of it is the same question: is optimism something that happens to you, or something you choose? And if you could calibrate yours up or down — would you? ⏳Chapters 0:00 – Intro + optimism bias 0:25 – How optimistic are we? 3:19 – Ambition vs optimism vs just needing the money 5:02 – Isaac's med school hustle era 7:57 – What one night of nursing work does to an aspiring doctor 10:00 – Why faith started a blog (it wasn't really about optimism) 18:21 – Writing as a way of rewiring how you feel 21:06 – The things we always underestimate (time, sleep, emotional bandwidth) 25:25 – Becoming a freelance doctor and regaining optimism 26:45 – Does surviving hard things make you more or less hopeful? 27:09 – Pain caves, canoeing sprints, and the resilience mindset 29:59 – On-call coping + 5am carbonara 31:12 – Optimism bias in medicine: when patients go rogue 35:02 – What are we optimistic about right now? 36:59 – Would we calibrate our optimism up or down?

8. 

   4 Jul 2026

   From Cadaver Lab to Breaking Bad News: What Medical Training Really Teaches You

   We started medical school by walking into a room with donated human bodies and a scalpel. And if you ask most doctors about it now, years later, there's this thing that happens — the memory is still vivid, but the weight of it has somehow… shifted. This episode is about that shift. Faith and Isaac talk through what cadaver lab was actually like — the smell, the pledge, the strange intimacy of returning to the same silent mentor week after week. But what starts in that room doesn't stay there. From the first time you realise you're treating someone's worst day like a Tuesday, to the 4am calls where you have to find enough human warmth to deliver devastating news on barely any sleep — the emotional recalibration that comes with working in medicine is something nobody really prepares you for. They get into patients rejecting life-saving dialysis, dark humour as a coping mechanism, what it means to "pace" with a dying patient's family, and what the best and worst examples of clinical communication have taught them about who they want to become. By the end of it, the question isn't really whether doctors are desensitised. It's whether some version of that numbness is necessary — and whether, if you're honest with yourself, it's started showing up in places it probably shouldn't. ⏳Chapters 0:00 - Intro & what this episode is about 0:58 - What actually happens in cadaver lab (for non-medical viewers) 2:45 - Our first day: the pledge, the white coats, and the moment the bodies were unveiled 5:00 - The difference between Faith's experience and Isaac's (dissecting vs. observing) 6:20 - Developing a "relationship" with your silent mentor over weeks 7:05 - How that emotional weight slowly evolves as you start seeing real patients 9:45 - The first time you start feeling like you're becoming someone you don't like 12:00 - Dialysis, difficult conversations, and learning what pacing with patients means 15:00 - The overnight call that made it feel real: a stroke patient our own age 16:00 - Processing heavier conversations — and why 10 seconds is sometimes all you get 18:45 - Did med school actually prepare us for any of this? 22:30 - Staying up overnight to practice breaking bad news at 5am (our proposal to faculty) 24:00 - Desensitisation and colleagues: dark humour, "rocks," and what outsiders don't get 26:00 - Code-switching: from hospital to real life (and the velvet glove problem) 27:30 - When a senior doctor loses it — and what that taught us about who we want to be 30:10 - How numb are we, really? (Isaac's answer: 80%) 32:00 - "Microdosing emotion": what the best seniors actually do 34:00 - SBAR: when clinical communication becomes your default personality 36:00 - Does the numbness follow you home? The paternalism trap 37:00 - Patient stories that stuck: the man who refused dialysis 38:30 - The "pleasantly confused" auntie who gave us Korean hearts — and then didn't make it 41:00 - Closing thoughts: striking the balance between empathy and function

9. 

   20 Jun 2026

   Milestone Anxiety, Regrets & Side Quests: Two Doctors Questioning The Singaporean Dream

   Somewhere between a therapy session and a sparring match, this episode has Faith and Isaac putting each other on the spot with questions they actually want answered. No guest, no agenda — just two doctors who've both strayed pretty far from the expected path, asking each other the hard stuff: Was there a moment you knew the default wasn't for you? What did you have to unlearn to get here? And what's the biggest misconception people have about your life right now? They get into the Singaporean timeline pressure most of us grew up with — the relentless march from JC to uni to job to BTO — and what it actually feels like when you clock out of that race. Faith talks about going from "squash those feelings down, deal with them later" at 17, to eventually forcing herself off the path; Isaac opens up about the chaos underneath what looks like a stable multi-hyphenate life. There are side quests that turned into unexpected vocations (Faith's blog accidentally becoming a go-to resource for med school applicants; Isaac's scuba diving becoming a masterclass in building systems), stories about friends who became professional barbers at 18 or aerospace engineers in Alabama, and a genuine conversation about whether doctors — of all people — are the worst at taking care of themselves. Then it closes with the hypothetical that sticks: if $10 million dropped out of the sky, what wouldn't you change? It sounds like a fun icebreaker, but the answers end up being a pretty good map for how both of them actually want to live — and a nudge for viewers to think about it too. ⏳Chapters 0:00 – Welcome & what we're doing differently today 1:00 – The Singaporean default path: school → job → BTO → repeat 3:10 – Milestone anxiety & why A-levels was collective trauma 6:20 – "What would you tell your 18-year-old self?" 8:05 – The big misconception: our lives are NOT that stable 10:55 – Unlearning: why you don't need a full plan before you start 14:00 – The "B-student vs A-student" paradox & jumping in early 17:20 – Side quests that stuck around: Faith's blog, Isaac's scuba 21:50 – What would you have done if not medicine? 24:00 – When your blog goes viral overnight (and you can't kill it) 27:00 – Entrepreneurship lessons: building systems, not just hustle 29:30 – Faith's "Don't Die" longevity community & lifestyle medicine 32:00 – Doctors giving the worst health advice (5am carbonara, anyone?) 34:10 – Side quests vs identity: imposter syndrome & going public 36:00 – The unexpected superpower medicine gave us: communication 38:05 – Rapid fire hypotheticals: the $10 million question 41:30 – Wrapping up

10. 

    6 Jun 2026

    We Chose Medicine — But Did We Actually Choose? | The Script We Didn't Write

    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?

11. 

    1 May 2026

    Singaporean Doctors by Day, Side Questers by Night: Did We Let Singapore's Education System Plan Our Lives?

    Welcome to the first episode of We Didn't Plan This — a podcast for people who ditched their five-year plan. We really didn't plan this. It started with a lunch conversation a few months ago, and somehow became a full-fledged podcast. In our first episode, we (Faith and Isaac) share our backstories. Faith, a locum GP juggling a blog, side quests, and too many creative projects, and Isaac, a house officer who took the scenic route through law school before landing in medicine, while running an education consulting business as his side gig. We talk about how we both ended up in healthcare, what it felt like to follow a script we never consciously chose, and why it's worth asking whether you actually wanted the path you're on. Topics covered: - Our career and personal journeys - Law school to medicine - The blog that started it all - Singapore's meritocracy and education system - Side hustles, bonds, and balance - What it means to not just be defined by your job ⏳Chapters 0:00 — Intro 0:38 — Our backstories: 2 very different routes into Medicine 7:34 — How we met + navigating professional vs personal identities 14:46 — What shaped our career choices + schooling years 21:10 — The pivot: what made us change course 30:49 — How we juggle work and our side quests

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