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Synopsis
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.
Episode Transcript
Isaac
Hello, I’m Isaac.
Faith
And I’m Faith.
Isaac
And welcome to the We Didn’t Plan This podcast. So Faith, today we are fast-forwarding to the present. We’ve been doing a lot of reminiscing in the past few episodes about growing up in the system, about university, about different versions of the fetal us that were dreaming, hoping, got disappointed, got excited. So now we’re talking a little bit more about adulthood as we are navigating it right now. I don’t know, do you feel like an adult?
Faith
Well apparently we are. I mean we’re about to turn 29 or 30 soon but yeah adulting doesn’t feel quite real until you know you’re following everyone’s milestones right like getting married getting a house, I don’t know, paying your own bills and managing life.
Isaac
Yeah and you know sometimes I don’t even 100% feel like adulting has happened full time yet and and then I realized that not only are we definitely in adulthood, we’ve been so for a few years, quite a few years.
Faith
It’s okay, it only counts once you start working. So you’ve been an adult for one year, I’ve been an adult for five, even though I hardly feel that way.
Isaac
Supposedly. So 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?
Faith
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 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 oh have a kid after that. Everything so meticulously planned out, but somehow here I am, turning 29 soon and i do not have any of that figured out no house and like you know no marriage or kids nothing so it’s a blank slate and it’s scary but exciting yeah how about you?
Isaac
I think when I was a kid, the age 30 didn’t even exist in my realm of imagination you know. Like you know to me, turning 21 was adulthood and that signified a few things okay maybe a job a degree. Like 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 I basically I think the theme to all that was that when 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 would be 100% sort of 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 when you thought about that, was there an a version of you – 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?
Faith
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. In the end, I decided, oh, this path is not for me. I don’t want to specialize. Heck, I don’t even want to work full-time. And heck, I need more freedom. I don’t want to necessarily be tied down in the way that a lot of our peers are. Like every time you open Instagram nowadays, it’s probably like a wedding or a birth announcement or someone’s pregnant or someone’s kid is turning like one or two years old. I’m like, oh my, I don’t feel ready for that yet at this stage. There’s so much more we want to do that, you know, we don’t want to limit ourselves that quickly.
Isaac
And do you think that a lot of this, I mean, where you’re at right now, how much of it do you think was entirely of your choosing? And how much of it do you think was guided by things you went through in your early career? Like, you know, you felt as if, okay, things are bad in wherever you were at. So you must leave or there must be another way.
Faith
Yeah, I think I didn’t want to lock myself into that, you know, that particular narrative that my younger self had told myself to stick to. when I realised that things weren’t working for me I decided like why should I stay in a situation that isn’t optimal. I have free will, I should use it, and I should explore to minimise future regrets.
Isaac
And with great power comes great responsibility. And with any of those choices did you ever feel like you were setting yourself back or that you failed at something you know any time point leaving the hospital after you finished your housemanship starting a clinic but not being with it throughout the whole way, etc. Were any of those things, do any of those things feel like a failure or a setback?
Faith
I wouldn’t really call them failures or setbacks as much as learning opportunities. Maybe that’s a very euphemistic way of saying it, but I would consider myself pretty optimistic and excited towards my future, like ever since I left the hospital. When I was in the hospital, I was on a one-track mind of like, oh no, I’m going to be just stuck here and there’s no freedom. But now that I’m out here and able to explore options, even when one option doesn’t work out, I tell myself, there’s still an infinite number of possibilities out there for me. So why should I waste time being demoralized about one option not working out when there’s an entire world out there for me?
Isaac
So it feels like the world’s your oyster.
Faith
Yeah, it does feel that way. Because I mean, financial freedom, plus being able to just take off and travel whenever I want to, plus also having good enough health to be able to maintain an exciting and adventurous lifestyle. So what about you? I mean, you’re a house officer running a business on weekends, running on a caffeine and thinking like, when’s your next diving trip going to be? Is this what you imagined when you decided to go from law to post-grad med?
Isaac
I don’t think so. I don’t think so. But I think I would be lying to myself if I said that I had any idea of how things would go after I jumped into it. Because I think at a point in time, what I felt was that this was maybe one of the more major decisions I would take in my lifetime that I’m really taking it into my own hands, right? Where maybe before that, I don’t think I was a very, very mature, very foresighted kid, right? So I think all along, you just go into the flow quite a lot.
So I jumped into it with obviously the right informed decision-making and having talked to a decent number of people. But I left the conclusion to that relatively open-ended because to me, once after landing in this job, I would then hope that the rest of the things fall into place. And I think what surprised me then was that actually, after that fell into place, so did a lot of other things. Because for better or for worse, I like the job, but I also feel that there’s a lot of other things I like. And with one thing anchoring everything down, what I’m lacking outside or what I like outside becomes even more obvious. And then that led me to the things that I pursue outside, be it leisurely or be it professional. And that’s kind of that stage of reckoning that I’m at right now. And I mean, you mentioned that it felt like a world of opportunity after you left the system. You have more freedom for yourself. You have more professional opportunities for growth. Was there a particular moment in time that you really felt, wow, this is my life right now. I didn’t imagine it would be like this, in a good way. What do you smell? What do you see? What do you hear in that moment?
Faith
I think the first time that moment really sank in was, you know, the end of housemanship. I think slightly afterwards, we had a D&D or something for our batch. I’m not sure why we had it or something, but it was around the time when I was the only one who knew that I was going to break my bond and that I was literally resigning within a few days. No one else knew that, but suddenly I felt just so strangely liberated. I was like, wow. In a few days, I’m going to be flying off to New Zealand for six weeks to just enjoy and travel and take my first step towards adulthood and freedom and autonomy over my career and life, whereas everyone is still happily floating in their own career paths in the system.
So I was like, wow, this is the start of something new. And I think since then, every single day or every single major choice that I’ve been allowed and granted the freedom to make, it’s just been like a pinch me moment because I didn’t think that I would have this much freedom before turning 30 and before finishing my bond psychologically.
Isaac
That sounded like a really meta kind of moment, right? When you’re there, but then you’re watching yourself on film.
Faith
Yeah, it’s like an out-of-body experience. You’re like, wow, this is the future. Did you have something like that?
Isaac
Yeah, I feel like I’ve had a few moments like that here and there. Maybe one of them that really hit home for me was a very, very ordinary day-to-day life moment where I remember I was sort of standing in my balcony at home and I was just looking at the scenery outside at night, right? And for context, I moved out a while ago, so I rented a few places. And I think this was the fourth place that I rented a shared apartment somewhere. And this is also the first time that I moved in with my partner. So my girlfriend and I, we’ve been together for like a while. But then this is the first time we are staying together properly. And also it was a decent house upgrade from the last one. Out of a lot of deal hunting on Facebook and a lot of touring, we found a place that we really, really liked.
So then, I think it was in that moment where it really hit home that everything felt the same yet different all at once, where I’m still waking up at some ungodly hour to do something, this time going to work at a hospital somewhere, instead of waking up for school or waking up for a lecture or waking up for work in some other setting. And then I’m going to do the same thing before the end of the day. I’m probably going to go for a run sometime. probably going to be talking to my friends, probably be having dinner. But then it just felt like, actually, a lot of things have happened. And as I stared at the ocean very, very far away, I started thinking about next time I go diving, it felt a very nice moment.
Faith
So, I mean, we both grew up in these kind of educational systems, like, you know, Raffles, Hwach for you, right? And then med and law, everyone else was just always hustling and gunning for something. Like, they’re always just running and never stopping. So how much of your ambition do you think was genuinely something that you wanted versus what society or what others were peer-pressuring us into?
Isaac
I think we’ve touched on this theme so many times over, and I think the answer will always be the same, which is that you definitely feel like it’s not entirely yours. And for all we want to say about the system is like this, or the culture is like that, a lot of times then you start realizing, looking inwards, maybe to some extent, I myself wasn’t looking very hard either, right? Because you get prescribed a certain thing. No one is putting a gun to our heads saying that you must study. No one’s putting a gun to our heads to say that you must enter this school. But yet, you do feel like it’s the only thing or one of a very limited self-options to do, right?
Like you feel as if when you’re in secondary school, you have to do well so that you go to JC. JC have to do well because you have to go somewhere in uni and at that point in time I realized in your 17 18 year old brain you don’t know where it ends you just know that there is a next step but you don’t know what’s at the end of the staircase and I think 100% I was on a treadmill like that with no end in sight and I don’t know it feels like you might agree with that too?
Faith
I mean if we think about it, how do we truly disentangle how much of the ambition came from us how much came from our parents or how much came from society because it all just feels so interconnected because of how we grew up in the system every day you’re exposed to it it’s like where does it where does one thing start and why does one thing end and is it really that bad that our ambitions were influenced by those around us since it actually probably led us to better outcomes if we appear pressured in this positive direction.
Isaac
This whole thought made me often question the idea of what is normal and what is default, because you know you grow up and you feel as if that, okay you know this person is doing something a bit different they started their own business somewhere. The other person’s a bit different because they dropped out of school they went somewhere else to study or something like that, and then you don’t necessarily look down on it – you know you sometimes you look at it with a lot of admiration in fact – and then you say that wow this person is very unconventional, very interesting very groundbreaking, but then at some point in time I think especially when I went abroad and people were studying the same thing but with very different goals and very different values, it made me question the idea of “Is there even such thing as a normal?”, is there even such thing as a default. Do you ever feel like there was a moment where it stopped being a default path for you or do you think that that’s still a lingering reflex somewhere? Like you see a bunch of people having children or you know moving into their homes.
Faith
I mean it’s hard to avoid, especially at this kind of age in our late 20s to early 30s our entire feed will just constantly be the majority of people following the majority path. I mean it’s nice and cozy for them, but I guess sometimes if you yourself, or due to life circumstances you’re not on that same path, there’s always the question of “do I want to be on that path” or like “do I regret not being on that path”, or is this an opportunity that the universe has sent for us to try something new something entirely different, which could open up a different door from you know what we thought was previously possible?
Isaac
And I think that that instinct never leaves you entirely, in that when I see milestones being hit by the people around me, it’s not that you know I see people moving into a new flat I mean obviously I’m not gonna say that it’s boring – I’d love to have my own – or a bad thing, right? It’s not a bad thing by any stretch of view.
Faith
We celebrate them, you don’t get us wrong.
Isaac
But then you also sort of wonder, okay, at the end of the day, then it’s not that I don’t want some of these milestones. I sure as hell want a house too. But then you just want to make sure that it’s a deliberate, intentional decision. As long as you own it. Like I could look at person A and person B and I want half the things that person A wants and the other half is what person B wants. I think as long as you can call it your own, then it’s all good, right?
Faith
Yeah, I mean, for sure. So, I mean, your entire friend group went into like, what, PPE, politics, law, consulting, right? Do you ever, you know, check on what they’re doing now, like stock their IG feed and feel envy, relief or something else?
Isaac
Well, I mean, I guess now it’s LinkedIn, right?
Faith
I guess now it’s LinkedIn, yes. Everyone’s posting new career updates and new promotions and new salary raises.
Isaac
Well, I mean, I think that, Definitely. So I would say that I felt that, I came to realize that compared to a lot of the people I work with, a very large majority of my friend group isn’t in medicine. And that was like a bit of an anomaly. But then I felt as if it makes my life a little bit richer in the sense that I kind of hear about what they’re doing in different spaces.
Some people are in creative industries, some of them are in government, some people are doing some other things, right? And I think, yes, there’s definitely a sense of negativity sometimes because you compare any job A and job B, right? There’s going to be something that’s better about one compared to the other unless there’s like 20 years of seniority gap, right?
And I think one thing that predominantly hit home very often was the idea of how nascent or how small my professional identity feels compared to what some people around me might be doing. Partially time delay, partially how our profession is structured. You feel like other people are shaping policies or leading teams or creating products, right?
Faith
Some social impact and doing something great that ends up in the news.
Isaac
Yeah, and then, you know,
Faith
like making millions of dollars.
Isaac
We copy, paste notes and decide how much phosphate to top up for someone.
Faith
And then we queue to become a specialist and we just start rotating in the same few hospitals like some ping pong balls.
Isaac
Yeah, and I mean, that’s the instinct at first instance. I’m not going to pretend that I have this like Nirvana state where, wow, it’s amazing. I love my job and nothing else compares to it. But I think when you reflect a little bit on that as well, you also start putting yourself in other people’s shoes. And when you apply that to yourself, you also start figuring out, well, actually, maybe there’s some things about my job that, some things about my existence that I might prefer, right?
Because I think to me, something that I’ve always reckoned with is the idea of how much impact your actual role makes versus how large the role is in context of your organization. What I mean by that is that on a day-to-day basis, a junior medical officer or a houseman, they do very tiny things, right? Like you are a tiny cog in a tiny team led by a consultant specialist who’s quite senior. But actually, they are a very tiny part of just one department whose department head is like a very important person if you meet them in the hospital. But actually they are just one department head out of many medical departments, under one department of medicine, under one hospital. And you get how this whole goes, right? All the way up to the ministry or national level.
And then so there’s that contrast, right? Where you feel that, okay, you’re very small, but actually you do things that have a very immediate effect. You know, you push the lorazepam, the seizure kind of stops, right? I think that’s pretty immediate gratification. And on the other hand, you might have someone who’s leading a team of consultants, financial advisors, whatever, right? Or someone who’s shaping policy at a larger level, but you don’t see as immediate of an effect as well. And then you kind of reckon with, “Okay, obviously these different structures are built up for their own reasons, and where do I see myself in each of them?” And that’s where you start making a little bit more peace. But I don’t know, when you look at your peers and where they’re at right now, in medicine or otherwise, how do you feel?
Faith
Honestly, I think career-wise, I’ve never really been that ambitious or competitive, partly because of the way I was raised. My dad’s a chill GP. He’s very happy with a 9-5 job. My mom quit work when I was born to take care of me, and then now she’s working part-time in a hospital. So for me, work was never a priority, and I never really felt competitive about climbing the career ladder higher than others.
I think I was always strangely competitive about like having more free time than others, which is what I am trying very hard to do right now. I’m literally like, you know, side questing so hard because I think that’s the most exciting thing that life gives us. I mean, we have finite time. So what we do with it and like how much joy we can squeeze from our finite time on earth is more important to me than like, you know, a fancy title or money or prestige. What about you? What’s the most ridiculous thing that you’re competitive about?
Isaac
Oh, I feel like there might have been a point in time. Definitely not now because I’m tired and older. But I remember, especially when I was in NS, that there was a period where, and for context, I was in a very lazy job in NS. I wasn’t one of those officer or special unit kind of people. So I had a super, super slack job in NS. So I think there was a period where me and some of my friends who were kind of getting very competitive about how many things can we fit into a weekend, right? Or in your limited spare time, can you zip off to the gym, go and do some work, and then find a group of friends, and then another group of friends, and then you go out at night, and then after that, you wake up really early the next day to go and do something else.
And then it’s like that sense of how many side quests, or how much you can really maximize your time. And I don’t know, does that idea of how free time maxxing, as the Gen Alpha might say, everything maxxing, How does the idea of free time maxing or side quest maxing look for you right now?
Faith
Yeah, so the danger with free time maxing is that sometimes you end up in a lazy state where you’re just lying down and Netflixing and whining instead of going out and doing things. But on the other hand, you also don’t want to over-hustle to the point where you burn out from all your hobbies or enjoy yourself physically if, let’s say, all your hobbies are sporty. So I don’t know, I’m just enjoying my free time maxing because it gives me… I can’t believe I’m using that phrase, but now you’ve coined it. I guess we’re stuck using it.
The joys of free time maxing is that there’s no one to give you a structure and telling you that, oh, you must achieve X, Y, Z for this particular side quest. It’s not like hospital where you have to do monthly assessments with your supervisor and apply to a certain role or apply for a certain job posting. So the idea of unstructured play as an adult is honestly quite enjoyable because it also lets us realise other dimensions of our personality outside of work. and help create a more whole version of us as a human versus just one career stat and being really, really high.
Isaac
And I feel that a lot as well. I feel like sometimes you structure your things because you look forward to them. After work, I look forward to exercise, look forward to meeting my friends. But then at the same time, as I’ve grown up, you feel like adding in a structured piece of unstructured play gets very, very liberating. Like you said, in this one hour between one thing and the next or going home on dinner, I am going to window shop aimlessly at ION.
Faith
Yes, I do that.
Isaac
I’m just going to take a long route to somewhere or take the slower elevator up or something like that. And that feels oddly liberating, right? And I guess since we’re going to the opposite end of the spectrum from trying to maximise things and trying to hit milestones, right? Has there been any milestones you’ve hit that you succeeded quite neatly, but then you felt not much after that? You felt it was oddly flat.
Faith
Let me think about it, but do you have anything that comes to mind?
Isaac
I think maybe if I think about it all the way back into the past, I think a lot of these come from academic milestones when I was much younger that really, I think the silence was deafening in the sense that, you know, there were some things that you worked towards that are really, really, they feel really big, right? I don’t know, secondary for end of year exams, it’s pretty much, you know, like it feels like O-levels or something, or even getting A-level results back, or maybe even getting, you know, in your CCA to go for national school games and you work hours and hours just for like a gold medal or something and I think those were things that at that point in time you only have these two jobs CCA and studies and you work really hard towards them and I felt like there were not just one but a couple of milestones that I felt I wouldn’t even say relief instead of joy it’s just nothing much period and I think those really collectively really told me that further on in life, just kind of chill out about some of these things.
Obviously, there is a minimum level of sufficiency I would try to hit and you would try to hit that pretty aggressively as well. But it’s about not just hitting the maximum of everything you can possibly do, be it grades, be it career milestones and all that, finding where my goal is. And that’s where the lacklusterness let me, I suppose.
Faith
Yeah, I mean, if we’re going down the academics route, I would say that, yeah, honestly, all the exam results that we’ve achieved over the years, like in the moment, it felt so important to us, right? Like our lives would end off. We just would be ruined if we didn’t get an A, we got a B or like, I don’t know, a B3 or something. And I mean, now if you think about it, there’s no more emotional impact. Like we’re just like, oh, okay, it was just an exam. It was actually not life and death, even though given our perspective as teenagers back then, it really felt like it was the whole world.
Isaac
Yeah. And I think it gets difficult as well when you realize the kind of person it makes you into. And what I mean is that I think many times in more competitive academic environments, because you impose these expectations on yourself, you look at other people who maybe don’t hit those milestones. You don’t look down on them, but when you see them happy or you see that they don’t care, then there’s a little bit of jealousy. And I mean, once you grow out of it, you realize how crazy of a thought that is. back then, sometimes, you know, in the workplace, you also see people who still maybe carry that mentality and, you know, workplace culture and dynamics is another thing we’ll talk about in another episode. But, you know, sometimes you see people who are still striving that hard, which is totally fine. And I think you get really happy for them when they hit their milestones, right? Like, well, I want to be a surgeon, I want to be an anesthesiologist, I want to become a whatever, whatever.
Faith
Yeah, it’s exciting to see everyone progress through life at their own pace and achieve their own unique set of dreams.
Isaac
Yeah, the only problem comes when they look at, if you look at other people and then…
Faith
Yeah, and then if you get FOMO or you get jealous, unless it ruins your emotional state for the day.
Isaac
Yeah, or you hear the, oh, this person is just a GP, or this person is just a this or just a that. That’s, I think, something that is not very nice byproduct of that kind of system that hopefully one grows out of. So I guess when it comes to all these milestones and all that, do you think there was one point that you can tell your younger self, okay, that’s when you stop being obsessed? Or that’s when you maybe grew out of it a little?
Faith
I think getting into med school was probably the milestone where I decided, okay, I have achieved what I really need to achieve in life. As long as I pass med school, I don’t have to get an A for med school. I just need to pass. And I’ll be a doctor and I can just like chill and, you know, cruise through life and start exploring the rest of life, like everything else that life has to offer, which we were kind of deprived of in our school days. Or at least I was deprived of. So yeah, now I’m happily side quest maxing. What about you?
Isaac
I think that like you, it came pretty gradually. You know, I think you definitely get out of that 11 robot phase pretty fast once A-levels finish us. And then for the rest of it, with things like professional identity, professional FOMO, someone gets a better internship than you, someone gets a better job than you. Can I say that, you know, graduated fully from that and I’m in this transcendent state where I don’t care about what other people do. No, absolutely not. Absolutely not. But I think we slowly find our peace and we slowly find where we want to stand amongst in the world and amongst our peers and amongst everyone else. Yes, we can call it a day.
Faith
Yeah, and we’ll see you in the next episode.
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