Q&A: Student Career Planning, Exploration vs. Exploitation & Navigating Uncertainty Across First Job, Passion & Mid-life Crisis - E283

· Q and A,Southeast Asia,Positivity,Mentorship,Purpose

“It's nice to feel the anxiety and nervousness. Don't penalize yourself for telling people that you feel uncertain. It's not a popular emotion to share out loud, but I challenge you to feel it and take action because its purpose is to solidify certainty. Do the bound exploration pathing, the butterfly testing, and the experiments. When you do those things, you don’t only acknowledge your feeling of uncertainty, but you are also solving it.” - Jeremy Au


“Half of the folks who have midlife crises already had the signals all the way back at university or at their first job but they kept brushing it off. It’s been happening for a long time, but it wasn't allowed to be felt. They end up being locked into that path they don't like and then they have to do a rupture move where they jump entirely to a different path. You can save yourself the pain of a midlife crisis by being in touch with your feelings, the tribe you want to be with, and the lifestyle you want to build, and acknowledging and accepting the trade-offs of that passion or hobby. Go out there and slowly build the life that you want. You can have a happy life no matter what role you have.” - Jeremy Au


“It's much harder to explore careers when you're 50 years old. It’s more ideal and socially acceptable to do that when you're in your 20s. You’d want to create a very bounded exploration path. You have more energy, and fewer obligations in terms of family and salary, and you are part of a tribe where everyone’s doing the same thing. People expect you to explore new geographies, and do different things, and you don't get penalized for it.” - Jeremy Au


In their discussion, Jeremy Au and Adriel Yong offer valuable insights for individuals seeking personal fulfillment and making career choices. They advise approaching career decisions as a series of experiments and being open to exploring different paths. Rather than getting locked into a job that doesn't align with one's true passions and values, they suggest embracing feelings of uncertainty and seeking diverse perspectives from a wide range of people.

Jeremy stresses the importance of gathering insights from various individuals before committing to a particular path, particularly for university graduates. The speakers highlight that uncertainty is a signal for change and growth, and individuals should acknowledge and discuss this openly. They both caution against ignoring early signals of dissatisfaction and emphasize the significance of pursuing personal happiness and fulfillment over external expectations. By gradually experimenting and exploring different options, individuals can potentially save themselves from drastic career changes or midlife crises down the line.

The discussion encourages self-reflection, open-mindedness, and the pursuit of personal satisfaction in one's career. By embracing uncertainty, seeking diverse perspectives, and prioritizing personal fulfillment, individuals can navigate their professional journeys with purpose and build lives that bring them genuine happiness.

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Jeremy Au: (01:41)

I think there are a lot of questions from folks who are seniors and looking for new jobs, about life and jobs. So I figured, let's do a Q&A about that.

I think the last case we had is, we had a Singaporean graduate in Computer Science, it was based in the US, and weighing a decision between the US and the current drop market there versus Singapore's job market. That's one story. But also, there are many other stories, right? I think there are folks who are running a small business and deciding whether to keep growing after that, after graduation. There are folks who want to do consulting. I think lots of different stories. What do you want to ask Adriel?


Adriel Yong: (02:15)

Yeah, I think there are multiple ways to approach this. I think the first common question is what should I actually do, should I be a corporate slave? Going to consulting? Join a large MNC? Or should I do something more entrepreneurial, whether it's my own small business, a startup, or a nonprofit? You went through the debt decision path because you are thinking between Conjunct Consulting, you're thinking between Bain, and starting your own company. So how do you approach that? The first question is about what exactly to do after graduation.


Jeremy Au: (02:45)

Yeah, it is not an easy position to have. I'll start off with the personal story before we talk about frameworks and the key takeaways. For me in junior college, I had wanted to be a vaccine researcher, and my side job, I wanted to be a poet, and I initially told folks and family about that. And I think I went through some experiences, I think we shared about this before. I went through the loss of my first girlfriend, but also, had some exposure to the medical field and I basically said that wasn't really one of the paths I wanted to be at.

So I went to university with a thesis that I wanted to eventually work at Gates Foundation on vaccine strategy, or Bridgespan Group on Social Event Consulting because I had joined this consulting club that was doing social impact in university called The Berkeley Group, and it's a tremendous alumni community now, and I think it was just so warm and so helpful that I was able to say Hey, this is the path I want to do.

I didn't get those jobs because I didn't have enough experience, and also from their perspective, I was an international. They wanted US citizens, so I went for my third choice, which was applying for jobs at Bain. And I had opportunities to either apply and get selected for either the US or Southeast Asia. I was very happy to actually apply for Bain because, even though it was my third choice, I felt like I was going to learn a lot, and I knew that it was a real rockstar group of folks that I could learn from, and get training. So for me, I think it was a little bit clearer to me that going to Bain was a bit of a no-brainer.

I think in the back of my head there were also opportunities to work in tech in SF, Google, and Facebook, but at that time, I think it was a little bit less obvious because this was back in 2010, 2011, right after the global financial crisis. So it was just starting to open up opportunities for, from their perspective, Economics majors.

Before they had primarily been engineering jobs. So, you know, in that context, imagine, I'm doing internships in 2010, 2011, and the global financial crisis has just happened. A lot of my seniors had graduated into the worst job market in the US ever.

So, I eventually made a decision and said Hey, I'm happy to go back to Southeast Asia and work. There's a great group of people that are going to be great mentors and training there. And I remember there was that conversation I had actually where, the Bain team was like, Hey, you can either work in the Bain US office on the West Coast, or you can work on the Bain Southeast Asia office.

But in Southeast Asia, it's all about growth because we're still growing as an economy, so you're going to be learning about growth cases, et cetera. But if you work at Bain on the West Coast, you are going to be working on projects that are focused on cost-cutting, and headcount reduction. It's just a different type of learning that you're going to get.

That stuck with me since then, which is true, right? Because even though technically it's the same company, we have a great equally rockstar group of folks. I think the geography and the title projects you got to work on actually train you about your future opportunities, right? And so, when I worked at Bain Southeast Asia and China, I actually ended up learning a lot about tech, about consumers. I learned about growth, and I learned about strategy. I learned multi-country strategy and market expansion. So these are all skill sets that actually turned out to be still relevant to my career, over 10 years down the road, which is in VC, which is about growth, leadership, hard decisions, market expansion, all these others, and the same geographies actually.

So taking a step back and I'm just saying, what are the lessons that I take away from it? I think there is actually a lot of path dependency, which is that I think it's very non-obvious. It's that I think you want to make some decisions in your life now, but the truth is the decisions that you make 10 years down the road are very dependent on what are the decisions you make today.

Now, it doesn't necessarily mean that the decisions that you make today mean that you box a certain career down the road, but it means that you just have to be hyper-aware about what exactly you're taking away. So it's less about job roles, which I think a lot of people are very concerned about. It's like marketing versus consulting versus things. But also, I think a lot of non-obvious stuff that is much more obvious to me now is geography is actually a big part. Are you choosing to be in a frontier market, for example, like Indonesia or the Philippines? Are you doing this in Singapore or the US?

So, which market are you in? Who's the boss that you're going to have? Your mentor is so key about what kind of work attitudes you learn from, both the positive and the negative, and what you like and dislike. Who's the tribe they hang out with? Who's your cohort, right? What are they going to do with their lives? Because, there are a lot of psychological studies that show, Hey, if your friend gets fat, you have a 30% chance of getting fat because obesity and obesigenic behaviors are socially contagious, and we see that, for example, in social media radicalization in terms of violence in, against schools or religions. Social networks have a huge amount of sway. And obviously, we think about it when they are negative behaviors, but the truth is, there are also positive behaviors that we get from the tribes that we work with.

I think optimizing for who you're going to become is really the key if that was the real layout. And what I mean by that is if you know that one day you would like to be a CEO, I'm just saying as an example. You would like to be a founder. Then, there are different paths to get there. You could be, for example, highly technical. You could be an engineer. You work at a bunch of startups, late-stage startups, then you will get early-stage startups, and then eventually become a co-founder, CTO, or could be a technical founder who's the CEO.

There's a path that is quite well-trodden and clear about the archetype, about what the strengths and weaknesses are their approach, and what you need to work on. Or you want to be a CEO of a large multinational corporation. When you look at their LinkedIn profiles today, a lot of them, for example, joined a multinational corporation. They joined consulting, eventually, they probably did a Masters, an MBA. A lot of them did that, and then they joined a company and then they stayed.

If you look at most public company CEOs, most of them have been at a company for 20 years, so all these public companies are all promoting from within. They're not necessarily promoting a CEO that comes from a different company. So if you want to be a CEO you're to work your way up through the key functions like corporate strategy, finance, whatever is the core revenue driver of the business.

And so that's, I think a lot of implicit paths to that role that are there, and there are multiple types, but you have to be aligned. And so, I think a lot of folks are very much oh, I want to be a consultant. I wanted to be a marketer. Those are the job titles that you're going to take on in the next two years, but, I think the question is like, who are you going to be? Who do you respect? Who do you not want to be? Who do you want to be? And take a look at their LinkedIn. Take a look at their profile, right? What did they do? What did they achieve? Who did they learn from? And I think that's how you work backward and you create that. Path dependency becomes an asset rather than finding yourself boxed out.


Adriel Yong: (09:22)

You obviously touched on how and why you chose to go to Bain Southeast Asia. So that's I guess the consulting plus the geographical angle to some extent, but at the same time, you're doing Conjunct Consulting, right? You started your own non-profit. What do you think about doing that full-time versus doing consulting? How do you weigh those two options?


Jeremy Au: (09:41)

The reality was that I had been thinking about Conjunct Consulting as a nonprofit at that point of time. I founded it because I was coming back to Singapore and I wanted to volunteer at a social impact consulting firm or organization. It didn't exist, right? So JC and I, Kwok Jia Chuan, had that conversation and we said, we were good friends back then, and then we talked about it and said, yeah, why don't we just do it together? And it was very natural. We made it happen. And at that point in time it was a nonprofit, so we always envisioned it, at the time, to be volunteer around and so forth. But I think the decision was really, once I got Bain I was like happy and had that, and I wanted to volunteer at Conjunct at that point in time.

What happened, of course, is like, went in a year was I realized hey, this is not going to be sustainable unless we make it a social enterprise. We need to think very clearly about our money, revenue streams. We had to think very clearly about who's going to be the succession planning, who's the executive director, who's the talent, and who's the pipeline of talent for folks who are going to be passionate about eventually coming back to the role.

Because it's not an easy role to do as well. So I think creating that internal decision was like, okay. Actually, at some point, it was like, okay, in order for this to keep going, I should probably leave Bain at some point and take this full-time role, so that I can, solidify everything. Solidify the revenue, be full-time, be committed, but also actually honestly create a cultural precedent for somebody to be a leader who is a paid professional then. Of course, nobody at that point of time complained about me, becoming a full-time employee because they knew that I was working so hard all the time as the founder.

So I had that implicit organizational trust. So I wanted the transition to happen with me first, so I could carve our path, and eventually, Samantha, who was a Conjunct volunteer got trained and eventually became my successor in the open bidding process, in our search process. When she took over, she had an easier time because I already had proven this transition from a volunteer-run organization to a more professional organization. Frankly, at the time it was more like my decision was to work at Bain, and on the side, create this nonprofit at the time, called Conjunct Consulting. But then, we didn't work. I was like, look, this organization is going to die if I don't go full-time at some point, to again, carve out the social enterprise nature of Conjunct Consulting.


Adriel Yong: (12:00)

And, I think that question was worth asking and thinking about because there are a lot of students out there thinking about whether they should continue on with maybe it's a small business, e-commerce, or marketing agency, or start one right after graduation. There are also some people who were thinking of scaling up the nonprofits that they built in school after graduation.

It's like, is after graduation the right time to go be a founder, go and build a company or is it better to go and pick up skills somewhere else first? How do you think about that?


Jeremy Au: (12:32)

Yeah. I think when I was a student, I asked the same question and obviously, there were all these older folks who were like, Hey, you should learn stuff, and I was very unpopular. I was like, no. I want to build this nonprofit. In retrospect it was like, yeah, all the managers and all the mentors were like, Jeremy's just going to learn and explore first, and then none of them were like, go build straight away. I was founded very unsatisfactory with the answer and advice. I think what I want to do is I want to give the same advice, but I want to give a little bit more nuance, so hopefully, I, can understand the nuance behind it.

I think life is long, and assuming that you don't get hit by a bus or something bad happens to you, but I think actually for most folks, you actually have a pretty long career. From your twenties all the way to your seventies, there are 50 years of life that you can actually build a career. And the truth is, on average people state have a job for four years. So there's like 10 different jobs that you're going to have across that timeframe. What I mean by that is the question then becomes, what's the sequence of the jobs that you want to do, in that sense?

You have a choice to explore or you have a chance to build. In business school, they call it explore versus exploit. Your exploration mode means that you're searching, you're learning, you're not committing, you're very shallow, you're very breakfast, you're very divergent, you're brainstorming, and you're okay to ask questions. So it's exploration mode and it's using it to describe companies that are in the exploration phase.

It talks about companies and teams who are in the exploitation phase, which is after this exploration, they discover something that is a secret, a hidden advantage. There's something they really enjoy doing, as a clear product-market fit. So they choose to exploit it.They choose to build very aggressively and they're a hundred percent laser-focus and they're no longer in exploration mode, and of course, attention to yin and yang here a little bit is when you are exploring, there's always going to be some people who are like, oh, we should this focus and blah, blah, blah.

The thing is, when you explore, you want to really explore the solution space very thoroughly, and then when you exploit, you want to exploit and you don't want to get distracted by a bunch of different things. The tricky part is that a lot of companies, teams, or people end up being very muddled. They're exploring, but then they're actually trying to focus, or they're busy trying to exploit something, but they don't carve out a business division to explore separately. So, they're neither here nor there.

The best practice in that scenario, for example, is that if you are exploiting something like a monopoly or you are like an oligopoly, you're exploiting it, you should create sub-teams where they're protected culturally too. Explore and venture build or invest, but you're giving that, and you can call it a spiky shape. You can call it a T-shape, but that's how you should be thinking about it from a company level. It’s quite true outside the individual level actually, that you get to explore careers.

I think it's much harder to explore careers when you're 50 years old, but it's much easier to explore careers when you're 20 years old. It's more socially acceptable. You have more energy. You have fewer obligations in terms of family and salary, and also, you are part of a tribe where everybody's exploring as well. So your twenties is really your time to explore because people expect you to take a sabbatical. People expect you to explore new geographies. People expect you to do those different things, and you don't get penalized for exploring as well. What I mean by that is then, you want to create a very bounded exploration path which is okay.

We met somebody that you introduced, and the person was like, okay, I set up a marketing agency and it turns out I don't like marketing, but I do think about the future. I do think about what the world needs and I think about Southeast Asia, and so I want to do something in tech, but I don't want to do marketing. And I'm like, yeah, maybe you should try sales, because you said you like talking to people and building relationships, so yeah, why not sales? Adjacent to that, it might be lobbying and government affairs. Maybe adjacent to that is product management. So there's a bunch of different roles that are adjacent, you don't like doing brand marketing. You don't want to run an agency, you want to do something in tech. There's actually a bounded space, right? You're not doing oil and gas, you're not doing logistics. Actually, the space is quite bounded. So explore, maybe do two years as a sales role, as a business development representative, junior sales role. And then it turns like you don't like it, then transfer and do product management in tech, and startups are quite generous and open for generalists and flexibility. and you are in your twenties, so this is a great time to do the exploration.

What I'm trying to say here is you really get to explore. That being said, it turns out, maybe you already know a secret. Maybe you've been, and we talked, we had a previous episode where we had Evan Heng at Zenith Education. So he started a teaching agency pretty much as a freshman. And then he is done well over those four years, and now he wants to keep going and make this a full education tech startup upon graduation.

So if you already know something about yourself, you really like education, you know that you already have a secret that you want to exploit fully, you want to build, then yeah, you get to focus, I think The tricky part for me is like, the truth is my side was, I was in exploration mode in the sense that in freshman year, I was doing all kinds of different clubs and societies and then, it turns out I really like having a sense of mission, having a strong tribe that is very passionate about a larger cause and high performance and that performance turned out to be problem-solving and consulting. So there was a good group of people, and the truth is I've continued to build and exploit that inside of mine, right? Which is, I used that to join Bain. I used that to work and build Conjunct Consulting, to build that community as well, and then I found that at Harvard, in business school. And I found that in building a company of my own as a founder in education tech, which also again, had all these things: a strong sense of mission, high performance, and, like clear vision direction.

And then similarly for VC, right? And now I get to hang out with founders who have that same sense of purpose and hunger and ambition, and logical work that needs to be done. So, I've continued to exploit that insight of mine personally in terms of how I think about my career and where I want to work, and what I want to do.

But I also continued to explore. I did TaeKwonDo in secondary school. I did judo in JC. Army, actually was pretty good as a sport, in terms of fitness, and then our cycling and a bit of hiking in university, and then I got tremendously unhealthy over the two companies I built because I didn't have the balance. And it turns out now, know, I'm in my thirties, but then, at a second company, I was in Boston. My wife recommended, Hey, I took out this class in improvisational comedy, for example. So I said, okay, you're trying it out. Yeah, I like it, it was nice anyway, as a show, I explored it. I went into this, I took a one-on-one course, and then turns out I really enjoy it. I'm getting better at it. There's a pathway for me to get good at it, or excellent over the long term. There's a certain cadence that I like to do it at, every week or every other week. It took me 10, to 20 years to explore what the right hobby was, in that sense. But now, I'm happy to continue building and so, now I know I can do improv comedy in Singapore for the next 10, 20, 30 years, and that's a skill set that is helpful for public speaking and for conversations. The active listening component is very helpful for our business and so forth. So these are all things that are adjacent to my job, it took me 10 years to explore and then later exploit, right? So I think that's the nuance I have, in terms of the framework is that if you're a university student, do you actually know that you really want to do something?

And if you know you really want to do something, then do it. But if it turns out that you don't know and you're still exploring, then give yourself permission to explore. Do a two-year bound experiment in a job and industry and geography that you think you're most likely going to do well or enjoy and do it for two years. And then if you don't like it, change it. And if you like it, do more of it.


Adriel Yong: (20:21)

Yeah. I really like that explore versus exploit mental model. In fact, I was just having dinner with two juniors from school last night and then, we were having the exact same conversation, which is what to do after graduation? How do I really know I like something?

And, it reminded me of what Steve Jobs said about, things only making sense in hindsight, or the dots only connecting how you look at them in hindsight. And the truth is when I look at my whole undergraduate career, I've done government internships, trust, and safety in big tech, FMB, tech, nonprofit, the entire gamut.

I think it's really only after going through the entire gamut of things, then I have a clearer idea of what I like and dislike, what are the types of people I enjoy working with, what're the types of people I don't enjoy working with, who are people that I'd love to work with, from my boss, my colleagues, et cetera.

And I think a lot of undergraduates don't actually do that. As we are discussing, one interesting thing was that a lot of, undergraduates who have a certain internship or an outcome in the university, say consulting, or investment banking, want to get that year three internship there in a bank or consulting firm. And so they like reverse engineer everything that needs to happen before that. So year one, I do, an internship at a small consulting firm. In year two, I do an internship at a larger, mid-science consulting firm, and hopefully, by year three I get an internship from Bain or Oliver Whiteman that then converts very nicely into a full-time job after graduation.

But that's like a very linear pathway, and it's also very constraining, cause you then, remove the opportunity from yourself to explore adjacent fields or random spaces in your first and second year when you should really be exploring. And a lot of people actually also don't do the more upstream stuff in figuring out whether they would really be happy in banking, consulting, which is, level one is, go to events, hear how consultants, bankers talk about their jobs, their lives. And then level two is to have one-on-one deep dive conversations with them. Level three, maybe work, work with them on a site project and see if there are people that you would enjoy working with, both in terms of working style and how you think about issues and problems.

And then the level four stuff is really getting an internship at a consulting firm. So there are a lot of things you could do beforehand before you actually commit three months of exploration time in college to a specific industry or career, which I think a lot of people don't think about right now.


Jeremy Au: (22:50)

Yeah, I get it. I had the privilege of joining a social impact consulting club that was very selective because they really liked me, and I always tell people the luck I had was, this is a very selective club, and they did a case study for, a case interview. And the case interview that was very hard that everybody couldn't pass was about, Hey, this nonprofit has received a hundred thousand doses of vaccine and they needed to figure out how to distribute it across the city. And I was like, oh, I don't know how to do a case interview, but I could talk to you all day about vaccines because I wanted to be a vaccine researcher in JC, right? And I aced the interview and I lucked into it. And so I got qualified, and of course, I think I disappointed them in semester two because I was like working on Vietnamese microfinance, which I had no interest or exposure to prior, previously.

But we did a good job. So I had a little bit of that luck, right? I was willing to explore because for me, I had previously heard about this club from somebody who was an alumnus, who had just come back from UC Berkeley, and she just told me, Hey, check out this club. If you really like volunteering with nonprofits and you like medical stuff, this is a good place to join.

So I think that serendipity and luck components are really hard to do if you really know what you're going to do. And don't get me wrong, I think there are also good reasons to know why you're already going to do what you do. Some folks I know now, in retrospect, I think back then I didn't understand, they came from very poor backgrounds and so they want a very stable, high-paying job. And that makes sense. Back then I'll be like, oh, so corporate, so transactional, but then you're like, okay, now in retrospect, I'm older. I'm like, okay, I get it. It gave them the stability and the income to get to the point where they're like, okay, now I can start thinking about the rest of my life.

And then that's when they start changing their career because now they feel like they got some stability underneath them. So what I'm trying to say is that, if you have the ability to explore in your freshman year and sophomore year, really take the opportunity to explore, do as many internships as you can, and do as many informational calls as you can.

Go try stuff, different stuff. Be a butterfly and do different things. And I think a lot of people like shame you cause oh, you should be, shouldn't you already know you want to be a doctor or a lawyer or this or that, because it's true. I mean it's more clear glide path for status and rewards. But I think goes back to global maxima, local maxima. You know what they say, right? It's you can work very hard to climb a local hill maxima, and then you realize, that turns out you're climbing the wrong hill, right? For yourself. So I think there's the tricky part that is like, the explorations phase is basically saying okay, which hill do I really want to climb and be there? Because when you find a hill that you really want to you can get good at it over a very long period of time.

So for example, I think, you and I have talked about it should people be VCs, right? And I'm like VC is a very apprenticeship structure. There's not a lot of training, so there are a lot of difficult moments I think for young, fresh grads to enter the job. They're going to face a lot of problems because they don't get trained properly and therefore they can't do a lot of different other types of jobs. But that's okay. But if you explore for two years, that's fine, and then you can do something else and that's okay.

But the truth is, If you know you're going to do 40 years in the same geography, the same verticals, the truth is you're probably going to get at least above average to good, to even great because you have that time horizon and that comfort level to keep building your network, your skills, your knowledge expertise, your credibility, your reputation in that space, you can really do it over the long term.

I've actually met folks who did, I don't know, six years of VC, and then they're changing geography or verticals, and then, it doesn't port right? The networks don't port and the main knowledge that doesn't import is selling from scratch. And in retrospect, for what it's worth, a more efficient way, I've been able to do VC for two years, realize you don't ever want to become a partner and then go do something else, which is totally fine,

so what I'm just trying to say here is you don't want to end up spending a lot of time climbing three-quarters up the hill or even the top of the hill, and they realize, they're like, oh, I'm, I've climbed the wrong hill, and it happens a lot in life.


Adriel Yong: (26:43)

Yeah. I think that's a very good way to think about it. Being very clear about the experiment that you're taking with your own career, and not going too deep into it without having very high conviction in it. And I think, for university graduates out there, go out and speak to as many people as possible before you even make a three-month commitment to something or a two-year commitment to something after graduation.


Jeremy Au: (27:06)

I think my last piece of advice is, it's okay to feel uncertain. In fact, it's great to feel uncertainty because when you feel uncertain, it means that you have discomfort with your present reality, and you have hopes and fears for the future. It's an amazing feeling to have because I can tell you now that I'm older, I have a lot of certainty and I don't feel the uncertainty anymore.

It's nice to feel that anxiety. It's nice to feel that nervousness. It's okay to be at peace about uncertainty. Don't blame yourself for feeling uncertain. Don't penalize yourself for saying and telling people that you feel uncertain. That's okay. Obviously, it's not a popular emotion to share out loud, but it's okay. What I challenge you to do is to feel the uncertainty and then take action, because you feel it, it is to reduce and solidify the certainty. Do that bound exploration pathing. Do that sequence of work. Do that butterfly testing. Do the experiments, because when you do those things, then you are actually acknowledging your feeling of uncertainty, and you are also solving it.

I think a lot of folks I've met feel uncertainty, and they're locked. Like you said, they're locked into this path of becoming a consultant, or a banker, and they feel the uncertainty. And I'm sitting with them and they're like, I'm really uncertain about this job, but I'm working very hard to do this job.

And I'm like, have you already done an internship? Or are you uncertain because you've done it? And then they're like, oh yeah, I did two internships and I secure a third internship, and I feel uncertain about this job. And I'm like, whoa. If you've done effectively two and a half internships in a job, and you feel uncertain about this job, that's probably a sign that you would not like this job.

I am saying that you can take a job that you don't like because you want to feed your family. That's totally fine. But it was just interesting that, when people get locked in, they don't let themselves feel the uncertainty and they don't let the body tell them what the reality of the situation actually is, and then that's when it gets stuck. You're doing a job that you don't like and you feel uncertain and you force yourself not to feel uncertain, but actually get uncertain, and then that's how you end up lawyers who set up a cupcake shop brand.

There's a joke they have. It's like all the lawyers who set up bakeries in their forties because they did 10 years of law. And I'm like, whoa. It took you 10 years of law school and doing law to set up a bakery. Like. You know what I mean? You could have discovered that maybe in year two, and then, yeah, you had to eat the bullet, don't get me wrong, it's super tough, right? Can you imagine you tell your parents, you're like, Hey, I'm dropping out of law school and I want to join, become a baker. I think you're going to get scolded for sure. But, that's the reality, right?

People have this conception of the law degree, but the actual reality of studying law, the actual reality of practicing law, the actual types of law, commercial versus trial law, I'm just giving this as an example, right? Go test it as fast as you can, and if you can test it within two years, and it turns out that you really don't like it, then let yourself be okay with it. Or maybe graduate with it so everybody's happy and then you go do a generous role in startups or something else.

What I'm trying to say here is, there are a lot of people who say there's a "midlife crisis", and I'm very empathetic to my friends and folks who experience it. I would say a solid half of the folks who have midlife crises actually had signals or feelings about this crisis all the way back at university or at their first job. It's more like they kept pushing it down and pushing it off, and this feeling eventually became a midlife crisis where they suddenly were asked, for example, the job to commit to work towards being a principal or partner. There's that very clear inflection point that forces them, and then everybody looks at them and they’re like, wow, this crazy person changed countries, changed jobs, change everything about their life, change families in their thirties or whatever, and then you're like it's not like the guy woke up in the morning or the lady woke up in the morning, was like, oh, I have a midlife crisis today.

The midlife crisis was happening for a long time, but it wasn't allowed to be felt and because of it, instead of being a set of bounded career experiments where you gradually work your way towards what you want, they end up being locked into that path they don't like and then they have to do a rupture move where they jump entirely. They have to do an MBA, they have to re-skill, and they do something very different because the pain of continuing down that path is worse than the pain of changing.

So, if you're listening to this podcast and you have 10 years of a midlife crisis, don't feel bad. It's okay. Lots of people have a midlife crisis, but if you can save yourself the pain of a midlife crisis by feeling and being in touch with your feelings and being in touch with the tribe of people you want to be with, and being in touch with the lifestyle you want to build, and acknowledging the trade-offs of that passion or hobby, what that means in terms of financials and lifestyle, and you're able to be bringing yourself to peace and accept those trade-offs, then you can have a happy life no matter what you are. So go out there and slowly build the life that you want to be happy with.


Adriel Yong: (32:00)

Yeah, I think that really wraps things up very nicely. I think people need to first understand what fundamentally makes them happy, and too many people focus on what makes other people happy rather than what makes them happy. That's the first cardinal sin when you are thinking about what to do with your life.