7 mental models for making the right career choices
A few of the underlying foundations of making stronger job decisions moving forward borrowing from algorithmic theory and other first principles.
Since my last post about making the decisive choice to leave Bain after only a year (metaphorically considered a sin to quit before 2-3 years) to join GovTech Education Indonesia, and explaining my personal principles on why it was undoubtedly the right decision for me— I’ve received a lot of messages from people who viewed the move as “bold”, “empowering”, and “exactly in line with what I expected from you”. A few students and early professionals reached out expressing a desire to understand how they can make stronger career decisions of their own, to think strongly on their two feet rather than relying on the status quo or societal influence.
Given that I run a professional development non-profit Cornerstone Careers, I thought it would be a good idea to write an article that students, early professionals, and even older professionals can use to think through their long-term professional journey. In Indonesia, a BCG article states that “New employees leave for better offers but also because they are disengaged. Only 20 percent of employees say they are satisfied in their jobs”. It’s sad, and I’ve seen this firsthand observing early professionals that I work with — especially if they’ve chosen careers because it’s what they observed other people did. At the same time, the world of the past is vastly different than the world of the future. When I asked Wafa Taftazani — the CEO of UpBanx — about what he wishes for new graduates to know, it’s the fact that the road to a traditionally successful path is unlike anything the past generations has known. It’s better that students and early professionals are able to be rapidly observe, experiment, and adapt to the new paradigm on their own terms. No one knows and can dictate what will happen down the road.
Thus, this article will delineate some of the mental models (not necessarily in order) that you can use in order to build stronger conviction and intention towards making decisions in your professional career:
Hill-climbing
Behavioral economists — in a theory called temporal discounting — suggest that humans tend to systematically overvalue near-term rewards over long-term rewards (https://www.sciencedirect.com/topics/psychology/temporal-discounting). This trait exacerbates amongst ambitious people. This has major implications for our career choices, as it seems we are always looking for continuously upward paths in our professional lives. As an ex-consultant, I see this play out a lot. People want to achieve the next available milestone (“it’s only a year away!”) and tend to overemphasize titles vs. responsibilities even in their early careers — even if it means a shift towards another role would represent getting closer to where they really want to be (e.g. a Senior Associate Consultant at Bain is reluctant to take an Associate Product Manager job even though they know they want to go into product management because they are “so close to a post-MBA title”).
Consider the plane above. What we see are two distinct hills but imagine that there are many hills. Now imagine your job was to create an algorithm to find the highest possible point in the plane without knowledge of the landscape if you were dropped off at a random point. In Computer Science, this job is called hill-climbing. A “naive” approach would be to try to keep going up based on what you can see in front of you. However, that approach might lead you up the smaller hill (a representation of missed potential). The optimal, and more sophisticated approach is to build an algorithm that can scout up hills to learn, and use that testing to reassess the heights of other hills. In the optimal version of hill-climbing where you get to the highest hill amongst many hills in your landscape — taking steps back or laterally is simply part of the process of getting to the top. We should not be afraid of doing so.
Our professional careers are no different, except that in most cases our human minds have the added instinct of knowing whether or not we’re at the right hill for us. We should listen to those instincts more. You can keep going higher and higher up a given path — but know that it might not lead you where you ultimately can get to and that it’s a lot harder to go down once you’re already high up (believe me, I’ve hiked enough mountains to know).
The paradox of optionality and the power of the straight line
Optionality is often a word consultants and investment bankers use to discuss the broad horizons of opportunities available to them after a couple years in the job. “The world is your oyster and you’ll be well trained to do anything you want” is the often used (paraphrased) marketing line. For ambitious people that come out of university not knowing what they want to do with their life — this is seen as incredibly attractive. It’s great getting a job that can really do it all, where you can not be specific but still gain career knowledge that is relevant to everything else. Let me tell you why this is a paradox with a simple, real personal example from a friend, and elaborate on that in more detail.
This friend was a top performer in a top consulting firm — and has spent almost four years at the particular firm working on a multitude of projects, from technology to consumer products to environmental strategy. He started to sense that consulting was not for him, but the moment he started on his career search he was as lost as he was after graduating from university going into consulting (then with the aspiration that consulting would magically provide him the clear insight on what he wanted to do in the long-term). He applied to all jobs available to him in a wide variety of roles (from business development to corporate strategy), but the moment he got his offers was equally lost and stressed on what the “optimal” path is. He ended up taking the one with the highest pay (see “Hill Climbing”) but it was clear that he wasn’t sure it was the best possible path.
The paradox of choice, by psychologist Barry Schwartz, is described as the following:
“He found that instead of increasing decision satisfaction, having too many options made people less likely to be satisfied that they had made the best decision. While freedom is important, Schwartz explains that there is a fine line between having the freedom to choose what you want and being paralyzed in the face of too many options.”
Simply, the reason why stressing the benefit of optionality can be a curse is because it reduces the need for us to make concrete, personal reflections on what we want / don’t want in a career. Stressed with an abundance of choices, we’re vulnerable to biases from societal influences or naive hill-climbing (as seen above). We also live in a world where people with specific skillsets are rewarded (see below: specific knowledge). If what Malcolm Gladwell states is true — that putting in 10,000 hours is what it takes to truly achieve “mastery” of something — then the closer we are to a position where we feel confident putting in the time to get to that mastery the better. Optionality can be great, but don’t let that distract you from the fact that it takes genuine personal work to get to an understanding of the path that is right for you.
Limiting yourself from n-to-1 paths with the expectation of one in a kind results
When Peter Thiel, investor and entrepreneur (founder of Palantir, Paypal), interviews someone he likes to ask the following question: “What important truth do very few people agree with you on?” He asks this for the following reason:
“This question sounds easy because it’s straightforward. Actually, it’s very hard to answer. It’s intellectually difficult because the knowledge that everyone is taught in school is by definition agreed upon. And it’s psychologically difficult because anyone trying to answer must say something she knows to be unpopular. Brilliant thinking is rare, but courage is in even shorter supply than genius.”
Many ambitious people, especially out of prestige paths (e.g. top universities), are seeking one of a kind outcomes but are limiting themselves to picking prestigious paths that everyone goes down on. Winner Takes All by Anand Giriharadas tells the real-life story of Cohen, who joins McKinsey right out of her undergraduate studies at Georgetown University with a passion for public policy and community organizing:
“She joined McKinsey by reassuring herself: “Now that I’ve been trained to structure, break down, and solve business problems, I can apply those same skills to any issue or challenge I chose.” Once inside, though, she realized that while this way of thinking was indeed useful for helping a tire company shave costs or a solar panel maker select a promising market for global expansion, it didn’t deserve its status as a cure-all among domains. Accountancy, medicine, education, espionage, and seafaring all have their own tools and modes of analysis, but none of those approaches was widely promoted as a the solution to virtually everything else. Cohen began to worry that this idea of business training as a way station to world-changing was just a recruiter’s ruse.”
It’s almost a paradox that the most ambitious people are in fact also some of the most vulnerable to picking paths that only align with continuing down the track of being seen as the most prestigious (wow, hill climbing appears again! https://medium.com/s/story/a-culture-of-prestige-98c8671ceade). You don’t have to have the aspiration of changing the world, but not knowing where your biases are leading you especially if they are fueled by societal influence and not by your own first principles will just lead you to an undifferentiated path. This won’t really change unless you recognize it and shift course. McKinsey doesn’t churn out executives — it’s the ex-consultants who differentiated themselves in other ways and built up their own unique credentials (let’s say Sundar Pichai) that ended up going down one in a kind paths. In most cases, consultants exit to corporate strategy positions or go down the Partner track. Obviously these are extremely high-paying, rewarding careers — but it’s not the “CEO launch pad” that some people come in expecting.
This is not meant to discredit the “prestigious path” altogether. Sometimes, it can be extremely beneficial especially for those who come from backgrounds that require some safety nets (e.g. due to socioeconomic circumstances). What is important to highlight though is to not take these paths for granted and assuming that it will get you to become “one in a kind”. To do that, you need much more than just an MBB or bulge-bracket stamp on your resume.
Build specific knowledge and create luck
As Naval Ravikant put it so eloquently (https://nav.al/money-luck), the strongest form of success (in his case wealth creation, but generalizable) should to be to strive for “Level 4 Luck” — a position where you’ve created such a unique embodiment of your truest self, such that luck finds you. It’s a position in which no one else has the ability to replicate what you offer to the world. It’s where 99.9% of others have given up due to the difficulty, lack of interest, or lack of fulfillment from the pursuit of the journey. This comes from what Naval calls specific knowledge. According to Scott Adams — the creator of Dilbert — this can be done in two ways:
Become the best at one specific thing
Become very good (top 25% at two or more things)
“The first strategy is difficult to the point of near impossibility. Few people will ever play in the NBA or make a platinum album. I don’t recommend anyone even try.
The second strategy is fairly easy. Everyone has at least a few areas in which they could be in the top 25% with some effort. In my case, I can draw better than most people, but I’m hardly an artist. And I’m not any funnier than the average standup comedian who never makes it big, but I’m funnier than most people. The magic is that few people can draw well and write jokes. It’s the combination of the two that makes what I do so rare. And when you add in my business background, suddenly I had a topic that few cartoonists could hope to understand without living it.
...Get a degree in business on top of your engineering degree, law degree, medical degree, science degree, or whatever. Suddenly you’re in charge, or maybe you’re starting your own company using your combined knowledge.
Capitalism rewards things that are both rare and valuable. You make yourself rare by combining two or more “pretty goods” until no one else has your mix...
It sounds like generic advice, but you’d be hard pressed to find any successful person who didn’t have about three skills in the top 25%.”
This explanation is self explanatory. If you’re one of the rare and gifted few who can truly be the best at one thing — then you should go for it with all of your spirit. Otherwise, taking the opportunity to continuously develop and broaden your base of skills (be a double/triple/quadruple threat in a way that is unique to you) will be your strongest and most reliable way of being someone that people value. But again, you shouldn’t underestimate how hard it even is to be the top 25% at something. It still will take consistency and targeted hard work to get there (which is why understanding yourself — a theme of this article that I hope you see starting to emerge — is extremely important).
Long-term games with long-term people
“I only play long term games with long term people. All returns in life, whether in wealth, relationships, or knowledge, come from compound interest.” - Naval Ravikant
“Compound interest is the eighth wonder of the world. He who understands it, earns it. He who doesn’t, pays it.” - Albert Einstein
Building and contributing to a challenging, unified effort over a sustained period of time with people that are intrinsically also long-term minded reaps the strongest rewards because: (1) you’re optimizing for a longer period of time where people aren’t maximizing for quick gains and instead are empowering each other to succeed for the benefit of the mission, (2) over time you are able to solve increasingly challenging problems because of a compounding knowledge base, and (3) you reduce friction and increase trust between the people that are building with you — enabling stronger teamwork and potential opportunities / serendipity down the line.
With all the theories that we learned so far in this article, this is a natural extension of getting to path of the “hill” that is truly optimal for you to climb. It has two implications in terms of our career search. The first implication is that we should experiment, fail, and learn in order to get to our most optimal career path as fast as we can. What this means is that our early career is absolutely the most important time for us to not just “take risk” but be systematic at eliminating career choices that are not enduring for who we discover we are. The second implication is that it is vital to pick a career where you can benefit from compounding rewards and that the people in the industry stay in the industry in the long-term, and that the industry is one that will endure in the long run.
Portfolio theory of career choices
Aaron Brown — a legendary Morgan Stanley derivatives trader — writes the following in his book The Poker Face of Wall Street, when talking about hiring traders at an investment bank:
“What I listen for is someone who really wanted something that could be obtained only through taking the risk, whether that risk was big or small.
It’s not even important that she managed the risk skillfully; it’s only important that she knew it was there, respected it, but took it anyway.
Most people wander through life, carelessly taking whatever risk crosses their path without compensation, but never consciously accepting extra risk to pick up the money and other good things lying all around them.
Other people reflexively avoid every risk or grab every loose dollar without caution.
I don’t mean to belittle these strategies; I’m sure they make sense to the people who pursue them. I just don’t understand them myself.
I do know that none of these people will be successful traders.”
While Aaron was talking about investment strategy, the same principle can apply to our lives and especially our career decisions — which is where the portfolio theory comes into play, helping us make systematic, principle-based decisions on our career and when / how to take risk. Risk is vital because without risk, it is impossible to exploit any extraordinary opportunities. As Marc Andreessen states: “You can live a quiet and reasonably happy life, but you are unlikely to create something new, and you are unlikely to make your mark on the world.” However, there are real and legitimate reasons why you might not want to take risks at a particular time — which is why all of this should be analyzed in terms of a portfolio of a lifetime of career decisions.
Each role you take, each opportunity you pursue will have a return (benefits you get like income, skills development, etc.) alongside a corresponding risk profile (things that could go wrong including getting fired, company failing, geographic risk, opportunity cost). Once you start thinking in terms of these options as simply parts of a portfolio of a 50+ year long career, you’re able to think strategically about your career over its lifespan as opposed to just thinking about decisions from a one-off perspective. You should put decisions in context with all the other risks you are likely to take throughout your entire career and decide whether this opportunity fits into your portfolio.
For example, when you’re just out of school — there’s an argument to be made to optimize for developing skills and acquiring experiences, even if that means taking income risk. Once you’re married and have kids then you’ll take opportunities with a different risk and return profile. However, when you zoom out over the course of your career — you should have parts risky and safe decisions, constituting what is ultimately the portfolio of your career.
Understand yourself deeply and be ruthless in pursuing that
You’ll notice — and I reiterate this over and over again through this article — that a lot of these principles rely on the very foundation of deep, personal reflection that you must do continuously over your career. I know a lot of friends that rely on their MBA’s as the first time that they’re genuinely thinking about what they want to get out of their lives and what matters to them. The more effort you can put into this as early as possible, the earlier you can get on the hill that optimizes your potential and reap the benefits of compounding rewards and the luck built through specific knowledge. You can do this by reflecting on the following exercise (although definitely not limited to this — just a way to get started):
What are the most important values to you that make you who you are? How did you develop these values? How do you implement and show them in your day to day actions?
What do you perceive are your greatest strengths? What about your greatest weaknesses? What do peers say about you based on these? Do they align to your expectations?
What are your long-term goals — not just from a professional standpoint but also from a personal standpoint? As Clayton Christensen mentioned — we often optimize only for our career without realizing that it has inter-tangled effects with other (equally important) elements of our lives.
What have you learned you liked or didn’t like about career choices that you’ve made (or if you’re a student - internship choices)?
What are other stories that are important in shaping the person that you are today? Walk yourself through these stories. What can you learn from them?
Write the answers to these five questions down — and deeply think about these in a way that is beyond just fluff. Seriously, get in deep and spend a few hours reflecting, writing, and thinking. And when you finish doing it — don’t just throw it away. Read it, and in a months time, reflect on it, and constantly revise it to fit the current model of how you think about the world. I cannot think of a better, most valuable, high-impact way to generate outcomes for yourself beyond this. And use this to guide your decision-making, and build integrity for yourself and what you believe in the process.
At the end of the day — mental models are just tools to make sense of the world around us — and are context dependent based on the state of our lives. I encourage you to apply these when you’re in the process of job-searching / making a career move, but also pressure test and apply your own principles to your decision making process. Good luck!
This the good stuff, Nate! I need to know what you're on to be able to write this! 😂
Completely agree on the last and most important peace; I always advise youngsters to get used to being alone and using that time to get to know themselves better. And really really loving the quotes form Scott Adams and Aaron Brown!
One thing that I'm unsure of is - what is "n-to-1 paths"? I can't seem to infer the meaning from the article.
Looking forward to more bro and all the best in GovTech! 🙏🏽