No doubt 2022 was one of my most challenging years. I was consumed by work in ways I never thought was possible. I think I even lost myself for a while. One good thing (of many) that came out this experience was that it crystalized several career lessons that had long been on my mind.
This post walks through 15 of my most important lessons on the topic of career development. This is also Part 3 in the 10 Areas of Life series.
Lesson #1: The Ikigai framework is a great starting point
For years, the Ikigai concept has served me well as a starting point for making career-related choices.
Basically it’s saying find a role that overlaps the four areas as much as possible:
- What you enjoy
- What you’re great at
- What the world needs
- What pays well
While all this seems sensible, I faced a number of challenges when attempting to apply it in practice. Particularly in the early years of my career.
First, I didn’t really know what I “loved” – at least in a career sense. Halfway into my engineering degree, I recognized I was more drawn to solving complex business problems as opposed to more narrowly domained technical ones. Yet I had little to no idea on what kind of business roles were out there. Let alone which could be suitable for me.
Second, whatever I was good at kept changing over time. I felt like my strengths were more of a byproduct of wherever my energy happened to be channeled to, as opposed to some persistent or innate talent.
Third, the world seemed to need a lot of things. I read. I travelled. I exchanged countless conversations with hundreds of people. To my surprise, the more I learned and experienced, the more confused I was about which “problem to fall in love with.” Ah, it’s Dunning-Kruger and Imposter Syndrome at it again.
Fourth, what pays well seemed more like a lag measure of the above two points. Become highly skilled at a solving a critical need and the rewards will follow.
Here’s how I oriented myself amidst this confusion.
Lesson #2: Nurture your pre-existing strengths
I figured, the world was in perpetual need of so many things regardless. So I honed in on the what-you-are-great-at point.
One by one, I pieced together the hints that revealed what I might be good at. I pushed aside more grandiose questions like “What can I be the best in the world at?” and opted instead for the more grounded ones like “What am I generally better at compared to those around me?”
I embraced the little boy inside me that would get excited about drawing patterns between concepts, events – across time, place, and discipline. I recognized that I was pretty good at reducing complex ideas and situations into its atomic units. Then by, first principles, reassembling and repackaging them into something more relatable. I also realized that I enjoyed explaining complicated concepts in the simplest way possible. Perhaps an undoing of being a high school math and science tutor for 6 years. And despite my fickle ambiversion, I loved working in highly cross-functional and interdisciplinary teams, embedded in fast-paced environments, taking on the most existential problems facing the organization. Being among smart people. All these things made me feel most alive.
The hard part for me from here was figuring out what kind of roles would get the most out of me. In all honesty, I’m still finding my footing in many ways. But I’m now more confident than ever with the general direction I’m heading in.
So if there’s anything that seems difficult to most people but is somehow less difficult for you, I encourage you to explore that further. Nurture your pre-existing strengths.
Eventually, I noticed that every career question I pondered on always came down to just 2 things: value creation and value capture.
Value creation is what the world needs and what you’re good at.
Value capture is what you enjoy and what pays well.
Reducing every career question into this intentionally simplistic dichotomy has proven remarkably useful.
Lesson #3: Focus on creating value rather than capturing value.
Most people obsess over capturing value: “I want work-life balance. I want to work for an organisation that sees its employees like business partners, and compensates them generously. I want to be in a role that brings out the best in me.”
It’s better to instead focus on creating value: “I want to play an integral part in building a valuable company. I want to be world-class in my area of work. I want to make a real difference.”
Value capture tends to be about having this and that. It often attends to lag measures – passive downstream effects of upstream causes.
Value creation, in contrast, tends to be about being and doing. It usually attends to lead measures – actionable upstream inputs that cascade into downstream outcomes.
Placing more attention towards value creation is exactly what helped me embrace the mantra: “be, do, have”. One must first do in order to have, and be in order to do.
Rather than asking “What do I want to have? What do I want to do?” instead ask “What can I have? What can I do?”
Rather than starting with self-centered motives, ask “What does the world need?”
Then ask “Which of these best align with what I want and what I can?” This overlap is what should be your contribution. This is the Ikigai.
There’s more to this than advocating selflessness over selfishness though. You see, the world is a funny place. It’s marvelously fair at times, and unapologetically unfair in others.
Lesson #4: Recognize that the world values outputs over inputs – and to a broader extent – outcomes over outputs.
Life’s not fair in a sense. There’s a brutal mismatch between your inputs and the rewards you get.
“I’ve been here the longest so I’m entitled to that promotion. I worked the hardest so I deserve that bonus.” These are common career misconceptions of the hourly worker mindset.
I’m sorry, but this is just not how the world works. You’re not always going to be compensated based on your inputs. Especially as you move into more senior roles.
Nor does the world care all that much about your outputs. Number of reports published, projects completed, code deployed etc are all vanity metrics at the end of the day.
Instead, the world rewards you based on the outcomes you generate.
Entrepreneurs would understand this. The free market doesn’t care about who worked the hardest. You’re rewarded for your ability to solve the latent problems as opposed to the hours and energy you’ve put in.
The sooner you realize and accept this, the sooner you’ll be on a more productive path.
Indeed, there are countless instances where meritocracy is broken. The more political an organization is, the less efficient its input-to-output-to-outcome ratios. Tragically, many organizations promote based on more visible, tangible, and individually attestable outputs rather than more subtle, intangible, and individually unattestable outcomes.
On the other hand, the world is also fair in a sense. It’s generally meritocratic on an outcome basis. The more value you create, the more opportunities you tend to get to create even more value. Perhaps I’ve been lucky. But at least in my own experience, I’ve seen a high degree of correlation between inputs, outputs, and outcomes. So if you’re giving it your all (high inputs) and continually refining your mental models of reality (high outcome-to-input ratio), keep at it. You’re on the right path to being more useful to the world.
Ok, so create value by generating outcomes. Now how does one go about quantifying such nebulous concepts?
Lesson #5: One proxy for value creation centers on the scale and complexity of the problem you’re capable of solving
Since it’s difficult to answer “How much value am I creating?” I like to proxy this by asking “How big and/or complex of a mandate am I capable of leading?” And check that how much it grows over time.
When starting out, my contributions could only ripple out so far. I was responsible for executing tactical level initiatives. Conduct a data refresh and reformat this deck. Draw out the ‘so whats’ from this 100-page report into 3 slides. Given that these are the inputs we have, and these are the outputs we want, create the Excel model such that we can easily play around with the assumption parameters. These mandates would range from several hours to several days.
Then I was responsible for managing work at the project level. Prepare the RFP for this tender. Lead a 3 FTE project team to deliver a 6-week $250k client engagement. Design our pricing model and schedule. Our biggest client is at significant churn risk – find a way to keep them. These mandates would range from several days to weeks.
Later, I’m responsible for managing work at an even more holistic, company-wide level. Assess whether now is a good time to expand into the US, and if so, draft the GTM strategy. Here’s a pilot client and a MVP. Now go set up a new business vertical – establish all the SOPs, refine the product, acquire suppliers, hire and build the team. Oh and try not to spend more than half a million dollars. These mandates would range from several weeks to months.
So as my career progressed, the scale and complexity of the problems I was solving kept increasing. In doing so, I knew I was adding more and more value over time. (By “I” here, of course I’m including the teams I was coordinating and leading. They were not individual achievements.).
As the mandates I took on became scarier and hairier, I noticed certain commonalities amongst these problems.
They were entangled with other problems. They were a subsystem within a broader set of systems. They were fraught with subtle non-linearities, hidden dependencies, and non-ergodic processes. They were bounded by an endless list of hard constraints, such that every local optimisation had to be carefully weighed against broader global optimisations. They were time-sensitive – no decision was itself a decision, and often a subpar one at that. They were path dependent – most choices were irreversible. There’d be insufficient information available, and even when raw data was attainable, or insights calculatable, the cost of measurement was too high. They were NP-hard problems in a business context. They were wicked. Oftentimes, the initial solution would make the problem even worse.
Above all, all of these hairy problems required an excellent orchestration of teams of teams.
Lesson #6: The most complex problems requires exceptional vertical and horizontal competence
As an organization grows, the scale and complexity of its problems grows even faster. Even simple headcount additions multiples communication complexity. (Because the combination of linkages in a network grows faster than the number of nodes added).
This is why the dictator-genius with a thousand helpers model can only get so far. No one can be a specialist at everything. No one can keep up with what’s going on. A network of 100 billion neurons in a single human brain just doesn’t have the processing power. And even if someone somehow could, they wouldn’t be able to act fast enough to have materiality.
So problem solving at the highest levels requires deep, technical domain expertise – I call this specialization vertical competence. It also requires rich horizontal competence. Which I think of as the ability to deploy the most applicable mental models to observe, orient, act, and decide. This includes having excellent soft skills and leadership qualities. Horizontal competence is about generalization.
So big problems need lots of people focused, aligned, and committed. In fact, this is the definition of an organization or business. It’s getting people together to create a ridiculous amount of value for the world, and capture some of this value – in a way that’s impossible to do alone. Organisations, businesses, and teams are vehicles to achieve this.
While I won’t diverge too much on how to build competence, I’ll share just one key point that has worked wonders for me.
Lesson #7: Apply leverage to accelerate
While your career will grow naturally over time, one way to supercharge it is to apply leverage.
Leverage knowledge and experience by learning from others that have already gone through similar journeys. Read articles, essays, and books. Watch explainer videos and documentaries. Listen to talks, and debates. Engage in productive conversations. Apply the lessons learned. Experiment. Adapt.
Also leverage your time. Figure out how to gain 2-3 years’ worth of experience every year.
Figure out ways to do things at twice the speed without compromising quality.
Work a little longer. Not double the hours, but something like 20-30% more than most. If you start at 7.30am and engage in 2-3 hours of deep flow-state work, you’ll get more done in that one morning than what most get done in their entire meeting-and-procrastination-ravaged workday.
Run towards the ugliest problems rather than shying away from them. Appreciate that the sink-or-swim situations are usually the most transformative periods. But only if you process and interpret it that way. Get into a habit of frequent microreflections. Continually refine your approach.
Also figure out where your mental health danger zone is. Then keep a 20% safety margin away from it.
Reject the default organic growth rate. Stretch yourself to hack in as much inorganic growth as possible.
Working for a fast paced start-up is a great way to do this by the way.
Let’s now go into value capture.
Lesson #8: Be brutally honest with yourself on what value capture means to you.
Who’s the most successful person you know?
What makes them so?
So what exactly does ‘successful’ mean to you?
Most people would interpret ‘value capture’ through the len’s of society’s conventional definition of ‘success’. A respectable occupation. A fancy job title in a prestigious organization. Lucrative salaries and bonuses. High net worth. In particular, high self-made net worth. Plus a panoply of material-based social status indicating cues like the car you drive and clothes you wear. All age-adjusted of course.
I won’t bore you by telling you what you already know: that there’s more to life than chasing social prestige. I’ve already written about this here.
While it’s fashionable to bash on these conventional success measures, there’s nothing fundamentally wrong or immoral about wanting some of these things. It’s ok to want a beautiful home, travel to incredible places in style, and indulge in amazing food. Just beware of the common happiness traps in chasing social status.
More importantly, be honest with yourself on how you measure progress. You are your only judge here.
Create your own definition of success, without overly glorifying or vilifying the conventional definition.
What is it that’s truly important to you?
Lesson #9: Benchmark for inspiration
I admit freely that I’ve frequently compared myself to peers on career progress. Even more so in my mid 20s. He landed this incredible role. She got an astronomical pay raise. I couldn’t help but ask: “Am I doing well? Am I where I need to be at this point in my life?” On countless occasions I felt like I was behind.
I knew much of this insecurity was rooted in my personal experiences growing up poor. While I knew that the comparison mental battle was futile, I just couldn’t help myself.
Even as recently as early 2020, I remember ending a day on a low after learning that my pay would be reduced by 30% due to the pandemic uncertainty. That evening, I learned that one of my friends just earned a $200k bonus. I was ecstatic for him. But also got hit by a toxic dose of “Oh man, what am I doing with my life.”
As I gradually I chipped away my cognitive dissonance over the years, I found an even better way to handle all this. Rather than cutting out comparisons wholesale, transform the the insecure-envious variants into healthy inspirational comparisons. Career insecurities can eat you up inside. But this power can also be harnessed into a productive force that propels you forward.
Compare yourself to others to be inspired, not envious. They reveal paths that you didn’t know could be taken or even existed. They turn your “Damn, that seems out of reach” moments into “Wow, if they can do it so can I.”
Lesson #10: Embrace the full package
Loving your job doesn’t mean you have to love every aspect of your job.
You will encounter assholes. Apply Hanlon’s razor – “never attribute to malice that which can adequately be explained by stupidity”.
You will face on some dark moments. Apply antifragility – walk through the mud and come out stronger than ever.
“If you’re going to eat a shit sandwich, don’t nibble” – Ben Horowitz
Embrace the full package. Especially if you signed up for a challenging role in the first place.
Lesson #11: Consciously choose your place on the Striver-Settler Spectrum
Strivers are your classic A-types. They’re ambitious. They’re proactive. They pour their whole heart into their work. They’re energized by fast pace and intensity. But they’re also more susceptible to stress and tend to be impatient.
Settlers keep the machine running. They’re chill. They have a more lackadaisical outlook on work. They value peace and simplicity. They have clear boundaries between work and life that needs to be respected. Their motivation to work usually revolves around the amazing people they work with, more so than the problem the organization is solving.
Indeed the striver-settler tendencies are on a spectrum. Everyone sits somewhere in between these extremes. I find myself hanging out on the striver end more often, but I embrace my settler moments too.
There’s nothing wrong with being more of a settler. Everyone has different goals, values, and priorities. What really matters is that you’re making a conscious choice on where on the spectrum you want to be.
If you’re more of a settler, appreciate that you can’t always have it all. If strictly-no-work-outside-9-5 is your religion, I sincerely respect that. But also accept that this approach will narrow down the kinds of roles that are suitable for you.
If you’re more of a striver, don’t be surprised that fulfilling this ambition comes with more sacrifices. More hours. More energy. More stress. Be prepared to make some trade-offs. Having said that, call out and protect the aspects of your life you’re not willing to give up.
Lesson #12: Play the long game
I’ve always liked to tell people and myself “When in doubt, zoom out.”
What I mean by this is to focus more on the pace and direction you’re heading rather than where you’re currently at.
Speed over location. Rather asking “Am I happy with where I am?” ask “Am I happy with the pace I’m moving at?”
Velocity over speed. Rather asking “Am I happy with the pace I’m moving at?” ask “Am I moving in the right direction?”
Acceleration over velocity. “Am I happy with how fast my pace is increasing?”
Never underestimate the power of compounding. Play the long game.
I might also add: journey over destination. Enjoy the process of creating value, independent of the quantity you’re creating.
Lesson #13: It’s rational to be slightly naively optimistic than safely pessimistic
So many people construct narratives to protect themselves from failure. They employ self-bashing pessimism to cap their emotional downside. They’re afraid of telling themselves that they can do amazing things. This is cheap insurance against the agonizing pain of disappointment and embarassment.
But this cocoon of denial is counterproductive. It erects a glass ceiling on the potential upside. If one thinks “I”ll never get there”, there’s no point in giving 100%. The sacrifices involved with taking their career to the next level will be too intolerable. This way, “I can’t do it. I’m not capable.” becomes a self-fulfilling prophecy.
Instead, optimism about one’s future – a generous serving of excitement with a healthy dose of fear – invites a more inspiring state of mind to work in. This increases the odds in your favour. “I’m not sure how I’ll end up in that role, but I’ll figure it out” is more likely to succeed.
So it’s rational to be optimistic. Even if a bit of naivety gets mixed in there.
Lesson #14: Be grateful for the opportunities you have
Recognize that the value you’re able to create and capture is largely a function of the opportunities that have been presented to you. The role you’re in is far from a guarantee on how much value you can generate. It’s merely a platform, a vehicle, a potential to create and amplify.
Chances are, there’s a lot of people out there that would love to be given the opportunities you currently have in your role. Chances are you’re in a privileged position. So make the most of where you’re at now. Be grateful for what you have and where you’re at, rather than being disappointed with what you don’t yet.
Lesson #15: It’s convenient if your career is your contribution, but it doesn’t have to be.
Throughout this post, I’ve intentionally used the word value in the broadest sense. It extends much further beyond financial value, which is just a proxy, and a shabby one at that.
For some people, Career and Contribution overlap a lot. Their job and their work is exactly how they create value for the world. Even if it’s not clear what their individual contribution is, if the organization they work for does useful things for the world, and the team they work for does useful things for the organization, and if they do useful things for that team, what more could you ask for?
For others, say stay-at-home parents for instance, their means of value creation occurs very differently. There’s people that do their fair share on weekdays 9-5, but propel most of their energy into their evening side hustle, or weekend community activities. These are all equally valid and valuable contributions.
This is why Career and Contribution have been split out in my version of the 10 Areas of Life.
So regardless of how you create value, take pride in it.
Social merit should be given value creation not just value capture. This is something I wish the world did more of.
Recap of the 15 lessons:
- Ikigai is a great starting point
- Start with what you’re good at
- Focus on value creation over value capture
- Measure outcomes over outputs over inputs
- Consider problem scale and complexity
- Build vertical and horizontal competence
- Apply leverage to accelerate
- Be honest with yourself on value capture
- Benchmark for inspiration
- Embrace the full package
- Consciously choose your place in the striver-settler spectrum
- Be rationally optimistic about your career
- Play the long game
- Be grateful
- Recognize that career and contribution can be separate
Take pride in creating value for the world. Don’t be shy in capturing some of this value. And enjoy this cyclic process of creating and capturing value.
Enjoy being useful to the world.
Career and Contribution questions for introspection:
- When someone asks you what you do for work how articulate are you? Do you like talking about work outside of work?
- What are the 3 things you like most about your job? 3 things you dislike most? Which could you think of faster – likes or dislikes?
- Do you find the need to escape from work every weekend? How much does “Build a life you don’t need to escape from?” resonate with you?
- By continuing on the path you’re on, where are you hoping to get to? How confident are you about this? What gives you confidence or lack thereof?
- How much more value are you adding to your organization compared to a year ago? Would your colleagues say the same?
- If you could start your career all over again, what would you do differently?
- What are things you want to do differently but struggle to?
- What would it take for you to leave your role/organization? Would you jump ship for a 50% salary increase?
- Is your current role turning you into a better person?
- What’s really hindering you? Honestly, what are your deepest insecurities slowing down your career progress?
- What value is your organization contributing to the world? How does your department or team contribute to the organization you work for? How do you contribute to the team you’re part of?
- How important is your career relative to other aspects in your life?
10 Areas of Life Series:
- Part 1 introduces the 10 Areas of Life goes into 3 sustainability enablers: Physical, Mental, and Financial Health.
- Part 2 covers the people and relationship elements: Partner, Family, and Friends.
- Part 3 covers the value creation elements: Career and Contribution.
- Part 4 (coming soon) will cover the experience elements: Intellectual and Adventure.
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