Careers and Hills

2140 words, 12202 characters

As I’ve grown older, one question consistently comes back to haunt me. What am I to make of my career?

I’ve heard plenty of the common advice, optimize for money, for impact, for prestige, for mentors, for a high-growth company, for a great culture, for passion. What I’ve learned is these are all good career anchors, but it’s one of those situations where the high degree of randomness forces every answer to be both right and wrong. Needless to say, the grass is always greener on the other side. Working in finance? Tech has a better work-life balance with the same pay. Working in tech? Quant traders get paid more, much more. Working as a quant? Job security is worse than those working in finance.

Yet, amid this sea of uncertainty, I’ve gleaned one fundamental tenet. I can count on one hand (maybe two) the number of people I’ve met that genuinely enjoy their jobs. In percentage terms, less than 1% of people that I’ve met are actually happy with their job. Work doesn’t seem to get more fun or more rewarding as we age. Instead, it seems that we become more accustomed to trading time for money and more patient with the shortcomings in our professional lives.

To me, that’s incredibly scary. Does this mean that I’ll have to pick a line of work now, not knowing if that’s really what I want to do? Over the next few decades, do I adjust myself to the work, all the while ignoring any wisps of doubt? Or does it underline an inevitable tradeoff between money and happiness, magnetizing the mutual exclusivity of both? The popular entrepreneurship myths sell the story of building your own company as the perfect intersection between happiness and wealth. The reality that I’ve experienced building two moderately successful startups is that entrepreneurship simply ties your happiness to your wealth. You celebrate when your company does well, you grit your teeth and work harder when your company doesn’t. You smile after a milestone but there’s always the next obstacle, the next hurdle, or the other companies that grow faster than yours.

As I’ve read more of different successful, and hopefully happy, people give advice, the only conclusion that I came to was that very few have contemplated or questioned the concept of careers. Advice given, in one form or another, is always optimized with the intention of outlining a path to some ill-defined high point of a career. But what are careers?

What are careers?

Definition-wise, careers are defined as the linear progression of jobs with increasing levels of responsibility. It’s a path starting with titles like Junior or Associate and ending with titles like MD, VP, C-suite.

Or, careers are simply a path that we walk down, with a start, an end, and a very long journey in between.

Some describe this journey as a series of dots waiting to be connected. And others talk of it as a trail with a thousand different forks. Whether dots or trails, each career path might start at different starting points, but they all end with the hope of a happy ending. Maybe that starts with working at McDonalds, finding the love of your life there, and progressing to store manager where you’re surrounded by loving friends and family throughout your career. Or that path starts in finance where you’re continually promoted from youngest principal to VP, partner, and onwards until you can look back at your career and say that it was a life well spent.

We define success in compensation and power, rather than happiness. Happiness is qualitative, squishy, and hard to measure. Is the janitor that hums on his way to work better off than the CEO that eternally wears a scowl? With ambiguity around what a successful career means, we orient to metrics we can track.

But that isn’t a complete view. At a basic level, careers are meant to maximize a person’s potential “output”. Career progression is the combination of responsibility, risk, and outcome. Tactically, what this means it that early in a person’s career, the risks are limited and likewise, potential outcomes are rather narrow. The focus is more on learning the ropes and observing more experienced members. Mid-career, the risks are more pronounced though the potential outcomes are still generally positive. It’s also a period where responsibilities such as leadership and abstract decision-making start to pile on. Finally, the tail part of the career is where risk is now fully exposed and outcomes range from wildly positive to wildly negative. The experience accumulated through a long and fruitful career helps those in their twilight years guide younger generations and enable decision-making with much smaller margins of error.

These yardsticks of responsibility, outcome, and risk are only appropriate for knowledge workers. Output is defined on a different plane between a CEO and a janitor. I use the example of a janitor because the tasks involved are relatively simple and experience plays a small part in outcome. In other words, there’s comparatively little difference between a janitor cleaning for three versus thirty years. As a result, this framework is woefully inadequate for many and can in fact be dangerous, dangling some mythic happiness fruit at the top of a long ladder of work and responsibilities. The story of a janitor becoming a CEO is celebrated. The inverse narrative, where a CEO becomes a janitor, is scoffed at even if the person is happier as a janitor.

Further, understanding the macro direction of careers means very little on a personal level. For someone struggling to comprehend the purpose of realigning powerpoint margins, career is a poor consolation.

Careers are meant to help you build. In the same way that entrepreneurs build companies or construction workers build bridges, careers are meant to help you build your own fiefdom of accomplishments. Rather than having to start from scratch or investing decades of your life into a monolithic creation, your career allows you to pile up smaller, shorter-term projects together. The resume is marketed as a representation of a career. It acts as a trophy case where each trophy can be unique and different from the others but assembled together, they become a beautiful collage of achievement - of “a life well spent”.

So is a career just a trophy case?

To me, the answer is no. A career, time spent over forty to fifty years, should be more than the two-dimensional view of a trophy case. In reading through biographies of famous people (definitely a biased sample set), I saw how success for many wasn’t a carefully choreographed dance but rather serendipitous. They put in the work and ended up at the right place at the right time. There’s another place where serendipity happens, hiking.

From that, the best definition that I’ve come up with for careers is that a career is a series of hills. Some people climb up a hill and decide they like the view at the top. They settle down, build a house atop the hill and improve upon it year over year, adding trees, gardens, and paths to help others climb the hill. Sometimes, it’s not even at the top of the hill. They find the right height with the right view and call it a day. Some want to explore the view of taller hills which make for a more arduous climb. Some want to try something new and climb a hill in another area, one that might not be taller but is definitely different. Finally, some reminiscence about their previous views and retreat back to the previous hill.

To put it all together, a career is simply a journey of climbing hills, collecting and assembling the views at the top of the hills, until the desired view is found.

What is my career?

Under this lens, I can finally attempt to answer the original question, “what am I to make of my career?” Or more specifically and morbidly, “what views do I want to see before I die?”

When I was younger, I had a burning desire to climb further and faster than others. Rather than some specific view atop a certain hill, I wanted to see views that were simply higher than others. I was willing to pay dearly in pursuit of this.

As a result, I took huge gambles on non-traditional paths of success, such as starting an underground gaming service where I bought and sold game accounts and hedged different risks rather than do my homework. In these gambles, I was also willing to place a stupid amount of effort into them. Even to this day, I can name the market price for every single skin in League of Legends issued before 2018.

At the same time, I was extremely lucky and found a yet-unexplored niche in publishing. To borrow from poker terminology, I went all-in on this opportunity. Beyond just homework, I started to bring different papers to read in class and furiously scribble over. I even borrowed time from studying for the SATs and writing college admission essays to work on the venture. I tried to outwork everyone around me.

It worked. These efforts led to my first company that was eventually acquired while I was still in college. The combination of luck and hard work helped me climb to heights that few others saw. Yet the views there meant little to me. Celebrating the acquisition over a fancy meal, my only thoughts were around how I could build the company to be better. Like before, my motivation came from staying one step ahead of others rather than finding some specific view.

And so, I kept climbing. Since the acquisition, I left the company I founded, learned a bit of venture capital, joined another venture-backed startup, and started another company. One after another, I was searching for a view that was always a bit out of reach. Yet, as soon as I found any view, I would realize that I wanted something better, something higher. I was continuously climbing.

It’s really been the past few months where I slowed down both by circumstance and choice that I’ve gotten a chance to really examine what I was searching for and let the question of careers catch up to me. For so much of my life, I had been avoiding the question and simply been ambitious without ambition.

After mulling the question for the past few months, my answer is astoundingly cheesy. I want my career to be fun. I want to find the views that will bring a smile to my face.

The other day I bought a wood chisel set and started to carve a ball out of pine - I nicked myself a couple times in the process. Is woodworking going to be my long-term career? Probably not, but the view from the top of a hill, no matter how small, counts and for me, I’m ready to appreciate that view.

I’ve also begun to write more. In the past few years, my writing muscles have become so familiar with company strategy docs and process outlines that the first five hundred words of this blog post took nearly a week to perfect. But I believe this is some of the best and most important writing that I’ve ever done. I’ve been able to take vague trains of thought that have been nagging at me for years and put them on paper, something I’m really proud of.

Beyond writing, I run a small private equity firm called Fund22 where I buy small companies and build them into sustainable, friendly companies. In other words, private equity without the cost-cutting. I’m not sure if it’ll work, but I’m enjoying almost every second of it and know that I’ll treasure the successes so much more than before.

With a mix of wood chiseling and starting a PE firm, the line between hobbies and profession has started to blur. I guess nothing is off-limits in the pursuit of happiness. And perhaps, this just might be the right climb for me.

PS: Writing this may have been one of the most challenging things I’ve done in my life. Starting in February, I typed, edited, mulled, and fretted over every word and multiple drafts. Looking through and adding up all the various drafts, I had typed over 15,000 words to compile this short blog post of 2,000 words. No wonder it took me such a long time.

Writing this was also inspired by the Billy Williams Story → “So…I guess, on my bucket list, what I really wanna do is-s, drop…a project. Like, nobody has to even listen to it. I just, wanna know that, I did it. Be able to say, I went out there and, did that and I chased my dreams. And that’s really it.”