The Unstructured Path

I am a little lost with my career.

This is probably a common feeling for people my age, but it is an unfamiliar one for me. For the majority of my life and the entirety of my adulthood, I’ve clung to the idea of following a long-term plan; a life with clear precedents to mirror and defined parameters to follow. I am now approaching the end of an incredibly rigid path and I don’t feel particularly comfortable with the uncertainty that comes next.

I’ll be honest – all options that lie ahead seem to kind of suck, which is sad, but I suppose hilarious in a Shakespearean dark comedy sort of way. It’s not as though I haven’t spent hours and years laboring over this question. All the typical options pursued by people in my position – business school, staying in private equity, going to a hedge fund, trying out a start-up – they just don’t really appeal to me.

One of the most consistent realizations I’ve made since graduating is that most jobs and paths appear to sort of suck, at least a little bit. There are certainly exceptions, but it is my opinion that most people are probably at least a little disappointed with what work and the real world is really like.

It’s actually entertaining to witness the juxtaposition between my own career expectations and career reality, because I had been such a vocal supporter of finance when I was in university. Perhaps a little bit of self-delusion is necessary to succeed in life.

I think if you genuinely like your job (and you have been working there for more than a year), you should be ecstatic or at least very grateful.

In my view, it feels like most of the options I have in front of me require making clear wildly extreme trade-offs (such as work / life balance for prestige or ownership for risk). It’s a tough juncture and an uncomfortable feeling for someone who has consistently tried to optimize and preserve optionality.

The Power of Inertia

I got glimpses that I wasn’t suited for a grind-y and tough corporate life back during my junior year internship a few years ago. I interned at what Google searches have described as a leading private equity firm in San Francisco and found it to be pretty challenging. People were very bright, the commute was gruesome, the learning curve was steep, and I wasn’t handling the lifestyle very well. Unfortunately, I was unhappy. But, it almost didn’t matter what I thought by that point – it was probabilistically too late for me to really switch paths.

Recruiting for finance is this incredibly fragile and annoying thing (though I think recruiting is one of those universally crappy things). Finance recruiting requires a lot of premeditated work and careful planning to navigate well, particularly if you’re from a non-target program (which all Canadian schools are if your goal is the U.S.).

At the end of my internship, having already invested so much of my life into finance, I did what I think most immigrant children with inferiority complexes would do and tried to just tough it out. I ended up grinding it out for four more years in investment banking and then private equity (collectively), which brings us to the present.

To be completely fair, it’s a bit unclear how exactly I will feel about things when all is said and done, as I haven’t yet worked in other industries. But I think I realized that the work/life balance required for a high-pressure corporate job is not for me. I often lacked any control over my work and schedule, which I think deprived me of my sense of intrinsic self-worth. From my observations, the path to success seems to require a lot of lonely, labor-intensive hours.

I will say it has been relieving realizing that virtually all successful people had to grind to get there.

Separately, I found that my personal utility for money was much lower than I had anticipated back in school. Coming from a pretty frugal family has probably biased me a little bit, but I just don’t care that much about luxury. I think it’s fine and natural to like nice things, I just don’t have those particular preferences. I’ve noticed that from a psychological perspective, as long as my quality of life is modestly improving or staying the same, I am generally content.

I think I desperately sought some metric to derive my self-worth from after graduating (which had been academics and prestige as a kid), but I found that incremental money just wasn’t making me incrementally happier.

I’ve had these notions for a long time, but really settling and internalizing the conclusion to try something else with my career was a painful lesson on inertia:

Without conscious and deliberate effort, inertia always wins.

Tony Hsieh in Delivering Happiness

The vast majority of my peers will probably stay in finance. It’s honestly a great career path if you can handle it. People tend to think that you’re sick / smart and I think you can dismiss many of life’s problems by throwing money at it. It appears that is why finance is so incredibly difficult to break away from. The golden handcuffs are a compelling burden to bear and they appear to only become… more gold later in life.

There are times when I am confused with how so many of my peers are willing to deal with a life of brutally hard work. I think I came to peace with my decision to try something else once I found that my values no longer aligned with those around me. After four years of grinding, the ones who remain focused are those who genuinely like the work or those with psychopathic quantities of ambition.

Is it OK if I pick a more adventurous life?

I’m really not certain yet what I will do. I can feel the inertia (and my parents) pushing me to stay in finance, but I really don’t want to do Future Me a disservice.

I think I’ve received enough hints of foreshadowing along the way to know what those typical paths are like. I want to optimize for what I think will make me “happy” or fulfilled, which is a painfully intuitive but apparently a practically difficult thing to do.

I view these upcoming years as one of the last opportunities to steer the course and direction of my life. That might sound overly dramatic and cruel, but when I view the lives of some of the older peers I have, there doesn’t seem to be a lot of movement for most people after you’re 30 or so. I presume that when you have a kid or mortgage, it becomes harder to quit your job and act rebelliously.

As rough heuristics, I looked up the typical age for various life milestones: marriage (28 for men / 26 for women); getting an MBA (28); buying your first home (32). Those are huge life decisions just around the bell-curved corner for me and I think each of those decisions impair your ability to take risk. My finance friends sometimes joke that if you want to leave the industry, you should speak now or forever hold your peace.

Perhaps it’s a naïve and childish view to hold, but I remember hearing this on one of my favorite podcasts:

When I was in college, I had this revelation that I wanted to live my life like a character in a book. I wanted to make decisions for the most interesting story. So many decisions don’t seem linear (from a career point of view). I made those decisions because I want to be on an adventure. I love adventure.

Scott Norton on Khe Hy’s Rad Awakenings Podcast

I wouldn’t say I love adventure – I probably just… like it compared to some people. But I think I need to start embracing the possibilities that come with non-linear thinking and exploring different career paths. It’s taken years of incubating these ideas and trying to train my mind to think differently about risk.

I’m giving myself a one-to-two-year sabbatical to figure things out. I’m going to experiment with various forms of entrepreneurship to see whether aligning incentives will fix my career apathy. I also plan on devoting significant time to producing music, writing, learning Chinese, and becoming a more well-rounded, healthier person.

I’m finally getting off the path.

(1) Median age for marriage (
(2) Average age for full-time MBA (
(3) Average age of first-time buyer (CNBC).

5 thoughts on “The Unstructured Path

  1. Good for you Matt, you’re a leader. I have no doubt that as you seek, you’ll find what it is that you’re made for.


  2. I’m proud of you, Matt. Thank you for being so vulnerable and candid. I’ve always looked up to you so this means all that much more..

  3. Money can’t buy happiness.. thanks for the insight and I hope you find what you are looking for on your sabbatical

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