The Path
5 min read

The Path

For me, The Path started when I began my career in finance in 2002. Actually, I've probably been on The Path even longer, since middle school. Get good grades, get on the honors track, do extracurriculars. Get into a good college. Get a good job. Get promoted. Get a better job. Get promoted. Get a better job. Get promoted.

By the time I turned thirty, I had begun to question The Path. I wasn't satisfied. I felt bored. Work was tedious. People would tell me "That's why they call it work!" or "It'll be worth it in the long run!"

There were always good reasons to trust The Path. Once I find the right company, I'll like my job. Once I find the right position, I'll be satisfied. I'll leave work at work and I can do whatever I want on my own time. But those reasons just didn't sit right. There was a slow grind of discomfort that finally led to a realization.

The work wasn't stressful, it wasn't even hard.

It was just pointless.

I don't even mean a "this won't change the world" pointless. I mean a "Dwight Schrute" style of pointlessness. And this level of senselessness permeated all of my jobs.

There was the job where management didn't even use the analysis that my group created. Decisions were made and then we would come up with analysis that justified a preconceived decision. I could have done nothing and there would have been the same result. I know it's true because I tested it.

There was the job where twice a day, everyday, all 30 people had to do a manual process (literally checking off boxes) for 5 minutes to run a report. I asked for them to automate it, even diagrammed out exactly what needed to be done. This fix would take a day to implement and save everyone days each year. By the time I left a year later, it hadn't moved from the bottom of the Kafka-esque priority list.

There was the job where we consistently stayed until 2 in the morning in order for our manager to give feedback the next day. Of course, that feedback didn't come until the afternoon the next day, necessitating us to stay until 2 in the morning again in an absurd time loop.

It was Performance Art.

There's a concept named Pournelle's Law - "in any bureaucratic organization there will be two kinds of people: those who work to further the actual goals of the organization, and those who work for the organization itself." The second group are the ones that control the organization and get rewarded, while the first group provides the horsepower.

How could this exist? Because it doesn't hurt the bottom line. Actually, it can help - our analysis group was the shiny toy they could show off to raise money, even if the analysis itself did not matter. Since what we did was superficial, ambitious managers didn't have to apply real thought or effort. They could make arbitrary decisions that benefited themselves rather than the company and use the rank and file as hard working pawns.

At another job, there was a team bonding event at an Escape Room. I played "good little soldier" and followed the crowd until we got bogged down. My competitive side came out and I started solving puzzles and delegating tasks. My boss (who I was friendly with) later jokingly said that he didn't realize how much I was sandbagging at the regular job. I wanted to ask him why management sandbagged us last week when we stayed in the office until 11 figuring out a plan to save an investment only to get vetoed the next day with no explanation.

I still didn’t even know where The Path led. I realized I didn't want my job, I didn't want my boss' job, and I didn't even want my boss' boss' job. I was making a significant amount of money, but I wasn't actually creating value. To be successful in this industry was not by creating value but by making your boss look good. That didn't come naturally to me. I had already undermined my career by not putting in face time and by questioning my superiors.

James Altucher says that there are good reasons and there are real reasons. The good reasons, such as "It's prestigious", or "People would kill to have that job" didn't hold up to examination but kept me on The Path.

The good reasons were the bribes your parents gave you to get you to behave.

The real reasons were that the money was good and The Path was a siren's call to a life of comfort. The money to me was security and optionality. But I wasn't using the optionality to do anything and because I had already stopped spending money on things I didn't enjoy, I had a degree of financial security. Why be inauthentic to myself in order to pursue goals that didn't interest me? In finance, the answer to the interview question "Why do you want this job?" is a dirty open secret. You are not allowed to say money. Even though that is everyone's real answer. You must make up an answer to prove that you are not a masochistic psychopath. I couldn't lie anymore. The only reason to stay in this job was money, but to me cash was the applause of Performance Art and I would rather put on my own show in an empty theater.

I realized The Path is a fairy tale, surrounded by boogeymen in the form of "good reasons".

A year ago, I stepped off The Path.

I quit my job.

The world didn't end. I saw a bald child who told me there was no spoon. The numbness disappeared.

Looking for The Right Path was like waiting for Godot. Not just my job, not just the industry, The Path itself is Performance Art. The Path is full of "Gets" to check off and show off. I had chosen The Path, but I hadn't created it. Now, I knew I could not even choose The Path.

I’m not going to say I wasted eighteen years in a finance career. It took me that long to figure out what I don't want. Thankfully, I also gained perspective, life-long friendships, and the security to look for what I do want.

So for the past year I've been exploring what interests me. Cooking with my wife. Long walks. Writing on a blog that no one will find. Figuring out different ways to learn. Taking online courses. Teaching my wife how to snowboard. Doing things that I think are important, not things other people tell me are important. Things that I enjoy intrinsically. Things that I think improve me or that I can improve in the world.

Even the most prosaic things can be interesting. A month ago, I spent hours shoveling through a twenty inch blizzard. Figuring out the most effective process was an interesting problem (we have a gravel driveway so you can't pile the snow up on the grass and you can't block the cars) and then physically implementing and iterating was hugely satisfying. I honestly can't wait for another big snowfall so I can see if I can clear the driveway faster.

The contrast to my working experience is remarkable. Instead of constantly questioning "What am I even doing here?", I'm questioning "What can I do here?" Anything I do now doesn't feel like a burden, it feels like a puzzle to be solved.

So why did I leave The Path, my career in finance? I hadn't understood what I actually cared about. I hadn't understood my true motivations. Once I understood that my motivations were not actualized by my career there was no reason for me to stay. The Path was full of other people's wants and needs. My needs were different: I needed to create value, to have a process and pair good thinking and conscious effort. I can only do that by pursuing what is interesting to me, by exploring my curiosity. And now I can do what I really want to do at 2AM: sleep.