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What My Spectacular Failures Taught Me About Jobs, Passions, and Finding My “Life’s Work”

How NOT to be naïve about your passion and find something you love doing.

Photo by Clark Tibbs on Unsplash

My father worked for almost 40 years — for 12–16 hours per day, at a job that he hated. He worked all sorts of crazy hours, was shuffled from location to location, and by his account — hated every minute of it.

Also by his account, he was in this situation for 2 reasons:

  • He didn’t go to college, but rather chased after an immediate paycheck
  • He didn’t pursue his passion, and so ended up working only for money

As a result, my primary directives in live came to center around not repeating those two mistakes. My journey into work thus began not through money, but through trying to find my passion, my “life’s work”.

Unfortunately, my naïve understanding of that concept did me more harm than good. And it took me a lot of mistakes and pain to learn a better way to look at the idea of passion, loving what you do, and the concept of “life’s work”.

The First Mistakes

From the time I was about 5, art seemed to be the candidate for my passion. I had been drawing since I could remember doing anything. I loved reading comic books, and created my own characters and stories.

This continued throughout school, but during that time I began to really embrace more scholastic and intellectual subject matter. I began really enjoying the critiquing of art — the examination of themes, concepts, and ideas. I began procrastinating on my own work, turning in technically shoddy pieces, and explaining away the shoddiness with flowering, interpretive prose.

This was the first of many missed signals that I was on the wrong path.

My senior honors art portfolio was sparse and filled with sub-par work. I just couldn’t get motivated to put in the time — and it showed. The only area in which I shined, according to the feedback from the board, was the essay explaining my portfolio.

It was clear to my teacher that I didn’t have the time or energy to waste on my supposed passion, but I could devote plenty of time and energy to putting words together to explain it. I should’ve learned something from that, but I was 17, so I just applied to art school instead.

Once at art school, I began to feel completely outclassed by the people in the illustration program. From the introductory drawing classes onward, I was out-shined every time we put work up to critique. The only time that I didn’t feel out-shined was when I was talking or writing about the ideas and concepts surrounding works of art. I received numerous compliments on my critiques and insights, but because I still was so sure I was an artist, I ignored what was right in front of me.

Spectacular Failure…and Something New

After 2 years of art school, I finally received a message I couldn’t ignore or explain away: I failed my art classes. I couldn’t move on in the program. I was done.

But then something weird happened.

I had been taking Philosophy 101, and liked it a lot. I loved the stuff we were reading, I loved writing the papers, I loved the discussions in class.

On the day of the final written exam, after I had handed in mine, the professor made it a point to follow me out of the room and chase me down to talk with me. He said he saw a lot potential in me, and suggested that I pursue philosophy as a major. Had I not just failed my art classes, the message might have fallen upon deaf ears. But alas, the timing was right.

Days later, I decided to change course, and formally declared philosophy as my new major.

I proceeded to fall in love with philosophy, and because I really wanted to continue doing it, I looked for the narrow and well-worn path to make it my job. That path is to get a master’s degree, a PhD, and become an academic.

So in starting to take that path, I narrowed my vision, and made my success contingent upon following an unnecessarily narrow path. I began work toward my master’s degree, and dreaming of PhD programs. My mindset was that my life’s work was to be a philosophy professor. Nothing else would suffice. By thinking in this narrow way, all I did was give myself a shortcut to severe disappointment.

I essentially crafted an ultimatum for myself: either do exactly this one thing or be miserable at any other job. So when — for financial reasons — I made the decision not to pursue a PhD, I found myself hurtling into doom and gloom as I drove to my regular salaried job, which I had convinced myself that I hated.

The Problem of Narrow Passions

Having a passion is great. But that passion cannot be too narrow.

Where I thought I had been setting myself up for success, I was really increasing the probability that I would fail. After all, good jobs in academia are becoming fewer by the day. Good academic jobs in philosophy even more so. So when my financial situation demanded that I turn down 3 funded offers to do doctoral work in philosophy, I initially felt a wave of regret and sadness at having lost my shot at doing what I love. Was I doing exactly what my dad had told me not to do? Was I leaving behind my passion for money?

Again, I was thinking too narrowly. At the behest of my wife(always the voice of reason), I began to re-frame the whole thing.

She asked what it was that I loved about the idea being a philosophy professor.

I replied: “I love thinking about interesting problems, teaching others how to try to solve hard problems, and writing about hard problems.”

She said “Okay, but do you have to be a professor to do those things?”

I didn’t have a ready answer, but it quickly became clear to me that the only correct one was an emphatic “absolutely not!”

In hindsight, I should have let myself benefit more from hindsight. After all, I had been down this road before. I used to be so sure that being an artist was my passion — my “life’s work”. But the whole time when I felt so sure, there was a better fit for me lurking just around the bend.

As it turns out, I didn’t need to be a professor. That wasn’t my life’s work. Nor was it my passion. What I really wanted was what Merlin Mann has called “sharp tools and interesting problems”. I just wanted to think, talk, and teach others. Fortunately for me, opportunities to do that are everywhere, and perhaps in even greater supply outside of academia.

I don’t need a fancy postgraduate degree or permission from academic journal editors to explore these problems. I could begin writing about the persistent interesting problems in any arena I choose, today, right now. All I had to do was give myself permission to think more openly about what work is out there for me.

The overarching lesson I learned is this: Yes, to lead a fulfilling life, you should do what you love to do. However, you must be as inclusive as possible in defining what that is.

Open Wide and Dive In

To assume that there’s only one job to match your passion is foolish. Think about it: jobs appeared long after people started pursuing their passions, not the other way around. So don’t attach your notion of what your life’s work is to an existing job. It’s unnecessarily limiting, and often disappointing.

Instead, take your interests. obsessions, enthusiasms, and curiosities, and shop them around. Do so with an open mind — at whatever job you can shoehorn your way into.

Embrace the hustle, look for interesting things to work on, even things you know nothing about (yet). Get yourself in a bit over your head, so you have to learn, and learn quickly. Then take a step back, and look at what you’re doing now that really moves you. If you do this right, you can begin to realize your broader passion — the more eternal, overarching thing that drives you. And I can guarantee you it isn’t limited to one specific job.

You could also fall flat on your face. In fact, you probably will. And when you do, good on you. I pity the person who has not been fed the wholesome and rejuvenating fruit of failure. Feast on those failures. Lick your plate clean, and rise from the table — armed with the knowledge you’ve gained. The younger you are, and the more narrowly you think about your passion, the more this advice applies.

In the end, the only real mistake you can make is to act in fear of making mistakes. Mistakes aren’t to be feared. In fact, quite the opposite. Mistakes are always accompanied by lessons — lessons as shallow as tweaks to your workflow or as deep as rethinking your life’s meaning. Look for all of them, and then really look at them. It could mean the difference between merely working all your life and doing your life’s work.