td;dr:
I got attention at work for doing a good job, so doing a good job became my entire personality. It was very toxic and it eventually burned me out. Then I switched to financial security as an entire personality, but that wasn't much better. Don't do what I did.

The Exceptionalism Bug

I grew up with the American exceptionalism bug. I valued aggressive personal and economic growth at the expense of hard work. Anything less than toil and progress felt like failure. Imperceptible process meant stagnation and that concept seemed to be something like death. I didn’t know how to choose a career, but I knew that I needed to make money to be independent.

The bug has a good root, you should want to improve yourself and your condition in life; but it also results in bullshit chest-beating and people needlessly toiling in unhappiness. We internalize statements like “I like to work hard and play hard” and confuse finding a good career with finding meaning in life.

Not everyone has this bug. Few people take their job as seriously as the infected. The others will still talk around the Keurig machine about how they’re “crushing it” but they’re actually making puppies until the weekend. That includes people working jobs you’d hope would be special: medical, police, military, your boss, etc. Those people are right! This bug ties up your feeling of self-worth with how hard you work and produce. It’s likely to leave you unhappy with a high blood pressure.

The Bug’s Promises are Lies

To someone who gets their reason for being from outside of work, the infected seem stiff and overly concerned with detail. The bug can produce better results, but the uninfected can ask: “who cares?”. Unless you’re working in a fulfilling field where you have direct impact on people’s lives, good enough is probably as much as should be done. There’s no guarantee others will agree on your conception of better, either. Your flawless Word template might not impress anyone but yourself.

Imagine having this bug in a job you hate (I hope you have to imagine it). Does anyone love writing parking tickets or calling residential customers for collections? Is collecting urine samples from athletes for drug testing anyone’s treasure? If you work in a job that makes you the bad guy and you don’t have a deep fountain of validation to draw from elsewhere, you’re going to have a bad time.

How I Was Mislead

As a student I was taught nothing about careers besides outdated advice delivered with the same passion that any of us muster when clicking “I agree” on an end-user agreement. I hope it’s better today, but I doubt it.

My family didn’t have much guidance for me. Work hard, get a good job with benefits, keep your head down, end of goals. I don’t blame them; my parents and grandparents worked in harder situations with fewer resources. I needed different advice to live a happy life.

How I Was Cured, Maybe

The financial independence movement is a group of mostly high-earners that plan to save enough money to live off forever. This dream of escaping the rat race became my reason to work for about a decade. I ultimately fell far short of financial independence (it takes a lot of money to be financially independent) but the financial security that goal brought me gave me the breathing room to come to terms with what I was doing to myself. I was burning myself out to escape the grind and it was making me deeply unhappy. This is when I stopped worrying about how to choose a career and started thinking about living my life.

Armed with a long-term budget and a healthy emergency savings account, I realize my burning for the next dollar was done out of insecurity. In hindsight, I realize that the insecurity I feared was never really there. Look at the pages of applications on Modest Needs and you’ll find people that are one car payment away from poverty. I am remarkably privileged and have no rational reason to be this insecure.

That fear kept me from thinking charitably, and I wonder how many successful, wealthy people were driven to their wealth with that same bug that infected me. It never feels like enough, and your fortune seems ready to turn to ash at the next moment. The wealthy are the best doomsday preppers on the planet. You can buy all kinds of weird insurance that includes rescue by helicopter. The wealthy are at least in part deeply insecure people.

What About Everyone Else?

I’m privileged to have had grown up with marketable skills that allowed me to earn a high income. I also had mostly positive influences and references for success that allowed me to leverage that for a better future that I could believe was possible. I also pursued my goals in a culture that is white male centered, loading all the dice I rolled in my favour. Not everyone will have that same privilege.

The first step towards a more charitable world is early therapy for people like me. Before people think about how to choose a career, they need to know themselves. It’s trite, but true. It’s unfortunately pretty expensive. I think almost everyone would benefit from it.

If you’re wondering how to choose a career in my opinion you’re best off doing what will pay you the most for the least work. Your life outside of work should be rich and memorable. When you have some financial security, you can afford to choose lower paying work that you enjoy more.

If you grind to financial security, you will find that the grind has changed you. It will harden your heart and raise your blood pressure. You will forget your old passions and interests. Be careful.