Figure out what you actually want to do, not what you think you should

• Here's some career and life advice: Beware "the tyranny of the should."
• We often do things not because we want to but because we and others think we should.

Back when I was "finding myself" in my mid-20s, a friend of my father's gave me a piece of advice I've remembered since — one that has helped me not only in my career but in life.

In those days, I was confused and stuck. I had done what I thought I was supposed to do — have adventures and follow my bliss. I had lived in rural Japan. I had written a book. I was trying to get the book published. And I was trying to figure out what to do next.

I also had little income and no health insurance and was living in my dad's spare bedroom — a feature of bliss-following that I wasn't enjoying much. And my dad was trying to help me by introducing me to some of his wise friends.

One of the wise friends he introduced me to was a college classmate named Gene Prakapas. "Prakapas," as my father called him, had apparently experienced some career angst of his own. And he had been a book editor. So maybe, my father said, in addition to sharing some career wisdom, Prakapas might have some thoughts about my book.

Prakapas did have some thoughts about my book.

"It's competent," he said, over lunch in a New York City deli.

I wasn't all that tuned into subtext in those days, but even I recognized what Prakapas was saying:

My book wasn't terrible. There had (probably) been worse ones written. But there was a long way between "competent" and something someone would actually buy and publish. So, I shouldn't expect some editor or agent to solve my career problems by launching me into a life of literary stardom.

I asked Prakapas what he thought I should do next.

"Take another step," Prakapas said.

I must have looked confused, because Prakapas elaborated. He extended his hand toward the thick draft of my book, which was on the table between us.

"This was a step," Prakapas said, patting the draft. "Now take another step."

Then he gave me the advice I have found useful ever since:

"And beware the tyranny of the should."

The what?

"We often do things because we think we should," Prakapas explained. "Or because others think we should. The key is to figure out what we actually want."

Prakapas then went on to describe his own experience with the concept, which psychologist Karen Horney coined in 1950.

Back in school, Prakapas said, there had been nothing he and his friends had admired more than books. And there had been no professions he and his friends had admired more than books. So when it came time to pick a profession, Prakapas chose… books.

Specifically, he became a book editor.

And he must have become a really good one, because, in less than a decade, he was the editor in chief of two imprints at one of the major publishing houses.

An amazing success story, right?

Apparently not.

Despite his success, Prakapas said, he was miserable.

The source of his misery, he eventually realized, was that he didn't actually want to be a book editor. He just thought he should be one.

So he quit his job at the publishing house and opened an art gallery.

Prakapas didn't say it, but one reason he told me that story was to help me think about whether I was pursuing a freelance writing career because I wanted to… or because I thought I should. (Also, as a former book editor, he undoubtedly knew that, if I continued down that path, it would be a long and arduous one.)

Over the coming months, I thought about that.

And I realized that Prakapas had a point.

I certainly thought I should be a writer. After all, that was the profession that I and many of my friends in college had admired most.

But I didn't want to be a writer, at least not now that I had learned how hard it was — and how many more years of loneliness, uncertainty, and impoverishment it would take for me to become more than "competent."

What I wanted to do, I eventually realized, was work in finance — a profession that struck me as fascinating and fun and that would give me the financial flexibility to move out of my dad's house. Most of my college friends had zero interest in finance and were mystified about why I claimed to find it interesting. It was also a profession that, back in college, none of us had admired and that none of us had thought a responsible, well-meaning person should work in.

But it was time for me to move past the tyranny of the should.

So I got a job on Wall Street.

You can see more of my career advice here.