A Typical Career Versus... What?

In recent posts, I’ve used this blog to start a public conversation about my career doldrums. Even though that was a scary and risky move – you will be judged, threatens the inner monologue – it has had several benefits.  For one, it has elicited advice from some of my smartest, kindest friends and acquaintances. They’re a diverse group of people with varied perspectives, so when their thoughts start to align, it’s a sign that they might be on to something particularly true. Last week, I talked to two friends on separate occasions who both shared this idea: you don’t need to have a “career” in the traditional sense to have a good life.

“It sounds like you don’t even really want a career,” my friend Leo* pronounced with his usual perceptiveness.  We’ve been friends since we were college freshmen, which means we’ve known each other for a decade.  He's a conventionally successful guy with an unconventional outlook who never fails to make every party, place, and project better when he touches it.

“I mean, why don’t you just keep trying things you like and learning from them?" he continued. "You’ll eventually figure out how to monetize something, how to turn something you care about into a job that can support you in the lifestyle you want. You don't have to have a career in an office with a desk and nine-to-five hours.“

I nodded and studied my hands, wanting to agree but feeling slightly uncomfortable.  I simultaneously loathed and longed for a successful career path along a traditional trajectory.  I had read too many issues of Forbes magazine as a kid (I stayed at my dad’s office most afternoons and would get bored and devour any literature I could find from front to back many times over, with Forbes, Popular Mechanics, Newsweek, and the Oriental Trading catalog being some of my favorites) not to absorb dreams of climbing the corporate ladder to business stardom. But Leo was right. I had tried to have a typical career, but even when I came closer to achieving it, I hadn’t felt happy. Like many other nonconformists, my need for a kind of intellectual and physical freedom that you can’t find in most corporate environments is far stronger than my desire for job security and the respect of fellow Forbes readers.

But admitting to yourself that you no longer want what you always thought you wanted, especially if it is what everyone else seems to want, feels strange, foolish, and almost mournful. When you give up on a dream, no matter what the reason, you are giving up on one aspect of your being and choosing another. That makes it a kind of death and rebirth of a portion of your spirit.  What will grow to replace it? How will it fit?

There are so many dreams you can pursue, so many different ways that you can support yourself. I idolize people who forge their own non-traditional careers by working hard – and working smart – on things they care about. They're the hosts and guests of podcasts like Andrew Warner's "Mixergy," Jaime Tardy's "Eventual Millionaire," and Tim Ferris' eponymous "The Tim Ferris Show." These are people who become experts in their niche while mastering the art learning a little about everything. They seem to have arrived at their own definition of success after traveling strange and difficult paths in work and life.

“I’m at the point,” Leo continued, “where I don’t really want to keep climbing the ladder. I’m happy. I’m set. I like my job, I love my company, and I really love my life when I’m not working. But I can’t let them know that,” he laughs.

“Yeah, you gotta keep pretending that you want to ‘grow your career,’” I said, making finger quotes.

“That’s just part of it,” he nods. “You just have reach the point of equilibrium between the stuff you don’t like doing and the stuff you like doing. Make your job work for you to live the life you want. It’s about balance. You don’t need a career to do that.”

As Leo spoke, a familiar motivational glow washed over me, same as I feel when I listen to my favorite interview-with-an-amazing-person podcasts. Like I said before, he's the kind of guy who leaves everything he touches a little bit better. Once again I felt enthusiastic instead of intimidated by the possibility of building a livelihood as a bonafide maverick.

In another conversation, my friend Chuck* pointed out that a lot of his peers in the film industry get stuck in traditional careers and miss out on the harmony he’s struck between working on bill-paying freelance projects and un-paying personal projects. But it’s late here, so I’ll tell you about that tomorrow.

* These are not their real names. ;)