On the blog Study Hacks, Cal Newport looks at why some people end up leading successful, enjoyable, meaningful lives, while so many others don’t. True to his intellectual roots (he’s an Assistant Professor of Computer Science at Georgetown, has a Ph.D. in Electrical Engineering and Computer Science from MIT, and graduated Phi Beta Kappa from Dartmouth), Cal looks beyond simplistic slogans like “Follow your passion!” and tries to decode the underlying patterns of success. In his latest book, So Good They Can’t Ignore You, he takes a contrarian approach to helping people find work they’ll love.

What does this have to do with your career as an oddball pilot? Everything.

In a post from 2011 titled, On the Possibility of Non-Conformity in a Conformist Career, Cal notes that many of the most prolific proponents of the “lifestyle design” movement draw a sharp distinction: “Either you reject everything traditional … or you’re a conformist drone.”

But, he says, if you want to have a really interesting, really rewarding life, it’s not that simple. “Some of the most interesting, non-conformist opportunities, require a foundation of ability gained through unabashedly conformist means,” he says.

It’s true. Especially in aviation. Talk to the most unconventional pilots around, and you’ll find that some of them landed their dream jobs only as a direct result of decades spent paying their dues on a more conventional path. The fact is, some really fascinating flying work requires advanced education, specialized training, or the ability to work in a more conservative environment.

So stay open-minded. We will too.

“While some writers … do a good job of separating the spirit of non-conformity from a strict collection of ‘acceptable’ and ‘non-acceptable’ paths,” says Cal, “too many others treat traditional accomplishment as the enemy.”

No matter what you hear in a specific interview on Oddball Pilot, in the end there’s no “best path” to an unconventional flying career. For every bush pilot who headed for the hills fresh out of high school with a backpack and a dream, there’s another pilot with a really interesting job who got it because he or she took a more traditional route.

Food for thought.

Super cool photo by cheb. odegaard licensed under Creative Commons Attribution 2.0 Generic.