Leaving the Good Life to Hit The Road

Gregg Bleakney crossing into Argentina from Chile. Photo by Gregg Bleakney.

The latest episode of Patagonia’s Dirtbag Diaries podcast is about a young man who left a high paying, white collar career to ride his bike from Alaska to Argentina. Gregg Bleakney had a successful and lucrative job at a Seattle software company. By the time he was in his mid-20s he owned a big house, fancy car, and all the other luxuries one might associate with a rich young guy. He also felt a deep dissatisfaction with the work he was doing and spent many sleepless nights pacing around his house stressing about it.

His solution: set off on a year long, 19,000+ mile bike tour with a friend. Bleakney figured the trip would be just the experience he needed to return to his software career with a renewed sense of vigor and satisfaction. Instead, he wound up spending almost two years on the road, discovered a new passion for photography, and realized he would never find satisfaction in his old life.

Now Bleakney makes his living traveling the world as a freelance photographer and writer for publications like Adventure Cycling magazine, National Geographic Adventure, and Velo News.

The podcast is well produced and a quick listen. You should go check it out for yourself.

Though the parallels are not perfect, as I listened I found myself thinking about Matthew Crawford’s Shop Class as Soulcraft, a book I’ve slowly been reading for the last few weeks. In short, Soulcraft argues that we place too much emphasis on four-year degrees and white-collar office job career paths. Crawford himself left his high-paying, but dissatisfying job at a Washington DC think tank to start a motorcycle repair business in Richmond, VA which he finds significantly more fulfilling.

Crawford wants to see a cultural shift in America that removes the stigma of not attending a four year college and places greater value on vocational training and skilled labor careers. He’s not arguing that everyone should give up pursuing white collar careers. He’s saying that there’s great satisfaction and as much (if not more in certain situations) intellectual challenge to be had in skilled labor as there is at a desk job, so we as a society need to do more to present alternative paths through life.

Bleakney doesn’t exactly match Crawford’s argument (and is, in fact, living the life thousands of liberal-arts college students dream of living). But, he is certainly further proof that there’s much more to life than riding a desk and bringing home a big paycheck.

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