Tag Archives: gregg bleakney

Gregg Bleakney: From Software Sales to Cycling Adventures

Gregg crossing from Argentina to Chile. Self portrait by Gregg.

In the early 2000s, Gregg Bleakney was on a strong path to (one type of) success. He was earning a six-figure salary as a software salesman, owned a house in Seattle, and was generally enjoying his career. Then Gregg and his best friend from college set out on a two-year bike tour from Prudhoe Bay, Alaska to Tierra del Fuego, Argentina to raise money for the American Diabetes Association. Towards the end of the ride, Gregg realized he couldn’t go back to his old life. He quit his job, sold his house and started making inroads to a new career as a self-described visual storyteller focused on adventure travel. Now he’s traveling around the world telling stories as a photographer and writer, often with a focus on bikes. I spoke to Gregg on a short break he was taking in the United States after covering the Tour de Langkawi in Malaysia. We talked about his Alaska to Argentina ride and its sea-change effect on him, his new career and world travels, and more.

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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.

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