The Perfect Career Path? An Interview with Derek Bouchard Hall ’92
“I never really picked the career of a professional bike racer, it kind of just dawned on me one day that I was a professional bike racer.”

These words were spoken by Derek Bouchard-Hall, Princeton ‘92, in reference to his decision to become a professional cyclist following his graduation from Stanford as a graduate student in structural engineering. Derek is currently the CEO and President of USA Cycling, the governing body for amateur cycling in the United States. After college, Derek was riding monuments like the Paris-Roubaix and the Ghent-Wevelgem. He won a gold medal in the Pan-American Games and represented the United States in the 2000 Sydney Olympic Games. After retiring from cycling in 2002, Derek received an MBA from Harvard Business School, worked for McKinsey in London, and then moved on to become an executive for Wiggle, the world’s largest online cycling retailer. Derek left Wiggle and became the president of USA cycling in June of 2015. In my 45 minutes with Derek, I came to realize that this man led what could be said is the “perfect” professional life. Derek managed to follow his passion as a professional cyclist for many years, and when he retired, still became a smashing success in the world of business. Yet he didn’t divorce cycling from business; instead he may have cracked the code on how to lead a successful and fulfilling professional life.

Without a doubt Derek’s career path isn’t “conventional,” but it is evident that Derek masterfully married his living with his passion. “I’d like to think that I am a living example of successfully doing this [joining one’s passion and career].” Yet Derek does warn of two innate risks in trying to merge these two parts of one’s life together. Derek first warns of “the high costs” that come from pursuing one’s passion, and the risk one takes in “accepting a very different level of financial security.” In reference to athletics itself as a career, Derek commented on how “athletics are dead-end careers” and how after his retirement, he felt like he “was a successful athlete, but not financially successful.” Derek commented on how “I didn’t have a skill set” and that “I had built nothing from a career standpoint.” The second risk that Derek warns of is that “your passion ceases to be your passion.” When your passion (i.e. riding bikes) becomes your work, it “stops being a gift, and it becomes real work and tedious.” Our passions, according to Derek, are our passions because they give us a release from the other stresses of day to day life. In making your passion your living, that escape that was a “gift” when you could do it stops being a release. So when Derek moved on to business, cycling still was the gift that it had been to a hopeful collegiate racer, but his life lost the excitement that comes with competition. “My love is riding bikes and racing, not managing people.” So in his pursuit to create his optimal work-life balance, Derek indirectly brought these two things together to make his professional life truly fulfilling.

So when I asked Derek, the man who worked outside the “traditional” career path, his opinion about the traditional career path, his response seemed rather counter intuitive. “There is a lot to be said for the traditional career path. I would certainly never knock it. When I left cycling, I did take a very traditional path, and that has given me great benefits- that’s the reason why I’m in the world I am in today. But let me tell you, those first years were miserable years. But they were incredibly skill building, and they laid the foundation for where I am today.” Derek stated how there is no right or wrong way to choose one’s career path, but “it’s up to the person to decide what is more valuable, the destination or the journey”- meaning, when deciding one’s career path, one must decide what he or she values more; the end result or payout, or the life experience of working. For Derek in his initial pursuit of professional cycling, “liking what I was doing with no clear destination was very valuable to me” and in reflecting on his post formational years, he said that he “was very pleased in choosing the exciting route, instead of doing a more financially rewarding route.”

Don’t be mistaken; Derek didn’t go straight from the peloton to the executive offices of Wiggle and USA Cycling. Derek said “when I left cycling, I did take a traditional career path. I went from Harvard Business School to consulting. Those were miserable years, but incredibly skill building.” Just because a non-traditional career path led Derek to success doesn’t mean that the traditional career path is obsolete. Derek’s ultimate advice to students is to “find what you value” and be “thoughtful of the trade offs you are making so you can appreciate the positive things you are getting.”

There is no one correct way to approach one’s post-college life. Derek took a step back to find what he valued the most, and pursued that career as long as he could. Derek also realized that in order to make a name for himself in the business world, he would have to make up for his time spent racing, which he did with his time at Harvard Business School. Just because Derek left cycling professionally doesn’t mean he had to abandon it altogether. Derek merged what he learned at Harvard Business School and consulting to create a career that is fulfilling in every sense of the word.


  • Richard

    I agree. A wise businessman in the Caribbean named Sir Kyffin Simpson always said that the key to success is progression and humility, and clearly he’s done very well for himself as a self made man!

  • John Andrews

    The Airgain IPO launches this week, and they’re a one-brand company.

    Some investors don’t think it’s a good stock though:

    http://seekingalpha.com/article/3997291-risky-signals-antenna-maker-airgain-launches-ipo

  • Cincinnati World Cinema

    Well said, Joe, and worth rereading on a regular basis! Another advantage of small-to-midsize city living is pace and competition. Living in NYC, LA and SF entailed a hectic pace, hallmarked by capital S striving, as one realized there were a ton of others doing what I do. Spending so much time in one’s car in SoCal meant much less time for quality pursuits and pleasures. A smaller pond with relaxed pace allows one to savor life and special moments.


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