The Problem With Building a Portfolio Career

Diversifying your professional life like a financial portfolio isn’t always a good idea.

Illustration: Sarah Cliff for Bloomberg

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Over the last decade or so, I’ve been struck by a recurring theme in conversations with former students. Typically, they are in their late 30s or early 40s, successful in their corporate, investing, legal or consulting careers, and now they’re feeling itchy. The path they seek inevitably sounds something like this: “I think I would really like to shift to doing some part-time consulting work that can enable me to pursue other avenues. I’ve had entrepreneurial ideas. I could perhaps take on a board seat and also do some not-for-profit work.”

More recently, I’ve started to hear similar thinking from current students and young alums, who are already vigorously pursuing side gigs in addition to their main job. Either way, this plan usually gets labeled as living “the portfolio life.”