What do you regret most about your career?
I had just finished a guest lecture on business and innovation at Parson's School for Design, and a particularly attentive front-row audience member kicked off question time with the curliest one of the day. I answered quickly with the hope of getting back on target. But judging from the scores of follow-up questions and the volume of post-lecture emails I received, a talk on career regret would have been the real bull's-eye.
Ever since that afternoon, I've been on a mission to categorically answer the awkward but significant question of exactly what we'd do if we could magically rewind our careers. The hope? That by exposing what others are most disappointed about in their professional lives, we're maximizing our chances of minimizing regret in our own.
To this end, I sat down with 30 professionals between the ages of 28 and 58, and asked each what they regretted most about their careers to date. The group was diverse: I spoke with a 39-year-old managing director of a large investment bank, a failing self-employed photographer, a millionaire entrepreneur, and a Fortune 500 CEO. Disappointment doesn't discriminate; no matter what industry the individual operated in, what role they had been given, or whether they were soaring successes or mired in failure, five dominant themes shone through. Importantly, the effects of bad career decisions and disconfirmed expectancies were felt equally across age groups.
