What do you regret most about your career?

I had just finished a guest lecture on business and innovation at Parsons 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.

Here were the group’s top five career regrets:

1. I wish I hadn’t taken the job for the money. By far the biggest regret of all came from those who opted into high-paying but ultimately dissatisfying careers. Classic research proves that compensation is a “hygiene” factor, not a true motivator. What was surprising, though, were the feelings of helplessness these individuals were facing. Lamented one investment banker, “I dream of quitting every day, but I have too many commitments.” Another consultant said, “I’d love to leave the stress behind, but I don’t think I’d be good at anything else.” Whoever called them golden handcuffs wasn’t joking.

2. I wish I had quit earlier. Almost uniformly, those who had actually quit their jobs to pursue their passions wished they had done so earlier. Variable reinforcement schedules prevalent in large corporations, the visibility of social media, and the desire to log incremental gains are three reasons that the 80% of people dissatisfied with their jobs don’t quit when they know they should. Said one sales executive, “Those years could have been spent working on problems that mattered to me. You can’t ever get those years back.”

3. I wish I had the confidence to start my own business. As their personal finances shored up, professionals I surveyed yearned for more control over their lives. The logical answer? To become an owner, not an employee in someone else’s company. But in the words of Artful Dodger, wanting it ain’t enough. A recent study found that 70% of workers wished their current job would help them with starting a business in the future, yet only 15% said they had what it takes to actually venture out on their own. Even Fortune 500 CEOs dream of entrepreneurial freedom. Admitted one: “My biggest regret is that I’m a ‘wantrepreneur.’ I never got to prove myself by starting something from scratch.”

4. I wish I had used my time at school more productively. Despite all the controversy currently surrounding student loans, roughly 86% of students still view college as a worthwhile investment. This is reflected in the growing popularity of college: In writing Passion & Purpose, my coauthors and I found that 54% of Millennials have college degrees, compared to 36% of Boomers. Although more students are attending college, many of the group’s participants wished they had thoughtfully parlayed their school years into a truly rewarding first job. A biology researcher recounted her college experience as being “in a ridiculous hurry to complete what in hindsight were the best and most delightfully unstructured years of my life.” After starting a family and signing up for a mortgage, many were unable to carve out the space to return to school for advanced study to reset their careers.

5. I wish I had acted on my career hunches. Several individuals recounted windows of opportunity in their careers, or as one professional described, “now-or-never moments.” In 2005, an investment banker was asked to lead a small team in (now) rapidly growing Latin America. Sensing that the move might be an upward step, he still declined. Crushingly, the individual brave enough to accept the offer was promoted shortly to division head, then to CEO. Recent theories of psychology articulate the importance of identifying these sometimes unpredictable but potentially rewarding moments of change, and jumping on these opportunities to non-linearly advance your professional life.

Far from being suppressed, career regrets should hold a privileged place in your emotional repertoire. Research shows (PDF) that regret can be a powerful catalyst for change, far outweighing the short-term emotional downsides. As famed psychologist Dr. Neal Roese recently stated, “On average, regret is a helpful emotion.” It can even be an inspiring one. But it means that we must articulate and celebrate our disappointments, understanding that it’s our capacity to experience regret deeply, and learn from it constructively to ultimately frame our future success.