A few years ago, tech entrepreneur Daniel Gulati sat down with 30 professionals between the ages of 28 and 58 and asked each of them what they regretted most about their careers to date.

The group was diverse, made up of an investment banker, a failing self-employed photographer, a millionaire entrepreneur, and a Fortune 500 CEO. Across all age groups – and despite success level – they all shared 5 themes in common when it came to their top career regrets.

Here is what Gulati determined to be the top 5 career regrets of the group:

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. 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.'”

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. 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. 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. “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.'”

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.”


How many of these career regrets do you share? What lessons have you learned from your own career regrets? Share them with us below!

Read this article in its entirety over at HBR. [Image]



  • For me, 2 and 3 really stand out as things that I am struggling with now. Currently, I am in a job where growth and opportunity are unavailable and where I do not see a future. I am at the point that I may need to quit before I find another job (as close to 10 people have quit or been let go since May) and I just am not sure I can shoulder more responsibilities.

    Ideally, I would love to break out on my own and support myself doing what I love: Art & Design. But, my family is not supportive of that and only celebrate success as having a large income (which I gave up in 2011 to travel and study abroad for 2.5 years). Now that I am struggling in a dead-end entry-level position after having completed my MFA (and giving up a great salary), it seems I have even more to prove to my family.

    Thanks for listening. Any suggestions are welcome.

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