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Coping with Career Regret


Fall is a time when career regrets tug more strongly than during the laid-back summer months. New jobs appear on job boards, and many colleagues and friends move on to new careers or go off to graduate school. If you aren't moving with them, you can become vulnerable to "should have" thinking.

The should haves are hard to turn off. "I should have gotten that promotion." "I should have never chosen Public Relations." "I should have left my job long ago." These should haves eat at you, particularly if you are comparing your career to the careers of others.

Dwelling what you should have done is especially destructive because it carries a feeling of futility. Once that happens, anger and resentment build up, and you quit trying. This is painfully obvious to others — you won't get the best assignments, and honestly, people avoid those who have palpably bad attitudes. Instead of toiling through the negativity, you have to change your thinking altogether.

 The right approach is to replace the "should haves" with "what ifs."


  1. Start with the regret, for example, "I should have never chosen Public Relations."
  2. Try getting some trusted friends or colleagues to brainstorm with you, as their valuable outside perspective can help you think differently about your regrets. Choose confidants who are imaginative and positive — not cynical and snarky.
  3. Pile up as many "what if" questions that relate to the regret as possible. Some possibilities for the PR example might be: What if you did PR for a cause you passionately believed in? What if you coached your clients on PR strategy? What if you taught business executives PR basics?
  4. Explore those what ifs for ideas to act on. Just that exploration will re-invigorate you and set you on a better path. If you find yourself getting excited about one possibility, keep working on it until it pays off.


To see how this plays out, take this example:

 Evelyn's family persuaded her to go into accounting, but after five miserable years at a financial services firm she still regretted not following her passion into music. She believed it was "too late to change now, and I'd never be able to support myself."

 But when she started thinking about what ifs instead of should haves, Evelyn's attitude changed. She asked, "What if I work in an environment where there are lots of musicians and music? What if I could help musicians with my financial skills?" The what ifs lead her to target accounting jobs in music departments of universities or in other music organizations. While she was looking, she volunteered to help a local music school put its books on QuickBooks. She loved it, and they loved her, too. When she mentioned her interest in a career change to some people on the board of the music school, they helped her get started networking in the music world. Now she is the financial administrator of a large music festival, where she gets free music lessons and sometimes even jams with the performers.

 If career regrets attack you this fall (or any time of year), get a few friends together, gain a little perspective on yourself, and try asking a different question: What if?

Coping with Career Regret
Priscilla Claman
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