Avoid Making Career Decisions You’ll Later Regret

Many people wander through their career without direction, moving from one job to the next without a clear sense of purpose. Then one day—usually around mid-career—they wake up and wonder how they ended up where they are.

Most times, the emotion expressed is regret. They feel disappointed over lost opportunities, and, not surprisingly, blame themselves for not doing things differently when they could have chosen a different path.

You don’t want to live with regrets.

Here is a short writing exercise that involves reflecting on your past as a way of moving ahead in your career without regret.

1Find yourself a good place and time to write. Turn all your attention to the activity and avoid distractions such as phones, television, kids, or social media. You should also write your story. Writing is a more effective way of processing thoughts than simply thinking about them.

2. Be brutally honest with yourself. Robert Steven Kaplan in his excellent book What You’re Really Meant To Do points out that everyone has competing narratives. Your “Success Narrative” is one you tell most often, usually to impress people in job interviews, when you meet new people, when you go on a date, or when you talk to your children. But you also have a “Failure Narrative”, which rarely gets told. This narrative is about self-doubts, worries, fears, and struggles that influence your actions and career decisions. Both are important to acknowledge.

3. Answer the questions below clearly and honestly. Feel free to add to the list if you want. Remember the purpose of this exercise is to learn about yourself, so be specific.

  1. What were you parents like? What beliefs did they hold about life and work?
  2. What were your brothers and sisters like?
  3. Who were your best friends and how did they influence you?
  4. What were your hobbies and interests?
  5. What subjects interested you in school?
  6. How did you do in school?
  7. Who were your childhood heroes?
  8. What did you always want to be when you grow up?
  9. Who are – or were – your role models? Why did you select them?
  10. What are some highlights from your school years?
  11. Why did you pursue your chosen courses of study in college or university?
  12. What experiences in life have been most gratifying for you?
  13. What experiences have been most difficult for you?
  14. How have your early career jobs influenced who you are today?
  15. What three people have had the greatest influence on your life and why?
  16. Who were your best bosses and why?
  17. Who were your worst bosses and why?
  18. If you have children, how have they affected your outlook on life?
  19. What jobs have been your best ones? What jobs have been your worst ones? Why?
  20. How well do you get along with your co-workers and bosses?
  21. Are there any career moves you regret?
  22. How have any volunteer or community activities affected your outlook on life?
  23. What worries you most about the future?
  24. What matters most in your life?
  25. What do you need to change about yourself?

This writing your “life story” exercise is all about understanding yourself and becoming more self-aware.

When you’re complete, take time to reflect on what you have written. What have you learned about yourself? How have your career choices been influenced by your story? What insights have you gleaned? How will your future behaviours change as a result of this story?