Avoid Making Career Decisions You’ll Later Regret

By Gerald Walsh ©           

Many people wander through their career aimlessly. They move from one job to the next without a clear sense of purpose until one day – usually around mid-career – they wake up and wonder how they got to where they are.

Frequently, the emotion expressed is one of regret and a feeling of disappointment over lost or missed opportunities. They blame themselves for not doing things differently when they could have chosen a different path.

You don’t want to live with regrets.

Today, I am going to suggest a short exercise that involves reflecting on your past as a strategy for moving ahead in your career without regret.

I call it writing your Life Story.

How to write your story

1. Find yourself a good place and time to write. You should turn all your attention to the activity and avoid distraction such as 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 we all have competing narratives in our own lives. Your Success Narrative is the one you tell most often, usually to impress people in job interviews, when you meet new people, when you go on a date, when you talk to your children, and so forth. But we also have a Failure Narrative, which rarely gets told. This narrative is about self-doubts, worries, fears, and struggles we have that influence our 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. Where were you born? Describe your upbringing.

2. What were you parents like? What did they do? What beliefs did they hold?

3. Describe what your brothers and sisters were like.

4. Who were your best friends and how did they influence you?

5. What were your hobbies and interests?

6. What subjects interested you in school?

7. How did you do in school?

8. Who were your childhood heroes?

9. What did you always want to be “when you grow up”?

10. Who are – or were – your models? Why did you select them?

11. What are some highlights from your school years?

12. Why did you pursue your chosen courses of study in college or university?

13. What experiences in life have been most gratifying for you?

14. What experiences have been most difficult for you?

15. How have your early career jobs influenced who you are today?

16. What three people have had the greatest influence on your life and why?

17. Who were your best bosses and why?

18. Who were your worst bosses and why?

19. If you have children, how have they affected your outlook on life? How have your behaviours changed?

20. What jobs have been your best ones? What jobs have been your worst ones? Why?

21. How well do you get along with your co-workers and bosses?

22. Are there any career moves you regretted?

23. Have you ever done something on the job that sabotaged your goals?

24. How have any volunteer or community activities affected your outlook on life or work?

25. What worries me most about the future?

26. What matters most in my life?

27. What do I need to change about myself?

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 from the past? What have you learned about yourself? How has your story impacted your behaviours and values? 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?


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Gerald Walsh is an executive recruiter, career coach, public speaker and author. He is the author of PINNACLE: How to Land the Right Job and Find Fulfillment in Your Career.” You can follow Gerry on Twitter @@Gerald_Walsh