21 Great Questions to Ask Yourself When Changing Careers

21 Great Questions to Ask Yourself When Changing Careers

In my last post, I presented seven reasons why I believe that “Do What You Love” is bad career advice.  And at the end of that post, I promised to present what I felt were better alternatives in terms of career advice.

And now, as I sit down in front of my keyboard, I’m wondering if I’ve bitten off too much.

As I mentioned on my Facebook wall, my big issue with “do what you love” is that it’s an overly simplistic way of choosing a career path.

Do what you love might be okay as a starting point, but it’s not sufficient in and of itself.

Yet any alternative advice that I might offer is likely to suffer from the same problem.

The truth is this: A successful career choice generally involves a comprehensive process that looks at a variety of factors.

If you only consider one or two factors, you’re more likely to make a choice that you end up regretting. And the next thing you know you’re back at the starting point.

So after giving this considerable thought, I think the best thing to do is to present a series of questions that you might consider when changing careers.

And just to be clear, a career is general whereas a job is specific. So working as a nurse is a career. Working as the Director of Nursing at the Canton City Health Department, as my aunt did for many years, is a job.

The following questions are presented in no particular order. And you don’t have to consider all of them, just the ones that resonate the most with you.

21 Great Questions to Ask Yourself When Changing Careers

1. Besides making money, what motivates you to want to work?

2. What kind of knowledge or skills would you like to be using all day long?

3. How do your career goals fit with your personal and family goals?

4. What is your definition of career success?

5. What have other people (family or friends) told you that you’d be good at?

6. What are you doing when you feel most on purpose?

7. Who are you when you’re at your best?

8. What would you do if you knew that you absolutely couldn’t fail?

9. What sort of activities do you most enjoy doing?

10. What kind of skills do you have (or are willing to learn) that might be marketable?

11. What kind of activities lead you to losing track of all time?

12. When you daydream about work, what do you envision yourself doing?

13. What sort of work environment(s) do you picture yourself in?

14. What activities lead you to feeling totally immersed in and exited by your work?

15. When was a time that you used your gifts or talents to make a difference – a difference that truly mattered to yourself or someone else?

16. What social problems are you interested in making a positive contribution to through your work?

17. What are your 3-5 most important values and how do you want to express them via work?

18. Based on your personality type, what sort of careers might be a good fit for you?

19. What are you doing when you feel most fulfilled?

20. What things are most important in your life and how can your choices of work support these?

21. How do you want to use your career to add value to the world around you?


As you can hopefully see from this list of questions, there are a variety of factors that you can (and probably should) consider when changing careers, not just what you love to do.

You can consider what you’re good at, what you enjoy, your personality characteristics, your values, and how you want to make a contribution. As well as how your career fits into the bigger picture of your life.

I don’t expect any single one of these questions to provide the proverbial “magic bullet” to selecting a new career. Rather my aim is to provide you with a broader perspective for changing careers than simply “do what you love”.

The questions above will open you up, give you new possibilities, allow you to see patterns that you haven’t noticed before, and understand what’s truly matters to you in a career.

And by the way, the list above is by NO means exhaustive. If you have other great questions that can be used when changing careers, please list them in the comments below!

This Post Has 2 Comments

  1. Great post, Ed. I like your questions and ask them of those I coach frequently.

    1. Thanks Bev, appreciate the positive feedback.

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