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21 Powerful Questions to Help you Uncover Your Dream Career

“You do not merely want to be considered just the best of the best. You want to be considered the only one who does what you do.” – Jerry Garcia

How do we discover what we’re meant to do with our life?

Do you believe everyone has a calling? If so, how do we uncover it?

Identifying our “dream career” is a lofty ideal that can feel a little paralyzing to think about.

The good news is, you don’t need the perfect answer to have a fulfilling career.

You may never have absolute certainty about your career calling, but you can at least grow self-awareness and learn as much as possible about who you are and what you want.

If you’re in a situation where you feel lost and confused about your life path, it can be helpful to reflect on and ponder some deep questions.

So here’s a challenge for you: Over the next 3 weeks, answer one of these 21 question per day. Take 5-10 minutes to answer and reflect on each question over the next 3 weeks and see what emerges.

At the end of the 21 days review your answers and see what themes overlap and recur.

21 powerful questions to help you gain clarity on your dream career

1. You’re on your deathbed looking back on your life. What did you like best about it?

2. What is the one problem you were born to understand?

3. If you had only three wishes, what powers, possessions or qualities would you wish for?

4. If you were granted three life mentors, who would they be and why?

5. If you had one hour of prime time TV to address the world, what would you do?

6. If you had an opportunity to teach every child one life lesson, what would it be?

7. If you knew with certainty that you would not fail at doing this, what would it be?

8. What is the single most important thing missing from your life right now?

9. If you could predict the next big choice your life would present you, what would it be?

10. What would be your single greatest regret if you died tomorrow?

11. What is the “unlived life” of each of your parents and what effect has it had on your life?

12. What are your top three talents?

13. When were you the happiest and what were you up to?

14. What is your most memorable break with tradition or taboo, and what were you after?

15. What do you want to be remembered for after you die?

16. What have you rejected that seems determined to claim you?

17. If you could choose one friend to trade careers with who would it be?

18. If you had to go back to college tomorrow what classes would you take?

19. What is the most consistent message; impulse or prompting you’ve been getting about following a departure from the status quo in your work life?

20. What do you love most about your current job?

21. When was the last time you were in a state of flow, in the zone and totally lost track of time? What were you doing?

There are a lot of questions here so don’t get overwhelmed. Just pick one of the questions to answer each day.

Try to write your answer quickly and automatically without much thought.

If the question is difficult to answer that’s okay too. Give yourself time to see what emerges as you start contemplating these deeper possibilities.

“To succeed … you need to find something to hold on to, something to motivate you, something to inspire you.” – Tony Dorsett

Photo credit: lukestehr

21 Powerful Questions to Help you Uncover Your Dream Career

Joe Wilner

Joe Wilner is a life coach, licensed clinical psychotherapist (LCP), and drummer from the band Yes You Are. He is also creator of You Have a Calling, a blog and online community helping people discover and pursue their life’s work and mission. Through deep and personalized coaching, he helps ambitious, creative, and spiritually minded individuals make a greater impact, grow as leaders, and design a soulful life they are inspired by.

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APA Reference
Wilner, J. (2017). 21 Powerful Questions to Help you Uncover Your Dream Career. Psych Central. Retrieved on October 28, 2020, from


Last updated: 9 Jan 2017
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