20 Questions To Help You Figure Out What To Do When You “Grow-Up”

photo: david schap


Where your deep gladness and the world’s deep hunger meet –

there you will find your vocation.

Frederick Buechner


Since the beginning of the year I’ve had four new clients approach me with the refrain, “I need help figuring out what I want to do when I grow-up!”


Each of these folks has graduated college (one is a post graduate) and each works at an established company. And each is deeply uncomfortable where they are in life.


So how do you figure out what to do when you “grow-up”?


The first thing is to acknowledge that – You already ARE grown-up!


You are an adult – even if you may not always feel like one or act like one.


In addition, although you have a job or had a job, it’s critical to keep in mind that you are not your job – no matter what you do.


You are the sum of your relationships and your obligations to those relationships, along with your feelings and beliefs, your spirituality and psychology, your values and habits.


All of that guides and influences what you do and how you do it and why you do it.


The legendary theologian John Henry Newman believed that “To live is to change, and to be perfect is to have changed often.”


When someone says they want to figure out what to do when they “grow up” they are muddling the issue because the issue is not “when I grow-up.”


The issue is “given that I am today this grown-up, how will I reinvent myself?”


In the early years of my adult life I lived in a religious community and prepared for ordained ministry as a priest. When I resigned from ministry after twenty years of community life I had only a hazy notion of who I was. (And, yes, that it is a startling thing to admit)


My therapist told me that I had to find new ways of being “priest.” That required I do things that would force me to become realistically acquainted with the skills and talents I’d acquired and had taken for granted. I had to experiment, try on, risk and reevaluate.


Reinvention doesn’t necessarily require new skills. It does, though, require you to be familiar with the skills you currently have and become comfortable using them in new and possibly unfamiliar ways.


So how do you reinvent yourself – now that you are grown-up?


Cristina Nehring in her book, A Vindication of Love, writes that when she was in high school,

My English teacher told our class that the most important thing about life was to live it as if it were a good novel – as if, she said, it were a good film script. ‘Would audiences walk out during the movie of your life?’ She believes that by living deliberately, gracefully, inventively, and fearlessly any one of us can be “a piece of art.”


Here are 20 questions for you to consider as you create the “piece of art” that is YOU


  1. In your present job, what skills do you enjoy putting to use? What comes easy to you?

  2. For what skills do you get your most compliments?

  3. When you last were looking for work, what had you really wanted to do?

  4. What or who pushed you into taking this job?

  5. How do you think you’ll emotionally be if you remain in your current job for another five years? Ten years?

  6. What are the practical reasons for you remaining in your current job? How important are those needs? Are those needs really “needed”?

  7. Who else is involved in your decision to reinvent yourself?

  8. What needs do they have? What fears are attached to those needs?

  9. Is there a specific field you’re interested in? Does it require new training?

  10. Do you know anyone who is doing what you want to do? Do you know anyone who knows someone doing what you want to do?

  11. Are you most excited by the idea of a new job or by having the opportunity to use skills you currently under-use?

  12. Is there any place within your current company that would let you tap more into the skills you want to be immersed in?

  13. A dream job is just a dream without a strategy. Do you have a dream or a strategy? What does your strategy look like?

  14. How will your life be different in your new job? Is this new job crucial to making your life different in the way you imagine?

  15. What will you miss from your current job and do you think you’ll find it in your new one?

  16. How will the new job make you more “grown-up” than your current one? What “grown-up” responsibilities will you have in your new job that you don’t have in your current?

  17. How are you sabotaging yourself now and would those techniques carry over in whatever new job you take?

  18. Do you have a tolerance for ambiguity, along with a dose of patience and grit?

  19. What is one skill you have that will come in handy as you reinvent yourself? What is one skill you need to develop?

  20. What do you want to be remembered for in this life? Will your future job help you be remembered for all the right reasons?


Answer these questions and you will have more insight into your next possible job and clarity into who you want to be, doing what you’ll be doing.


If you strategize with these questions, you will not just find a new job. You will experience transformation.


Leadership guru John Maxwell calls transformation the “journey to significance.”


Significance, according to Maxwell, is all about adding value to people.


Angela Duckworth, author and expert on “grit” believes that,

“Rather than ask, ‘What do I want to be when I grow up?’ ask, ‘In what way do I wish the world were different? What problem can I help solve?’


This puts the focus where it should be — on how you can serve other people.


Deep. Yes, I know!


Going deep, though, is what adults do. . .


I help people find their voice, showing professionals how to communicate in smart, healthy ways so as to develop successful relationships.

To explore how I can help you present you with enhanced confidence, please contact me at: JP@thebusinessofconfidence.com

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