A New Career: 34 Probing Questions to Prepare for Work You Love

Doing what you love is the cornerstone of having abundance in your life. ~ Dr. Wayne Dyer

Follow your bliss. Do what you love. Live your passion.

You know the truth in those words. You’ve heard them many times and have probably cogitated on how they apply to your life, your job.

Am I doing what I love? Am I passionate about my job?

In this economy, with the jobless rate hovering near 10%, many of us feel lucky just to have a job.

Thinking about changing careers to do something you love feels indulgent, if not downright dangerous.

Why tempt fate when that paycheck is coming in every month? Doing what you love and following your bliss seem like concepts for bumper stickers or refrigerator magnets — not for today’s economic reality.

In a 2010 study conducted by The Conference Board, a business research association, only 45% of Americans are satisfied with their work (just satisfied, not passionate).

This is the lowest level recorded in the 22 years of this survey. And sadly, 20-somethings,  with all of their youthful enthusiasm and energy, are the least happy at work. 64% of workers under 25 are dissatisfied with their jobs.

So what does this mean for you? Are you dissatisfied with your job or even somewhat satisfied but not passionate?

Do you feel trapped and stuck where you are until the economic situation improves? If you do, that’s understandable, but I’d like to invite you to shift your thinking a bit.

Open the door to the possibility that you can change careers and have a job you totally love, even in this economy.

Think about this: you spend 8-10 hours a day at your job. That’s more than half of your waking hours in a day. If you don’t like your job, you are spending half of your day in a state of unhappiness or at best, toleration.

What are you doing with the other half of your day — anything really fulfilling or exciting? More than likely, many of those hours are spent doing tasks, driving, eating, and vegging out in front of the TV or computer.

In my very humble opinion, that stinks. I would sacrifice a whole lot of extraneous lifestyle in order to reclaim some passion in my work and life. For me personally, there are many things I would sacrifice before I’d give up half of my day to a lackluster job.

I know that’s easier said than done, but if you ask yourself the right questions, you can uncover how much of your life you are willing and able to reclaim for passionate living and work.

It is all about making choices based on what is most important in your life. You can’t have everything, but you can make enough change to create a fulfilling life with fulfilling work.

Just creating some clarity around these choices will create a sense of control over your destiny and momentum for taking action.

So grab a pencil and paper, and answer these probing questions to help you prepare to make a shift and find work you love.

1. On a 1-10 scale, with 10 being total passion and fulfillment and 1 being complete job dissatisfaction, how would you rate your current job?

2. What elements of your current job do you enjoy and would you want to keep in any future career? List everything you can think of, including your commute time, the physical environment, the people you work with, etc.

3. What elements of your current job would you wish never to have again in any future job?

4. Do you know or have an inkling about the kind of work that would excite and fulfill you?

5. If so, why have you not pursued this work or found a career in it?

6. If not, would you be willing and able to invest a few hours a week into research and self-discovery to find the type of work that would excite you?

7. Do you currently live within your financial means and have a cushion of savings?

8. If not, would you be willing to adjust your lifestyle and spending habits to live within your means and/or save money?

9. If so, what elements of your current lifestyle are more important to you than job satisfaction. List everything that trumps job satisfaction for you (ie: children’s education, taking care of elderly parents, living in a particular neighborhood or house).

10. Would you be willing to downsize your home for a job you love?

11. Would you be willing to move to another city for a job you love?

12. Would you be willing to disappoint or upset someone close to you to change careers for a job you love?

13. Is there anything you could change about your current job that would make it more exciting and fulfilling?

14. What are the possible consequences of asking for change at your current job? Could you live with those consequences?

15. If you were to lose your current job today, what would you do?

16. How long could you maintain your current lifestyle if you were unemployed?

17. If you were starting over right out of school, what career would you pursue?

18. Would you be willing and/or able to get additional education or training for a job you love?

19. Would your spouse support you in a career change?

20. Would your spouse be willing to make lifestyle sacrifices in order for you to make a career change?

21. What have you done toward finding a job or career that you love? (ie: research, updating your resume, looking at job openings, etc.)

22. How could you find or create the time to research and/or look for a job you love?

23. In the past, when have you felt the most fulfilled in your personal and professional life?

24. If you were writing a vision for your ideal life and work, what would it look like?

25. Do you believe it is possible to create your life in a way that is close to that ideal?

26. If you were aged 90, looking back on your life, what would you like to have accomplished personally and professionally?

27. Would you be willing and able to try out a few jobs before you found one that is deeply fulfilling?

28. Do you feel like you know yourself well enough to know what makes you happy and fulfilled? If not, where do you need some self-discovery work?

29. Do you have beliefs or fears about yourself or your abilities that prevent you from acting? If so, how could you begin to address these?

30. What is the least amount of money you’d be willing to make?

31. What is most important to you, job satisfaction or prestige?

32. How is your dissatisfaction with your current job impacting the rest of your life? (ie: stress, relationships, life balance, etc.)

33. If you didn’t have to work at all, what would you do?

34. What one thing could you do today to move toward finding work you love?

Here are some ways you can use this information to begin making a shift toward finding work you love.

  • Look at all of the non-negotiables you have listed in your answers. Are they absolutely non-negotiable or is there any wiggle room? Think about how these will impact your potential career change.
  • Review the areas you listed that you enjoy and find fulfilling in life and work. Where do you see a pattern? How can these areas translate into a career?
  • Think realistically about the potential lifestyle changes that would be involved in finding and taking a job that would make you really happy. For example, would you be willing to sell your house, pack up and move, and live more frugally if it meant you could be happy most of the day, every day?
  • If you are unsure about the kind of work you would feel passionate about, take the time to do some self-discovery work. Read books, take courses, take some career assessments, meet with a career coach or counselor.
  • Talk with your significant other, friend, or family member to discuss your ideas and the potential repercussions and necessary actions involved in changing careers.
  • If you have some personal issues holding you back related to self-esteem or fear, make an appointment with a counselor to work through these. They will keep you trapped if you don’t address them.

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27 thoughts on “A New Career: 34 Probing Questions to Prepare for Work You Love”

  1. Thanks for the comprehensive questionnaire. It’s a shame that most people are dissatisfied with their jobs. After all, there’s nothing inherently bad (quite the opposite!) about being productive and giving value.

    • You are so welcome. No, being productive and giving value can be very rewarding. But passion for what you are doing makes it sustainable and infused with purpose.

  2. First of all, I always love to read your posts—the quality of content is amazing. The 34 questions are a great step to finding your true passion in life. Answering these questions will take reflection and some time—and once you get the answers—your life will change and opportunities will begin to spring up around you—you will bloom. Please take the action towards the life you dream of—we all need to share our gifts with the world.

    • Thank you so much Cris. I agree that you will bloom once you open yourself to responding to these questions. A person “in bloom” is a gift to the world!

  3. Thanks Barrie for yet another thought provoking post. You have a way of nudging people to get beyond “comfort zones” and into more challenging modes of thought. This is a good thing as most of us tend to be content with languishing in our secure and safe places. Change is certainly possible for those with the passion and resources to take those critical first steps :-)!

    All the best,


    • Hi Jon,
      That is what I hope to be — a nice “nudger.” 🙂 Even if we take baby steps, the momentum is exciting and powerful. Just thinking about positive change is moving you toward it.

  4. Thanks for these questions – I went through them and found them helpful and indeed probing. What job would you do right now if you graduated is a great question. That question by itself says a lot. The other questions are also good guides to figuring out what direction one should take towards finding the job they are passionate about.

    • Hi Vishnu,
      So what conclusions did the questions lead you to? Anything exciting? Thank you for your kind comments.

    • Nothing big – just gave me the answer to what I should be doing with my life right now. Lol – thank you:)

  5. Hi Barrie,
    Love this post topic. I am currently the happiest in my work I have ever been and I can vouch for the fact that it is life changing and well worth any sacrifices or changes that may need to be made.
    Thanks for all the great information!!
    Shona. xx

    • That’s wonderful Shona! I am so thrilled for you that you have found what you love to do and a way to do it.

  6. Hi Barrie,
    Thought provoking list. I ask my clients this simple question…..”If you are doing something that you don’t like…..then why?” Drill down & find the real “why” and see if it truly serves you. We only live in our bodies for a finite time, no time for regrets. Thank you &
    be good to yourself

    • David that’s a excellent question to add to the list. I would imagine fear of something is the most common answer — which rarely serves us. Thank you for sharing this.

  7. Great post!i love my work by mt work i survive,and i enjoy because i meet friends through online.thanks for sharing your tips.happy working!

    • Hi Katherine,
      I’m so glad you liked it, and I’m glad you have found work you love. Online work is so gratifying because you can meet so many interesting people from all over the world! Best wishes to you. 🙂

  8. Such great questions to prepare for a work we love.It’s difficult to find a favorite job.I have ever got many trouble with in when I have just graduated from college and I work in the fifth company:d.

    • Hi Suteki,
      If you have just graduated from college, this is a great time to do the “inner work” I mention in my post. Take a look at some of the books and resources I list as they might help you clarify the kind of work that would be meaningful for you.

  9. Hi Barrie.
    I initially postponed reading your post because a casual look at it revealed that this was not material to scan through in a hurry. So I saved it to read it when my mind was at its best. I did that a few moments ago (six in the morning-Kenya) and once again you have succeeded in bringing out a positively thought-provoking post. I believe these questions are relevant to all people at whatever stage of life- age, financial or relationship they are in. Thank you and have a great day.

    • Hi Murigi,
      First, thank you so much for your kind comments. I am so amazed that a gentleman in Kenya is reading what I’ve written hear in Atlanta! 🙂 Technology still amazes me. I’m glad you found the questions relevant and hope they helped you in some way. I hope you are doing something you love!

  10. I have so many friends who doesn’t know what to do in their lives. Once it was easy to to decide because you had no much choice so I can’t decide which is better… Thank you for this quality post!


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