27 Questions to a Rewarding and Meaningful Job

by | Mar 19, 2012 | Coaching Skills | 0 comments

Feeling stuck in your job?

I’m always sadly amazed at how many people are stuck in the trap of working a job that is slowly sucking their souls dry. Especially when I know here is another way!

What I often see in my new coaching clients is – smart, educated, successful professionals who loved their work once-upon-a-time. But as the years passed they found themselves giving more and more to their jobs (i.e more time and more emotional energy) and settling for a diminishing return on that investment (i.e. less time with friends and family, poor health and fitness, compromised values and a feeling of not living one’s full potential).

To combat this, I’ve developed a short career exercise that helps people discover the type of work they need to be doing to be happy. We can can get out of bed each morning, inspired for the day and ready to get started!

Feel free to use this with your clients and make any changes you like! 🙂



Part 1: Your Authentic Self

What are your natural skills? What do you love doing? What really matters to you?

To be happy and fullfilled, you must reacquaint your self what really matters to you. This will empower you to make a good decisions on how you are going to spend 1/3 of your life (i.e. doing work).

Please answer the following questions:


1. What are your top skills and interests?


2. What are your top values?


3. What do you love doing?


4. What things do you do that are fun easy and satisfying?


5. What really matters to you?


6. How does your current job align with your authentic self?


7. How does your current job NOT align with your authentic self?


8. How could you better align your current job with your authentic self?


9. How could you align a NEW job with your authentic self?



Part 2: Your Work’s Purpose

It’s important to be honest with yourself about what you’re working for.

For example, is it: high pay, a job you enjoy, security, a good environment, excitement, interesting colleagues, variety,  etc.? Knowing this truth will help to keep you resilient through any hard times in the future.

There is no ‘right’ answer with this. Just be as honest as you can with yourself.


10. Choose the top 3-7 factors that matter most to you about your work.
  • High pay
  • A job you enjoy
  • Security
  • A good working environment
  • Excitement
  • Interesting colleagues
  • Freedom to do things your own way
  • Great benefits
  • Potential of promotion
  • Opportunity to expand your skills
  • A decent boss
  • An inspiring boss
  • Working 9:00 am to 5:00 pm
  • Work when you like
  • Work from home
  • Reputation of the employer
  • Prestige of your job
  • Variety
  • Other (_________________)
  • Other (_________________)
  • Other (_________________)


WARNING!!! The next 4 questions are intentionally brain twisting. Don’t dwell on them. Let your unconscious mind answer the question by going with the first answer that comes to mind.



11. What will happen if your job does deliver these factors?


12. What won’t happen if your job does deliver these factors?


13. What will happen if your job doesn’t deliver these factors?


14. What won’t happen if your job doesn’t deliver these factors?


Part 3: Understanding Success

The definition that I like for success is, “the favorable or prosperous termination of attempts or endeavors”.

This means that if you achieve whatever you have decided to attempt you are successful.

Therefore, to know if you are a success of not, you need to know what do you want to achieve in your life.

If you achieve what you have set out to achieve, you are a success no matter what anyone else may attribute to being “successful”.


15. In 3-7 sentences, paint a picture and tell yourself how you would like each of the follwing Life Areas to be. Write it down.
  1. Career/Business
  2. Finances and Wealth
  3. Friends and Family
  4. Fun, Recreation and Entertainment
  5. Health and Fitness
  6. Love Life
  7. Personal/Spiritual Development
  8. Physical Environment


16. Given what you want to achieve (see above), how will you know when you are successful?



17. List 5 people who have different ideas about success to you. Then list 5 people who have the same ideas of success as you do.



18. How will you interact differently with each of these people in the future?





Part 4: 80/20 Thinking

By completing the first 3 parts of this exercise you may be now telling yourself that you are already pretty close to your ideal job and some tweaking around the edges is all you need to do OR you may have discovered that you are way off track and need to make many changes from where you are currently.

Aweness is the first step! The next step is to take action!

The 80/20 rule states that that 80% of results flow from just 20% of your action. So, when you are planning your next career move, focus on the results you want. Once you know what you want, find the easiest way to get what you want with:

  • the least effort
  • the least sacrifice
  • the MOST pleasure

For more reading on this topic, I highly recommend, Richard Koch’s book, Living the 80/20 Way.


19. What types of jobs will best align with your authentic self, key factors for work and regularly be able to satisfy your definition of success?


20. List at least 5 people you could talk to that will help you better understand the types of jobs you’ve listed above. What specifically can they help you with?
Example: Sue Smith, Recruitment Manager – can help me to understand salaries and current demand for the types of roles I’m looking for.Answer:


21. How many days/hours a week do you want to work? For what purpose?


22. How much money do you want to earn per week/month/year? For what purpose have you chosen this amount?


23. Where do you want to be in your career 3 months from today?


24. Where do you want to be in your career in 5 years?


25. Where do you want to be in your career in 10 years?


26. What is the easiest and most fun way to obtain the results you want in this area of your life?


27. What steps are you prepared to commit to today to get your ideal career started?



In Conclusion

If you managed to get though all these questions, I take my hat off to you because it means you are committed to trying new things to change your current situation.

I hope you found the exercise helpful in shaking up your thinking enough to start to see a new path in your career.

Most of us spend 1/3 of our life doing some sort of work. This time can be miserable, drudgery or it can be rewarding and meaningful. The cool and the scary part is that when it comes down to it, it’s your choice. 😉



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