10 Questions To Ask Yourself If You Want To Leave Your Job

10 Questions To Ask Yourself If You Want To Leave Your Job Hero Image

Everyone desires a meaningful and fulfilling professional life. When you're happy with your work, you feel more content, purposeful, and complete. When you're unhappy at work, the days seem long, Mondays are dreaded, and stress and negativity can affect all areas of your life. 

As an executive coach, I've worked with many clients to help them find more fulfillment in their work. This process has different parameters for each person: it could involve negotiating change in a current role, leaving a job, changing careers, or even making massive life changes toward an entirely new way of living and working. Many people aren’t sure what they what they want to change, but are motivated to figure it out so that they're happier in their work. Whatever the initial motivation, the first step I take with all my clients is a simple and effective self-exploration process, which includes the following questions:

1. Why am I unhappy in this job?

Understand where your unhappiness comes from — is it specific to the type of work you do, who you work for, or the industry you work in? Understanding your unhappiness is the starting point for making change.

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2. Do I need a job change, or a life change? 

Ask yourself: Is my unhappiness about my job, or life in general? Unhappiness in one part of life can have a cascading effect on the rest of what we do. Before taking action, make sure your focus is to resolve the primary cause of your discontent. 

3. If you could have anything quickly, easily and now, what would that look like?

This is about making a simple change that will positively affect your job. What one thing, if it happened today, would make your job more fulfilling? Can you negotiate this in your current position, or find a way to make it happen? If not, keep this at the top of your list of non-negotiable factors in your job search. Then ask yourself this question about your life also. What one thing, if you could have it quickly and easily, would make a big difference in your life? How can you make that happen?

4. What are your professional goals?

What do you want to achieve professionally, and when? Are you currently on path to achieve those goals? If not, what do you need to do or change about your current job and career path to get there?

5. What’s been missing for you professionally?

What are you lacking in your professional life? Recognition, compensation, advancement, or interesting assignments? When you know what's missing, you can make plans to fill in the gaps, in your current position or elsewhere. 

6. What values matter to you in work? 

Our values underlie our actions and behaviors. When we live through our values, choices become easy. Examples of work values are integrity, honesty, creativity, recognition, risk-taking, security, respect, work/life balance, power, and financial gain. Are your work values supported in your current job? Make a list of the values that matter to you and note which ones are missing. Consider any future job opportunity with your values in mind.

7. Where do you see yourself in 5 years? 10? 20?

Envisioning your future self is a great way to keep the bigger picture in mind. A simple envisioning exercise: close your eyes, clear the mind with a few minutes of breath awareness meditation, and then look ahead five, 10 or 20 years. Where are you working? What have you achieved? What does the rest of your life look like? When you open your eyes, jot down what you saw. You can then take actions to align your present life with the future. 

8. What would you like to be known for in life?

Recognition is important to most of us at work, but the more important question is: what do you want to be known for in life? If that recognition is related to your current career, then keep working towards it. If that recognition is about an entirely different idea (such as being a great parent, or being an inspiring local leader), then bring that perspective to your current situation. Where can you put your energy given this insight?

9. What do you feel you were put on this earth to do?

This question is hard for many people, but warrants deep thought if you're considering a career change. What do you feel in your heart you're meant to do? What work would bring you deep happiness and meaning to your life? This may be something you can do outside of your current job – as a hobby or part-time interest. Or it might be worth pursuing wholeheartedly as a career. 

10. What would you do if you knew you couldn’t fail?

We all have dreams that we believe (usually incorrectly) are unattainable. What is your dream? Perhaps you've never told anyone about this dream, but you carry around in your heart. Know that you can make a plan to achieve that dream. Break it down into small steps — what can I do today, next week, this year? Whatever actions you take to move closer to your dreams will open up new positive energy and opportunities in your life. If you can’t get past the obstacles you see in your way, find someone with an objective perspective on how you can start to overcome those hurdles. 

Undertaking self-exploration work will allow you to understand what you need to be more fulfilled professionally. If you have financial obligations and other considerations that preclude making a significant job change, look for ways to incorporate what you learned about yourself in other areas of life. Take action. Move towards the activities, interests, and people that resonate with you, and fulfillment will follow.  


Photo Credit: Shutterstock.com


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