Should I stay or should I go?

This is a question many of us mull over for many months, years or even decades. In my role as a career coach, I often hear executives use the term ‘golden handcuffs’ to explain their feeling of being tied to a job or lifestyle that affords them status and financial stability, even when it no longer provides a sense of happiness.

My expertise and experience tells me that if the term ‘golden handcuffs’ rings true to you then you’ve likely spent many hours lamenting your position. You feel tethered to your current situation because of relative financial and emotional safety.

There are always snippets of hope. Have you ever caught yourself lazing on your holiday sun lounger, allowing your mind and heart to open to the potential of life… without the shackles you have placed on yourself?

In these moments you may feel free, excited and hopeful. Then, as you return to work and fall back into the rat race, you again allow fear to be your operating model.

You revert to the status quo of living a comfortable lifestyle, with discomfort lurking beneath the façade.


Sometimes these uncomfortable feelings hang around because you don’t yet have clarity on potential ways forward. As a career coach, I find clients regularly gain important insights by honouring themselves and diving deeper through questions that deliver lucidity.

These questions will provide answers, depth and intention around that all important question:

“Should I stay or should I go?”


13 Powerful Questions To Ask Yourself…

Give yourself some quiet unencumbered space to think and write down your answers, without interruption. I use these key questions in my coaching work to spark awareness, direction and shine light on the truth.

 1.    Do you wake up energised and raring to go to work?

Why or why not?

2.    How is your mental and physical health?

Is your wellbeing negatively affected by your work choices? How is your current work situation impacting on family and friends? What are the benefits that you and your family could receive if, instead, you followed your passion?

3.    Have you ever given yourself the opportunity to imagine, even visualise, the life you truly want? (Focus goes where energy flows.)

4.    What is your current mindset?

Are you coming from a scarcity mindset or an abundant mindset? What are all the things you have to gain by making a change?

5.    Are you being gentle on yourself? Letting go can be hard. Have you acknowledged and honoured those feeling? Are you looking at your thoughts as if you were a third person to gain some perspective?

6.    You have been successful in your current role. What positive traits could you amplify in a new position?

7.    Are there people waiting in the ranks, ready to do a kick-ass job in the position you no longer enjoy?

8.    What is the worst thing that could happen? What steps can you implement to cushion against this? (List these steps).


9.    Visualise 5 years from now.

Describe the scene:

1) If you stay


2) If you go and discover new possibilities


10. If a friend or family member was in this position how would you coach them through this question (‘should I stay or should I go’)?

11. In times of change, it is really important to have a good group of supporters.

Who will be your supporters?


12. What legacy do you want to leave?

What example do you want to provide for your children about the life you lead? Not only in terms of any perceived job success but in terms of following your dreams, passions and being the person you want to be?

13. Could you engage a career coach to offer their experience and expertise? An objective and balanced viewpoint that takes into account your personality, skills and wishes can open up possibilities, smooth the way forward and help you to finally answer the important question, “Should you stay or should you go?”

We’ve been helping people — just like you — to uncover their right option. Should you stay in your current job? Are there strategies to boost happiness in your present role? Or do you need to make a serious change and seek out a new position?

If you could benefit from expert support and guidance, we are ready to help you.

Book an appointment today.

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