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On The Write Path: Navigating Career Crossroads


Are you currently at a career crossroad? Torn between staying in your current job or taking the leap into something new and unknown?

The decision to stay or go is a challenging and pivotal moment that many of us face at some point in our professional lives. The choices we make during these times can have a profound impact on our happiness, well-being, and future.

One tool that can help you navigate this important decision-making process is journalling. Journalling provides a safe and introspective space to explore your thoughts, feelings, and aspirations. It allows you to gain clarity about your current situation and the path ahead.

To assist you with your career adventure, I've compiled a set of powerful journalling prompts specifically designed to guide you through the process of deciding whether to stay in your current role or seek new opportunities. These prompts will help you uncover insights, reflect on your values and priorities, and make an informed decision that aligns with your goals.

I encourage you to set aside some quiet time for self-reflection as you consider your career options. Whether you're feeling stuck, overwhelmed, or simply in need of some clarity, these questions will serve as a valuable compass on your career path.

Below are 18 prompts and begin your adventure of self-discovery, which is quite a lot. If you are choosing to dive in,there are two ways you can do so. Firstly, you can dedicate the time and answer them all one by one, or you can (with journal and pen poised and ready) run down the list and only respond to the prompt(s) that call out to you.


Remember, your career decisions are a reflection of your aspirations and values, and it's essential to make choices that resonate with your true self. Also, there is no right or wrong way to journal - take note of whatever comes up for you. Have fun!

  1. What initially drew you to this role, and what were your expectations when you started?

  2. How do you currently feel about your job on a daily basis? Describe both the positive and negative aspects.

  3. What are the specific things that make you want to leave your current role? List them in detail.

  4. What are the aspects of your job that you still find fulfilling or enjoyable?

  5. Have you communicated your concerns or dissatisfaction with your current role to your supervisor or HR department? If not, why?

  6. What are your career goals and aspirations, and how does your current role align with them?

  7. What are the financial implications of leaving your current job, such as changes in income, benefits, or retirement plans?

  8. Have you considered the potential opportunities for growth or advancement within your current organisation? If so, what steps can you take to pursue them?

  9. How does your current job affect your work-life balance and overall well-being? Are there specific aspects that are causing stress or dissatisfaction?

  10. If you were to leave your current role, what steps would you need to take to transition smoothly to a new job or career?

  11. What are your values and priorities in life, and how does your current job align with them? Are there any values or priorities that your job is currently conflicting with?

  12. Have you sought advice or feedback from trusted friends, family members, mentors, coaches or colleagues about your decision? What insights have they offered?

  13. Consider the worst-case scenario if you were to leave your current role. What steps could you take to mitigate potential risks or challenges?

  14. What are the potential benefits and drawbacks of staying in your current role for another year? How about for the next five years?

  15. If you were to make a list of pros and cons for both staying and leaving, what would each list look like? Which one seems to outweigh the other?

  16. Can you identify any patterns or recurring issues in your past jobs or career decisions that might be influencing your current dilemma?

  17. What steps can you take to improve your current job satisfaction, even if you decide to stay for the time being?

  18. How confident do you feel about your ability to find a new job or career opportunity if you decide to leave your current role? What skills or resources can you leverage to enhance your job search?

Finally, remember it's okay to feel uncertain. Trust that the clarity will come. Wishing you health, happiness and career fulfillment. PS. If you would like some support with your career aspirations and development, with me as your coach, there are some opportunities available right now. The Leadership Lounge is now open! Up to $10K in bonuses available. CLICK HERE The Intensive is now open (earlybird + bonuses still available) CLICK HERE I currently have one place available for Private 1:1 Coaching CLICK HERE


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