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On The Write Path: Navigating Career Crossroads

Writer's picture: Janelle RyanJanelle Ryan

Updated: Nov 8, 2024


Are you at a career crossroads, wondering whether to stay in your current role or leap into something new? This question can feel especially relevant at the end of the year, a time when many people pause to reassess their career paths and future goals.


The choice to stay or move on is a pivotal moment, often impacting our happiness, well-being, and sense of fulfillment. During this time, journaling can be a powerful tool to guide you through this decision-making process, offering a safe and reflective space to explore your thoughts, feelings, and aspirations. Through journaling, you can gain deeper clarity about your current situation and the path that lies ahead.


To support you in this journey, I’ve compiled a set of journalling prompts designed to help you decide whether to stay in your role or seek new opportunities. These prompts will guide you to reflect on your values, priorities, and the direction you want for your future.


As you consider your career options, set aside some quiet time for self-reflection. Whether you feel stuck, overwhelmed, or just in need of clarity, these prompts can serve as a valuable compass on your career path.


There are 18 prompts below, so you have options for diving in. You can either dedicate time to answer each one individually or simply respond to the ones that resonate most deeply with you.


Remember, your career choices are a reflection of your values and aspirations, and it’s essential to make decisions that align with your true self. There’s no right or wrong way to journal—allow yourself to note whatever thoughts or feelings come up.


Take a moment, reflect, and begin your journey of self-discovery. 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. Salon X 2025 is now open for applications! Up to $10K in bonuses available. CLICK HERE The Australian Intensive is now open (earlybird still available) CLICK HERE I currently have one place available for Private 1:1 Coaching CLICK HERE

Join the Debut: Leading from the Start online course for ambitious professionals CLICK HERE

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