Journaling Prompts:
Career and Purpose

REFLECTION & JOURNALING TOOLS

Prompts for examining what your work means, where it is going,
and who you are becoming through it.

Where This Tool Helps

Career reflection tends to happen in two moments: when something is wrong, and when a decision has to be made. This tool is designed for a third moment - before something is wrong, before the pressure of a decision narrows what you can see.

The prompts here are not about strategy. They are about orientation. Where are you relative to what actually matters to you professionally? The gap between the career you are building and the work that would fully engage you is often visible in how long it takes to answer certain questions on these pages.

Leaders who do this kind of reflection consistently report something consistent: not that it changed their direction immediately, but that it made the current situation harder to ignore. That is the point.

Work through each prompt in order. The sequence moves from past to present to future - anchoring in what has already been true before reaching toward what you want.

How to Use These Prompts

  1. Write in a single sitting if possible. The context accumulates as you go, and the later prompts benefit from having the earlier ones fresh.
  2. Do not answer what you think the right answer should be. Answer what is actually true.
  3. If a prompt feels disconnected from your current role, note that. The gap itself is information.
  4. Mark the two or three prompts that produce the most discomfort or energy. These are worth discussing with your coach.
  5. Return to this tool at major transitions - role changes, performance reviews, year-end.
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Journaling Prompts: Career and Purpose

1. What did you want to be when you grew up, and how has that vision evolved over time?

2. If money, status, and other people's expectations were removed from the equation, what work would you pursue?

3. What does meaningful work look like for you? Can you point to a specific time you experienced it?

4. What are the professional accomplishments you are most proud of, and why those specifically?

5. What skills or strengths do you consistently underuse in your current role?

6. Where do you feel the biggest gap between who you are professionally and who you want to become?

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Career and Purpose (continued)

7. What kind of legacy do you want to create through your work?

8. What would you need to believe about yourself to make your most ambitious career goal possible?

9. What values most need to be present in your work for you to feel aligned - not just productive?

10. Who in your field do you most admire, and what specifically do you want to emulate?

11. What has your career path taught you about yourself that surprised you?

12. If you could redesign your current role, what would you change first?

Before Your Next Session

Look at prompts 5 and 12 together. What would have to be true about your work for the underused strengths to find expression and the redesign to feel possible? What is the smallest structural change that would move in that direction?

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