Journaling for Clarity: 5 Prompts to Navigate Career Shifts

A few years ago, I hit a wall in my career.

I was working in a large organization, doing work I was good at, but it all started to feel… monotonous. Uninspired. Stagnant. I knew something needed to change, and not just a little tweak—I needed a drastic shift.

When I found myself stuck in that season of professional uncertainty, my journal became the space where I started asking harder, deeper questions:

• What do I really want?

• What’s no longer working for me?

• What would it look like to build something different?

That clarity didn’t come all at once, but over time, through reflection, exploration, and being honest with myself, I began to design a new path. Now, I am doing work that excites me, and through my businesses, I support others in designing lives and careers that feel aligned and fulfilling, too.

Whether you’re navigating a shift, considering a new role, or just trying to grow where you are, these journal prompts can help you cut through the noise and reconnect with what matters.

1. What does “success” look like for me in this season of my career?

Success isn’t static. It evolves as we grow. This prompt helps you redefine success on your own terms—right now. What does it look like for you in this moment, not based on external expectations or past definitions?

2. What do I want to learn, experience, or strengthen this year?

This is your invitation to check in with what growth means to you. Maybe it’s leading with more confidence, deepening your subject-matter expertise, or learning to navigate uncertainty with more ease. When you name it, you can start to pursue it.

3. When do I feel most energized at work? When do I feel drained?

Energy is one of the best feedback tools we have. Start paying attention to the patterns—what gives you life, and what consistently wears you down. This insight can help you shape your workload, career direction, or leadership style.

4. What stories am I telling myself about my capabilities—and are they true?

We often internalize doubts or outdated narratives that quietly hold us back. This prompt is about noticing them and challenging them. Because growth isn’t just about learning something new—it’s about unlearning what no longer serves you.

5. What’s one bold move I could take in the next 30 days?

You don’t need to overhaul your entire career to move forward. Just take one step. One experiment. One conversation. Use this prompt to identify a bold (not necessarily big) move that helps you build momentum and confidence.

Journaling as a Tool for Growth

I’ve seen how powerful journaling can be—not just for myself, but for the clients and leaders I coach. It helps you access clarity, build confidence, and make intentional decisions about your next steps.

Because sometimes, the clarity you’re looking for isn’t out there—it’s already within you. You just need a place to see it and hear it.

If you’re looking for a place to start, these prompts are a great entry point. And if you want a structured tool to guide your growth, check out Pen and Purpose Journal Co. We help you write with intention and live with purpose.

Connect with me on LinkedIn.