3 Questions That Help You Step Into Your Boldest Version Yet

Welcome to the first episode of Boldish! Today we’re breaking down the Odyssey Plan, a powerful clarity tool for anyone navigating career pivots, life transitions, or the “what’s next?” moment. You’ll learn how to build three possible paths for your future, evaluate them honestly, and use the insights to move forward with confidence and bold intention.

If you’re feeling pulled toward change but aren’t sure where to start, this episode will help you uncover what’s possible, what’s aligned, and what’s next.

The 3 Odyssey Plan Questions

1. What would your life look like if you continued on your current path?

Describe your next five years if nothing major changes — same career direction, same routines, same trajectory. What does that version of your life look and feel like?

2. What would your life look like if your current path was no longer an option?

If your job disappeared tomorrow or you had to choose something entirely different, what path would you take? What does that five-year future look like?

3. What would your life look like if nothing were off the table?

If fear, money, time, and expectations weren’t limiting you — what is the bold, dream-filled five-year vision you would choose? What excites you, scares you (in a good way), and feels expansive?

If this episode sparks something in you, subscribe to Boldish and share it with someone who’s also ready for their next bold move. And if you create your own Odyssey Plan after listening, send me a message — I’d love to hear where your clarity takes you.

If you’re looking for more support as you grow your confidence and leadership skills, head to www.theboldroom.com . Inside the Bold Room, you’ll find a community and course experiences built to accelerate your career growth with clarity, courage, and connection.