From Wonder to What’s Next: Exploring Career Possibilities This Summer
July 23, 2025
Odyssey Plans and conversations can help you design your future before September.
Why Summer Is the Season to Explore
By now, if you’ve taken time this summer to reflect—to consider what matters most to you—you may be feeling a sense of... openness. That openness is a gift. So use it with intention. Once we’ve clarified what we need to thrive (your Life Design Criteria), the next phase is exploration. Not committing, not applying, just exploring. Think of summer as your personal R&D lab.
Discover Your Nine Lives
In a podcast episode titled "How to Break Out of Autopilot and Create the Life You Want," featuring Graham Weaver, a Stanford Graduate School of Business professor and CEO of Alpine Investors, Weaver introduced me to the “Nine Lives Exercise.” I use it to help people start exploring. Try it: Set your timer for five minutes. Brainstorm on a piece of paper nine different careers/lives that you might possibly want to live—variations of your current job to wild and crazy new possibilities. In all, just assume you have the skills and experience and that they’ll all compensate you comfortably. Don’t stop until you get to nine. Now, analyze your results. What themes do you see? What energizes you most? Cross check these with your design criteria. Your goal is to converge on three ideas—not casting aside the others but just starting your exploration with the three that give you the most energy.
Odyssey Plans
The next step employs a tool from Designing Your Life, by Bill Burnett and Dave Evans: the Odyssey Plan. Try it: Sketch out three different 5-year plans, using the three possible lives from the nine-lives exercise. In your plans, consider your path in your career as well as its impact on the other major aspects of your life. From each of the 5-year plans, create a set of questions that you need answered about the plan before you are ready to pursue it. These questions become the basis of your learning plan—your prototyping, as Burnett and Evans call it.
Prototyping Possibilities (Yes, That Means Talking to People)
Once you've drafted those paths, it’s time to test them—not by jumping into a new job, but by having conversations. This is what designers call prototyping. In career terms, it’s a low-risk, high-insight experiment. Here's how: • Find someone doing work that matches one of your Odyssey Plans. • Ask for 20 minutes to learn about their path. • Don’t ask for a job. Ask for insight. Ask for their story. Questions to try: • What do you love about your work? • What surprised you when you started? • What do you wish you had known before entering this field? Summer is a great time for this. People are often more relaxed, flexible, and open to connecting over coffee or Zoom.
Exploration Isn’t Indulgent—It’s Intentional
If you’ve been achievement-oriented your whole life, this part may feel soft or “unproductive.” It’s not. It’s essential. Most bad career moves come from rushing into action before deeply exploring options. Exploration creates context. It shows you what’s actually out there—and what calls to you. Keep a notebook. Track your energy. Write down insights after every conversation. This is the real work—building momentum toward decisions that feel aligned.
What Comes After Exploration?
Come August, I’ll post the final article in this series: how to turn your insights into action. I’ll share how to: • Sharpen your story. • Clarify your job targets. • Build a search strategy rooted in clarity, not desperation. For now, use the rest of July to explore broadly and deeply. It’s not about locking in. It’s about trying things on - lightly, intentionally, and with curiosity. And if you want a guide for that journey. I'll be back August 20, ready to work with those who are ready to move from exploration to action.
—Everette
