I Quit Without Knowing What Was Next

How I used design thinking to prototype my next chapter and follow the joy.

Around 4pm three years ago today, I shut down my work laptop, left it on my desk, and walked out of the office for the last time as a consultant. I had chosen to step away, and I also had no plan for what came next.

Up until then, I had followed the expected path: college, graduate school, a respectable career. Yet I felt like I was treading water in roles that didn’t fit. Deep down I knew something was off, but the misalignment left me feeling both trapped and paralyzed. My body was continually tense, heavy, constricted.

I didn’t have a big vision for my life or even a clear articulation of what I really wanted. But over time, I began to clear the fog and sketch the outline of a different life.

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Designing My Life

About four months after quitting, the gravity of returning to a 9–5 job began to set in. I started interviewing and networking with that in mind. Around the same time, I picked up Designing Your Life by Bill Burnett and Dave Evans.

Burnett and Evans, colleagues at Stanford’s d.school, teach readers how to apply design thinking to careers and lives that feel joyful and meaningful. They frame design thinking through five mindsets:

• Curiosity: see opportunities everywhere

• Bias to Action: get in the game

• Reframing: let go of dysfunctional beliefs

• Awareness of the Process: enjoy the ride

• Radical Collaboration: lean on your community

Each chapter includes reflections and exercises, which most readers probably skim and think, “I’ll do that later.” For once, I actually paused and completed every exercise, even the daunting one about writing a personal philosophy of the meaning of life. The process culminates in what the authors call Odyssey Planning: sketching three alternative versions of your life over the next five years.

Odyssey Planning: My Three Lives

If you begin with only one idea, in this case, the life you’re already living, you’re likely to get stuck there. The power of this exercise lies in creating three distinct lives, each with its own title, work, location, relationships, and guiding questions.

• Life One is the obvious path: the one you’re already on.

• Life Two is what you’d pursue if Life One were suddenly no longer an option.

• Life Three is the fantasy path that feels bold and a little unrealistic.

Here’s a snapshot of what I dreamed up:

Life One: W-2 Employee, Looking for What’s Next
In this version, I accept an account manager role at a healthcare firm, stay in the city where we already live, take weeklong trips to Europe, save half my income, and feel bored. My big questions: How early can I retire? and Will this ever feel meaningful?

Life Two: Slow Build to Location-Independent Coaching
Here, I return part-time as a trainer at Orangetheory while pursuing a life and executive coaching certification. By year four, I’m mostly coaching in my own business, with OTF as a fun side gig. I also launch a newsletter. My questions: Will I actually like coaching? and Will people pay for it?

Life Three: Downtown Portland’s Community Wine Shop
In my fantasy life, I secure investors and a small business loan to open a wine shop in the Old Port. By year three, I’m hosting community events, serving on city committees, and leading wine trips abroad. My newsletter becomes the go-to for local foodies. My questions: Am I comfortable promoting alcohol? and Do I know enough about wine?

What Happened Next

The design process doesn’t stop with imagining. It continues with prototyping, or taking small, low-cost steps to test aspects of each life. I began experimenting and checking in with my energy.

Life One (W-2): While networking and interviewing, I noticed a pattern. On nights after meetings, I barely slept and often woke in sweats. My body was sending a clear signal that returning to corporate life might look safe and respectable, but it wasn’t aligned. I’ve kept this option in my back pocket, but it no longer feels like the path forward.

Life Three (Wine): I never prototyped this seriously. Looking back, it’s striking that my original question was about promoting alcohol, because today I’ve been alcohol-free for more than 18 months. Still, the elements of community building and group travel are interesting to me.

Life Two (Coaching): This is where the energy flowed. My first prototypes were small—reading coaching books, listening to podcasts, and signing up as a guest client for coaches-in-training. Each left me feeling more energized. That energy carried me into a rigorous year-long certification program, the launch of my practice, and earning my ACC credential with the International Coaching Federation.

Following the Joy

For me, life design distills into one principle: follow the joy. Pay attention to what excites and sustains you, and let that energy guide your next step.

I’m still experimenting. Last spring, I prototyped a small-group coaching program inspired by the book itself. I wanted to share the process in a supportive, expansive space where folks could explore alongside each other. Together, we worked through the core reflections and exercises, including Odyssey Planning. I checked in with my energy at every stage and found joy all along the way, from building the website to sending the final follow-up email.

The participants, too, found joy. One shared:

“This program helped me to see that the changes I want and need to make are smaller and more attainable than I had been feeling. I have a renewed sense of possibility for my own life.”

This fall, I’m offering the program again, with new cohorts beginning the week of October 7. If you’re at a crossroads, or simply seeking more energy and alignment for your next chapter, I’d love for you to join us.