My First Two Years as an Entrepreneur: A Journey of Lightness and Joy
I took this photo the day I turned in my resignation letter two years ago, feeling a mix of nerves, exhaustion, and quiet hope. This selfie reminds me just how much I’ve learned in the past two years, and I feel deeply proud of her—for leaping before she felt ready, and for choosing to build something that honors her values every step of the way.
Sometimes the biggest journeys begin with a shove rather than a carefully planned leap. My own origin story as a leadership coach and business owner started that way. A swirl of life circumstances nudged me—okay, shoved me—out of the comfort of a salaried role and into the wide‑open sea of entrepreneurship.
Year One: Lightness Amid the Heaviness
Those first months were personally heavy—I was squarely in a caretaking role for multiple family members. Because my emotional bandwidth was stretched thin, I made a quiet promise to myself:
I will only do what feels light and right.
That simple filter changed everything. The moments of “I-need-to-figure-out-this-business-thing” still existed, but my coaching sessions with clients became like oxygen to me—pure lightness and joy. Supporting leaders through overthinking and self-doubt filled me up in a way nothing else could. I pursued that feeling above all, and it carried me through the turbulence of Year One.
Year Two: Surprise, It’s a Thriving Business
I entered Year Two with cautious optimism and a spreadsheet that still felt more aspirational than factual. Then the numbers caught up to the vision: month by month, my coaching practice expanded until I’d quietly replaced almost all of my old W‑2 income.
The funny thing? The bottom line on the spreadsheet wasn’t even the headline. What mattered more were the new metrics I’d started tracking:
Weekdays off that aren’t official holidays. Midweek beach mornings with my dog felt like a too-good-to-be-true treat
Flexible scheduling. Being able to take doctor’s appointments during the workday, freeing up evenings for family time—an unexpected delight
“Netfunking” meetings = fun networking. If a conversation felt light and interesting, I said yes; if it felt heavy, I didn’t
Exercise classes attended. I found a Barre studio that sparks genuine enjoyment—and that renewed energy flows directly into how I show up for my clients
Collaborating and creating. Working with other entrepreneurs to co-create programs, retreats, and classes that light us all up
These might sound unconventional, but they tell a truer story of success than revenue ever could.
My Guiding Word for 2025: Enjoyment
Each December, I choose a word to guide the next year. For 2025, the word practically chose me: enjoyment. It’s a reminder that I didn’t leave a steady paycheck just to recreate hustle culture in a different outfit.
Enjoyment means:
Taking on work that feels energizing, not draining
Leaving space for drumming lessons (yes, really) and unstructured time with visiting friends
Building systems so the business can hum while I’m away—because…
Looking Ahead: My First Ever Sabbatical
Next spring, I’ll take my first ever sabbatical: three months of van-life wandering through the Pacific Northwest with my wife and dog. The plan is equal parts camping, hiking, connecting with myself and nature, and simply being. I’m setting the business up now—automations, client timelines, trusted collaborators—so I can step away without worry and return restored, ready to dive back into meaningful work.
Lessons I’m Taking With Me
Joy is a strategic advantage. When my calendar includes activities that restore me, my coaching is sharper and more impactful.
Lightness is a compass. If something feels heavy or “off,” I say no—even when the money looks good. That single practice has protected both my energy and my brand.
What I track shapes what I value. I’ve learned that intentionally tracking joy, wellbeing, and flexibility changes how I design my business—and it’s made everything more sustainable.
It’s okay to do something just because I want to. I used to default to productivity-first. Now I’m learning that desire and enjoyment are reason enough. The paradox? More unstructured joy often leads to more creativity and momentum.
A Final Reflection
I share these milestones not as a playbook, but as a window into how I move through work and life. If my commitment to lightness, curiosity, and genuine connection resonates with you—and you’re wondering what enjoyment might look like in your own leadership—I’d be honored to explore that conversation with you.
