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- ⛰️ Trail & Error: Real Life Happens
⛰️ Trail & Error: Real Life Happens
How sick kids, RSV, and a sprained ankle fuel building a career on your terms.

Welcome back to ⛰️ Trail & Error, where we navigate the ups and downs of creating a life and career that truly align with who you are.
In this issue, I’m sharing how real-life challenges—from a sick baby to sprained ankles—aren’t roadblocks but reminders of why this path matters. Building a flexible, fulfilling life isn’t about perfection; it’s about showing up, adapting, and making space for what matters most.
If you’ve ever felt the pull to create a life that works for you—even when life happens—then this one’s for you. ⛰️
Real Life Happens
This newsletter didn’t land in your inbox last week. Life threw some curveballs: a stomach bug hit my entire family, and just as we recovered, Thanksgiving brought us to Santa Barbara for some much-needed family time. This week? My baby is sick with RSV. I’m writing this during one of his naps, squeezing in work while staying present for him and my family.

Baby Bowen with his grandfather, “Bop Bop”
It’s moments like these that remind me why I’m building this life and this business. It’s not about achieving perfection—it’s about creating the freedom to focus your energy where it’s needed most. My hope is to help you design a career that supports your values, your people, and the life you want to lead.
A Small Victory, A Big Milestone
This week, I experienced one of those small-but-mighty moments: I got back on my cargo e-bike after spraining my ankle and rode to pick up my kids from school. Later, I took my daughter to her piano lesson.
It felt like such a win—not just for the recovery, but for the reminder that even small steps forward can feel monumental. Given that we’re a one-car family, this is particularly important for logistics, but more importantly, it’s these little milestones that make the bigger picture come to life.
This is what I want for you, too: to build a life where even the small wins reflect a deeper alignment with what truly matters to you.
A Quick Thank You
This is the seventh issue of Trail & Error, and I want to take a moment to thank you. The first issue went out to just 7 subscribers; today, there are 77 of you. I couldn’t ignore the serendipity of those numbers—a sign, perhaps, that this journey is unfolding just as it should.
Your presence here inspires me to keep going. Your support means everything, and I’m so grateful you’ve joined me on this path.
If this resonates, hit reply and let me know what small win or big challenge you’re navigating right now. I’d LOVE to hear from you!

Our baby is sick but we’re all still feeling festive!
What’s Coming Next
I’m working on something I can’t wait to share: a group coaching program for people ready to build a career and life they truly own. It’s for those who are done playing by someone else’s rules and are ready to take charge of their future.
I’ll share more details in the next issue, so stay tuned! My goal is to help you take meaningful steps toward a life that feels like yours. If that sounds like something you’re ready for, this is just the beginning!
Thank you for being part of this journey. Together, we’ll keep moving forward—one step, one win, at a time.
See you next week,
Sean
Thanks for reading Trail & Error. If you enjoyed it, please share it. Together, we’ll help people build more resilient & fulfilling lives!
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