⛰️ Trail & Error: The Unexpected Joy of Building in Public

Welcome back to Trail & Error, where we explore the journey of designing work and life on your own terms.

In this issue, I’m diving into the surprising rewards of building in public—from learning to share imperfect moments to finding joy in the journey.

If you’re struggling to take action because you’re waiting for the “perfect” moment, read on.

The Unexpected Joy of Building in Public

For years, I held onto this idea that the “right time” would come along to start sharing my work more openly.

But I’ve learned that building in public isn’t about waiting until everything feels “ready” or “perfect.” It’s about sharing the process—mess and all—and it’s been one of the most surprising, rewarding changes in my life & career so far.

Just this week, I was talking to a new friend and fellow coach, Tim Schneider, a brilliant psychologist with only a small LinkedIn following. Tim’s insights could fill books, but he’s still getting comfortable sharing his story online.

Our conversation took me right back to the start of my own journey, remembering how challenging it was for me to share things before they felt polished. Looking back now, I can see how far I’ve come in making my work and life visible.

I vividly remember the first time I shared my thoughts online. It was 2016 and I’d just returned from a career break, traveling around the country in a refurbished Airstream with my now ex-wife and my oldest child, who was 1 year old.

I published a piece on Medium about our journey, and the most incredible part was the encouragement and stories I received in return.

Ashley reached out to say, “❤ this Sean, and so admire you and your wife for doing this! I’ve taken the past couple months off for a much needed break, and I have to say it’s been incredible.” That one piece even got picked up by When To Jump, a publication by a Dartmouth classmate, Mike Lewis.

This experience taught me that sharing even the smallest moments—before things are fully formed—can be powerful. It builds a community that’s along for the journey. Each imperfect step forward has created something real and lasting.

Launching Trail & Error last month, along with sharing more on LinkedIn, has brought that same feeling. The feedback has been both encouraging and humbling.

One recent favorite was a message from my friend and Trail & Error subscriber, Tim Miller, who said, “Thrilled to see this… proud of you for chasing what feels like the next right thing… also, you picked a GREAT name.”

There’s a magic in building publicly. Here’s what I’ve found along the way:

• Sharing decision-making moments – When I shared my decision to go from full-time to fractional work, it wasn’t just about a new role; it was a story of choosing freedom and ownership over my own time. Letting people into the “why” behind this decision has helped me connect with others who are making similar choices.

• Talking about failures – Early on, I hesitated to post about things that didn’t go as planned. But it turns out people connect even more with the parts that don’t work as they do with successes. Sharing my missteps has opened up countless 1:1 conversations, many of which have turned into lasting friendships.

• Celebrating small wins – I’ve started celebrating the smaller victories, like hitting my first subscriber milestones or getting client testimonials. These small moments add up, reminding me—and the people following along—that progress isn’t always about big leaps. Often, it’s made up of a hundred small steps. That’s certainly been true for mne.

Every time I share my thoughts, whether it's on LinkedIn, X, or here in Trail & Error, now feels like part of a larger journey. And, as Anne-Laure Le Cunff of Ness Labs reminded me last week, there’s something incredibly rewarding about building alongside others.

Building in public isn’t about waiting. It’s about showing up each day, sharing each step—no matter how imperfect—and inviting others along for the ride.

Building In Public - The #1 Takeaway

Building in public is about both action (sharing your thoughts) and mindset (overcoming fear & self-doubt 😉).

It’s not just sharing wins (though that’s great too!)— it’s inviting people into the messy, nonlinear process of growth.

Sound fun? Maybe a little terrifying? Both?

If the idea of building in public—posting videos, writing about your process—makes you shudder, working with a coach might help. Coaching can help you get to the root of that discomfort, and the transformation can often be quicker than you’d expect. (No pressure, but if you’re interested in working 1:1 with me, there’s more info below.👇)

One last thought: every interaction, piece of feedback, and new subscriber is a part of this journey we’re building together. It makes the whole experience more meaningful and, honestly, more fun. So thank you for being here, supporting my journey and growth.

I’m grateful to be learning alongside you.

If you’re feeling stuck in your life and career, if you’ve been laid off, and are looking to make a major transition in your life, I’d love to help you get unstuck.

Here’s feedback from one of my clients:

Thanks for reading Trail & Error. And thank you to Frank Chen for providing feedback on this week’s issue! If you enjoyed it, please share it. Together, we’ll help people build more resilient & fulfilling lives!