With a Little Help from My Friends

Everyone warns you about the hard parts of going out on your own. The uncertainty. The cash flow. The fact that you are now also your own IT department. What nobody really prepares you for — at least nobody warned me — is the boredom. Not the kind that comes from having nothing to do, but the kind that comes from doing things without anyone to do them with.

I spent fifteen years inside organizations, and what I remember most isn't the decks or the deliverables. It's the people. The friend who could read my face across a conference table and know exactly when to jump in. The team that had a standing lunch order, a group chat full of nonsense, a weird little ritual that made a hard week feel manageable. The colleague who stopped by your desk at 4 p.m. on a Friday insisting it’s time to stop work and start playing games. None of that makes it onto a résumé, but all of it made the work feel meaningful.

I didn't miss the meetings. I missed the people.

When you go solo, those things just stop. There's no team standup, no shared debrief after a tough call, no one to send you a meme when something goes sideways. And in their absence, a certain flatness can settle in — not crisis, just the low hum of missing something you didn't have a name for until it was gone. I found myself getting bored not with the work (the work is very exciting and keeping me very busy), but I was bored with the experience of it. Turns out the work had always been better because of the people doing it alongside me.

So, I started reaching out. Not strategically, not with an agenda — just genuinely reconnecting with the people who had mattered to me over the years. Former bosses. Old teammates. Clients from years ago and collaborators from just recently. People I'd worked with for a season and people I'd stayed close to over the span two decades. And to my genuine surprise, every single one of them showed up. They made time. They shared freely. They asked good questions and told honest stories and cheered me on in ways I will not forget.

What I've built from those conversations isn't quite a team and isn't quite a network in the traditional sense. It's more like a community. With real history, real warmth, and real investment in each other. It has replaced some of what I was missing. And it's taught me something about what I was actually looking for all along: it was never the structure. It was always the people.

Without fail, each has helped me, whether they know it or not. They’ve helped in tangible ways; reviewing my go-to-market deck, my first SOW, my website, my logo, introducing me to clients, sending me articles…. But more importantly in intangible ways. By showing up, they showed me that the relationship we built was valuable for them too. And I know that they believe in me in this new endeavor, which is a type of currency I didn’t know I needed.

I want to honor that. So I'm starting this blog series as a way to share what I've been learning, with gratitude to everyone who's been willing to share it with me. And as a reminder that relationships matter. There will be no editorial calendar, no pressure, no promises about frequency. Just an ongoing, open-ended conversation — much like the ones that inspired it.

If we’ve worked together hand haven’t connected in a while, or if you’re a solopreneur experiencing boredom or loneliness… let’s chat.

More soon. With deep gratitude.