Will you show up when life gets messy?
Three women, three cities, one dinner pact - and friendship that emerged from the chaos...
Sometimes, real friendships rise from the ashes of the worst situations.
Two years ago, Kimberlee and I were colleagues at Scribe Media—a remote-first company with a toxic culture that eventually went bankrupt and laid off 80% of us. (You can read about that one here.) We'd only met in person once, at a company offsite, but we stayed connected after the whole thing imploded.
Around the same time, Jenn Ruwart was running her branding agency, Roger That, and had done some work for Scribe. That's how she and Kimberlee knew each other. Fast forward to this year, and Jenn needed a copywriter for a project. Kimberlee recommended me.
The project wasn't a good fit. But Jenn and I hit it off anyway.
"Want to stay in touch?" we asked each other. And we meant it.
What started as Friday coffee Zoom chats turned into something more. We pulled Kimberlee in, and suddenly we had this little trio of support.
Jenn talked through challenging clients and business decisions. I vented about a mastermind that wasn't working out like I'd hoped. Kimberlee was navigating finding a full-time job that felt like a good fit.
We became each other's sounding boards. The kind of friends who hold space for who you're becoming, not just where you are right now.
Then, on one of those Zoom calls, Kimberlee mentioned she had an extra room in her house on Fidalgo Island outside Seattle. "You're welcome to visit," she said.
I'm always up for a weekend adventure. "Sure!"
Jenn jumped in: "Hey, I could come up from Portland for a night and we can all have dinner in Seattle."
And just like that, it was on. We all wanted to meet in person.
Two months later, I texted the group. We picked a weekend. I bought the plane ticket from Austin to Seattle. The date was set.
But as the weekend got closer, I started second-guessing. We all had things competing for our attention. Life was doing its usual chaos dance. Jenn was taking a 3.5-hour train ride and staying overnight in a hotel—all for a few hours of dinner.
Was this really a good idea?
Here's what I love about these two: we all stayed the course.
I caught my flights. Jenn took the train. Kimberlee drove almost two hours from the San Juan Islands into the city.
We met at Matsu, this great sushi place, ordered rosé, and talked about everything. Life, families, where work is right now, how we all want to feel about what we're building.
Then we walked a few blocks to the rooftop bar at Jenn's hotel, Populus, and kept talking under the Seattle skyline until way too late.
Meeting IRL shifted something. It gave us all the feels. Like we'd invested our energy in the right people—professional friends you actually want as personal friends. Finding that blend is such a rare and beautiful way to create your life.
There's something special about online business support friends. They're the ones who show up and follow through. Who support you in creating the life you're imagining, especially when things are falling apart.
They hold the space to trust that things will come back together in ways that feel more like who you want to become.
Sometimes the best connections come from failed projects, toxic workplaces, and promises you almost don't keep.
Tell me - do you have online business friends who've become real-life support systems? The ones who hold space for who you're becoming, not just who you are right now?
Hit reply and share a story - I love hearing about the connections that matter.







I am still in touch with friends I made at (go figure) a remote workplace in 2017. We met in person during the company retreat (THAT was eye-opening) and through quarterly meetings. One lady was my housemate for a year and we're all still in touch. Some of the best friendships come out of toxic places. We all got our alive.
This is amazing, Jen! So incredible the people you meet along the way and how they evolve into our lives!