Hi Reader,
As Co-Founders, every time we get together in person, it's different. The season we're in shapes everything — what we talk about, what we need, what the business needs from us.
This one was different in a way we can't fully describe without sharing more intimately where we actually are in our own business journey.
The early days of Supported CEO had a particular kind of energy — a long list of things that needed to exist that didn't yet, and a worker bee momentum that made it easy to stay heads-down. There was always something to build, create, launch, and figure out.
However, we're not in the building phase anymore.
What nobody really warns you about is what comes after. And even though we are both seasoned business owners, we still didn't fully recognize this until we came face-to-face with it.
When you're no longer building from scratch, a different kind of conversation has to happen. And it's harder, honestly. Because now the question isn't what needs to exist — it's why aren't we showing up for the goals we say we have?
That's the conversation we had in Milan. Over a lot of pizza, of course.
We talk about this with our clients constantly. There comes a point in every business where the next level of growth requires a different version of you — not more systems, not a better strategy, but a real reckoning with the places you've been playing it safe. The building phase is a great place to hide. There's always something urgent to do. But when the scaffolding is up, and the work is right there in front of you, you have to actually show up for it.
We coach women through this transition every day. And we are not exempt from it ourselves.
So that's what Milan was. Two co-founders, a lot of honest conversation, some excellent food, and a decision that the next six months are going to look different around here.
The truth is, we've grown comfortable staying busy — with our clients, our containers, the next system or strategy. But what we haven't been doing is actually showing up for the goals we say we have for the next year of this business and beyond. We have an incredible journaling membership that we love and talk about internally every single day — and yet we rarely share it outside the safety of our email funnels.
If we want to get where we're going, we can't keep choosing not to be seen. (Yes, this came straight from both of our personal journals)
Being in person allows us to have the conversations where we can be really honest with ourselves. But where it all comes together is sharing it out loud — here, with you.
It also gave us a much-needed reset that we both personally needed. Which is why we didn't start the trip with a tour or sightseeing at all. Instead, we ordered room service and started a documentary. Because showing up the way we had been in a building season also signaled something: we needed rest before reflection.
If any of this resonated, we'd love to leave you with a couple of journal prompts:
1. What's a goal I've been saying I have — but one I'm not actively taking action to prioritize?
2. What season am I in right now? Are there any areas where I'm hiding?
There are many other decisions we worked through on this four-day weekend that we plan to share with you — including how we are navigating accidentally running two businesses when we only planned to grow one.
More on that next week.
Stay Supported,
Elli + Ginny