Written by Rachel Stewart, Content Director and Co-Founder

The hotel room had become something between an art studio and a think tank. Eight giant posters covered the walls, each one filled with multi-coloured handwriting and arrows pointing in every direction. Piles of markers were scattered across the room, and my hands were speckled with ink. Empty paper cups. Crumpled post-its that didn’t make the cut. The chemical smell of permanent and scented markers hanging in the air. This is what it looks like when strategic planning starts getting real.

Ruby and I had blocked out one night (two days) for our first official strategic planning session. No distractions, no responsibilities pulling us away, just us and the future of ROSE. Luci couldn’t make it, but we promised a full debrief. We dove into SOAR frameworks, logic models, and 30-60-90 day plans with the kind of energy that can only come from building something you deeply believe in. But strategic planning, mission work, visioning… it’s all messy. Not just the post-its and markers kind of messy – though there was plenty of that – but the emotional, vulnerable, “are we really doing this?” kind of messy.

At one point during that first three-hour intensive session, Ruby teared up. They were happy tears. Five women had already submitted expressions of interest, each one sharing a unique story they hoped to tell through ROSE. We sat there together, reading through their submissions, and had a full-on pinch-me moment. This thing we’d been dreaming about? People wanted to be part of it. Real women with real stories were already saying yes.

We worked until we couldn’t think straight anymore, then traded our planning mode for PJs and Chinese food. Ruby ordered wonton soup, I got hot and sour, and we split an order of dumplings while talking into the night. We talked not about frameworks or timelines, but about everything else. We’ve been friends for over 12 years, and that night reminded us why we’re doing this together.

The next morning, we met back in that poster-covered room to wrap things up. That’s when I hit a wall. I stood there staring at those eight giant posters filled with our plans, our goals, our entire vision for ROSE, and suddenly felt small. The doubt crept in fast: Could we actually do this? Could I actually do this?

Ruby noticed immediately. “Are you feeling imposter syndrome right now?” she asked. I nodded. “Because what you’ve talked us through, what we are doing right now, is doing the work of building a business,” she said firmly. “You are an entrepreneur, Rachel.” I teared up, too. They were different tears than the night before, but just as necessary.

What came out of all that chaos and vulnerability? Clarity. We identified who we want as our first cover girl. We decided our first issue launches in May 2026. We made the hard call to shelve some exciting ideas because we needed to focus our energy where it matters most right now. We turned three hours of frantic brainstorming and two hours of focused execution into an actual roadmap.

I left the retreat knowing that building ROSE requires both the post-its and the pajamas, the strategic frameworks and the late night conversations, the happy tears and the scared ones. It takes showing up in hotel rooms that smell like markers and believing – even when imposter syndrome whispers otherwise – that you’re exactly where you’re supposed to be. 

So yes, we’re really doing this. Let’s build something beautiful together.