You Don’t Need More Strategy — You Need Space

All right, so today I want to talk about something that, honestly, founders have very strong opinions about, usually before they've ever experienced it: retreats. And I have to laugh a little bit when I say that word because the reactions I get from founders are always fascinating. And some people immediately picture yoga mats, green juice, and everyone sitting in a circle talking about their feelings. Other people think it's basically just a holiday disguised as work.

And then there's a third group who assume it's some kind of luxury mastermind where everyone is pretending their life is perfect on Instagram. And every time I hear those assumptions, I smile. Because the truth is, the best retreats are none of those things. They are actually something far more powerful.

Now let me tell you a quick story. A while ago, I was speaking to a founder who had been following my work for quite a while. She'd built a very successful business. She was doing well financially.

The team was growing. And she said something to me that I hear all the time. She said, Dawn, I keep seeing your retreats, and they look incredible, but I'm not really a retreat person. And I said, Interesting.

What does a retreat person look like? And she paused for a second, and then she said, I don't know. Someone who has time. And I laughed because that is exactly why the founders who benefit most from retreats are usually the ones who think they don't have time for them.

Because here's the irony: the more successful your business becomes, the harder it becomes to think. You're in meetings, you're in Slack, you're solving problems, you're making decisions, you're reacting to things, and before you know it, months have passed and you've been operating entirely inside the business instead of above it. Which is exactly why retreats are so powerful. They create something founders rarely get: space, actual thinking space.

And when founders arrive at one of my retreats, the first thing I notice is always the same. The first 24 hours, they're still in CEO mode, phones out, messages flying, checking emails, answering the team. And then something interesting happens. Their nervous system slows down.

Their brain starts thinking differently. They start having conversations with other founders who understand the game they're playing. And suddenly ideas start appearing that simply would not have surfaced in a normal working week. Now I remember one retreat in particular where we were sitting at dinner, incredible location, beautiful setting, amazing group of women around the table, and one of the founders suddenly said, Oh my God.

Now whenever a founder says that during a retreat, I know something interesting is about to happen. And she said, I've just realized something. And we all looked at her and she said, I've been solving the wrong problem for the last year. Now imagine that moment, 12 months of trying to fix something in the business, marketing tweaks and team tweaks, offer tweaks, and in one conversation over dinner, she realized the real issue wasn't any of those things.

It was the business model itself. That is the power of environment, because proximity changes perspective. When you put ambitious founders in the same room, incredible things happen. Ideas expand, beliefs expand, vision expand.

And honestly, this is something I've seen again and again over the years. Founders arrive thinking they're coming for strategy, and they leave with something much bigger: clarity, confidence, and connections. Because when you're building something ambitious, the room you're in matters. Now this is something I think a lot about when designing my retreats, because they're not just about location, although I do love choosing incredible places.

They're about who is in the room. Because when you sit next to someone who has scaled a business further than you, your thinking expands. When you hear someone share a challenge you've been quietly worrying about, you realize you're not alone. When you see how someone else solved a problem you're currently facing, suddenly the path forward becomes obvious.

And this is the thing founders often underestimate: the power of being around people who are playing at the same level. Because entrepreneurship can actually be quite lonely. Your team can't always relate to the pressure you carry. Your friends might not understand the decisions you're making.

Your family might support you, but they're not inside the business. And so founders often end up solving everything alone. But when you step into the right room, that changes instantly. Now I'll be honest as well.

Retreats aren't just about strategy sessions and whiteboards. Some of the most powerful moments actually happen in the in-between spaces: walking conversations, late-night chat. Chats, coffee in the morning, the moments where founders finally exhale and say, Okay, here's what's really going on. And those are the conversations that create breakthroughs.

Because when you take high-performing women out of their normal environment, remove the noise, remove the constant demands, and place them somewhere inspiring with other ambitious founders, their thinking expands in ways that simply can't happen on Zoom. And this is why retreats have become such an important part of my work. Because strategy is important, systems are important, execution is important, but perspective is everything. And sometimes the biggest breakthrough in a business doesn't come from doing more.

It comes from stepping away long enough to see things clearly again. And the founders who allow themselves that space often come back with decisions that change the trajectory of their business entirely: new offers, new partnerships, new business models, sometimes even entirely new visions. And that's the moment I love most. When a founder arrives feeling slightly overwhelmed and leaves feeling completely re-energized, clear, focused, excited about what they're building again.

Because building a big business should feel expansive, not exhausting. So if you've ever looked at retreats and thought, That looks nice, but I don't really have time for that, just remember something: the founders who scale the fastest are not the ones who stay the busiest. They're the ones who create space to think bigger. Because sometimes the most productive thing a CEO can do is step away long enough to see the next level clearly.

Thank you for joining me for another episode of Dawn of a New Era, The Billionaire Brain. And if this episode made you think about the rooms you're currently in, share it with another founder who might need that reminder too. Because the right room can change everything.