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Picture this: I’m sitting poolside in Arizona with twelve incredible women who help make this business run. Some of them have been on this journey with me for nearly eight years, which in internet years might as well be a century.
And in that moment, surrounded by laughter, heartfelt conversations, and the gentle clink of glasses, I realized something huge: I never set out to be a boss. That wasn’t the dream when I started my little side hustle with a Craigslist camera.
But now, this role as a leader of a team is one I cherish deeply, and this retreat reminded me why. After skipping a year due to life, babies, and all the beautiful chaos in between, our fourth team retreat came together in the best way. It was part celebration, part strategy, and all heart.
In this episode, I’m giving you a behind-the-scenes look at how we planned it, what we focused on, and how even if you don’t have a team, you can still create this kind of intentional space for yourself.
The Intentionality Behind This Retreat
Over the years, we’ve tried different styles of retreats—from total relaxation vacations that felt like bachelorette parties without the wedding, to full-on working sessions where we were spread out with laptops and timers.
This year, I wanted a mix. I craved something that naturally flowed between business and life. We hadn’t seen each other in person for two years, and it felt important to make time for both meaningful work and quality connection.
Our goal wasn’t to solve a big problem or map out a massive promotion. It was to align on vision, reconnect as a team, and reignite that sense of shared purpose.
Marisa, my right-hand woman, tackled all the logistics like a pro, making the entire experience feel seamless and stress-free. We returned to a familiar retreat location, which made everything from the airport to dinner reservations feel easy.
And yes, I treated every team member to a spa appointment because I’m a robe-loving spa girly at heart! The investment of time and money was significant, but the ROI in alignment, morale, and creativity was worth every penny.
The Heart of Our Conversations
On our very first night, takeout boxes in hand and cozy in one hotel room, we found ourselves deep in a conversation that wasn’t even planned but turned out to be one of the most powerful.
We started talking about who we really are as a brand and who we’re here to serve. I found myself passionately reaffirming something I’ve always known in my gut: I love serving beginners.
Helping someone take that brave first step into business lights me up more than anything. And while many others are eager to move into advanced strategy, I’m still fully in love with helping people get their first win!
That conversation also sparked ideas around simplifying the journey for our audience. With so much content between our blog and podcast, we started thinking about how to make it easier for someone to find exactly what they need, right when they need it. It was honest, heartfelt, and exactly the kind of clarity I hoped this retreat would bring.
Thought-Provoking Team Discussions
Before the retreat, I asked each team member to come prepared with answers to three questions:
- What is one creative or strategic idea you have been itching to try either in your area or for the business as a whole? What (if anything) has held you back from testing it?
- Be honest. What is working really well in your area right now? What is one thing that feels like a roadblock? And could the team help you clear it? If yes, how?
- If there were no limitations (budget, time, etc.), what is one bold strategy you would love to see us try to drive big results this year?
These questions sparked incredible ideas and helped us identify a few initiatives to pursue together. We didn’t want to walk away overwhelmed with a laundry list of to-dos… the goal was to feel focused and centered.
What surprised me was how many ideas had already started bubbling up during our casual conversations, and this structure helped solidify them. We even reframed the big-dream question with the prompt, “Wouldn’t it be crazy if…” which led to some fun and unexpected brainstorming!
How I’ve Changed When It Comes to Leadership and Growth
One of the most powerful parts of the retreat for me was realizing just how much I’ve grown as a leader. I never set out to lead a team, let alone a team of twelve women spread across North America.
I started out solo, doing everything myself—writing emails, editing webinars, sending out replays. But now I get to support a team of women who each bring their unique genius to this business.
Some have been with me for over 8 years, walking through life’s biggest seasons with me, from losses and moves to motherhood and milestones.
It hit me in such a profound way that this business is not just mine anymore. It supports families and livelihoods, and the depth of those relationships goes far beyond work.
We truly love spending time together, and I feel so lucky to have built something that attracts and retains people I would choose to travel with even if we didn’t work together.
The Power of In-Person Connection
There’s something sacred about being in the same physical space. It’s the small things like laughing over inside jokes, spontaneous brainstorms in the hallway, and those heart-to-heart chats that just don’t happen on Zoom.
At one point, we were laughing so hard by the pool that other guests didn’t believe we were technically on a work trip. And honestly? I wouldn’t have it any other way!
Even though we all come from different backgrounds, belief systems, and seasons of life, we came together in love, respect, and shared purpose.
It reminded me that building a brand isn’t just about visuals and messaging… It’s about human connection. And being able to gather in person brought out a depth and creativity we wouldn’t have reached otherwise.
Why Team Building Retreats Matter for a Remote Team
As someone who built a business entirely remotely, I love the freedom that comes with that. My team is scattered across states and even countries, and we’re really good at getting things done from afar.
But remote work can also create silos, especially when team members own specific areas and don’t always collaborate. That’s why these in-person touchpoints matter so much. We uncovered hidden talents, built stronger relationships, and created new systems for working better together.
If you’re running a remote team, I encourage you to get creative. Maybe it’s a quarterly Zoom call with DoorDash for everyone, a co-working session with no agenda, or body doubling over Zoom for accountability.
And if you’re a solo entrepreneur, plan a mini retreat for yourself! Change your environment, check into a hotel for a night, or spend a day at a coffee shop. Create the space to reconnect with your vision and move a project across the finish line.
Final Thoughts
Whether you have a full team or you’re building your dream solo, you deserve a space to pause and zoom out. These retreats, whether group gatherings or solo resets, are where clarity is born and momentum begins.
Don’t underestimate the value of connection: not just through strategy sessions, but through shared meals, laughter, and honest conversations.
If you’ve been dreaming about hosting a team retreat or treating yourself to a CEO getaway, let this be your permission slip to go for it.
I’d love to hear your biggest takeaway or your dream retreat vision—DM me or tag me on Instagram so we can dream together!
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