Being a business owner can be lonely. Though event planning is inherently social, many planners spend their days making important decisions in isolation — pricing their services, fielding complex client requests, navigating tricky contracts — without a team to bounce ideas off of or a mentor to guide the way.
That’s exactly why we created the Chicago Planner Retreat (CPR).
In 2019 Sholeh Munion of Sholeh Events had the pleasure of being invited to a one-time local area planner retreat, where I was inspired and encouraged by other planners sharing their stories of personal and business growth, which is what propelled me continue pursuing my business, even while pregnant through the pandemic(!) with a toddler.
By 2023, I gathered a small group of local planners who all saw the need to fill a gap many had long felt in the industry: the need for real community among event professionals. Not just another networking event, but a space to slow down, dig deep, and learn from one another without ego or competition. A space where newer planners and seasoned pros could all come to the table as equals — to share tools, troubleshoot together, and maybe even laugh (or cry!) over snacks and spreadsheets.
The first retreat lit a spark. The second, held in early 2025, proved it was a valuable resource.
And now, with the help of returning planners-turned-co-creators — Sholeh, Blair, Rebecca, and Rojin — we finished round three in March 2026.
So, what is the retreat really about?
At its core, the Chicago Event Planner Retreat is a collaborative, off-the-grid gathering for Chicago-area wedding and event planners who want to invest in their businesses and in each other. Held at a vacation home no more than 90 minutes from Chicago in various vacation homes, the retreat is intentionally small (20 attendees), intimate, and full of intentional programming that hits on both the practical and the personal sides of business ownership.
Topics we’ve covered include:
Building sustainable pricing & packages
Managing client relationships
Sales and marketing strategies
Navigating team growth and staffing
Owning your time
Practicing inclusive planning
Letting go of perfectionism
…and more
We also make plenty of space for open conversation — and some late-night laughter in sweatpants, of course.
As planner Rebecca put it:
“It’s easy to get stuck at your desk and forget there’s a whole community out there that wants to see you succeed. This retreat gave me the chance to step away from the day-to-day and reinvest in myself and my business.”
What makes this retreat work?
There are a few special ingredients that keep this retreat real, approachable, and meaningful:
A clear schedule shared in advance — so you know what to expect and can be present.
Guidelines and values — to create a safe, welcoming space where vulnerability is honored.
Collaborative sessions — including real-time feedback on business ideas, time management practices, and more.
A “house mom” on site — someone who handles meals and clean-up so we can all focus on the work (and rest).
Staying under one roof — we all live together in a shared house to deepen connection and maximize the experience.
Ongoing support after the retreat — including Zoom check-ins for contract review, vendor challenges, and encouragement through the highs and lows of entrepreneurship. Our Whatsapp group has been key to help us navigate real-time challenges.
What our attendees are saying:
“I learned that pretty much everything I’ve ever felt as a business owner is universal. Everyone experiences it differently, but we’re not alone. There’s power in hearing how others work through the same things.”
— Retreat Attendee
“I’ve been doing events for almost 20 years, and I’m still learning. This retreat challenged how I think about pricing and how clients are purchasing right now.”
— Sholeh Munion, Sholeh Events
“Meeting this group of powerful women gave me so much confidence and encouragement. I feel way more equipped to go out and serve my clients with excellence.”
— Alexis, new to Chicagoland planning
“The time management section changed everything for me. I walked away with actual strategies I hadn’t heard before, and I know it’s going to help me run my business better.”
— Chayla, CC Ellison Events
Is this for me?
If you’re a Chicago-area wedding or event planner with at least one year in the industry and a desire to connect with others in a real way — yes. This retreat was built for you. Whether you’re in your first few years or your fifteenth, this is a place to step out of hustle mode and build something more sustainable. And you don’t have to do it alone. Reach out to us to see how you can participate.
A final word
This retreat isn’t fancy. It’s not about styled shoots, swag bags, or photo ops (though we do love a good group selfie). It’s about real talk with real planners, looking to grow together.
We’re not building a conference. We’re building a community.
And we’d love for you to be part of it.
