Finding Our People: 2nd Annual Chicago Event Planner Retreat

Photo Credit: Sholeh Munion | Sholeh Events

Being a high-end event planner is often seen as a social career — we're always surrounded by people, celebrations, and energy. But the reality of running an event planning business can feel surprisingly isolating. Many top 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.

There’s no manual for how to grow in this industry, no clear pipeline for new planners, and few opportunities to gather with others who really get it. That’s exactly why we created the Chicago Event Planner Retreat.

After years of navigating this work solo — and after attending a powerful local retreat back in 2019 that left a lasting impression — I wanted to create a space where planners could come together not to compete, but to connect. To be honest and vulnerable. To learn from each other. And to remind ourselves that we’re not alone in this work.

Planning the 2024 retreat was stressful, but I had help from a few great planners, and that retreat lit a spark! Several of the exceptional Chicago wedding planners that attended the first year, such as Emmanuelle, Blair, Rebecca, and Rojin, jumped in and offered to help co-create the 2025 experience. Together, we built something grounded in community, trust, and the kind of conversations we rarely have time for in our day-to-day lives.

Photo Credit: Sholeh Munion | Sholeh Events

Photo Credit: Rebecca Pope | Something Profound Weddings

Photo Credit: Sholeh Munion | Sholeh Events

Some of what makes this retreat so special:

• We set the tone early. Clear expectations, a shared meal plan, a “house mom” to help facilitate smooth transitions, and gentle guidelines helped everyone settle in and feel safe.

• We get out of the city. Hosting the retreat in a quiet, serene location gives us the space — physically and mentally — to really focus and be present.

• We keep it real. Topics range from time management and client red flags to pricing struggles, perfectionism, and burnout. No question is off-limits. No ego required.

• We reflect. The very last session at the end of each retreat is a designated safe space to welcome feedback, suggestions and ideas for improvements for the following year.

• We stay connected. After the retreat, we keep the conversation going through texts, emails, Zoom calls — sharing contract clauses, vetting vendors, and supporting each other when things get tough.

Sholeh showing off her massive Emergency Kit.

Photo Credit: Rojin Babayan | Baroj Events

Photo Credit: Rebecca Pope | Something Profound Weddings

Photo Credit: Sholeh Munion | Sholeh Events

The feedback from attendees says it best:

“In the past, I’ve felt siloed as a female entrepreneur in this industry. It’s easy to forget there’s a whole community that wants to see you succeed. This retreat helped me reconnect with that. I learned that pretty much everything I’ve ever felt as a business owner is universal. There’s so much value in hearing how others have worked through the same challenges.” — Rebecca

“I’m new to Chicago, and being in this room with so many seasoned planners gave me so much confidence and encouragement. I feel way more equipped to serve my clients with excellence.” — Alexis

“It was really amazing to see how similar our practices are — and how much we can still learn from one another.” — Michelle

Our goal isn’t to grow bigger. It’s to grow deeper — to hold space for honest dialogue, peer learning, and professional relationships built on trust. Whether you’ve been planning elegant Luxury wedding planning for two years or twenty, we believe there’s power in getting off the hamster wheel and sitting around a table together.

Planning is already underway for the 2026 retreat, and we’re excited to keep building on what’s been created. If you’re a Chicago area event planner looking for real connection, honest conversation, and a space to grow alongside others who get it: stay tuned.

More details will be shared soon, and we hope to see some new and familiar faces around the table next year.

Photo Credit: Sholeh Munion | Sholeh Events

— Sholeh & The Chicago Planner Retreat Team