On the Road Chicago was my first in-person Women in Retail Leadership Circle event, and it did not disappoint.

After months of getting to know this community through calls, emails and behind-the-scenes planning, it was so special to finally experience it in person. What struck me most was how honest the conversations were. Our speakers didn’t just share actionable advice. They shared the real stories, difficult decisions and lessons behind it.

Our keynotes, Monica Nassif, founder and former CEO of Mrs. Meyer’s Clean Day, and Jennifer DiMotta, managing partner and founder of Uprisors Growth Partners, gave us plenty to think about.

Nassif shared candid lessons from building a breakthrough brand, including the risks, decisions and entrepreneurial turning points that shaped her journey. DiMotta brought the conversation back to leadership and growth, challenging the audience to think about how they make decisions, move businesses forward and lead through change. Both offered the kind of real-world perspective that stays with you long after an event ends.

I also loved our Top Challenges session, facilitated by Stephanie Pugliese, president and CEO of Duluth Trading Co. We heard about what leaders are navigating right now, including adopting AI without losing creativity, attracting younger customers without alienating loyal ones, developing talent, driving change, and doing more with fewer resources.

The common thread? Leaders are making increasingly complex decisions without a perfect playbook. Sometimes the most valuable thing you can do is get in a room with women who understand those challenges and are willing to share what they’re learning.

As I write this, our team is about to head to the airport, Starbucks orders in hand, to get ready to do it all again. Boston, New York City, Seattle and San Francisco, we can’t wait to see you!

There are still tickets available for our West Coast events, so you can join us in Seattle (Nov. 3) or San Francisco (Nov. 5).

The On the Road Chicago event reminded me just how special it is to gather in person and what a strong community we have at Women in Retail Leadership Circle. The conversations may begin in a ballroom, but the relationships and ideas continue long after the event ends.