Funny thing about leading a retreat: sometimes you’re the one who walks away with the biggest lessons.
I co-facilitated a three-day retreat last week with my partner Danielle Wilkie alongside a small group of powerful female leaders. We were tucked into the central mountains of Mexico in the enchanting city of San Miguel de Allende. This retreat was the culmination of a year-long YPO-like forum, bringing together accomplished women connected by industry and life stage—each beginning to consider what’s next.
I never imagined how much I’d learn from and with these women, especially in these immersive days together.
Here are five lessons that stood out:
1. Less doing, more being
These women didn’t need business coaching—they had that mastered. Instead, they craved a space to simply be together, expressing their unique gifts. Looking ahead to the next 30 years, their focus had shifted from WHAT they could accomplish to WHO they could become.
2. Softening is the growth edge
This group was filled with Enneagram 8s and 3s—women whose ‘badass’ and ‘get shit done’ personas propelled them to the top. And yet, their next chapter (and challenge) wasn’t about pushing harder; it was about leading with love, vulnerability, and presence.
3. Connection = nourishment
Wealth, for these women, wasn’t measured in dollars alone. The deep, soul-filling connection within this group was the precious resource they now prioritized—some realizing they had ground to make up, others planning to double down on relationships in the coming years.
4. Presence is a gift
The simple act of our morning meditation had a surprising impact. We started each session with just one minute of stillness, and for these high-powered women constantly on the move, it became one of the most valuable moments of all. They all reflected that they wished they had been more present along the way.
5. It goes by fast—so make it big
On our last day, we did a ‘Future Life Walk,’ stepping into our future state visions one decade at a time. Their message was loud and clear: Life moves quickly. Don’t wait to make it as big as you want it to be. Big dreams. Big fun. Big love. Big impact.
What an incredibly energizing week. Surrounding yourself with wisdom and excellence unlocks some serious shortcuts to growth.
If you’re interested in joining our next Agent CEO forum, reach out to us directly at hello@the-helm.com.