An Experiment in Group Connection
I brought 70 people to Hawai'i to connect, and here's what I learned
Outcove was one of the biggest moments of my year.
Not just because I held space for seventy people, but because I witnessed something profound:
When you give business leaders permission to be real, they rise to meet it with incredible heart.
While I had the outline of my group talks planned, I gave myself space before each talk to open my heart and see what wanted to spring forth. What surprised me was my desire to share parts of my story that had seemingly little to do with business.
So I stood up in front of our group of 70 hard-charging achievers and shared the dark night of my soul when I broke a longstanding internal pattern.
I battled a mysterious illness from 2022-2024 that kicked off with a breakup (I got dumped), moving out of my dream home, and a COVID booster shot. What started with pre-flu like symptoms turned into one of the biggest horrors in my life.
I was at a phase where I couldn’t walk my dog, sit upright, or lie down without having heart palpitations. I had spent thousands of dollars on doctors who had no idea what was happening to my body. And I lived alone on an island where I didn’t yet have community or family.
In a moment of complete and wretched helplessness and fear, the answer emerged. I stared at my phone for 20 minutes, debating whether or not I should respond to the urge.
Eventually, I gave in. I called my best friend, Jess.
I said, “I don’t know what to ask for, but I need help.”
It still make me nauseous to think back to that moment. To remember the pain, fear, and utter vulnerability.
It was also the moment that I turned around the mindset that I have to do this life thing on my own. I challenged the CEO mindset that you can’t ask for help unless you are specific.
Over the following 8 weeks, Jess helped me find 6 people to stay at my house, cook for me, clean my spot, and drive me to doctors. I made half of my recovery gains in that window.
I was a little breathless sharing that story with 70 people in-person. Was it relevant to a business gathering? Was it a little too real?
Slowly but surely, I had several participants come up to me afterwards. They shared similar stories where illness followed crisis. One person in particular said they had the same mystery illness for 2 years that followed after a hugely stressful experience that blew out their nervous system.
This outpouring of warmth and camaraderie made me feel less lonely in my own pain. It built a kind of bridge of connection from their heart to my own.
This is the best way I can describe the magic of Outcove. It was a weekend of exposing internal surface area that we don’t normally share with others. Then seeing our fears met and held.
We had confidentiality rules and gave guidance during specific exercises NOT to try to fix or solve someone else’s problems. Instead we took a high achiever group and told them to give space for complete expression and witnessing.
In that magical space, where you aren’t rushed to a solution by a listener who is used to looking at a checklist of problems, healing occurs.
Because groups hold a secret power: to hold the energy and trauma that you as an individual struggle to carry.
Multiple people told me the first 24-48 hours they were feeling sick, old pains in their neck were flaring up, or they just felt physical discomfort. By 48-72 hours in, most of these people finally landed in their nervous systems. They went from the speedy energy of LA, SF, NY, etc. to the rooted, slower energy of Hawai’i.
In a group container, people feel physical manifestations of stress because their nervous systems are scanning and adjusting. But the autonomic nervous system is constantly tuning in - and even synchronizing - with others in more subtle ways. Through nonverbal cues, breathing rates, and micro expressions.
So when the group has enough stability and slows down, we as a herd slow down together. This might explain why group energies (good or bad) are “contagious.”
When people slow down, clarity emerges.
I noticed a trend of participants having mini epiphanies. Quiet realizations about their businesses or lives that didn’t have the space before to emerge. It took the slowing down and safety of a large, compassionate group of people to let their intuition unfold.
1:1 group work is powerful, no doubt. But to be in the safety of a gathering of people going through similar crap to you (selling their company, divorce, breakups, and everything in between), there’s a healing to that. You aren’t broken or alone. You’re simply living the human experience.
I read somewhere that social wounds are best healed socially. That means if we had pain inflicted on us by others, it’s difficult to heal that on our own. It’s way more powerful if we can find a safe “other” to support us through that journey.
As Ram Dass explains, “We’re all just walking each other home.”
On the journey of building companies and leading with impact, we stumble and stress out and make mistakes. It’s part of the journey of living courageously and authentically. To work and live differently.
In our independent culture, we operate in vacuums of support. Outcove is a chance to invite other like-minded, kind, self-aware people into your inner circle for a few days and feel the difference. What does it feel like in your nervous system to know others share your experience? What’s it like to feel inspiration by someone living their truth deeply?
As media outlets plaster our fellow humans with labels of otherness, events and communities like Outcove give us a chance to drop the mask and see the human in front of us. To engage not just from the intellectual but to meet someone at an emotional and nervous system level. To deeply plug in with others and the land to find nourishment.
I challenge the idea that we’re all so different from one another. In my experience of human hearts and souls, we are more similar than we are different. We simply need reminders so we don’t drift away from our human family.
Who needs these reminders more than the entrepreneurs and visionaries guiding our economy? The ones who lock themselves away from human connection to power the tools and services we use daily. These are the ones who will shape AI, medicine, therapy, and even wars to come.
The private sector holds a lot of power, but if the leaders are devoid of human connection, we are at deep risk of losing our inner compass. If all we have guiding us is the attainment of wealth and status, we will surely guide our next seven generations wrong.
As for me, this doesn’t change a lot of my day-to-day. I still happily coach business leaders 1:1. I still answer emails and write blog posts.
But underneath, I feel the gentle hum of a call: to build unforgettable experiences of human connection that elevate consciousness. If you’d like to play with me in that realm or join a future event like this one, please let me know.
So sad I missed this! Could not agree more on all of it. Much love to you 🫶