In the holiday season of 2003 Joell and I started a journey together.
From our second or third date in 2001, we were hardly apart, but for our various jobs. Joell was teaching riding and doing sales for equestrian products. I was doing tech sales and failing at my new consulting business.
I found plenty of meaning in my work in tech, where our products were used by brilliant people doing extraordinary things. I’m fascinated by technology, and the big hook for me is giving people tools that enable important work that changes lives and society. I had that meaning in work, especially at Sage/Stride and Silicon Graphics, and I wanted more.
On Christmas Day 2003, Joell and I decided we would both commit full-time to build this thing we created called Square Peg Foundation. Friends thought we were crazy, though several provided invaluable counsel and support. We were energized and headed down this new path, together.
In the early years, I managed the office and went out to help with the barn a couple days a week. For both of us it was commonly a seven day week. 
We knew what we didn’t want to be – a program where families came for 60 minutes, rode the horses and left. We wanted to build a true community – where the shared work of caring for the horses who needed a second chance was empowering for everyone. We wanted to give struggling families the confidence and the support to do extraordinary things.
We learned every day about the running of a non profit, but there were so many things we didn’t know. We knew we were committed to being fiscally transparent and true to our mission. We pressed on and kept learning.
Every evening, Joell would bring home stories from the barn. Our long conversations connected me to the Square Peg work, to the families and the horses. As we dreamed, we were making a significant difference. Parents raved about how their kids grew in confidence and how the experience was carrying over into their lives outside the ranch.
This time was hard for me. Mostly I worked alone isolated in our little house in the woods. For Joell it was a sanctuary, but for me started to feel like a prison.
At the end of the day, Joell would bring home those barn stories. We talked about the new kid’s first break-through on horseback, saying new words and stringing together phrases. I listened to her heartbreaking stories of parents who time and again would tearfully told her that this was the one place where they could take their child and not worry that he would be judged and rejected. We discussed the meaning of self. We saw the difference that modeling compassion and cultivating joy could make. The keystone was the importance of how kids see themselves, how they see the world, and how they see themselves in the world.
I was Joell’s sounding-board and trusted support, and she brought to me the heart of the work, and together we refined
our principles of Square Pegs, our practices, and the way we communicated what we do and who we are.
Those difficult years were a crucible for us. We came out of it clear about what Square Pegs is, and what it is not. Rather than our troubles driving Joell and I apart, our relationship deepened.
Ten crazy years later, we moved to our current location. Joell developed her dream team, and now that we live here at the ranch I’m involved again in the daily programs, meeting with parents and donors and planning new projects, and loving it.
Today I see myself differently from 15 years ago, or even five. My work is more focused and I understand more clearly my own motivations and contributions. I’ve regained my curiosity. I’m diving deep into technical topics, running my own servers and learning Python and Swift. I am working with great clients, and on writing projects that I love — I’m writing a book, and already thinking hard about the next one. I read voraciously, and I’m thinking deeply about meaning, compassion and learning and how they connect through Square Pegs and technology and business. I’m learning to surf and I’m healthier than I have been in years.
All this is a direct result of this complex and trying journey of building Square Peg Foundation together. More than ever, I have a clarity about myself. How I see myself in the world has grown, developed and I see exciting and endless possibilities on my path.
What we’d dreamed on Christmas day 2003 that Square Peg Ranch does for the kids, it has done for me.
