I’ve mentioned Overlap several times in this blog over the last five years, and I’ve always meant to do a more in-depth post about it, and it’s finally time to do that. The occasion of this post is that I attended my fifth Overlap retreat over Memorial Day weekend, and not only did I attend, I helped to organize it. It went exceedingly well, and I wanted to share some reflections on Overlap, and why it’s so important to me.

So what is Overlap?

Overlap started about ten years ago as a retreat organized by a bunch of Toronto designers to explore the overlap between design and business. They went off into the woods for a weekend, and had deep and meaningful conversations. At the end of the retreat, Michael Dila stood up and said “This was awesome, and needs to happen again. I will organize next year’s Overlap event!” And so he did. And then the next year, somebody else volunteered to organize it, and on it went, with new people volunteering each year to organize the next year’s event. For each retreat, the organizers invite around 50 people to escape into the woods and have deep conversations about design, community, life and impact. Typically, organizers aim for half of the attendees to be returning Overlappers and half to be people new to the Overlap community, generally recommended by somebody already in the community. There is also an associated mailing list where you can get a flavor of the group.

So what makes people Overlappers?

This is such a hard question to answer that it has become a joke in the Overlap community. At one point, an Overlapper invited his friends out for a happy hour in New York. His other friends asked “How do you know X?” and several people said “Overlap” and they asked “What is Overlap?” and each of the Overlappers gave a different answer. Each Overlapper’s experience is different and what they value about the community is different, and yet there’s some core quality that brings us together.

I like to describe Overlap as a community of misfits. We’re the people that don’t stay on the path laid out by others. We go exploring off-road to see and inhabit the in between places. We investigate the overlap between fields, rather than sticking to one field. Somebody commented at this year’s Overlap that none of us can describe what we do to our parents, because we combine different disciplines in our jobs or interests, as no single career path can contain us. Several times, I have met somebody for coffee or a drink, and 30 minutes after meeting them, I say “You should join Overlap!” because they say things like how nobody understands what they do, and they feel constrained by societal expectations, or whatever. And they often have a great time when they attend a retreat.

I first heard about Overlap through a friend, who had heard about it from her friend who attended the 2012 Overlap retreat. My friend joined the mailing list, lurked for a few weeks and said, based on the discussions, “These are totally not my people, but Eric, they are totally your people! You should meet them!” So I joined the mailing list. A couple weeks later, somebody posted to the list that they were attending a convention in San Jose and any Overlappers in the area should join them for dinner. So I went, met them and a couple other Overlappers, and had a lovely dinner and conversation with them, and they encouraged me to attend the 2013 retreat. And I did, and met some new people who became instant friends as part of an amazing experience, and came away feeling like I belonged with this group. I’ve been to the Overlap retreat each year since, and volunteered to co-organize this year’s retreat as a way to give back to this community that means so much to me. In fact, I attended last year’s retreat in a neck brace with my neck still being broken because it was so important to me to not miss my favorite weekend of the year.

So why is it so important to me to have this community in my life?

One theme I explored at this year’s retreat was the human need for belonging. According to Maslow’s hierarchy, belonging comes after physiological (food, shelter) and safety needs, but is next most important after those sets of needs. And those of us who pursue the generalist lifestyle where we don’t conform to the paths laid out by society often don’t feel like we belong; we struggle to answer the commonplace question “So what do you do?”. So having a community of other misfits who understand the challenges we face and know how it feels is amazing. Others in the community understand us, and encourage and challenge us to pursue our own path.

In fact, my current coaching focus is a direct result of 2016’s Overlap retreat. A few of us had gone for a hike together and were sitting by a river chatting about our lives. I mentioned that I was somewhat frustrated with my job because I felt like they were measuring me on the wrong things, and my new friend asked: “So what are the right things? How do you want to be measured?” This was an obvious question, and yet it blew my mind, so I spent a few weeks after Overlap pondering how I wanted to measure my life. My new friend became my accountability partner after Overlap, and after a few phone calls, I decided that I wanted to help people one-on-one to have more impact, and that’s when I increased my coaching and mentoring efforts last summer. Since those efforts continued to feel meaningful as I spent more time on them, I decided to take the next step of entering a training and certification program with New Ventures West. So a whole new direction in my life was spawned out of a single conversation at last year’s Overlap.

And my experience is not unique – many people have made big changes to their lives after attending an Overlap retreat. People expand their sense of what’s possible when surrounded by curious, compassionate, and supportive people. And when people share their deep vulnerable selves at Overlap, we also learn that we are not the only ones facing struggles or challenges, and that gives us the strength to continue forward. A large part of the need for belonging is feeling that we are not alone, and the Overlap community provides that.

Overlap has become a big part of my life over the past five years, and I decided it was time to finally write about it on the blog. Contact me if you’re interested in learning more, or check out the Overlap site created by last year’s organizers and updated by one of my co-organizers.

P.S. Themes of the last 5 Overlap retreats for those that are curious:

  • 2013: Make (including blacksmithing and pottery making)
  • 2014: Back to Basics (including survival shelter building and white water rafting)
  • 2015: Play with Purpose (including slip’n’slide, zip line, and mini golf)
  • 2016: In Service (including how we can serve each other as accountability partners)
  • 2017: Generations (how do we think about and instigate long-term change?)

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