Over the past couple of weekends, I attended two conferences, one in Nashville and one in the suburbs of Chicago. One was legal. One was not. Both were small events with less than 200 attendees. And while they were both different substantively, they both had the same informal, sharing type feel where real conversations can and do happen.




The first conference was put on by the Summit on Law and Innovation (SoLi) sponsored by Vanderbilt Law School’s School of Law and Innovation. If you don’t know SoLi, it’s the brainchild of Cat Moon and Larry Bridgesmith. If you don’t know these two, go to Twitter and follow them (@InspiredCat; @LarryBridgesmith). They always offer excellent and insightful comments about the practice of law and innovation.


“It is impossible to live without failing at something unless you live so cautiously that you might as well not have lived at all — in which case, you fail by default.”- JK Rowling


According to the SoLi website, “the annual Summit on Law and innovation(SoLI) exists to bring together people passionate about innovating across the legal spectrum to #makelawbetter…SoLI is about creating a moment that will lead to a movement that (we hope) will ripple across legal practice, legal education, and legal technology”. Tells you all you need to know, actually.


The conference was Soli’s 3rd and the theme this year was a failure, vulnerability, and how to learn from it. Larry and Cat deemed it “FailureCamp” hoping to give the conference (or “unconference” as they called it), a distinctive, summer camp-like feeling: SoLi2019 was “designed to explore our human relationship with the fear of failure, the power of intelligent failure, its (necessary?) role in driving innovation across the legal industry, and more.”


The conference was divided into two sections: storytelling section which gave those of us who have suffered failure from time to time the opportunity to talk about our experiences and how we overcame setbacks. (In the interest of full disclosure, Cat invited me to come and tell my story of failure, probably because of my ability to fail greatly). The second part of the conference was described as an “unconference.” Members of the audience had the chance to pitch ideas for the group to discuss. The audience then voted on the topics they most wanted to discuss in small groups. People could attend any of the top 4 or five vote-getters for as long as they wanted.


The day was topped off with a distinctive Nashville feel: Cat invited her good friend, James Gurule, a songwriter and successful business executive to tell his story of failing and succeeding in the Nashville music industry and to sing some original songs. (Here’s a link to some of his music).


What did I learn at FailureCamp? I thought my story was unique since I radically changed directions in my career three times to overcome perceived failures. Wrong.

I learned that we all have stories of failure and success hidden away in our lives that can inspire and teach others.


I learned that we all have stories of failure and success hidden away in our lives that can inspire and teach others. That we all have the ability to tell our stories in meaningful ways whether we are in the legal field or not. That we can inspire and strengthen one another with these stories if we are willing to and have the right format to tell them. Thanks, Cat and Larry for providing that format.


And thanks to my fellow storytellers for being willing to share. We made each other laugh, cry, and think. As the late Coach Jimmy Valvano put it, “If you laugh, you think, and you cry, that’s a full day. That’s a heck of a day”.


The “unconference” section of the day was also impressive. It consisted of several relatively unstructured discussions about the top topics the audience selected from the pitches. For the most part, these discussions were insightful and productive. But because they were unstructured, there were people so impressed with themselves that they felt compelled to dominate the conversation. (Btw, the typical big talker was a middle-aged white man).


On the plus side, Cat and Larry provided a forum for continued discussion by establishing a Slack channel for just that purpose.  Hopefully, this outlet will give others more of an opportunity to express themselves. I don’t know if other conferences (oops, sorry, unconferences) have adopted Slack or similar tools to continue good, robust discussions afterward, but it sure seems like a great idea.




The second weekend conference I attended was MacStock in suburban Chicago. This two-day conference was created after the late, great MacWorld ended. It’s not designed to replace MacWorld but to be a relaxed place for Apple enthusiasts to come together and talk, exchange stories, and learn new things.


The conference advertised itself as a place to “hear community-leading experts share innovative new ways to accomplish tasks, save time, and express yourself creatively while getting the most from your Apple devices and apps…” The theme of this year’s show was creativity.


I try to attend a couple of conferences a year that have nothing to do with law, just to see what else is going on. Hence, I found myself among the eclectic crowd at MacStock.


Usually, at small conferences like this, I know at least a few people. (While it’s easy to lose yourself at a big conference and not appear disconnected, it’s a little harder to pull this off at a small one like this). But the only person I sort of knew going into MacStock was David Sparks. David is well known for his website, MacSparky and his Mac Power Users, Free Agents, and Automators podcasts. He’s also written several multimedia field guides for using Apple technology and apps which I would strongly recommend.


If you don’t know David or listen to his podcasts, you should. Besides being knowledgeable about Macs, Apple products, and their impact on the practice of law and how to do work efficiently, he’s one of the nicest people you ever want to meet. But David is a rock star at a conference like this, so I was on my own, and frankly, I feared being left alone in the land of young geeks who talk at levels so far above me that keeping quiet was the only realistic option.


However, MacStock was precisely the opposite. Yes, several young geeks talked in tongues I only vaguely understood. But there were also gracefully aging boomer ex-hippies. Businesspeople dressed in the “business casual” that says “I’m only doing this for the weekend then its back to my suit and tie:. And there were a good number of women and people of color who attended and spoke.


We all seemed to share a fondness for Apple-related products and a healthy respect for how Apple has and can make our lives-both working and otherwise-better. The event was low-key, engaging and social, much like its organizer Mike Potter.

As is usually the case with technology, no one-especially conference speakers– know everything about a particular technology. However, collectively–speakers and audience- we often do know most everything.


Most sessions turned out to be discussions more than lectures about how to use apps like Siri Shortcuts and Ulysses to create content. There were discussions on workflows and how to better create content and art. As is usually the case with technology, no one-especially conference speakers– know everything about a particular technology. However, collectively–speakers and audience- we often do know most everything. That’s the exciting thing I have found about tech and good tech conferences: if you want to learn and teach, have crowdsourced sessions so people can learn from each other. To the organizers’ credit, this was precisely the atmosphere I found at MacStock.


So, what did I learn from these two conferences? To have a good SmallCon, make sure people have plenty of chances to engage with one another. Let people tell stories. Encourage people to participate in the conference sessions actively. Have enough time for networking in a relaxed setting commensurate with the conference. At MacStock, the networking receptions (if you can call them that; they were more like meetups) was in a bar and conference room next to a Hampton. It was a perfect setting. At SoLl, it was at the conference facility as played songs he had written during his Nashville songwriting sojourn. Exactly the right tone.


Make people feel welcome and that you are glad they came at both conferences, a slew of volunteers went out of their way to meet attendees, answer questions, and introduce them to others. Have content that lends itself to discussion and crowdsourcing as opposed to lectures. Also, figure out a way to keep the conversations going after the conference is over.


Come prepared to offer something. To put yourself out there and be vulnerable. Meet people. Tell your story.


Going to a SmallCon? Come prepared to offer something. To put yourself out there and be vulnerable. Meet people. Tell your story. Be ready to listen and learn from everyone, not just the speakers. If some of the programming sounds a little touchy-feely, go with the flow. SmallCon is not a spectator sport-it’s a participation sport, at least if you want to learn something.


I’ve been to lots of conferences. I go to big ones because that’s where a lot of the people I need to see to offer relevant content are. But if you want to learn and meet people with whom you can have meaningful relationships, go to some good SmallCons along the way. You won’t be sorry.