I stopped running CocoaLove after 3 years because the stress of executing a professional ~125 attendee conference is massive. Before I started I didn't realize how much the stress of being personally responsible for a $50k budget (when you're not out to make money, margins are kept thin. I broke even thankfully.) would affect me mentally during ticket sales. I loved planning it, and I loved seeing it all come together, but the process was quite taxing even with help.
The goal of CocoaLove was not to put on the "best technical conference" or something like that, but to bring the community together. Sure the talks were a highlight of the event, always wonderful and some of my favorite talks I've seen, but they were on topics that would help spark conversations between attendees. They were never technical / instructive in nature; the talks weren't the point per se. Lively conversations, with people not even once opening their laptop, was my metric for success at CocoaLove. Fortunately I was able to consider CocoaLove a success for 3 years straight.
Of course, I was sad to see it end. But turns out I just couldn't stay away from the idea of finding ways to bringing people together.
I started planning a new thing back in December, and it finally happened this weekend.
Fireside Cocoa: ⛷🏂 + 👩💻🔥👨💻
Simple premise: a long-weekend trip with a dozen people in the iOS / Mac community to ski / snowboard at Killington Vermont. Grab a private condo, provide transportation, and see what happens. It was largely an experiment to see how well something like this would work so I kept it small to start. My goal was to take the best parts of CocoaLove, the people and their interactions, and just do that. No speakers, no talks, no schedule. Not a conference, but a retreat.
Now that the event is over: I think this kind of event is my new jam. It was a blast and a huge success. I'm 99% sure I'm doing it again next year.
But, unlike a conference, I'm not sure about my path forward for next year. This event can't grow too much in size; keeping it under 20 people is likely ideal. I don't want public ticket sales per se, but I also don't want to keep this limited to just people I know.
But I've got a year to figure that out. In the mean time I'm glad I found a way to combine two of my passions: snowboarding and our community.