A Reclaim Trip to San Diego

About once a year we try to get the Reclaim team together in person to work alongside each other, brainstorm for the future, and spend some time together in a new city. In years past we have visited Portland, New York and Nashville, not including the trips for other workshops, conferences, and events. Every time we get together in person I always come away feeling really refreshed and motivated to work with such an awesome group of individuals. In Portland we came up with the idea to host our first conference, Domains17, and in New York we started thinking quite seriously about Cloudron, which ultimately put us on a path towards Reclaim Cloud. I think after the New York trip we really began to understand the value of making time for the Reclaim team to hang out in person without any other responsibilities. We also went through a lot of transition and growth– our team expanded, we traveled more for other conferences and workshops, and then later hosted Domains19. By the time we were ready for another team trip, COVID was in full effect, and like most, we turned inwards to recalibrate and focus on perfecting our virtual events. We co-hosted OERxDomains21, an event that I still look back on with so much pride and excitement, and then a virtual DoOO workshop later that year (which I’m realizing I never formally blogged about). When we felt comfortable enough to be in person again, our team had more than doubled and the Nashville trip required a bit more planning to make the most of our time. Out of that trip came the foundations for Reclaim EdTech year 1, Reclaim Roundup, a tiered way of thinking about Domains, failover in Reclaim Cloud, and adjustments to internal team processes.

We used the goals set in Nashville as a cornerstone throughout 2022 to keep our work intentional and focused. Now with the year behind us, I’m so proud of all we were able to accomplish. We exceeded those goals and worked on setting healthy habits for learning & collaboration more so than ever before. Given our team has continued to grow and we were ready to start 2023 with a fresh plan, it was high time to meet again.

Touching down in San Diego

view from my hotel window

Though far from home, San Diego was a great city for a team trip. We stayed at the Moxy Hotel in the Gaslamp Quarter, ate a ton of great food, and had seemingly endless options for things to do in our free time. That Thursday night we grabbed a quick bite to eat at Prince Street Pizza after everyone made it into town and then prepped for a full day of working/brainstorming in person.

hotel lobby where we met up before exploring san diego – board games everywhere.
So many cool details in the hotel, but I think the room numbers were a favorite


brainstorming ideas for the day

Like in Nashville, Friday in San Diego was definitely the highlight for me. We rented out this working space and it turned out to be a pretty great experience. I really enjoyed having the opportunity to just think with the team for a while, especially since our daily work can be rather busy. Also like Nashville, I kicked off the morning with some icebreakers to ease folks into conversation. I tend to roll my eyes at the idea of forced fun and usually steer away from anything too cheesy, but there’s definitely value in having a bit of structure first thing, warming up and learning a little bit more about each other, and then slowly transitioning into aligned ideas for the day. Here are the starter questions I used, in order:

  1. What do your family and friends think you do all day?
  2. Would you rather stop watching movies or stop listening to music?
  3. What is something you are great at cooking?
  4. What is your go-to TV show at the moment?
  5. What is 1 non-work related goal that you hope to achieve in the next 5 years?
  6. What are 3 words you hope a customer would use to describe Reclaim?
  7. Where/When is Reclaim Hosting the expert? Similarly, when/where is Reclaim Hosting not the expert?

The first 5 questions took our group about ~30 min to get through, and we spent the remainder of that hour tackling the last 2 questions. We wrote answers down on a whiteboard– a visual during trips that is becoming increasingly helpful for us. Even before jumping into all the various topics that could have been discussed, I wanted folks to remember the why we do what we do, and the who we do it for.

For question #6, we saw words like empathetic, trustworthy, collaborative, responsive, innovative, welcoming, and helpful. In coming up with this initial list, I thought it was interesting that words like speedy or fast didn’t come up, yet they’re extremely important to us. The team agreed that being timely was the natural result of acting with empathy and respect when working with customers, and the trip was already worth it for me at that point. This is something that I want to hold close and reinforce often for our team and anyone else that we hope to hire in the future.

Tim, Goutam, and I – photo by Tom Woodward

One of the other things that became abundantly clear on this day, besides the sheer amount awesome work happening, is the fact that it’s not really possible for us to break out into strict teams for brainstorming. This is certainly a change from where we were in Nashville, and one that I think is indicative of the intentional habits we set last year to encourage collaboration around the work that we do. This doesn’t mean that internal Reclaim teams don’t exist, but each person has their foot in projects that impact some or all teams. To say, “ok Support, Infrastructure, Sales, and EdTech folks– split out and talk about what’s working/not working in your team,” is simply not possible, or at the very least, not helpful. For example, Infrastructure and EdTech folks are regularly assisting in Support, and Support is heavily mixed in with Infrastructure and Sales. EdTech and Sales work in close collaboration, and they both have a hand in the work that’s pushed to Infrastructure.

The cross-collaboration that’s happening at Reclaim gives everyone a voice for new ideas and handling challenges. This past January 2023 was also our largest month for internal professional development with at least 1-2 sessions scheduled each week. That kind of open, regular learning is something that we had dreamed about for our team only a few short years ago. Instilling healthy working practices (something I spent most of the summer thinking about) can take time to introduce, and even more time for habits to form. It has been so amazing to see this gradual transition over the last year, and even cooler to have that culminate on Friday.

One of the things I want to be mindful about as we kick off a new year is that we don’t let this collaboration work against us. For example, in order to make decisions or progress forward, does someone have to wait for approval from all teams? Ingrained collaboration means that no particular person or team is siloed or left to own work without the support of their peers. But we still want to make sure that someone is owning and pushing the work forward, and that things aren’t slowing down because of processes we’ve put in place. I suppose this is a symptom of growing pains more than anything, but I think being aware of those dangers will be important.

We’re missing Gordon, but cool to have almost everyone in one picture! Thanks Tom Woodward for capturing this.

Last thing I’ll say about Friday– there was SO many things to chat about! A larger group = more work happening = more to discuss. There was definitely too much to cover for one single working day, which may be a sign that we need an extended trip in future years (two working days?) or that maybe there’s a need for more regular planning conversations like this throughout the year. We have also refreshed how we are handling meetings in 2023 – something for a future post – and perhaps that will play a role in what’s needed for next year’s trip. We shall see!

After some downtime at the hotel, we ended the evening with dinner & games at Punch Bowl Social. I don’t have many pictures from this evening, but it was fun to grab a bite to eat while we were waiting our turn for some bowling lanes to open up. After bowling, some folks even stayed around karaoke. I really recommend this space if you’re looking for a little something for everyone!


The next morning, we met for breakfast at Fig Tree Cafe (delicious by the way) and then headed to the San Diego Zoo! This was the biggest zoo that I’ve visited, and I’ll admit that I may have gotten a little too excited about the koalas and giraffes. :) I thought the layout of the zoo was really well thought out, and it allowed our team to leisurely walk through different exhibits & stop for food breaks along the way. I’ll spare you the shaky animal photos I took and instead share some photos that Tom captured:

reclaim team at the zoo – photo link
Goutam, Meredith, Taylor, Amanda, and Noah scoping out a game plan – photo link
taking a quick break with the OG reclaimers – photo link
killing time before axe throwing

About halfway through the day some people wanted to split and go check out the Comic-Con Museum while the rest continued on with the full zoo experience. I don’t think anyone planned on being at the zoo (or even in this part of San Diego) all day, but it worked out! There was great weather, a lot of walking around, and a lot of down time to hang out.

After making it back to the hotel for a little break, we met for dinner at La Puerta. I think this might’ve been my favorite meal of the whole weekend… the food and drinks were amazing.

From there we said goodbye to the early morning travelers and then walked over to a place called Throw It! for some good ole fashioned axe throwing. LOL. It also just so happened that there was a line of arcade games right when you walk in the door, so I have to think that everyone felt right at home!

Overall, I’m feeling really thankful that I was able to attend this trip, and equally thankful that I get to work with such a creative, impressive team. Looking forward to all the projects and ideas that came from this weekend, and already can’t wait for the next trip!

One comment

  1. This is freaking awesome, and these photos are so awesome. San Diego was too quick because it was so awesome, this is a great write-up and really appreciate you capturing the magic. So much of what worked about San Diego was your doing, so major kudos for another amazing Reclaim event.

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