A Bo(u)lder offsite
Notes on planning a unique company offsite in Boulder, Colorado
Spelling bees. Chautauquas. Trail mail. Morning pages. Friendship bracelets. A lot of work time. An elaborate, extended climbing metaphor. BEARS.
At Medium, we are fully remote, but we have in-person weeklong offsites twice a year. This balance works for us. It’s an in-person anchor to our days of Zoom rooms and async collaboration.
Our last offsite was in Boulder, Colorado and it was great.
We believe in human connection; we do not believe in gatekeeping our offsite planning! We’ve written about our offsites in the past (see: A tale of two offsites, 2024; Scenes from a work retreat). This was one of my favorite offsites that we’ve ever had (our ninth!), so I wanted to share a little window into how we planned it and what we did.
Ops folks, offsite planners, remote companies: feel free to steal this and make it your own :)
The location: The Colorado Chautauqua in Boulder, CO
Our home base for the week was the Colorado Chautauqua, in the foothills of the Flatirons in Boulder, CO. We love picking places with a cool history and an alignment to our mission. Brik Olson suggested this location, and it happened to be one of our teammate’s favorite places in the world, too. Win-win. (A side note, we love picking offsite locations that are also someone’s hometown on the team.)
The Chautauqua movement created gathering places for “rather earnest, but high-minded, activities that aimed at intellectual and moral self-improvement and civic involvement.” It was designed to make information and education more accessible for everyone. Just like Medium! The meeting space we had for the week was gorgeous, plus we had a few cabins we could use for breakout sessions and house parties*. The staff were super helpful and folks enjoyed being in nature, but just a 20-minute walk from downtown Boulder. Folks took ad-hoc nature walks and hikes throughout the week on the nearby trails.
Travel logistics: The travel from Denver airport was easy. We encouraged people to take the shuttle or take Ubers/Lyfts together, and coordinated rides out via a sign-up sheet.
One potential flag: the wifi was a bit spotty, even with a dedicated network that the property set up for our group. This was not a big deal for us because we often orient offsites towards in-person convos and physical media (stickies, big pieces of paper) rather than screens, but if you’re doing a lot of work that requires a strong wifi connection, or hosting a hackathon or something, be warned!
*late night arts and craft sessions. “rather earnest”, you say…
Swag and vibe: Outdoorsy, summer camp
The summer camp, adventure-outdoors vibe was the main vibe we leaned into. A few ways this showed up:
- Hand-painted signs
- Beautiful stickers from Medium writer Sophie Lucido Johnson
- A “trail mail” table with a little bag for everyone (labeled with polaroids we took at the offsite, a nice keepsake in itself) and folks could drop notes, crafts, and letters to each other throughout the week
- An arts and crafts night with friendship bracelets, painted rocks, and more
- Tie-dye of our new TK t-shirts
- An (optional) company-wide hike
- A DIY granola bar with “granola notes” (we use granola.ai for notes a lot, this is a silly joke)
Our previous offsite leaned heavily into AI fluency as our focus concept and learning objective, so I think the focus on physical, hands-on, human-made art was a welcome contrast. Every night, people ended up back at the arts and craft table.
If you’re into company-branded swag, this is your time to get backpacks. I ordered some embroidered ones as a last-minute team gift for our Ops team, which started a cascade of other team orders. We worked with BDub Branding in Boulder and they were awesome. They even met up with us on their day off to give us our backpacks!
The work arc of the week: Rock climbing
At our offsites, nothing else matters if the work part feels bad. These are, after all, work days, and we get a lot of work done. We learned early in our offsite planning that the way people bond at Medium is often through the work they’re doing together. This is, I think, because people at Medium really care about the work they do. It is a privilege to work at a place where people care. At other companies, more retreat-style offsites are a better fit, but we… like talking about work. (Ah, there’s the “rather earnest”, again.)
So, we put a lot of thought into how to spend that work time. Sometimes it’s simple and we want to spend as much time as possible in project teams; sometimes we have an idea or strategy question to understand together as a company, or a shared goal to orient around.
This time, our overall theme was around thinking more boldly (er, bo(u)ldly) about Medium’s place in the world and our ambitions as a company.
The week before the offsite, I pitched a rock climbing metaphor, based on the outline of what we’d already planned to do with teams. I’ve climbed on and off for a couple of years and was giddy with excitement once this clicked into place. Like all big metaphors about sports-y stuff, it ran the risk of being cheesy or forced, but I think it really worked, in large part because we asked some of our team members who are climbers to introduce the concepts themselves.
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Without giving too much away work-wise, here are my quick notes on the climbing terms and themes we used:
- Day 1: Work the problem (Climbing 101). Intro concepts: bouldering vs. climbing. Climbing is the one where you climb up with a rope and bouldering is when you climb a big rock without ropes. In bouldering, they don’t call it a bouldering route, they call it a problem. You figure it out by trying. Try a sequence, fall, try again. That's this whole day's point: explore by attempting, not just talking.
- Day 2: Share the beta (Climbing 201). “Share the beta” means give another climber advice or tips on the climb they’re working on. Social habit of climbing. Origin story: Texas climber Jack Mileski, 1970s, would use a Betamax video recorder to film himself and his friends navigating tough climbing routes. He would then share these tapes with other climbers. “Beta spraying” is when someone tells you how to do the climb, without being asked. It is unsolicited advice. Not cool.
- Day 3: Send It (Climbing 301). Explain two types of climbing: sport climbing and trad (traditional) climbing (explain difference). In trad climbing, you have to trust your own intuition and judgment to make a new path. You have to follow your gut. And then: Send it. Climbing’s term for finally completing a route, a shout of celebration and encouragement.
Those are my rough notes; my coworkers made it way better. They demoed with actual climbing gear; a call-and-response “send it!” chant occurred. I think this metaphor has a lot of different ways you could take it! For other terms and ideas, REI has a good glossary.
We love: Reading and writing!
When you plan an offsite, I think it’s important to use it as a way to emphasize your shared values as a company. For us, that is reading and writing. Here are some fun ways we wove that through the week:
- “WE <3 WRITING” and “WE <3 READING” banners in the main area
- Shared time writing morning pages for 15 minutes together every morning, with optional writing prompts around the themes of fear, hope, and belief (again, we asked teammates to lead those prompts and make them our own, which led to a much more meaningful result)
- A Medium Imagination Library, sponsored by the Women’s ERG (employee resource group), with enough books for everyone to take one home from the Staff Picks library and a book swap. (Thanks Boulder Bookstore for your help!)
- An after-dinner spelling bee, which our VP of Content won because he is the only person who knew how to spell rigmarole, though later we learned that the way I spelled it is also technically correct and so I think he does not deserve this title
- Pencils and notebooks as swag items. This included left-handed Field Notes notebooks for lefties. As a left-hander myself, I felt very included by this <3
Miscellaneous other unique things from the week
- Meet a New Median IRL (our new-hire intro from all-hands, done live)
- Early-morning trips to a coworker’s favorite coffeeshop
- A new offsite pin
- Peer learning sessions
- A vote to rename our company all-hands meeting
- Many bear sightings
- Team-specific fun time, a block where teams could do what they wanted together for fun
- A lot of snacks
- Porch hangs (everyone stayed in cute cabins and some of them had great porches!)
- ERG meet-ups during mealtimes
- A birthday celebration every day somehow
- Thursday night karaoke
- Late-night werewolf games
- Chautauqua performances by David Lee Roth, Benjamin Franklin, and Divine
Why we do offsites
Offsites are weird, magical little work worlds. They’re a big part of how we help make working remotely feel more humans-first.
Planning them is a group effort, a co-ownership, a collaboration — not just with our ops team and leadership team, but with everyone at the company. By the end of the offsite, more than half of the company will have helped plan, lead, or facilitate a piece of the week.
They’re also fun, and we think work should be fun.
If you’re reading this for the purpose of planning your own offsite and have questions about this one, reply in the comments! I would be so happy to share details and trade ideas.
