Invoke fun at work
Issue 93: Fun and play leads to sustainable creativity
“Productivity” is a term thrown around at the workplace frequently. It makes sense as the company’s purpose is to deliver value to customers. In theory, the more productivity can increase, the more value is delivered. However, machines and systems are productive, not humans. If the designer is engaged, effective, and energetic, the outcome will lead to productive systems.
Christine was a designer on my team at One Medical. On every team, there is someone who is the heart and exudes culture—she was one of them. Though there are loads of wonderful attributes I can express about Christine, "fun" is the one coming to mind. Fun is not a nice to have, it’s a requirement for in the workplace, particularly for designers and builders.
"We need to make this more fun!", Christine would say in our 1:1s. My philosophy about work is to take your work seriously but not yourself. Design, creativity, and building are not linear production lines and requires multiple require multiple facets of your mind and skill. When you are too constrained with a certain approach, it stunts creativity and can lead to burnout.
Kyle, one of the most tenured designers at Webflow, conducts weekly cool-downs. In the last one, he created an image of Webflow imagined in the 80s/90s style of Microsoft Paint.


Like Christine, Kyle is the heart of our team—encouraging others to have fun. The mind is elastic like muscles. You need to stretch, warm-up, cool down, and tend to it in order to do your best work. If not, injury and burnout can occur—one you might not recover from.
Having fun builds better teams
Combining making and fun are ways to build strong bonds with your teammates. The more you know someone as a human being, the better collaboration model you'll have when you're doing work. This is why NFL quarterbacks fly their entire offensive unit during the offseason to some exotic location to practice. A huge part is bonding and getting to know each other. You start understanding the habits of designers. In a drawing session, do they sit and noodle on the idea before starting? Do they YOLO it and start drawing a bunch of ideas? This helps you get a sense of habits. Exploring different methods of making together helps you express and learn different angles from your teammates. Though the Zoom icebreaker adds value, it can only go so far. Let's look at some ways to invoke fun.
Invoking fun
What are some ways to invoke fun at the workplace while focusing on the mission at hand? Let's look at a few ideas from original ones I've tried and inspired by others.
Fun onboarding by (Christine Chang)
When I was on our Product Leadership team at One Medical, an initiative I was responsible for was new hire onboarding. I assembled a working group, and to no surprise, Christine was on it. "Let's make it fun!" I said to Christine, and she ran with it. What resulted was building out an experience where new hires would tour a clinic in their first 30 days, swag and goodies, and a balloon for their first week in the office. You might think a balloon might be a minor deal, but the small gesture created a Bat-Signal for people to come by and say hello.
This proved exceptionally helpful for people who may be shyer and weren't comfortable introducing themselves and invoked tenured team members to say hello.
Library hours by (Tony Dihmes)
Tony is a Sr. Product Designer at One Medical and leads library hours, a time for designers to come and foster focus time together. Like every designer ever, Dihmes would spin some lo-fi beats and facilitates time for people to put their phones away and do some deep work. Dihme’s library hours remind me of when Kimber Lockhart, my manager at the time at One Medical, would host writing workshops. Kimber would host sessions with people on the Technology team to spend an hour writing. Whether it was a blog post about a UI framework or someone’s novel, we could write anything and share. It meant a lot to see a leader at that level make time for creative work as a way to recharge. Kimber is the most influential manager I’ve had when it comes to encouraging my writing, and I’d probably not have this newsletter if it wasn’t for the space she carved out for us.
Figma jam sessions (Kyle Lambert)
Kyle and co. facilitate Figma jam sessions on Fridays at Webflow. It's a safe space for people on the team to gather and work on ideas together—low stakes without stakeholders. It’s a routine time where people can expect mandatory fun and is built out in our schedule.
Sketchbook swaps
One of the great things about One Medical's culture was these types of ideas were encouraged as long as it was inclusive to everyone. I invited a small group, set a budget for people to buy their favorite sketchbook and pen, and we'd do a swap. It was interesting to learn from each person what made their favorite sketchbook and encouraged each other to try different methods.
Meme your roadmap and milestones
In the previous issue, I wrote about metaphors and allegories. I should have added memes as well. When taking a break from heaps of meetings, I like making memes about our roadmap or product strategy. Though I’d love to share some of the Webflow ones I’ve made, it’ll give away our roadmap. Here’s how you can see them earlier.
At One Medical, I made this relevant meme in the spring of 2017 about FHIR, a healthcare interoperability protocol across Electronic Health Records combined with the disastrous Fyre Festival. I created this to root on the data interoperability team. A quick break in the day to have some fun can give teams a break to laugh and celebrate.
Foster fun, make it a habit and ritual
It's hard to find time to create fun activities and attend them all. Foster an environment where fun can happen and be shaped by your team. When I see people like Kyle, Christine, and Tony create an environment of fun and care, that's leadership. A one-week vacation is not going to fix burnout. It requires behavior change to build in breaks, and give people a chance to loosen up and have some fun. Hope you have a fun week at work!
Tweet of the week
The Webflow community never ceases to amaze me. #Flowchella was a hit and didn’t need Harry Styles.


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