Can work and play really coexist?

At With, we have a culture where play is encouraged, sometimes as a means of inspiration and co-creation, or not even a means to an end, but rather a process to embrace for its own sake. 

Sometimes, we organize playtime or playdates as a way of being curious, experimental, or creative. It’s not viewed as a distraction or something that takes away from our work, but something that contributes to the success of our work. 

So far this year, play has looked like: our 2-day retreat at the Toronto Islands, remote-friendly play experiments like our digital zine-making activity, and even a creative team photoshoot during our retreat. 

While play is often reserved for one’s personal life, slivers of time carved out from daily responsibilities and workload, With has proven that play and productivity don’t need to clash - the two can go hand-in-hand. 

What play has looked like lately

Earlier this June, With had its 2-day annual team retreat: a time for us to get together to pause, take a moment to reflect on the growth of the studio, celebrate milestones, and look forward to what’s to come. 

We spent one day on the Toronto Islands, biking across the island together, spending time in nature while chatting about the growth of the studio. We swapped desks for a park bench, and replaced slide decks with sticky notes. It felt more like an afternoon hangout, rather than a growth meeting with an agenda. 

On the first day, I set up an unstructured art activity for everyone on the team to sit down and contribute to, in between our schedule for the day. The purpose was to draw or create anything without a theme, an end goal, or a specific vision in mind, rather to show up as our whole selves and put pen to paper. Since there was no pressure to create anything specific or showcase our art skills in any way, the process of playing was relaxing, low pressure, and accessible for all. We played freely, without the comparison or competition that can often creep into group activities. We set up craft paper in the backyard of our co-working space, laid out our mixed media supplies, and just played. The result was colorful, full of whimsy and character. It felt freeing to escape the shackles of 21st-century technologies and opt for the beautiful, childlike simplicity of crayons, markers, and paper.

For our second afternoon of play, we kept the momentum going with a photoshoot that Josiah, one of our Design Directors, facilitated. In true With spirit, we paired up and took each other’s headshots, whether we were experienced photographers or complete beginners. We set up and played around with lighting, angles, and video, making the typically intimidating and nerve-wracking process of “getting a headshot done” into a unique experience. Folks who had never taken portraits before were encouraged to try it, which fostered collaboration and play. 

Aside from the retreat, play has taken other forms too. A couple of months ago, I facilitated a remote digital zine-making workshop on FigJam, with a theme in mind called “one-day”. The purpose of that was to put together a digital zine featuring things we’d like to do one day. It was something new for the studio, but it ended up being an enjoyable way to bring play into our day.

Okay, but why does this matter?

Work doesn’t always have to be so serious; it’s also important to find time to play. 

When playtime is relaxed and unstructured, I’ve noticed it creates unexpected connections, conversations, and fosters moments of pure joy. Playing in a low-stakes activity allows us to let our guards down and be our true selves without thinking twice. Showing up authentically when playing helps build trust and safety within the team. If we can play together with our guards down, we can feel safe to take risks and collaborate authentically on work projects too. 

Play breaks down the hierarchy, so everyone shows up equally. Aside from that, over the last 2 years at the studio, finding time to play with my team has sparked creativity within myself and has also helped normalize creating without the fear of failing, which has carried into how I approach work. Work and play seem like antonyms, but this doesn’t have to be the case. In this era of productivity, vibe coding, and building fast to break things, it’s been super valuable to find moments to pause and play. 

For most tech companies, it’s build, build, build. Break, break, break. Ship, ship, ship. A robotic pace to keep up with hustle culture. 

We do not subscribe to the same beliefs at With. We remember that we, as designers, are organic human beings full of creativity, craving joy and connection, so we do not neglect that side of ourselves.

Play inspires creativity and connection within our team, which helps us deliver the best outcomes and build better futures with our partners.