The Importance of Play & Whimsy at Work

Children don’t solve for play or whimsy. It’s a natural state of being, and many experiences we have in our youth are linked to imagination in some way. When I was younger, to feel imaginative meant to change the world around me, and that immersion drove my definition, understanding, and interaction with the world as it was. I dare say the validation and invalidation of my imagination, over time, shaped the lens in which I view the world. In the workplace, I think we’ve lost our way. Play and whimsy have become deprioritized. That doesn’t diminish their importance, but it does dangerously shift our perspective.

I believe that play and whimsy are directly linked to both productivity and innovation. Together, they make up what I call the fun factor.

Whimsy, to me, is explorative: following ideas and sparks, investing in interests. Play is the breather: a walk, a puzzle, a break with coworkers.

Here I’ll share my struggle with the fun factor in an agent-driven world, and how I’ve attempted to solve for it.

Struggles

Here are a few of my struggles.

Attention

Attention is a currency that we budget and allocate throughout the day. When I’m a horrible steward of that budget, I end up with several active agent sessions open, and I’m constantly tabbing between them. Between reading briefs, specs, and any other wall of text that Claude throws at me, I realized that I don’t have the attention to engage and digest all of these artifacts without pause. When I don’t pause, I am quietly overwhelmed. That impacts my judgment and understanding of what’s in front of me.

Pressure

The industry and the shape of work we do are changing rapidly, and with that comes the push to do things faster and more efficiently. These days it feels like the space for such play and whimsy is difficult to maintain or allow for, but that doesn’t mean it isn’t important. I sense a pressure to conform, and a natural (stubborn) inclination to fight that.

Fatigue

The size of the problems feels larger, or at least the lens is more zoomed out now. My brain has to process more definition, faster, between agent sessions, and that’s exhausting. I can only do one at a time, and I need something to recharge me in between.

Alleviating the Pain of Struggle with Play & Experimentation

I’m solving for two things:

1. How we feel at work (the experience)
2. How we do the work itself (the function of that experience)

The experience

It takes a lot of mental resources to engage with macro-level problems repeatedly. Macro used to get broken down, so there was often a much clearer point to stop or take a break. Lately, I’ve found that to be more of a decision I make intentionally.

So when I start to feel the mental drain and degradation of clarity, I try to take a break and come back fresh. I feel myself recharging when I step away from the screen. I go on walks, do puzzles, and talk to my coworkers. Sometimes I read or meditate. Real brain breaks help. Clarity, patience, and energy are all replenished a bit, and I feel ready to get back into problem solving.

Taking breaks has always been meaningful, even before the agentic era. I believe it matters even more now, because it gives you space to breathe and reflect on these experiences of rapid work.

The function

Talking to coworkers is also where whimsy starts for me. Those conversations about problems, ideas, and ways of thinking about what we do drive and inspire me to try things out.

Recently, a coworker and I talked about where humans should exist in the development loop. We had a whiteboard session and drew out a vision for the development cycle, which inspired me to write in more detail what each phase entailed. It’s something I’ve been interested in outside of our project, and the conversation helped me better visualize that flow and what steps and tooling are needed to support it. I went and built that pipeline for our project, and now our team is using it and continuing to iterate on it.

I’ve made it a habit to log ideas and topics of interest and lightly define them. I find ideas and interests in moments like that whiteboard session, and they fill a backlog for me internally of how I can make the process of work better. I would also argue that whimsy exercises our creative muscles, whether or not any given spark pays off.

I’ve been looking at AI tooling as an opportunity to exercise whimsy in brief moments of dedicated attention, because that’s the resource I have to work with. The moments of downtime I have are starting to shift from picking off new work tasks and context switching to ideating or executing on one of those logged ideas. It’s been a fun space for me to learn about new tooling, improve my development environment, and think about the ergonomics of my job in this new era of work.

Conclusion

I started this by saying that imagination leaves an imprint on the world around us. I’ve realized in time that this instinct has never disappeared, but just hasn’t been given the space to breathe. When we give that space, we put ourselves in a position to open new paths forward, just like we did in that whiteboarding conversation.

Both play and whimsy are critical to progress and innovation, and we must reframe our thinking to leave room for them in the workplace and in our lives.

That is the soapbox I’ll stand on forever, and the journey I’ll be on for the foreseeable future.

Thanks for reading. Fight the good fight.

Note

A blend of books contributed to my thinking here as I wrote this piece. I was inspired by both of these books and find them to be valuable reads for thinkers:

• The Creative Act by Rick Rubin
• What is Progress by Aldo Schiavone