Playing to Win

A Spoonful of Sugar is the Medicine

Work-life balance. 

Finish your homework before you play. 

That’s why they call it “work.”

As these phrases echo in our lives, they become accepted as truth without question. It feels justified. After all, what happens to the hunter-gatherer, who plays rather than farms all summer, when winter arrives? A hard work ethic is something to take pride in, and diligence can often pay off in careers, expanding our opportunities and responsibilities. We believe it is good for us, even though it does not always feel good. 

Work can be tedious, but reinforcing work as the opposite of “play” or “fun” is an unhelpful, destructive habit. 

First, we deny the importance of play to recharge our mental capacity and increase creativity, which allows us to work better. Second, we reward work as worthwhile while ascribing the act of work with feelings of “dull” or “obligation,” which conversely associates anything enjoyable as not valuable. 

Creeping Burnout

Insisting on work being “not fun” starts in small, seemingly harmless ways. For example, a boss will joke that employees should “get back to work” rather than socialize or comment too frequently about when workers are “on the clock” and not. 

A trusting team may take these comments as jokes, but others can interpret these comments as reminders to get back to work. 

Repeated in small ways, like remarking on the idle status of people on IM clients or commenting (even kindly) when an employee is uncharacteristically tardy to a meeting, an organization creates employees that are focused on appearing like they are working at all times. Of course, the energy put into keeping up appearances alone can take away from actual productivity, but that is only the surface cost.

As resentment and mistrust grow, employees begin to disconnect from the company, the mission, and the feeling of purpose they may have felt in the beginning. Acting without purpose is the foundation for burnout, a driving factor behind turnover.

Once burnout creeps in, it will only grow if not treated. Employees will rely more and more on willpower to get through the day. Some say willpower is like an emergency brake - great to have, but if you always use it, you’ll burn out.

Increase Enjoyment - Increase Engagement

From an early age, we see this “work must not be fun” mentality in school. Recess is timed and squished into the middle of the day. Fun lessons are exciting but often treated as “less important” than lectures and readings.

But which lessons are actually retained?

I do not remember what types of chemical bonds hold molecules together, but I distinctly recall my chemistry teacher dipping a tennis ball in liquid nitrogen and shattering it on the floor to demonstrate changes in the state of matter. 

I tutored math for several years, and I can say one thing with reasonable certainty - people hate math, and they will happily tell you about it. 

It’s understandable - it’s hard to look at the 50th word problem about trains leaving two cities at different speeds and believe this matters. 

Then one day, I met with a student I had tutored in high school and was now taking a business course in college. She wanted help on an assignment about taking a product to market. She needed to calculate how many boxes it would take to ship 100 units of a specific size, how much of the box would be space for packing material, how much each unit had to cost to cover the costs involved, etc. This student, who generally hated math classes in previous years, had already completed most of the work, understood the concepts, and even started doing similar calculations on a product she thought about making herself outside of class. 

She had found purpose. There was a reason to study math now, and the concept was interesting and provided the means to an end. While some learning may require repetition and practice, it’s easy to forget that “passing a test” is not the ultimate goal - the goal is to pass on skills that allow us to live better lives.

There will always be busy work and tedious administrative tasks in life, but why shy away from the excitement and creativity that create actual retention when we have the chance? What if, instead of wondering about the relative velocity of 2 trains, your new word problem was:

Your mom calls you to let you know she’s 15 minutes away from home. You’re supposed to be there working on your math homework, but you’re at your friend’s house, 5 miles away. How fast will you need to drive home to beat her there?

Companies can tap into this enthusiasm by understanding what excites their people and connecting the company’s purpose with an individual’s values. 

Fun Beyond Happy Hour

Organizations willing to infuse fun into their company culture create spaces people want to stay. “Play” engages our brain in different ways than work; it is less structured but ideally less stressful, allowing us to consider new strategies, think critically and problem-solve, and try out techniques we might otherwise avoid.

There are many ways to cultivate fun in the workplace:

  • Create competitions for who can give the most creative pitch

  • Try “ShipIt Days” (a concept from Atlassian), where employees have a 24-hour hackathon to solve whatever problem they feel like using whatever team they assemble

  • Host meme competitions during all-company meetings to see who can deliver the best meme about the topics at hand

  • Consider a 20% rule like Google - allowing for time employees can spend how they wish. With a trusting environment, they likely will not use always use the full 20%, but the flexibility removes stress for times when life happens


These flexible approaches foster creativity and connection that pay dividends not just in reduced turnover but increased engagement. This attitude is the foundation for the agile, self-sustaining team of any leader’s dreams.

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Are We Humans, or Are We Dancing Pigeons?

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Stopping Turnover with Acknowledgment