Give Your Business Team Permission to Play, Think, and Make Mistakes

Give Your Business Team Permission to Play, Think, and Make Mistakes

Something interesting has happened in my thinking lately that I thought was worth sharing. I’ve been having some fairly transformative insights into my own behavior and attitudes and mindsets, as well as those of others; some ideas that never occurred to me despite how obvious they now seem; breakthroughs through roadblocks; lightbulbs going off; A-Ha moments. Here’s what happened…

I was hanging out with my two-year-old and watching him get totally geeked out whenever a plane flew closely overhead, or whenever the garbage truck’s trash-compactor would crush all the bags in the back, or when someone did a backflip off our neighborhood diving board. These and a million other moments felt to my son the way I would feel if aliens suddenly landed in our backyard or if a genie offered me a hundred free wishes.

And yet, there was a time when I felt exactly like he felt about those same small things.

Until I didn’t.

And then I thought of my favorite entrepreneurs. Not the stressed-out ones who take themselves way too seriously and lose their minds when things don’t happen the way they want. My favorite entrepreneurs are the ones who act like kids when they’re working. Smiling, laughing, playing, exploring, excavating, and treating problems like games, all in the course of addressing monumental (and sometimes catastrophic) issues in their businesses.

Thomas Edison was supposed to have been like that. The story goes that when his lab exploded from a chemical fire and destroyed years of his team’s experiments and patent ideas and labor and effort, he stood outside, watched his dreams go up in smoke, turned to his son, and said, “Charles, go get your mother and all her friends. They’ll never see a fire like this again.”

previously wrote about the value of treating work like a game. In the past year, we’ve been incubating and building out a new, innovative service in our company that’s stretched our skills and talents, and knowledge beyond anything we have. There’s been a tremendous investment of time, money, and both physical and emotional energy from the team. There have been enormous highs and lows.

This “Kid Play” mindset has helped me weather these highs and lows really nicely.

We’ve tried to intentionally channel my two-year-old’s sense of exploration and freedom of thinking and wonder. Personally, I’ve inserted that phrase – “I wonder” – into my meditations, our brainstorms, and my journal.

  • “I wonder what being the top place to work in Ohio, or in the country, would look like in our company.”
  • “I wonder what incredible client service looks like.”
  • “I wonder what 30 days of exercise would feel like if I targeted a different area or skill each day.”
  • “I wonder what a four-day workweek in our company would be like.”


Some of these “wonderings” have led to actions, and some haven’t. But the act itself, the mindset shift, has added tremendous value to me personally and, I think, to my team. Giving permission to yourself and to them to play at work, to expand their thinking, and to make mistakes is energizing. And super-fun.

About Alex Gertsburg

At Gertsburg Law, our attorneys have a comprehensive understanding of the countless issues facing businesses on a daily basis. Most of our experienced attorneys in the Chagrin Falls and Cleveland offices are former business owners and in-house counsel, bringing a unique perspective and depth of knowledge to their skill set. We will work with you to understand your goals and to find the right solution for your organization. For more information visit