Recently, Ted and I witnessed a small moment in our neighborhood while on our daily walk that unexpectedly carried a big lesson about business — and life.
A group of little girls, probably around five or six years old, were playing together in the street. One child walked over to the group looking visibly upset and frustrated. Then she kicked a street sign.
Another little girl asked her gently, “Why aren’t you having fun?”
The upset child answered loudly: “Having fun is winning for me.”
One of the others immediately responded: “You should try to have fun anyway.”
As simple as it was, that exchange stayed with us and we talked about it later in the day, because many adults — especially business owners — feel exactly the same way, even if they don’t say it out loud.
For many entrepreneurs, “fun” becomes tied directly to winning, such as:
- Landing the client
- Closing the sale
- Growing revenue
- Beating competitors
- Getting recognition
- Winning awards
- Seeing constant upward momentum.
And when those things slow down or become harder to achieve, frustration quickly replaces enthusiasm.
Business starts to feel heavy and burdensome… (in other words, not fun!).
What often gets lost is the reason many people started their business in the first place. Most entrepreneurs began with excitement, creativity, independence, passion, or the desire to build something meaningful. But over time, stress, competition, economic pressure, staffing challenges, and constant comparison can slowly turn the experience into nothing more than chasing the next “win.”
That mindset creates a downward spiral.
If your happiness only comes from winning, then every setback feels personal. Every slow month feels like failure. Every competitor’s success feels threatening. Eventually, even meaningful accomplishments stop feeling satisfying because the goalposts constantly move.
The businesses that thrive long term are often led by people who still find value and enjoyment in the process itself. They enjoy solving problems, serving customers, creating new ideas, and building relationships.
Of course, results matter. Growth matters. Profit matters. No one is suggesting otherwise.
But there is an important difference between striving for success and believing success is the only thing that gives the work meaning.
Ironically, businesses often perform better when owners reconnect with curiosity, creativity, and purpose instead of operating in a constant state of pressure and frustration. Employees feel that energy. Customers feel it too.
Sometimes the clearest lessons come from unexpected places…like from a little girl who believed that fun only counted if she was winning and from the children around her who reminded her that maybe there was a better, more “fun” way to look at it.
That may be a lesson many adults in business need to hear too.
Yes, winning is important. But if it’s the only way you can have fun, you’re missing the best part of the game!