Entrepreneurship is supposed to be fun. It’s easy to forget that when you’re knee-deep in problems, but at the end of the day, we do this because we love it. My son was recently at a baseball camp, and his coach sent me a note that said, “I love how much he just loves to play everything!! I don't think it matters what sport—he just loves to play!” That’s the mindset we, as entrepreneurs, need to have. Hard times aren’t the end; they’re just part of the game.
Step One: Accept That You’ll Always Be Solving Another Problem
Entrepreneurship is a game with no end. If you think you’ll reach a point where all the problems disappear, I hate to break it to you—that moment isn’t coming. The finish line is a mirage. As Simon Sinek explains in The Infinite Game, business isn’t a game you win. It’s a game you keep playing. The goal isn’t to beat everyone else; it’s to stay in the game.
Every time you solve a problem, another one takes its place—usually bigger and more complicated. That’s just how it works. It’s not a sign that you’re failing; it’s proof that you’re growing. The most successful entrepreneurs understand this and learn how to roll with the punches. As Mike Tyson famously said, “Everyone has a plan until they get punched in the mouth.” The real question is: what do you do after that?
Control What You Can Control
We can’t control that problems will always need to be solved, but we can control how we respond. Some people get frustrated, some ignore the hard stuff, and some—usually the successful ones—lean in. They get curious, ask tough questions, and stress-test their ideas.
I’ve gotten good at asking hard questions—not to make anyone feel insecure, but to see if an idea can hold up under pressure. It’s okay to not know the answer. What’s not okay is pretending you don’t need one. Entrepreneurs need to think like detectives, constantly investigating, questioning, and adjusting.
The Danger of Ignoring Future Planning
Too many businesses get so caught up in the day-to-day that they ignore long-term planning. That’s a mistake. A study by FEMA found that 90% of small businesses that fail to reopen within five days of a disaster never reopen at all. Resilience planning isn’t just a “nice to have”—it’s what separates the businesses that survive from the ones that disappear.
Keep Playing the Game
If you’re an entrepreneur, you’re not chasing a finish line—you’re learning to run a never-ending race. The terrain will change, the obstacles will get bigger, and there will be days when it feels like too much. But that’s the game. And if you can embrace the uncertainty, ask the hard questions, and plan for what’s ahead, you’ll always have a shot at staying in it. Most importantly, remember to enjoy it. Like my son’s coach said—it’s not about the sport, it’s about the love of playing.
Now, GO PLAY!
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