Most business owners start with big dreams. They want to build something meaningful, something profitable, something that lasts. But somewhere along the way, many stop playing to win and start playing not to lose. They become risk-averse, cautious, and focused more on protecting what they have than pushing for what they want. And that, right […]
Most business owners start with big dreams. They want to build something meaningful, something profitable, something that lasts. But somewhere along the way, many stop playing to win and start playing not to lose. They become risk-averse, cautious, and focused more on protecting what they have than pushing for what they want. And that, right there, is the reason so many businesses stay small, stagnate, or fail.
Instead of planning and trying to make their best case scenario happen, business owners sometimes spend all their energy instead on trying to prevent the ‘bad’ outcome from happening. Reacting to their fears and inner desire for basic survival instead. It’s understandable when we face challenges to switch our focus to surviving and trying to prevent unfavorable outcomes, but we can end up pouring our energy into the wrong thing.
Blame it on your brain. Humans are wired for loss aversion—the tendency to fear losing something more than we desire to gain something new. Nobel Prize-winning research from Daniel Kahneman and Amos Tversky shows that losses feel twice as painful as equivalent gains feel pleasurable. In business terms, the fear of losing money, status, or stability often outweighs the excitement of making a bold move that could change everything.
Think about it: How many times have you hesitated to raise prices because you feared losing customers? How often have you kept a mediocre employee because firing them felt more painful than hiring someone better? How long have you put off a major investment—branding, advertising, hiring—because you were afraid it might not pay off?
How much time has passed since you have stalled in really pouring everything you have and more into your business to make things happen?
Consider two types of business owners:
Great businesses—the kind that break through ceilings, disrupt industries, and build loyal communities—play to win.
In the early 2000s, Blackberry dominated the mobile phone industry. Their strategy? Keep improving their keyboard-based phones. Apple, on the other hand, wasn’t interested in making incremental improvements. They scrapped the keyboard entirely and introduced the iPhone. Blackberry was playing not to lose, to keep the market they have; Apple was playing to win the future. We all know how that turned out.
Netflix started as a DVD rental company, but instead of doubling down on that model, they took a huge risk—moving into streaming before it was mainstream or accessible to everyone. Blockbuster, worried about cannibalizing their rental revenue, hesitated. The result? Netflix is worth over $200 billion today, and Blockbuster became a nostalgic lexicon.
Michael Jordan didn’t just want to be good—he wanted to be legendary. He took shots others wouldn’t, trained harder than anyone else, and refused to play a safe game. His offensive mindset made him the GOAT, while countless talented players faded into mediocrity because they weren’t willing to take the same risks. To be dedicated even when you risk failure.
If you realize you’ve been playing not to lose, don’t panic. You’re human, and your brain is wired to do this as a default. Here’s how to shift gears and start playing to win:
Every great move in business involves risk. Instead of fearing it, ask: What’s the upside if this works? Often, the potential reward far outweighs the worst-case scenario you’ve built up in your head. And really play out what you can do or adapt even if it fails, our spirits can be indomitable.
Businesses that play to win invest aggressively in branding, marketing, team-building, and product development. They don’t hoard cash out of fear; they put money where it will create more money. How long can you delay your gratification and take more wins later?
Keeping a weak employee because you’re afraid of hiring someone new? Sticking with a strategy that’s “good enough” but not great? Cut the dead weight. Winners don’t hold onto mediocrity just because it’s familiar. This also is an opportunity to look in the mirror objectively, if you’re underperforming-thats okay. You’re not a failure, this is a call to do what you believe in, thats it.
Playing to win doesn’t mean being reckless—it means taking calculated risks. Study the data and outcomes, make an informed choice, then commit to it fully. Stop second-guessing yourself.
Business is a game, and the most successful people enjoy playing it. They embrace the challenges, the pivots, and the big swings. If you’re constantly stressed and paralyzed by fear, you’re not playing to win—you’re just trying not to lose. When you feel yourself locking into it, come back to the same steps and start at the beginning, try to win first before preventing loss.
Look at your business right now. Are you making decisions based on growth and opportunity, or are you just trying to protect what you already have? Are you leading with confidence, or are you avoiding risks out of fear? If your answer leans toward the latter, you CAN make a shift.
The businesses that make history—the ones that thrive, scale, and dominate—don’t just survive. They take calculated risks, make bold moves, and play the game to win. Your business deserves more than just staying in the game. Your dream deserves a strategy that puts your business at the top of it.
