Why Successful Men Can’t Relax (Even When Life Is Going Well)
What if the real reason you can’t enjoy your success isn’t that you’re ungrateful, broken, or secretly miserable… but that you’re actually afraid of being happy? I know, it sounds ridiculous at first. Almost everyone believes they’re chasing happiness. So, the idea that you might be actively preventing it feels absurd. And yet, once you see this pattern, it explains most high-achiever behaviour almost perfectly. In today’s video, I unpack what I’ve seen repeatedly from years of coaching driven, intelligent, and successful people. People who look like they’ve won the game of life, but who are constantly anxious, restless, and unable to relax into anything they’ve built. I introduce a concept called cherophobia, which is essentially the fear of happiness, contentment, or enjoyment. I tell the story of a client, who if you looked at his life on paper, you’d probably feel jealous. He’s financially elite, physically fit, has a great family, and checks every box society tells us should equal fulfillment. But inside his head, it’s chaos. He’s constantly catastrophizing, scanning for threats, and imagining how everything could fall apart. He’s doing everything “right,” yet he hardly enjoys any of it. What’s going on here is a deeply ingrained belief that if things are going too well, something bad must be coming. Many high achievers live with an unspoken superstition that happiness invites punishment. That relaxing, celebrating, or acknowledging success will somehow tempt fate. So they stay tense, stressed, and dissatisfied, because that feels safer than enjoying themselves. This creates a bizarre dynamic where success and failure become fused together. You’re allowed to win, but it’s not allowed to feel like a win. Every achievement immediately resets the expectation bar. Your personal best becomes the new minimum, and anything less feels like failure. Over time, this erodes your ability to enjoy anything at all. Ironically, this fear is often what drives high achievement. These people are incredible problem-solvers because they never let themselves rest. When things are going well, they get suspicious. When there are no problems, they subconsciously create new ones. They don’t trust calm. They don’t trust ease.