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Dear High Performers,

Let me ask you something honest. When was the last time you actually let yourself go for it? Not the careful, calculated risk where you've hedged every possible downside. I mean really went for it. Fully committed. No backup plan. No safety net. Just pure execution without the constant mental calculation of what happens if you fail.

For most of you, the answer is probably "I can't remember." And that's the problem.

You're standing over a 180-yard approach shot with water short and right. You know you need to commit to a smooth 6-iron and trust it. But instead, your brain starts running disaster scenarios. What if you come up short? What if you pull it right? What will your playing partners think? Maybe you should play it safe and lay up. Except now you're not committed to anything, and you hit some weak, indecisive shot that finds the water anyway.

Or you're in a strategy meeting with a genuinely innovative idea that could change your company's trajectory. But instead of presenting it confidently, you start hedging. "This might be crazy, but… You've undermined your own idea before anyone else even had a chance to. You were so afraid of looking stupid that you made yourself look uncertain instead.

This is what fear of failure does. It doesn't just make you avoid risk. It makes you fail at the things you're actually capable of doing because you're so busy protecting yourself from judgment that you forget how to perform.

The Judgment Problem (That's All In Your Head)

Here's something that will either relieve you or irritate you: nobody is thinking about you as much as you think they are.

You hit a bad shot and immediately spiral into what everyone must be thinking. "They think I'm terrible. They're judging my swing. They're wondering why I'm even out here." Meanwhile, your playing partners have already forgotten about your shot because they're worried about their own game and whether they left the garage door open at home.

You stumble through a presentation and convince yourself everyone thinks you're incompetent. Meanwhile, half the room is thinking about lunch and the other half is rehearsing what they're going to say when it's their turn. Nobody is running a detailed analysis of your performance except you.

Dr. Thomas Gilovich at Cornell has studied this extensively. He calls it the "spotlight effect." We dramatically overestimate how much attention people pay to our actions and appearance. In his experiments, people consistently believed others noticed their mistakes, awkward moments, and failures far more than they actually did.

Here's the study that really drives this home. Gilovich had college students wear embarrassing t-shirts (Barry Manilow, if you're curious) into a room full of their peers. The students wearing the shirts estimated that about 50% of people would notice and remember the shirt. The actual number? Less than 25%. And these were bright, memorable, embarrassing shirts that participants were specifically told to notice.

If people don't even notice an embarrassing t-shirt you're actively wearing, why do you think they're carefully cataloging every bad golf shot or awkward moment in your presentation?

Ricky doesn’t give a rats ass what you think about his outfits. Why do you care if someone thinks you have a bad swing at your local $30 muni course?

The fear of judgment is almost entirely self-imposed. You're creating an audience in your head that doesn't exist in reality. You're playing to imaginary critics who are too busy worrying about their own performance to notice yours.

Playing Not to Lose (The Guaranteed Way to Lose)

There are two ways to approach high-stakes situations. You can play to win, or you can play not to lose. These sound similar, but they're neurologically opposite and they produce completely different results.

Playing to win means you're focused on the target, the goal, the outcome you want. Your attention is on execution and opportunity. You're thinking "I'm going to stick this approach close" or "I'm going to nail this presentation."

Playing not to lose means you're focused on avoiding mistakes, preventing disasters, and protecting yourself from judgment. Your attention is on all the things that could go wrong. You're thinking "don't hit it in the water" or "don't say something stupid."

Dr. Sian Beilock's research on choking under pressure shows that prevention-focused thinking (playing not to lose) consistently produces worse performance than promotion-focused thinking (playing to win). When your brain is oriented toward avoiding bad outcomes, you activate completely different neural circuits than when you're oriented toward achieving good outcomes.

Playing not to lose feels safer. It feels responsible. It feels like you're being smart and strategic. But it's actually the cognitive equivalent of driving with one foot on the gas and one foot on the brake. You're working against yourself.

I see this constantly on the golf course. Someone is playing well through 12 holes, then suddenly becomes terrified of ruining their round. They start playing conservative. They stop committing to shots. They're so focused on not making mistakes that they tense up and make mistakes anyway. They finish with a whimper instead of the round they were capable of shooting.

Doesn’t seem like he was just playing to “not lose” huh?

Same thing in business. A founder gets some early traction and suddenly becomes terrified of losing it. They stop taking the bold swings that got them there. They start making safe, conservative decisions. They're so worried about not screwing up their success that they stagnate and get passed by competitors who are still playing to win.

The irony is brutal. The very strategy you adopt to avoid failure becomes the mechanism that guarantees it.

Hunter vs Hunted: The Confidence That Changes Everything

Here's the truth about confidence and fear of failure: you're either a hunter or you're being hunted in your own head. And everyone around you can tell which one you are.

I've been fortunate enough to sit in meetings and rooms with some of the top tech executives in the country. You know what they wear to the nicest, most exclusive restaurants? White t-shirt and jeans. Not because they're trying to make a statement. Because they genuinely don't care about the judgment of a room full of people in suits.

When they present ideas, they don't hedge. They don't say "feel free to tear this apart." They present the idea, then ask for opinions on small implementation details. Why? Because they're confident in the fundamental premise and they're confident it's going to succeed. They're hunting for the best execution, not defending themselves from criticism.

That's what confidence actually looks like. It's not arrogance. It's not fake swagger. It's the complete absence of fear about what other people think, which frees up all your mental energy to focus on actual performance.

Fear of failure makes you the hunted. You're constantly scanning for threats. Protecting yourself from judgment. Playing defense. Every decision is filtered through "what will people think if this doesn't work?"

Click this photo and read the story. If you know, you know. This may have been the craziest fear of failure moment in golf history…

Confidence makes you the hunter. You're scanning for opportunities. Looking for ways to execute better. Playing offense. Your decisions are filtered through "what's the best way to make this happen?"

Same brain. Same situations. Completely different orientation. And it shows in everything you do, from how you walk into a room to how you stand over a golf shot.

The fascinating part? Confidence isn't about being certain you'll succeed. It's about being certain you'll be fine even if you fail. That subtle shift changes everything.

The Perfectionism Trap That Looks Like Excellence

Let's talk about perfectionism for a second, because most high performers think perfectionism is a strength. It's not. It's fear of failure wearing a fancy outfit.

Real excellence is about executing at your highest level. Perfectionism is about avoiding any situation where you might not be perfect. Excellence purses great outcomes. Perfectionism avoids potential judgment.

You know you're dealing with perfectionism instead of excellence when you find yourself:

  • Not attempting shots or strategies unless you're certain you can execute them perfectly

  • Spending excessive time planning and preparing because you're terrified of being unprepared

  • Avoiding situations where you might look bad, even if they'd help you improve

  • Obsessing over mistakes long after they're relevant

  • Comparing your behind-the-scenes struggles to everyone else's highlight reel

Dr. Thomas Curran's research on perfectionism shows that it's dramatically increased over the last 30 years, particularly among high achievers. And it's not making us better. It's making us more anxious, more risk-averse, and less resilient when we inevitably make mistakes.

Perfectionism on the golf course looks like refusing to hit driver because you might miss the fairway. It looks like not entering tournaments because you might not play well. It looks like practicing endlessly but never testing yourself in real competition.

Perfectionism in business looks like not launching until everything is perfect (so you never launch). It looks like not presenting ideas until they're bulletproof (so you never present). It looks like avoiding difficult conversations because you might not handle them perfectly (so nothing ever improves).

Here's the hard truth: perfectionism isn't about being excellent. It's about being safe. And safety is the enemy of growth.

You know how many memes I had to go through to find “the perfect” one lol?

You want proof? Have you seen the website for this newsletter? It's basically held together with digital duct tape and prayers. I launched this thing before it was "ready" because I realized I could spend six months making everything perfect, or I could start helping people now and improve as I go. Turns out launching imperfectly was the biggest blessing. I'm learning what actually matters to readers through doing, not through endless planning. The website still needs work. The newsletter is getting better every week. And that's exactly how it should be. Side not, thank you to all of you reading. It truly means the world to me and feel free to send me an email if you ever want a certain topic written about!

The Cost of Self-Protection

Every time you protect yourself from potential failure, you pay a cost. Sometimes the cost is obvious, like not going for a green you should go for, or not pitching an idea you should pitch. But often the cost is invisible. It's the compound effect of thousands of small moments where you chose safety over growth.

The self-protection instinct makes sense evolutionarily. Your ancestors who avoided all risks lived longer than your ancestors who took stupid risks. But your ancestors also lived in a world where the downside of failure was often death or exile from the tribe. You're living in a world where the downside of a bad golf shot is literally nothing, and the downside of a failed business idea is usually just "try again with better information."

You're applying stone age risk assessment to modern situations where the consequences of failure are minimal but the cost of never trying is massive.

What Actually Happens When You Let Go

I worked with an executive who was paralyzed by fear of judgment in meetings. He had great ideas but would only share them if he'd rehearsed them perfectly and anticipated every possible objection. He spent more energy managing how he'd be perceived than actually contributing value.

We did an exercise where he had to share ideas in real-time without preparation or hedging. Just raw thoughts, unpolished and imperfect. He was convinced it would be a disaster. Everyone would think he wasn't prepared. He'd look incompetent.

What actually happened? People engaged with his ideas more. They asked better questions. Conversations became more dynamic. Turns out when you stop performing perfection and start actually communicating, people respond to the substance instead of the polish.

Same thing happens in golf. I've seen countless players who are so afraid of embarrassing themselves that they play tight, mechanical golf that produces consistently mediocre results. Then something shifts. Maybe they stop caring as much. Maybe they get frustrated enough to say screw it and just swing. Suddenly they're striping it. Their tempo is smooth. Their commitment is total. They're actually playing golf instead of managing their fear. For all you weekend warriors reading this, it may be the time the front nine brews hit you after you stopped caring and you turn into 2000 Tiger haha.

The breakthrough isn't that they suddenly got better at golf or business. The breakthrough is that they stopped spending mental energy on self-protection and redirected it toward actual performance.

The Permission to Fail (That You've Been Waiting For)

Here's your permission: you are allowed to fail. You are allowed to hit it in the water. You are allowed to present an idea that doesn't land. You are allowed to look foolish sometimes. You are allowed to be imperfect at things that matter to you.

This isn't motivational poster nonsense. This is practical performance psychology. Dr. Albert Bandura's research on self-efficacy shows that people who give themselves permission to make mistakes while learning consistently outperform people who demand perfection from themselves.

The golfers who improve fastest aren't the ones who avoid mistakes. They're the ones who commit fully to shots within their capability instead of playing tentative, fearful golf. They trust their process, commit to their targets, and accept that sometimes good swings produce bad results. They're not trying hero shots they can't execute. They're fully committing to smart shots without fear.

The executives who build great companies aren't the ones who only move when they're certain of success. They're the ones who are willing to make bold decisions within their strategic framework, adjust quickly when needed, and keep moving forward.

Permission to fail doesn't mean being reckless. It means being honest about the fact that growth requires operating at the edge of your current capabilities, and operating at that edge means you're going to fail sometimes. The question is whether you're going to let that fear of failure keep you from ever reaching that edge in the first place.

But here's the critical part nobody talks about: if you fail and don't learn from it, then yes, that failure was completely pointless. Permission to fail isn't permission to be careless about what failure teaches you.

After a round where things went wrong, write it down. What actually happened? Not the emotional story you're telling yourself, but what actually occurred? What was your decision-making process? What would you do differently? This isn't wallowing in failure. This is extracting value from it.

Same thing in business. After a strategy that didn't work, a presentation that flopped, a decision that backfired, write down what you learned. What assumptions were wrong? What would you change? What's the actual lesson, not just the emotional bruise?

The golfers and executives who grow fastest aren't the ones who fail the most or the least. They're the ones who systematically extract lessons from failure instead of just moving on and hoping it doesn't happen again. Failure without reflection is just expensive randomness. Failure with reflection is education.

The Commitment Protocol

Here's how to start breaking the fear of failure pattern that's been running your life:

This week: Notice when you're playing not to lose. On the golf course, in meetings, in conversations. Just notice. Don't judge it, just become aware of when your brain shifts from "I'm going for this" to "I hope I don't screw this up."

This month: Practice full commitment in low-stakes situations. Pick one shot per round or one moment per week where you fully commit without hedging. No safety nets. No backup plans. Just pure execution. See what happens when you stop protecting yourself.

This season: Deliberately put yourself in situations where you might fail publicly. Enter a tournament where you're outmatched. Pitch an ambitious idea without hedging. Do something that terrifies you specifically because it terrifies you. Your brain needs evidence that failure isn't actually dangerous.

The people performing at the highest levels haven't eliminated their fear of failure. They've just decided that the cost of playing it safe is higher than the cost of occasionally failing. They'd rather swing freely and miss sometimes than spend their entire lives protecting themselves from judgment that mostly exists in their own heads.

Stop playing not to lose. Start playing to win. The score takes care of itself when you're actually trying to make something happen instead of trying not to screw up.

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