The Courage Gap

Why Most Never Bridge the Divide Between Good and Extraordinary

I remember the exact moment I realized that the way I was thinking about courage was all wrong.

It was back in my university days. I’m out at the local university pub with some friends including a friend-of-a-friend named Joe. Cheap beer, good music and a great university pub vibe…a night full of potential (and ending with poutine at 2 a.m. in a place that should have lost it’s liquor license years ago). Joe’s a good looking guy — tall, dark hair, athletic build and he’s got a natural charisma about him. Confident but not overdoing it. Joe spots an attractive girl on the other side of the room chatting with her friends. Without hesitation he gets up, walks over and starts talking to her. She looks up, smiles. They start talking. The rest of us watch in awe. I remember thinking to myself “I could never do that” — which is code for “I’m going to stand here clutching my beer like it's a safety blanket instead.”

My friend — the one who invited Joe — leans over and tells me something that changes how I think about courage forever. It turns out that Joe has a rule. When he goes out to a bar he finds the prettiest girl in the room and he goes to talk to her, no matter what. Joe’s reasoning is that one day the woman of his dreams is going to be on the other side of the bar and he wants to make sure that in that moment he has the courage to go up and talk to her. My mind is blown. It makes so much sense — and yet so hard to do.

Joe later confesses to me that he still feels nervous every time and when he gets rejected it stings. But he sticks to his rule because he can picture in his head that critical moment when he’ll need that courage. Every time he approaches a girl — each a rep — he's building the capacity to act through fear. While others wait around hoping to magically become "more confident" (guilty as charged) Joe's putting in the reps.

The Essential Insight

In order to do extraordinary things most people focus on the obvious: put in the hard work and develop your skills. Then great things will happen, right? The uncomfortable truth is that hard work and skill are not enough. That'll get you above average results - sure. But to do the extraordinary? You need something that’s in much shorter supply…

You need courage. The courage to act even when your emotions are telling you to run for the door.

"Life shrinks or expands in proportion to one's courage."

- Anais Nin

Think about it. That blog post you've been "polishing" for weeks? It's not about the writing anymore — it's about the fear of putting yourself out there. That app idea you can't stop thinking about? The code isn't what's holding you back — it's the fear of launching something that might fail. That person you want to reach out to for advice? You're afraid they'll reject you.

To do extraordinary things, you must seize opportunities before you feel ready. You have to make things happen. Yes, the prediction engine in your brain will go into full-on disaster mode, sketching out elaborate blueprints for every possible way things could go wrong. But that ability to act despite those feelings is what separates the extraordinary from the merely above average.

Is that you? Are you the person out there taking your shot? Or are you the one still perfecting your swing?

Courage as the Differentiator

It’s 2020. Danny Postma had just hit “send” on a cold email to Greg Brockman, the CEO of OpenAI, asking for access to a private tool called GPT3. Danny, a Dutch coder living the nomadic lifestyle in Bali, was making solid money…tens of thousands per year with his marketing headline generator “Headlime”. But getting access to GPT3 could transform it.

Danny hears the “ding” and sees that it’s a reply from Greg. His heart racing, Danny braces for rejection — but it’s a yes! He immediately gets to work building GPT3 into Headlime which makes it much more valuable and it quickly goes viral. In February 2021 Danny sells it for a life-changing 7-figures.

One key moment of courage — sending that cold email — turned a decent idea into a life-changing exit.

When we act with courage we expand our “luck surface area”. Each courageous act is like a lottery ticket — a chance to get lucky. That email Danny sent to Greg Brockman was a lottery ticket. Did he get lucky? Hell, yeah. But that’s the whole point — when you courageously put yourself out there you get more chances to be lucky.

Patrick Collison is another great example of this. At 13, this brilliant Irish teenager has the courage to reach out to Paul Graham about their shared interest in an obscure programming language called Lisp. Fast forward three years and another act of courage: asking Paul to meet for coffee in Boston. That coffee leads to dinner at Paul’s house with MIT professor Robert T. Morris and Aaron Swartz (who would later co-found Reddit). These meetings are formative to young Patrick encouraging him to think big. A few years later Patrick and his brother John start Stripe (through Paul Graham’s Y Combinator) which goes on to become a unicorn-level success — now worth $65B.

One act of courage leading to connections — an expanded luck surface area. Those connections leading to opportunities, guidance and inspiration. All of that leading to Stripe — a company that’s now enabled millions of small businesses to process payments online.

How do we develop that courage? Is it something you’re just born with — you’ve got it or you don’t? Many think that’s the case but it’s not true. Courage can be systematically developed. Think back to Joe…he exposed himself over and over to the chance of being rejected. Each was a rep that strengthened his capacity for courage….and he’s not the only one…

The Solution: Repeated Exposure

It’s early 2021. Kariza Santos posts a video “Why I’m Starting to Document My Life”. In that video Riza, as she’s known, launches a new chapter in her life triggered by an existential moment of questioning. She’d received a CD from a childhood friend full of old photos. Despite being a film maker, Riza realized she wasn’t capturing the moments of her life that mattered — from the big events to the everyday and mundane. And, more than that, she was living life small. Riza makes a courageous decision — to be the main character in her life. She had always wanted to be a YouTuber and had posted a video here and there. But, this time was different. She was going all-in.

“What we fear doing most is usually what we need to do.”

— Tim Ferriss

Riza starts a vlog capturing snapshots of her life. Each video was an act of courage both for the fact that she was documenting her life with vulnerability and also because she was going all-in on this as “her thing”. Each video was a rep — each requiring her to face her doubts.

At the start of the journey Riza had 7K subscribers. A year later 700K — her channel exploding as the world discovered Riza’s unique cinematic talent and commitment to living fully. Riza is a prime example of someone who has expressed courage over and over again to do something extraordinary. Each video a rep building her up to what she is today.

Riza, Danny, Joe — all of them, as Brené Brown notes forging their courage through action:

Courage is like—it’s a habitus, a habit, a virtue: You get it by courageous acts. It’s like you learn to swim by swimming. You learn courage by couraging.

― Brené Brown, The Gifts of Imperfection

This strategy of repeated exposure is something that many world-class performers figured out intuitively.

Early in Jerry Seinfeld’s career he had severe anxiety and stage fright. His solution was to book multiple shows per night to build up his tolerance. Today, his stage presence is legendary.

Warren Buffett had similar problems. Speaking was his greatest fear - he'd choose college classes based on whether he'd have to speak or not. "I would get physically ill if I even thought about having to do it."

Buffett knew this fear was holding him back so he signed up for a Dale Carnegie speaking course and then volunteered to teach at the University of Omaha, forcing himself to get up in front of people again and again. While others avoided public speaking whenever possible, Buffett deliberately sought it out. Today? He's one of the most compelling speakers in business.

This idea of repeated exposure, and more precisely progressive repeated exposure, to build our ‘courage capacity’ is backed up by science. Researchers at Ruhr University Bochum took 60 people who were afraid of both spiders and heights. Half the group got spider exposure therapy while half did nothing. The exposure therapy progressed each person through different levels of exposure. Level one was looking at a spider from five feet away. Level 14 was letting a spider walk on their hand. Each person was walked up this escalating ladder until they either got all the way to the end or two hours had passed. (Is this study still running? I’ve got a couple of kids I’d like to sign up).

The fascinating part? For the group that did the exposure therapy not only did their fear of spiders drop dramatically, but their fear of heights improved too — even though they never worked on it. The courage they built in one domain transferred to another.

This study shows that we can build courage in the same way we build bigger biceps: progressive overload. That is, lifting progressively heavier weights over time. Why does this work for building our courage capacity? I think there’s three reasons why:

1. We get used to the feelings of fear and uncertainty. The feelings don’t go away but they lose their debilitating edge.

2. We get used to failure and loss. When Joe got rejected by a girl it stung. But an hour later he realized that he’s okay — the failure wasn’t fatal. In fact, he interpreted it as a sign that he was moving closer to the girl of his dreams.

3. We get skilled at being courageous. We learn how to talk to ourself, how to shift our attention, and how to reframe our feelings.

Building Your Courage Practice

Let's take a moment to catch up on where we're at. First, we've covered why courage is the fundamental ingredient to extraordinary success. The success of Joe, Riza, Patrick, Danny, Seinfeld and Buffett all hinging on their ability to summon courage when they need it. And we've seen that courage can be systematically built through a process of repeated exposure.

So, how do we build up our own practice of repeated exposure? There’s three keys to making this work.

First, start small and progressively build up. What matters most is getting lots of reps in.

Second, treat this like a serious project, not a casual experiment. Don't just try it once or twice and then forget about it. The stakes are too high. This is something you must do if you want to do the extraordinary.

Finally, redefine what success means. When a rep leads to failure, whether it be rejection or embarrassment, be okay with that. Of course, this is easier said than done. We've all had some moment in high school where we were embarrassed — like when we tripped and got back up at super-human speeds. (To this day I swear that tile was intentionally moved). Those experiences get seared into our brains. But you know what? You're bigger than that now. You can handle it.

The fact of the matter is that when you do courageous things sometimes it's going to go badly. But, you have to keep reminding yourself that the rep itself is the win. It’s the reps that will transform you…as long as you don’t let failure stop you from continuing.

I challenge you: take a moment and think of one thing you could do today…preferably in the next hour…that would make you feel uncomfortable. Then go do it. Get this practice going.

The Stakes are High

As a kid, I lived and breathed baseball. I was pretty good too. I could field and throw with the best of them. But I had one fatal flaw: when I moved up to the level where kids were pitching with real velocity but questionable accuracy I was afraid of the ball. My response? I'd close my eyes. Pretty dumb strategy really. If the pitch is coming right at me I’m not going to see it and I’m going to take it in the ribs. My batting average? I don’t know the number but I do know that I had exactly one hit. One. And that was an accident — I was so surprised it took me a few seconds to realize I should run. That was my last year of playing baseball.

That fear - that instinct to close my eyes - cost me something I loved. But we all do this same thing now. We close our eyes to opportunities because we're afraid of getting hit. We tell ourselves 'someday I'll…’. or ‘I could if…’.

When we summon the courage to act, everything changes. Those ideas trapped in our heads get unleashed, turning potential energy into kinetic force. Each courageous action expands our luck surface area, creating connections and opportunities we couldn't see before.

You build that courage through repeated exposure. Joe approached the prettiest girl in the room as a rule so he’d be ready for that critical moment when the woman of his dreams was across that room (spoiler: he was ready). Each rep rewriting his story and building his courage capacity.

It’s your turn. The fact that it’s difficult is an opportunity. While others wait to feel ready, you’re out there systematically building your courage. The courage that turns potential into reality. The courage that builds a luck surface area so large that opportunities start coming in from every angle.

Don't close your eyes. Face the pitch head on and take a swing.