Risk Isn't Real

At 18, I had spent three years crushing on a girl I never had the courage to talk to. It was a dire situation.

To give you an idea of how desperate I was: I picked up guitar and lost fifteen pounds on a chicken breast and lettuce diet hoping she'd notice me.

I did all this and yet never even said a word to her.

Because if I did and things didn't work out, then the illusion of "if only I tried, I would've gotten her" would be all over.

But during the second half of senior year, with time running out, I decided it's now or never. I was going to ask her to prom by writing a song and singing it to her. It felt like years of pressure on my shoulders.

Yes, I'm cringing writing this.

I practiced for weeks. Got teacher approval. Heart pounding out my chest. All systems go.

Then word got out just minutes before my grand play. She cried from the pressure. I heard through a friend and canceled the whole thing.

I was crushed.

But here's the weird part: During prom weekend, she started hanging around me. Giving clear signs. My gambit had somehow paid off!

The problem was I was so butthurt from the original rejection that I completely ignored her.

But the actual outcome isn't the point. What mattered was I took the biggest risk (to 18-year-old me) of my life.

And the result? I didn't die after all. In fact, it went arguably as well as it could have. I'd been saved the embarrassment of the whole song and was handed a golden opportunity anyways (which I squandered).

After 18 years on autopilot, that cringe moment was the first real bet I ever made on myself.

And it was the beginning of my brain deprogramming what it saw as "risk".

Playing it safe is the riskiest play you can make.

I don't mean bungie jumping is safe or you should bet your life savings on red.

I mean the way your brain perceives risk -from asking your crush out to quitting your job- is completely backwards.

A few months ago, I met a guy who was having relentless panic attacks at his prestigious job. He could barely sleep. But he had a family to take care of. So he hired a hypnotist to hypnotize him every week into keeping him working.

Yeah, that's "safe" alright. Quitting would surely be riskier.

Well, eventually he did quit. And he now runs a 7-figure Amazon FBA coaching business and is financially free.

I "played it safe" my whole life. I optimized my entire life around safety. And it was after living that life to its logical end that I stood in my kitchen holding a chef's knife to my neck.

Society trains you to play not to lose. I still remember my parents telling me to stay even after telling them I had suicidal ideation. I remember the look in people's eyes who on the surface said they supported me but deep down saw someone throwing their life away.

It's this same backwards programming that holds people back from authentic desire. From asking the girl. From reaching for that dream job. From quitting once disillusioned. From sharing authentic thoughts online with the world.

Constant risk-aversion usually doesn’t end well. Here’s why:

Four years ago, I was headed to Thailand. The thing is, there are no direct flights to Thailand. And as fate would have it, my flight got severely delayed - meaning I'd miss my connecting flight.

I asked the attendant to reschedule me and if they had any money-back guarantees if I'd missed my connection.

She guffawed: "There are only two guarantees in life: death and taxes."

I'd always hated that saying. She solidified that hate.

Because in that very moment, tired and uncertain if I'd make it to Thailand, I thought to myself that we can boil this stupid quote down into one guarantee: “life is going to punch you in the mouth.”

When my parents and my brother were in California, a magnitude 7 earthquake leveled their apartment. They slept in their car.

At the 10-day meditation retreat, I met people from all walks of life - laid-off lawyers, struggling students, people in crisis.

And when I was at Google living the "dream life" on paper, I was considering death.

The earthquake doesn't care if you took a risk or played it safe. The layoff doesn't care if you were a "good employee." Your mental health doesn't look at your resume and say "nevermind!"

The punch is coming. You can run from it all your life like society will program you to do.

But there's no escape. As my psychologist says, "All paths lead through hell".

The question isn't if you'll get punched in the mouth. The only question is: who do you want to be when it lands?

Here’s the problem: we are programmed to play to not lose.

In behavioral psychology, they call this loss aversion. Studies find that people often reject even advantageous 50/50 gambles with a positive expected value e.g. win $20 vs lose $10 on a coin-flip.

Our brains are designed to catastrophize losses because we're evolutionarily wired for scarcity. But we're not in huts anymore. We live in a world of the internet, international flights, and AI.

When I committed to quitting Google, my brain did exactly what it's designed to do. I could only think about what I'd be losing.

Same with when I was about to press post on that first video.

Now? Six months later? It feels trivial. Almost silly that I agonized so much.

Let me show you the actual math on what I was so terrified of:

The "Catastrophic Failure" Scenario AKA what I thought would happen:

The Realistic Scenario:

The Actual Scenario:

When you're drowning in fear, your brain doesn’t work rationally. It just screams: "You're throwing your life away! Everyone will think you're insane! You'll end up homeless!"

All the things society programmed into you when you were a kid.

But the nightmare scenario isn't failing at something you choose.

It's living a life that you realized was never your own.

It's waking up at 65 and realizing you lived someone else's life and not your own. A lifetime optimizing for a "safety" and desperately running from life’s punch in the mouth.

Nope. It still lands. Now with compound interest.

The ocean of catastrophe you're imagining? It's a mile wide and an inch deep.

Whatever risk you're agonizing over right now, what’s the actual worst case? Don’t rely on the feelings and don’t fall for loss aversion - look at the facts.

For me: Worst case was traveling the world for a bit, trying entrepreneurship and failing, and… getting another job.

Maybe I could even find a remote role if it came to that.

Compare that “worst case” future to what I did know: a life where -despite the money- I didn’t care if I woke up in the mornings.

When I awkwardly recorded that first '50 Days to $1K' video in my living room, I thought that I’d be ending my social life as I knew it. But I knew not doing it would be to bury my truth. It ended up being quite a good decision.

Life is going to punch you in the mouth either way. Might as well throw one back.

Jim

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