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Too Many People Want Risk-Free Lives. Then They Wonder Why They’re Deeply Unhappy.

by | Nov 6, 2023 | Life

He shot him in the neck, fled the scene, and drove to Canada.

In Canada he got his filthy hands on a fake passport. It’s amazing what a bit of cash can buy you. That passport got him to Portugal then England.

He was a free man.

What an adventure. He killed one of the most influential people in history who started a cultural movement. While in England he booked a flight to Spain.

It was time for sun, fun, and babes. Ahhh the good life.

At the British airport he handed over his passport during a routine check. They gave it right back to him and he walked off. One security officer then yelled “Mate, is that a second passport falling out of your pocket?”

He walks back and says to security, “Nah, I’ve got two passports because they spelled my name wrong on the first one.”

Seemed legit.

The security officer asked him to come to the back room for a second check. It turns out they caught a fugitive.

90 days earlier he murdered Martin Luther King.

He almost got away with it and had plans to go to Africa, where he knew the government would treat him like a hero. His name was James Earl Ray.

I tell you this true story because James took a big risk and it didn’t pay off. The critics of risk-taking will argue this is why we shouldn’t take risks. They’re wrong.

The deep unhappiness in society is the result of people wanting to live risk-free lives.

You can take calculated risks…and not end up a fugitive.

Money is the one area we don’t want to take risks

I run an online business.

Last week a customer asked if he could pay at the end of my year-long program. He wanted a guarantee so he could pass all the risk in life over to me. I said no and he got mad. Real mad.

It’s not strange if you think about it. People enroll at Harvard University & don’t ask to pay at the end of their 4-year degree. The risk is on you.

Harvard can do their best to educate you, but if you don’t show up and smoke crack out the back of the library every day, nothing they say will matter. You’ll be high as a kite and learn nothing.

The same applies to our homes.

We buy a house for our family. Beforehand, we’ve done a bit of research and perhaps seen inside the house once or twice. But do we really know everything about the house and the neighborhood? Of course not.

Now, do we ask the real estate agent if we can live in the home for a year to try it out and then pay after that? Of course not. No one would let you do that deal. Buying a home carries a small amount of risk.

If it doesn’t work then you can sell your home and move. That’s the risk you take and there’s nothing you can do about it.

The same applies to refund policies. People want to use a product or service for as long as possible then get a refund if they’re not happy. Half the time it’s not the purchase they made that’s the problem. No.

  • It’s their expectations.
  • Or it’s user operation.

You can’t live a normal life if you don’t take risks. And you 100% can’t be successful if you want to live a risk-free life. Risk is everywhere (by design).

Just being alive is risky.

This is where the risk-free life leads

I’ve met many of these people immune to risk.

In fact, I made love to one of them. Just kidding. That person was me. I lived like this for 10+ years. Never wanting to take a risk. Always expecting others to take the risks for me and cop any downside.

So I chose to work a boring job in a call center. It gave me fake job security. I learned to hate work. Monday mornings felt like death.

I got paid less than I was worth and had the hidden tax of inflation (that I didn’t understand) destroy me.

Every year my cost of living increased. My pay stayed the same. Occasionally I got some $50 department store gift vouchers as a small reward. WOW. THANKS BOSS!

Getting fired showed me this risk-free life was actually a huge risk.

My pay got cut off same day. I was thrown out into the hell of the job market, where I met AI resume screeners and racist white boy recruiters.

For half a year I had no pay. I ate through my savings and had to stop going out and seeing friends. Even a $4 coffee was a stretch.

I became deeply unhappy. I thought I was living the good life by choosing job security, staying comfortable, and taking zero risks.

It was actually hell.

Why the risk-free life leads to unhappiness

Deep down we’re smart.

When we drown in comfort and refuse to take risks our mind knows we aren’t living up to our potential. We feel something is off. We know we’re born for more. We don’t feel free.

It feels like you’re wasting your life.

That realization leads to the breakthrough that you’re also wasting your precious time. Then that downward spiral makes you remember you can’t go back in time and change things.

And the fact you’re getting old makes everything 10x worse.

Now you know where the unhappiness comes from. It’s a better guarantee than the one risk-free people ask businesses to provide them whenever they’re asked to spend a little money on their future.

Take a risk or you’ll be doing the same boring stuff for life

This is gonna sound drastic…

Either take a risk or go down the dark path to eventual depression. That’s how I think about this serious topic as a former mental illness sufferer.

Not taking risks is boring as hell. Every day feels the same. You’re not experiencing any rejection or failure, so there’s no growth. That way of life makes you numb to almost everything.

Taking risks leads to the best type of learning.

Maybe things don’t work out, but you’ll learn better lessons than you can ever get from the biographies of successful people.

Unless you feel the pain the lesson doesn’t stick to your brain.

Taking risks forces you to have skin in the game.

It’s why I like risks that involve money. They give me financial accountability.

If someone gifts me a free ticket to a $2000 Tony Robbins seminar, I won’t value it as much as if I paid that cash out of my own wallet.

The financial pain forces me to show up early, pay attention, listen, and get some takeaways from the giant that is Tony.

Have a portfolio of small bets

What we don’t want to do is go from a risk-free life to a big-risk life, the way James Earl Ray did. That’d be stupid.

It’s like going to the casino and betting your house on black. The best approach I’ve found is to have a portfolio of small bets.

They’re a series of small risks you take to improve your life and get to the next level of the game.

The idea here is, no one risk should wipe you out and destroy your future. By spreading the risk across a few opportunities, you have the worst-case scenario covered and you can bounce back.

Small bets look like this:

  • A side hustle
  • Writing online
  • Launching a paid newsletter
  • An experimental new income stream
  • A secondment at work to try a different role
  • Attending Toastmasters to learn public speaking
  • Testing out consulting, freelancing, or contracting
  • Getting paid for an outcome instead of by the hour
  • Starting a side business to see if entrepreneurship is for you

The risk-free crowd won’t try any of these experiments. They’ll just hate on them because they’re too scared to try themselves and they want to feel justified with their decision.

Final Thought

The most unhappiest I’ve ever been is when I lived risk-free.

I lived a life of permission slips, gatekeepers, waiting for the right time, and hoping someone would tap me on the shoulder with a big break. It never happened.

If I could go back in time…I’d have taken more risks. Learn from my mistakes and set up a portfolio of small bets.

Maybe one risk will have a huge payoff. Or maybe the series of risks you take, over time, will transform who you are.

The possibilities are limitless when you take more risks.

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