Risks Worth Taking

Rainbow Rain Girl by Banksy

Whether or not the story is true, the man’s tale goes something like this. 

It was five hundred years ago when he set sail with a fleet of eleven ships for the Yucatán Peninsula. He left from Cuba without ever receiving permission from his governor. 

The time was that when such an act of disobedience was punishable by the type of death much worse than a clean and quick guillotine chop. That was reserved for the best of the worst. The worst of the worst, traitors, were punished with techniques designed to make them lose their mind before their life. 

You know, low simmer in big iron pot type stuff. 

So why did this man and his small fleet take such a risk?

There had been reports that this foreign peninsula held more gold than the world had ever seen, and he knew that if he were able to conquer the land, he would become one of the most important figures in all of the Spanish Empire. In fact, he was betting on it.

When his men started to push inland, however, they quickly realized they were not only far outnumbered by native forces but also ill-suited to fight in jungle climate. Their armor was hot and heavy, and their boots were too stiff for the soft terrain.

Uncertainty began to spread among the ranks. They spoke of leaving. Why should they be the ones to do the hard work? After all, they weren’t even supposed to be there. Perhaps the governor would forgive their pardons if they abandoned their leader and returned. Why should they be the ones taking a risk?

Sensing his men's waning spirits, the commander secretly assigned his closest guards to sneak out in the dead of the night and set fire to each of the ships.

By the time the alarmed soldiers stumbled onto the sticky and smoky beach, it was too late. Their ships, with all of their hopes of comfortably sailing back to safe lands, were nothing but charred skeletons sinking into oblivion.

Hernán Cortés and his 500 men would go on to lead the most influential campaign against the Aztec Empire.

***

Can you simplify the whole of people into two groups? Probably not. But this is my essay so I will.

There are two types of people in the world: those who have visions and take the risks required to bring them to fruition, and those who have visions.

That's it.

We often ask successful people how they reached the top, how they became so good at what they do. Questions like these couldn’t be a bigger waste of breath. We know exactly how they did it; we just don't want to do it ourselves. 

Evolution has wired humans to seek comfort and security rather than risks and sacrifices. That inclination is entirely natural, and there is nothing inherently wrong with it, as long as you are satisfied receiving the same outcome as everyone else.

What if you aren't satisfied? Isn’t it selfish and unjust to want something that the majority doesn't have? We've certainly been conditioned to think so.

Personally, I don't subscribe to self-limiting, communist ideals. Fighting to bring your own vision into existence isn't selfish; it's the contrary.

If you start making decisions to identify and align with what others deem as appropriate and fair rather than trusting your instincts, you not only betray yourself in the deepest way, but also cheat the rest of us by not becoming what you were destined to become.

People aren’t designed to be interchangeable.

Utopia isn’t some clean, orderly world where everyone sits around eating cakes and sleeping. Utopia is a place where everyone has the privilege to take the risks required to pursue their vision (and eat cakes). 

But we don't live in a utopia. Many of us will never be able to comfortably take risks.

Then again, risks were never meant to be comfortable. Even if you had the ships, sometimes the best strategy would be to burn them.

***

Unarticulated ideas aren’t worth a half-dime. That’s the first reason why I had to write this essay.

I’d been fumbling around with a vague conception that a risk appetite was somehow important. Now, I realize what an egregious understatement that was.

Taking risks is not merely important; it’s a necessary requirement for a meaningful life.

Take stock of the people you admire. It’s not a coincidence that every one of them at some point in their life took at least one major risk. Now reflect on your own life. Do you think it’s a coincidence that the periods where you grew the most followed a risk of some sort? 

Unlike your mother, fortune does pick favorites. Your boldness will be rewarded.

But oftentimes, pursuing risk means openly disregarding the advice most people offer.

It’s not that the risk-taker doesn’t care about these people and their opinions, but rather that they possess a radical trust in their own intuition. Or in Cortés’s case, a radical short-sighted ambition for glory and gold. 

Furthermore, the bulk of advice (especially when unsolicited) assumes that all parties are optimizing for the same end goal.

This passes as acceptable because most people do share the same definition of success. Most people also never take the time to define success for themselves.

The second reason for this essay was because, well, I’m burning the ships.

Life in Montana is simple, peaceful, and quiet. Long term, when risks become too risky, planting the flag here will be ideal. In the short term, however, this level of comfort doesn’t support my vision of growth.

In other words; I’ve got to ramble.

The new adventure is as follows: I am taking every dollar of my sweat-stained, waiter-boy savings ($15,000) and schlepping it abroad to see if I can monetize my mind before I run out of peanuts and popcorn.

More specifically, the immediate goal is to monetize my mind in a way that aligns with my definition of success. Depending on which country I’m in, my savings should provide eight to ten months of runway.

The journey will be documented in words (essays), videos (YouTube), and through a podcast that I’m launching. The goal is to publish two essays and one video each week, as well as one podcast every other week. My newsletter, Rambles from a Rogue, will highlight the best of these projects twice a month.

Since I am optimizing for production (reps), my previous road-ripping style of vagabonding will have to be stowed away. You don’t take a Land Cruiser to the race track. Wrestling hostel hydras while bouncing between countries like a pinball is not conducive to workflow.

I’ll spend two to three months in each location, and naturally, leave a small buffer for side-quests between each of these working blocks. After all, art can’t imitate life if there is no life.

The question I asked myself to determine if this idea was born from an unruly impulse or my intuition was:

If I knew this was going to fail, would I still do it?

Would I still set sail if it meant coming home broke and having to toil through yet another detestable job while I rebuild? 

The answer is, of course. I knew that immediately. The question hardly had to be asked.

I’m not satisfied with the standard rewards society offers. I don’t accept the gentle nudges pushing me onto the traditional and predictable path. My dice in life were not meant to lie dormant, collecting the dust of my forgotten dreams while I surrender to a life lived vicariously through others.

To hell with that!

Life is meant for the living. Bring on the sacrifices and risks and setbacks and failures and humiliations. If that’s what is required, then I welcome it all with open arms!

As for you, dear reader, if you made it this far, it’s either because you are worried for me and are gravely hanging on to each irrational word, or because you feel the same fire within yourself.

To the latter group, you might as well feed that fire. Let it spread to your ships. Find your curiosities, lean into them, look weird while pursuing them. This is the path to maximizing your value in society. I’d much rather have you create something of your own than sit back and follow my journey.

As for those who may have concerns for me and my uncertain future; I love you. How wonderful the world is when you know that others care for you.

If it helps, imagine that I am doing this so the conversations at Thanksgiving won’t be limited to weather and football. Besides, at this point, I’m afraid that it would be quite impossible for you to change my mind.

By the time you finish reading this, I’ll already be halfway across the world.

"The function of man is to live, not to exist. 

I shall not waste my days in trying to prolong them. 

I shall use my time."

 - Jack London

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Kill the Curious Cats!