Fortune Favors the Bold

Fortune favors the bold.

When I left for Amsterdam and Bangkok, skipping college for the first year, I had worries. Surely, it would make sense to be a college-student before I traveled. Before I become “de-institutionalized.” If I don’t head to college first I’ll lose everything I worked for!

I’m not saying that won’t happen. It might. But, I doubt it.

But, let me ask you a question.

What would be the word you would use to describe quitting a safe job to make a living off writing? The word would probably be foolhardy. Okay. Different situation: What word would you use to describe spontaneously booking a $1,100 ticket to Costa Rica on a whim?

Stupid. If you wanted to be delicate about it.

I’ve done those three things: Traveled at 18, quit a safe job, and booked a one-way flight to Costa Rica on a whim. For better reasons or for worse reasons; I’ve done them. And in the back of my head I’ve called myself stupid plenty of times. But, to be honest, if no one is calling you stupid you’re probably not doing cool shit.

The jury is out on how quitting my job to write and booking a spontaneous trip to surf, write, and travel will turn out. But, I want you to consider two mental models and look at these decisions in a new light.


Mental Models

The first: Consider whether or not you’re on the side of the majority. If you are, ask yourself why you’re on the side of the majority. It probably won’t be because it’s a decision you really believe in. It’ll probably be because everyone else is doing. That’s one of the reasons I forewent college to travel. Everyone else was doing it. Why wasn’t I? I’m not saying I’ll never head to college, but when I do, it’ll be because I want to head to college.

That’s one mental model — an immediate systems check whenever you’re on the side of the majority.

The second mental model is helpful for “risky” decisions. How would you classify quitting a safe job? ‘Risky.’ How would you classify spontaneously booking a trip to Costa Rica? ‘Risky.’

Is it really risky, though?

Ask yourself: “How difficult would it be to get back to where I am right now?”

On a similar note: “What’s the potential downside versus the potential upside?”

When I quit my job to write, the potential downside was: I go broke and pick up another hospitality job. So the potential downside is minimal. I can always get back to where I started.

The potential upside, however, is a COMPLETELY different story.

The potential upside is, if I make money from writing, I’ve unlocked a completely different financial inlet. If I can start a trickle here, I can make it grow into a stream. And then we can say goodbye to working at diners and restaurants. We can say hello to traveling all over the world and only needing a laptop.

Massive potential upside; minimal potential downside. See where I’m going with this? So, quitting a stable, safe job (so risky, oh my god) turns into an easy choice — quit and see what happens.


Risky Decision #3

And finally, we come to spontaneously booking a flight to Nicaragua / Costa Rica.

The ticket was $900. That’s a decent price for a ticket leaving in two weeks. I’d be leaving to travel about a month earlier than I thought; saving money on rent and expensive food. More importantly, I’d be able to spend every day surfing and writing.

Two weeks from now, instead of a month…

My mind flipped to a phrase — fortune favors the bold. I’d learned that from a biography on Alexander the Great. But I waited. I wanted to see what my parents thought of the idea. Queue me falling asleep, waking up at 3am, and checking the ticket prices. They’d jumped $600 in four hours. I almost threw a postcard across the room. Grumbling, I tried to close my eyes and fall back asleep.

But, what about other Central American countries? Smack open the laptop. Check other prices. Become more enraged. Slam the laptop closed again. Close my eyes.

You know, in a biography of Sir Alex Ferguson — the legendary football coach of Manchester United — he said if he woke up in the middle of the night his sleep was finished. He would wake up, start his day, and think about ways to make Manchester United better.

A glance at the clock. It read 3:47am. I sighed. I wouldn’t be able to sleep anyway and there HAD to be a cheap flight to Nicaragua somewhere. I wasn’t bold. I didn’t take advantage of the flight opportunity because of my indecision.

I vowed if I found a cheap flight across the world I would book it then and there. A second chance came my way — I seized it with both hands. And now a flight to Nicaragua has one seat reserved for me come 15th November.

In a biography of Alexander the Great one key element pops up over and over: Fortune favors the bold. Sure, things went wrong for Alexander from time to time. But also over and over his boldness and daring lead to great rewards. It’s why we remember him.

I almost missed the opportunity to spend the next few months surfing in Nicaragua because of indecision. When I was given a second chance — which we can never expect — I took full advantage of it. Sure, it could be considered foolish to spontaneously buy an $1,100 ticket halfway around the world and completely change the plans you’d made for the next month.

But, the most dangerous thing you can do is play it safe.

It only takes a closer examination to realize I wasn’t really clinging to safety; it wasn’t an incredible risk to book that flight. I was planning to head back to the Western hemisphere anyway, and would have had to book a flight soon.

It was my clinging to what was comfortable and safe that almost made me lose the opportunity to surf, travel, and write for an extra month. It was the spontaneity of the decision, the boldness it required, that almost startled me into inaction. And in the future I’ll remember — fortune favors the bold.

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