Just Do It! The How and Why of Risk Taking

Lessons From Latin America

A ship is safest in harbor, but that is not what ships are built for.  

Another thing that travelling Latin America (LATAM) taught me, which I simply would not have learned from living in Calgary, was how to take risk. A few particular experiences come to mind.

The most thrilling risk I took was riding motorcycles. I was both afraid of and prejudiced against motorcycles because they are coffins on wheels (to quote my grandfather) and because bikers are be annoying when they rev their bikes.

One day, I was late for a meetup on the other side of the island of Florianopolis, Brazil. A regular Uber would’ve taken 30 minutes, but a motorcycle Uber would’ve taken less time and money. So I ordered one. The guy pulled up on his bike and gave me a helmet. He didn’t speak English and I didn’t speak Portuguese. Away we drove! For 20 long minutes I clutched his bike’s rear handles hoping we wouldn’t crash, fall off, or skin our knees. We went up and down big hills and drove around bends and lakes. Fortunately, the guy was a good driver and drove safely. He sped up and slowed down gradually. We only weaved between cars when there was ample space. In the end, I got to the meetup in one piece, on time, and with shaking legs.

It was so fun that I kept doing it. I traveled frequently on motorcycle Ubers in Brazil and Argentina for the rest of my time there. After having so much fun on motorbikes, I came to feel bad for claiming that bikers who rev unnecessarily are just overcompensating for having small penises. So much of prejudice comes from ignorance. I had failed to see that the roaring motorcycle is one of the few remaining strongholds in our culture of unencumbered, free flowing masculinity. A roaring motorcycle, like raw masculinity, is brazen, assertive, intimidating, unapologetic, dangerous, and magnetic. Before riding them, bikers with their annoying roars made no sense. But now they do. And I want to roar too.

I concurrently learned to take risks from a good guard passing instructional. The secret to passing any guard (ie. how to get past someone’s legs when they’re pushing you away from the ground) is to put your weight on them at all times. When you first do this, you get reguarded and swept a lot because your weight is forward and you have no base. But the more you do it, the better you learn to balance on someone while they move. There’s an ugly period of learning where you fail repeatedly. But with patience and persistence, each of these failures turns into a greater gain: an instinct for balance. The only way to develop that instinct is to put in the reps. If you don’t, you won’t learn.

The lessons of jiu jitsu apply in life too. Turns out that I had been too risk-avoidant as a teenager and adult. So I swore to myself that I’d take as many risks as possible to catch up for lost time. That brought me to running by the beach in Lima, Peru.

Lima’s a beautiful ocean city. It’s protected from tsunamis by steep black cliffs of soil, on top of which are parks. But between the cliffs and the ocean is a highway.

Here’s a photo from a jog one evening. You can see the ocean, the highway, the cliffs, and then the lights of the park above it:

I would run after work at night in these parks because there was plenty of light and police officers. But I wanted to see the ocean, to run beside it and smell its fishiness and hear the waves crashing into the rocks. The only problem was that running on the highway seemed dangerous. In case a car stopped to mug me, there’d literally be nowhere for me to run!

One evening, I thought I’d taunt my inner bitch. That was a great day. I descended the long dark staircase leading down and found the ocean. Turns out that there were police around, that only some stretches of the beach were poorly lit, and that most of the people there were lovebirds enjoying a romantic night together. It was beautiful! Just as with motorcycles, my presuppositions and rationalizations were wrong. Taking that risk to go down falsified them and gave me new, better information. That wasn’t the most scary risk though.

The scariest risk I took was killing cockroaches. They’re huge, disgusting bugs. On nightly runs, one would always pop out of the bushes. My cockroach-phobia soon became a problem, because my phone would jump out of my shorts whenever I jumped away from the cockroach. Then I’d have to wait for the cockroach to go away to pick up my phone.

To fix, I had to learn how to step on a cockroach when one got in my way. It’s still hard for me to do this. They’re not soft and fragile like a mosquito. They’re big and structured, so there’s resistance if you step lightly. When you step heavily on one, you can feel and hear its exoskeleton crunching underneath your shoe. After you pick up your shoe, you see its juices in a blast radius around its shattered body. Disgusting. When I first started killing them on my runs, I’d stomp with the top-half of my shoe and back away immediately, in case it started to chase me. But I’d either miss the cockroach or wouldn’t apply enough force. So then I forced myself to step on it with my heel and body weight. That worked, and I finally learned to kill cockroaches.

JBPeterson once mentioned that initiation rituals are how societies calibrate the nerves of their young men to know the difference between danger and pseudo-danger. The initiation ritual of the navy seals, for example, is a swim through shark infested waters at night from an island near San Diego to the mainland’s shores. I didn’t do one singular thing that was as dangerous as that, but I did do a string of things that formed a continuous initiation ritual. As a result, killing cockroaches, running by the ocean, and riding on motorcycles made me less neurotic.

The last risk to mention is one that I almost missed. For context, strong, direct eye contact is a risk. Men usually only stare at each other before they fight (or f**k, but mostly fight). One Tuesday morning, a super hot guy walked into WeWork and sat down near me. I thought I saw a flash of anger in his eyes when we made eye contact, so I figured he was straight and upset that I was checking him out. I looked away and got back to work. How wrong I was! He messaged me on Grindr a few hours later and we went on a date later that evening. He turned out to be the hottest guy I had ever met. It turned out that in our first moment together, he was checking me out too and that he wasn’t angry - he was just eyeing me up. The experience was an eye-opener.

It was only because he reached out to me on Grindr that I learned that he liked me back. Thanks to him, I learned that I must’ve missed out on so many opportunities simply because I preferred the comfort of certainty that comes from pessimism over the discomfort of the unknown. When he first made eye contact with me, I chose to shrink away in fear instead of seeing where things could lead. Maybe there could’ve been a fight. But maybe there could’ve been an exchange of phone numbers too.

Now, I am now absolutely shameless in approaching people who lock eyes with me. There’s always a reason for why someone’s looking at me. Maybe they’re into me! Maybe they’re angry at me. Maybe they like my eyes. Maybe I have spinach in my teeth that they can tell me to remove. In any case, I want to find out why they looked at me. I now try to never break eye contact first, as I can’t know for certain why the other person is looking at me. If someone’s looking at me, I strike up a conversation with them to figure out why.

There are many pseudo-fears that pop up when maintaining eye contact or when starting a conversation: the fear of rejection, the displeasure of being seen suspiciously, or just being seen as weird. But after starting conversations with at least 20 strangers, I’ve learned that most people are focused all on themselves. Only one conversation that I struck up with a guy at a coffee shop didn’t go well, but that too was only temporary. An hour later, the guy came up to me and told me the real answer to my original question: the secret to dressing well is to get a girlfriend. If the conversation doesn’t go well, you can bail and never see that person again. There’s no downside.

When you’re faced with these pseudo-fears, the best thing you can do is throw yourself into the situation. Action is the antidote to anxiety. The more you throw yourself into the unknown, the more information you gain. And thus your bias for action should be directly proportional to your ignorance. This applies to things like riding motorcycles and picking up guys, but I suspect it also applies to things like speech: if something seems wrong or unethical or bizarre, say something! It doesn’t have to be perfect or well constructed. It can even be offensive, rude, or reputation destroying. You’ll undoubtedly learn how to better approach a situation like it and recalibrate for next time.

There’s a voice in me, as there is in you, that will rationalize you away from taking risks like jumping into a cold plunge or descending the dark stairs to run by the ocean. Whenever you notice this voice whining within you, you must endeavour to do whatever it tells you not to do. Taking risks will change your life for the better. It will be fun (motorcycles), it will cure your anxiety and neuroticism (cockroaches), and it will teach you the things you need to learn so quickly (meeting strangers).

Perhaps this is easy to write from the comfort of my couch, and that one day I will take a fatal risk. Maybe a drug cartel will abduct and kill me, maybe I’ll fall of a motorcycle and die. And then I’ll think “hmm, this wasn’t a great risk to take.” But perhaps it’s instead better to live a full life that leaves nothing on the table than it is to die without ever living at all. That is not to say that you should be stupid and careless. Just like investing, the ideal is to take risks that let you take more risk. But you cannot live a full life without taking risks, and you cannot know which risks are really stupid without taking risks to start. It’s not like avoiding risk is risk-free: you can end up in a car crash, you can end up dying through exposure to toxic mould that they only discover after your autopsy, you can get terminal cancer randomly and die in 6 months. There is no risk free life. You just get to pick the ones you take on. I suggest picking the voluntary risks.