Why do we fuck up, or more importantly, why are we so afraid of fucking up? It’s inevitable. We all do it. I’d challenge anyone to name someone they believe has never fucked up. If they think they can, they’d probably name someone whom they’d consider to be of great achievement, and in response, I’ll give them a pat on the back, and say, “Congratulations, you just fucked up. You’ve named one of the biggest fuck ups of all time.”

The path to achievement, success, whatever you’d prefer to call it, is completely fucked up. That’s a good thing. Humans are fallible. Regardless of your current position, look left, look right, look behind and you’ll see nothing but fuck ups. Be yourself and that self will fail. When you fail, you find out more about the world, and crucially, your place in it. The best place to fuck up, however, is that place you see when you look ahead and can’t see any fuck ups. But wait! Why are there no fuck ups there? Where’s this place?

Well, it’s been right in front of you your entire life. That place you’re looking at is where your fears live. It’s that dark-blanketed-scary-untraveled-wilderness of self-doubt, which is filled with all of the things you wish to do but would never dare. Why haven’t you stepped in? Because the world tells you that you shouldn’t so you’re paralyzed by the fear of fucking up, of breaking a few rules, and ultimately, of facing judgment.

You can’t move, but you should. You should stop worrying, find a backbone, tell the system to fuck off and step in NOW!

Here’s why:

1/ In your own wilderness of unknowns, no one else has been there to fuck things up yet, therefore, the noise and consequences of others’ fuck ups is diminished to a life-altering zero. You’re free to fuck up on your own without the confusion and distraction of the mess left behind by others and the resultant laws meant to clean them up on the path more frequently travelled. This is fundamental to figuring out, once and for all, who YOU are. The world would prefer if you stayed the common path and has gone so far as to create boundaries to keep you well behaved on the straight and narrow. The best of us know that these are merely ill defined guidelines.

2/ One of the reasons you’re SO afraid of fucking up is facing the judgment of others. What will John think of me? How will Jane react to this? Extremely, what will the judicial system say? If you’re like this, you should shut the fuck up and that’s different than fucking up. When you fuck up in your own wilderness you’d be surprised by how little anyone gives a fuck. Determining whether you’re a nudist in the wilderness vs. main-street will have considerably different reactions, or that dreadfully scary word, judgment. Nevertheless, you might be a nudist and you’ll never know it unless you try it out.

*/ You don’t own the wilderness. Sure, it’s yours for a time, but you’re leasing it. When your fleshy self turns to bones, will you wish to have left behind a clear path for others to follow, will you wish to have left behind an amusement park for others’ enjoyment, at the bare minimum, will you wish to have known what was on the other side of the edge? I bet you’ll have wished for at least one of those things. Believe me, you’ve walked down others’ paths and enjoyed their rides to arrive at your own wilderness, and I assure you, that while you’re alive, that little bit of wilderness is the only thing that’s truly yours.

“Freedom is something that dies unless it’s used.”

Hunter S. Thompson

Fuck Ups


Rules vs. Guidelines

Stop being such a coward, break a few rules, fuck up a bit, overcome your fears, and maybe, just maybe, you’ll live a little beyond the process.

“You don’t learn to walk by following the rules. You learn by doing, and by falling over.”

Sir. Richard Branson

You jump up and then fall back down, gravity. You build a rocket and then what?

Our lives our predefined by fixed rules, this is finite. Only when you begin exploring outside of those can you become acquainted with this expansive and beautiful place called infinity.

To understand this more clearly, you must think back to a time in your life when you said, “fuck you, I’m going to figure this shit out myself.” Can you remember that time or has it been too long? That time of course is childhood. Absolute freedom, fuck ups abound – you’ve no real responsibility. I’ll talk about responsibility a bit later on.

Back when I was in elementary school, we had this forest that stretched along the backfield where we were allowed to play during recess. One of the many rules during recess was that we weren’t allowed to leave the backfield to venture into the forest.

At that age, this seemed arbitrary, if not stupid, for I was a great explorer. I would not accept the world was flat, no matter what the school had tried to tell me. The rules were skewed against my own progress, and so, I would tip the scales.

My brother, our mutual best friend and myself decided that we’d like to see what was beyond the tree line one day. Not more than 50 feet in, we discovered the forest dropped into a ravine and at the bottom ran a small stream.

As young boys do, we got messy, creative, played with our surroundings and built a damn out of rocks and sticks. We must’ve got too caught up in what we were doing and out of earshot from the recess bell, because we didn’t make it back to class in time.

We received detention for disobeying the rules and as was the tradition at our private school, we were lined up outside along the main building for all the parents to judge and chastise during afterschool pickups.

For whatever reason, our principal was uniquely enraged by the incident. When our parents arrived, they were told what’d happened, and I suppose, they were meant to share his outrage – they didn’t. Instead, they argued that we were just young boys doing what young boys should do, explore.

The principal proceeded to tell them the three of us were delinquents that’d never accomplish anything in life. Our parents pulled us out of that school and we’ve all gone on to accomplish a great deal of amazing things with our lives ever since.

A few years ago, I went back to where the school had been. The forest had mostly become suburban sprawl. Yet, a small strip of it had been left behind, separating the new neighborhood from the old backfield. I climbed down the ravine into that small bit of forest and despite human progress, what we’d built as kids had stood the test of time, the school hadn’t.

The lesson – if you want to be a principal, follow the rules. If you’d prefer to be an astronaut, make your own.

Fuck Ups


Perception vs. Reality

Why do some paths seem less fearful than others, when inevitably, they both lead to fucking up, why one’s more valuable, but why you should always do both?

“The edge… there is no honest way to explain it because the only people who really know where it is are the ones who have gone over.”

Hunter S. Thompson

Let’s consider John for a moment. He completely buys into this absolutely moronic slogan, no doubt you’ve heard it before, “What happens in Vegas, stays in Vegas.” Cool right? Well… Yeah, sort of, except, not really, because it falls into that spectrum of commonly excepted human falsehoods.

What happens in Vegas follows you around for the rest of your life, which holds true anywhere and always. So why then is John at ease with going on this journey of fuck ups? More curiously, why’s it that John’s happy, if not elated, sharing his journey of fuck ups with the rest of the world?

The answer is, perception. Much of the world, the average world anyway, thinks Vegas is this really cool place, and therefore, so does John. Yet, going to Vegas is kind of the equivalent of vacationing in the fallout zone of an H-Bomb of fucks ups. That isn’t to say it isn’t cool, it just means, you’re very likely to fuck up there. Regardless, given the average person’s perception of Vegas, John thinks he’ll be perceived well, if not praised, whether he fucked up or not – he did, and still, he’s fearless.

Anyway, a month’s pay, 20 Instagram shares and many fuck ups later, what has John accomplished? Nothing really, he’s achieved what millions of douchebags before him have done with considerable ease, mediocrity, and now, he brags about it. He did little, if not nothing, for himself, or others.

This fearless journey of fuck ups was easy and resulted in little, if any, value to its journeyman. John’s journey didn’t change the world and it didn’t change his life, curiously, it possibly worsened both.

The perception of this journey was positive, and yet, no one will remember John for this specific fuck up.

/ /

Alternatively, let’s consider Jane. She’s a struggling and aspiring young actor. She’s been at it for years, landed a few small roles and the like. The figurative expression, “break a leg,” has become quite literal for her – the deeper she ventures along her journey, the more broken her body and soul become.

Many people, even those closest to her, have begun encouraging her to give up on her dream and start considering other options. They care about her. Their perception’s that it’s difficult to make it as an actor, and they’re right, this is also the reality. Why continue beating herself up?

Much like John before, she begins buying into this groupthink. She’s almost ready to step away from it all. She’s tired of being left behind. Her friends are well off down the road of normality, careers, marriage, and in some cases, even children. When she gets together with them, they have story after story, they’ve just got back from Mexico, perhaps, Vegas – they show off photos of their celebrated mediocrity, and she senses, they look down on her for not having anything comparable in her own life.

At last, she’s ready to throw in the towel. She goes to meet her agent to tell her the news. Her agent’s disappointed, however, she tells Jane she has one last role that she’d like her to audition for. It’s for the stage, the play itself isn’t fantastic, but she thinks Jane would be exceptional in the role – “it was made for her.”

Jane decides to give it one last chance. She get’s the role. Just as her agent had said, the play isn’t great, it’s perceived poorly, but there’s one bright point, Jane’s performance which gets rave reviews. A big-time Hollywood film producer is in town and reads the review in the paper. He decides he’s going to go see her because it sounds like she could be perfect for an upcoming film he’s working on. She is, and so, he offers her the lead in his film.

This fearful journey of fuck ups was hard but resulted in great value for Jane. Just when she felt like she was being left behind, she made one last leap and jumped out well in front of her peers. Her difficult journey changed the world and her life. She goes onto affect millions with her art.

The perception of this journey was negative, and yet, many will remember Jane for this specific fuck up.


I suppose that this is a bit of a modern interpretation of, “If it was easy, everyone would do it.” Here’s the thing. Life’s this big canyon that everyone must attempt to cross. Some things are easy, others, not so much. Nevertheless, everyone must leap at least once because those are the rules of life and everyone breaks a leg at least once.

Living is about accumulative experience. You should indeed go the Vegas, you should also, be at the forefront of something you believe in when others don’t, but perception should never be determinate in preventing you from doing one thing or another.

The world only remembers those who’ve leapt and made it to the other side of the canyon, only experience can get you there, there’s no such thing as luck. Even those who win the lottery played with everything stacked against them, you didn’t.

Fuck Ups


Case Studies in Fuck Ups

Let me tell you one of the greatest fuck up stories of all time.

“Move fast and break things. Unless you are breaking stuff, you are not moving fast enough.”

Mark Zuckerberg

There’s this kid back in 2003, he can write some code and decides, in a bit of a drunken stupor one night, to create a website. What brilliance is this? It’s a hot or not site. Nice! But wait. He’s in college, and in order to create his site, he’s hacked into the college database to collect the content for his site. Not so nice! So, the college considers expelling him because he’s broken the rules, if not, the law. Fuck up! He appeals, and thankfully, they don’t.

Wow, close call.

That was cool, he thinks, but what to do with it? He doesn’t really know, so that semester, he creates another site based on a similar codebase. It’s dumb though and not nearly as successful as his earlier effort because it’s not well perceived. He uploads 500 Augustan images that people can comment on, most people don’t because, well, let’s face it, it’s not quite as appealing as rating your peers on their physical appearance. Fuck up!

Hmm. Now what?

A year’s passed and he doesn’t know what to do with his mounting fuck ups, so, he sees if there are any good ideas floating around that he can sort of just build upon. He meets three people who do have an idea and it’s pretty good. Great, he thinks, he can apply his codebase to that. He does so, comes up with a really stupid name for his new site, and in 2004 launches it. The guys with the original idea don’t quite like that he’s stolen their idea, or differently, started building his amusement park on an edge of their wilderness. As such, they sue him and four years later, he settles for $300 million. Fuck up!

Hold on! Did you say $300 million? Did we miss something?

Well, as it turns out, this kid fucked up enough to figure out what he wanted to do with his life. He built an amusement park, membership to the park will cost you even though it appears free – that’s the brilliance of it. Turns out that a lot of people like it, in fact, one and half billion have memberships one decade later and his wilderness is worth a few hundred billion dollars.

Perhaps you’re familiar with this story. Had Mark Zuckerberg not decided to venture into his own wilderness, care little about perception and the rules outside of it, we’d never have Facebook.

Oh yeah, did I mention he dropped out of Harvard to do all this?

Now, let me tell you my own story of fuck ups.

The other night I was joking around with my girlfriend that I was getting old. On the one hand, I feel old in a figurative sense, but on the other, I feel young in a literal sense. I’ve gotten to this age and still feel young by proudly avoiding most responsibility that others haven’t. Perhaps, you’re thinking, well that’s an odd thing to have done, and specifically, to be proud of, what about a career, a house, a family, so forth and so on?

Well, let me explain.

Firstly, avoiding responsibility was a purposeful decision that I made several years ago to my parent’s chagrin. Secondly, you’re thinking about the results of responsibility avoidance incorrectly because you’re thinking like everyone else.

How so?

Well, I’ve had a better career than most because I explored many different things throughout the years, this has allowed me to not only become an expert generalist, but also, enjoy almost every aspect of what I was working on at the time. In this sense, notwithstanding, your earnings ceiling, your career is finite, mine is infinite. The deeper you go into your career, the more limited you become. This works in every aspect, but think of it more narrowly, as your responsibility increases so too does your risk aversion, you become scared, complacent, and ultimately, your progress reaches a plateau – the world moves on, you become a buffalo.

I’ve lived in many different places and in many different countries. The rest of the world looks very different from your downtown Toronto condo, or if you’ve played the normality game correctly, from your Forest Hill home. I’ve witnessed and experienced much of what the world has to offer. Believe me when I say, the rules change from place to place and you can’t possibly know the game you’re playing unless you know the entirety of it. We live in a growing period of globalization, if you’re local, you’re already dead – you just don’t know it yet, because you don’t know anything at all.

Lastly, my family is comprised of exceptional individuals only, those I’ve chosen, but much more importantly, those who’ve chosen me. Being able to move through a variety of experiences, both in work, as well as, locale, I’ve been able to create a strong, trustworthy and open network. Network in the tightest of senses here, because most of these people would go the distance for me. By traversing several places and aiming to be the best in each of those, even if I’ve failed or fucked up at times, I’ve inevitably encountered the best of what each place has to offer. Knowing when these worlds will collide is the greatest knowledge anyone can hold, causing it, the greatest power.

I started fucking up as it were, at a very young age, however, the most dramatic shift in my life occurred after I’d started feeling the weight of adult like responsibilities. I was in my final year at a very prestigious college where opportunity abounds. Still, there was a conflict, the more opportunity that presented itself to me, the narrower my freedom became – I had to make a life defining limiting decision.

As such, I dropped out in my final year during the worst economic climate since the great depression. My parents were perturbed, if not, enraged. My friends couldn’t understand, but I did, and that was all that mattered. Everything looked bleak to everyone else, but to me, bleak presented nothing but upward freedom – I was going to throw myself out into the world and take on every dark corner of it that literally scared the fuck out of me, and sadly, all of them.

Seven years later, I’ve done incredible things, and I’m only just getting started. I’ve had the most amazing experiences imaginable, things so obscure or protected I can’t even write about them here, things so unique, only a handful of people have ever experienced them themselves.

The world wants you to be the round hole, yet, what it really needs is the square pegs, and for your part in all of it, would you prefer to be the one doing the fucking, or the one getting fucked? There’s no such thing as life for those who sit around and just take it – you’re life’s bitch hooker.

Which of these would you prefer to be? Go out into that scary wilderness, break a few rules, fuck up a lot and find out for yourself.

Fuck Ups

“There is no such thing as paranoia. Your worst fears can come true at any moment.”

Hunter S. Thompson