Monopoly: An arena of opportunity

How board games inspire our real selves, imposter syndrome, and branding

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Monopoly: An arena of opportunity

You don’t know who you truly are until you play Monopoly.

Most of us have played Monopoly by now. The game’s tendency to devastate friendships and families has been an ongoing joke for some time now.

I’m a competitive guy. But I generally much prefer having a good time over winning. I show up for the banter and camaraderie that spawns from playing games with friends. 

I find myself staying despite raised tensions. Others around me start to escalate.

Then I play to crush my competition.

Two specific scenarios stick out with regards to this hell-ridden game. The first time was a bit over a year ago when I sat down with my friend and his family to engage in capitalism. 

My friend and his family are the most competitive people I know. It was undoubtedly the most I had ever gotten frustrated playing a board game. I was viscerally pissed when they didn’t pay rent while I was too distracted to call it out. 

I also grew more enraged each time they disrespected my trade offers.

I was losing quick and desperately didn’t want to encourage an ego-trip. As someone who has never played Monopoly much, I had to develop a strategy if I wanted to win. Quick.

The party complained about nearly every move I made. But that made me want victory more.

And to save you a long story, my strategy slowly evolved into paying attention, collecting rent, and swallowing property like a great white feeding on prey.

And I won. I will not lie to you. It was an amazing feeling. You bet your ass I rubbed it in.

The second memorable time was just the other night when I played it again. The night had already wound down but someone suggested we play Monopoly. There was a palpable feeling of uncertainty in the room.

Anyone that has played Monopoly knows that it’s both a massive time commitment as well as a fast-pass to aggression.

I knew two of the three other players very well. Or again, so I thought.

The quieter of two of my friends became a strategy mogul. He was plotting what a checkmate might look like well in advance of everyone else. The more amiable of the two swiftly became intense. And just like that, I have locked in again. 

The night evolved from a casual hangout into a conquest to take over the world. We argued rules and ethics. There was a shit ton of uncollected rent.

I watched idly by as my friend would pick up the dice, knowing full well tossing them would negate the meager $26 debt to his wife for Pacific Avenue. You have to pay attention.

And to save you another long story: I didn’t pull the win again. Like before, I slept in the beginning and waited too long to feed on property.

A few fundamentals through these experiences largely apply to life.

You have to pay attention

I often give the benefit of the doubt in life. When someone makes a mistake, I’m quick to abolish guilt and try to rectify the situation. True competition does not offer that luxury.

In the most recent game, I was poised to win pretty early. I had extremely lucky rolls and owned property of every type. I made one bad trade and blew up my leverage. I should have paid better attention. Play stupid games and win stupid prizes right?

I also observed almost every single person (including myself) miss out on collecting money when one another landed on properties. It’s easy to get distracted but it’s ultimately money left on the table.

Remember: everyone is playing to win, and no one will collect for you.

In life, it can be very similar. You need to pay attention to opportunities around you. Unless you’re in a strategy role, you’re primarily compensated for your efficacy to save your manager time and improve business. Make life easier on your manager, you’re guaranteed to do well.

Or it can be as simple as picking up additional skills. But you’ll never know if you’re not paying attention. You need to constantly look at the opportunity around you.

The game Monopoly is aptly named, as the winner generally ends up being the individual with the most property on the board. In life, and in Monopoly, you have to keep your eyes open to opportunity in order to seize it once it arrives.

And so when you land on an available property - you damn well better buy it.

Be prepared to play against the grain

When you don’t play by the book, people get pissed. In Monopoly, that’s no different. There are trades that will arguably make more sense over others. If you’re playing with seasoned experts as I have, you might feel like you’re occasionally dealing with a flailing toddler when the going gets tough.

But guess what? I never studied the playbook. I’ve played the game a handful of times in my life. And this actually felt as if it served a benefit to me. I wasn’t blindsided by a strategy I had developed over years. I wasn’t following the book, I was developing my own strategy on the fly that my friends often reminded me was inherently broken.

But in both scenarios, despite criticism, I rose to the top.

In life, doing what everyone else is doing is the best way to be rewarded like everyone else. 

Elon Musk’s proceeds in the PayPal acquisition netted him a cool $180 million. An amount to live an incredibly luscious life with enough to live off of investment dividends in perpetuity.

But he proceeded to invest $100 million in SpaceX, $70m in Tesla, and $10m in Solar City. He is quoted saying that he had to borrow money to pay rent.

On paper, this is outright idiotic. Anyone following a playbook would never encourage this erratic behavior. But we all know how this story plays out. The man is building rockets, digging out tunnels, selling flamethrowers, and amassing empires. 

So no, I won’t be trading my boardwalk for two of your properties. I don’t trust you.

Much like life, monopoly is ultimately a game of chance

The other night my friend had a clear advantage after I made a bad trade. I wasn’t paying attention and passed him a brown property for some needed cash.

On paper, my trade made all too much sense. By not paying attention, I couldn’t see the forest for the trees and gave him a one-way-ticket to building a hotel empire.

And so he did, and it was marvelous. He laughed, bragged, and ultimately made me feel like an idiot for my bad trade. It was undoubtedly a learning experience and a well-leveraged move on his part.

But then he miraculously landed on every single income tax space, turn after turn. The group almost died laughing every time he would roll and land on an expense. 

Even the chance cards would require him to pay each player. I’ve seen bad luck before, but this was truly a spectacle. I suggested to him that he not visit the casino that night.

And I wish so badly I could say that he won, despite having the obvious advantage. But it was my other friend’s wife who won. She played quietly, tactfully, and landed on all the right squares.

You need to be prepared for the reality that sometimes no matter how hard you try, or how much of an advantage you have, you run the risk of landing on the wrong squares.

And I wish so badly that I could tell you that life is fair. It is not. This reality should never discourage you from continuing to try.

When you start a fresh game of Monopoly, you’re given $1,500 and an open board. And the longer I look at that open board the more I realize that it’s an arena of opportunity. 

Life is a lot like that, too. We’re all in the same arena. Some approach it viciously, some approach is strategically, and some, can’t be bothered to approach it any way whatsoever.

But there is one absolute truth I’ve realized about this arena of life and Monopoly.

I’ve realized it’s mine for the taking.

Imposter Syndrome

The feeling of imposter syndrome is something that all creatives deal with from time to time. The psychological pattern that we aren’t actually competent enough to be working on our projects at hand. This is something I actively struggle with in my career - and everyone who knows me is well aware of it.

I’ve had managers from the past outright tell me that I needed to improve my confidence in decision making. I’ve had friends offer honest advice that I need to more effectively speak to my accomplishments. I’m working on it.

This story really resonated with me. I looked into it more and read this amazing oral history surrounding the inception of the legendary Goldeneye 007.

The entire team was less than 10 people, in their late 20s/early 30s. They were recent university graduates, bumbling with ambition, missing a resemblance of game development experience. When the game launched at a conference, it was hardly a memorable experience. The entire team struggled with imposter syndrome and architecture that everyone hadn’t worked with (as the N64 hadn’t been released yet).

You also likely know where this is going. The game is frequently cited as one of the greatest video games of all time. Pretty damn good for a group of fumbling graduates.

Newsletter Branding

I’ve really leaned into this newsletter as my creative outlet. It largely started as a means to distribute my work but has resulted in my primary outlet.

There’s also hundreds that read this each week - which is incredible.

I wanted to more accurately depict my love for this newsletter and decided to take the branding and messaging more seriously. So with that, here’s the new logo:

Would love to know what you think.


Building Writer’s Bloc

We now have over one hundred members that have joined our Slack community. Pretty incredible to think about considering it was built by three guys who didn’t know each other before this year.

We had a discussion earlier this week with the most people we’ve ever had. There was a pretty fun after-party. Next week, we’re hosting Carol to speak to everyone about writing a badass resume and cover letter.

Trying to build a thriving, paid community is unlike any other business.

Until next time,

Cullin