When I was a kid, if something didn’t go my way, my dad would say “Life’s not fair.” I can’t say I appreciated that at the time.
I’m not sure if there’s a fairness gene, but if there is, I have two copies and I can see it in my kids too (though I suppose there’s still a nature vs. nurture debate there). Don’t get me wrong, I’m competitive and I play to win (no, I’m not the parent who lets my kids win; this might have a tiny something to do with why my husband is usually their favorite). But I also find victory unsatisfying if I’ve taken advantage of an unfair loophole and I get pissed off when I realize someone else is “breaking the rules”. A former boss tried to knock this out of me by pointing me to a summary of “Scrubs” in the gaming world. I could relate to the scrubs, this wasn’t a compliment… I can’t say I appreciated that at the time, either.
A scrub is not just a bad player. Everyone needs time to learn a game and get to a point where they know what they're doing. The scrub mentality is to be so shackled by self-imposed handicaps as to never have any hope of being truly good at a game. You can practice forever, but if you can't get over these common hangups, in a sense you've lost before you even started. You've lost before you even picked which game to play. You aren't playing to win.
A scrub would disagree with this though. They'd say they are trying very hard. The problem is they are only trying hard within a construct of fictitious rules that prevent them from ever truly competing.
From “Playing to Win” by David Sirlin
But maybe I’m coming around to it, in my own way. Maybe not, I’m not sure.
My youngest is currently obsessed with the game Munchkin.
Every game has an “Objective”(typically called “Winning”).We aren’t handed a game objective when we emerge from the womb. It often takes several decades for us to figure out our ultimate aim and plenty of people have an opinion on the games we should be playing in the meantime. Throughout our lives we’ll play many different games and figuring out what strategy we’re optimizing for is a deeply personal journey,1 but I digress. At any given moment, we likely have some sense of an objective for the present moment (whether or not it sticks for the long term) - the question becomes: how are we going to play the game?
When you have different rules (and different luck)
A core assumption in any game is that every player has the same rules and the same opportunity. Sure, luck can play a (big!) role in any game (my mom has an uncanny ability to role double sixes in the end game of backgammon), but at t=0 everyone has the same potential for luck and what differentiates expected value is skill. To be clear, I’m totally fine exploiting flaws in game design (e.g. a single overpowered strategy) to win, I just find those games boring until everyone is aware of that strategy and it no longer works so I have to find another path to victory. But in the real world, the deck is stacked and there are MANY flaws in the game design.
Well designed rules keep luck in check. Multiple paths to victory counterbalance each other. When well studied, rules can be used to your advantage. But in life, not only is the deck stacked, but access to the rulebook (i.e. people who understand how to play the game) is often determined by luck as well. It’s as if at the beginning of the game, you roll a die to see how many pages of the rulebook you get to read first.
When we’re young, we rely on those around us to hand out rulebooks: parents, teachers, friends, bosses, VCs… We consider the lucky kids the ones who had lots of rulebooks to follow. They study hard, say no to drugs, run for student office or volunteer at a charity. They bask in the light of the gold stars awarded in the form of good grades, college acceptance letters, and proud parents. And then they realize that other folks are getting ahead and seem to be playing by a totally different set of rules.
The high school stoner who now has a booming local real estate business, married a cheerleader, and has two and a half perfect children
That kid who never showed up to that econ class is now the CEO of a hot fintech startup
A VC turns down funding an actual product while funding a competitor in your space with nothing more than a slick story
A convicted felon who brags about sexual assault is elected over a woman with a few decades of pretty clean-cut public service
So how do they do it? Are they playing a different game? Are they following a different set of rules?
I recently read The Third Door by Alex Banayan and found it both inspiring and infuriating. Without spoiling more than you learn in the first few pages, Alex decides to drop out of college in order to create his own leadership education by interviewing role models. Many trials, tribulations, and lessons ensue. Eventually, he interviews Bill Gates. Success! What I love most about this book is that it so clearly highlights his awakening to the realization that there new ways to play the game, new ways to stack the deck. Alex starts out following all the rules: hustling, drafting and re-drafting perfectly crafted emails over many days, researching as much as he can about his desired subjects - and he gets almost nowhere. He then cultivates a mentor (i.e. someone with a rulebook) who has successfully played this game himself and finds himself buying last minute plane tickets to exotic locations, staying up all night at clubs, and having hungover breakfasts with Tony Hsieh. Many fewer emails later, he finds himself almost effortlessly hanging out with people he wasn’t able to get meetings with “professionally.” He had learned the power (and staying power) of relationships and the new rules or cheat codes they unlock. He also unwittingly revealed how great it is to be a dude, but I digress once again…2
Stock vs. Flows
Most games involve both stocks and flows - you accumulate resources in a deck (stock) but only draw a handful of cards and have a limited number of actions per turn (flows). In personal finance, we have stocks (wealth/debt) and flows (income/expenses). In leadership, we have stocks (trust / relationships) and flows (actions). At the beginning of a game, flows are all that matter: everyone’s stocks are equivalent3 and the question is what actions you’re going to take now to maximize the chances of winning. In most games, this involves building stockpiles and delaying instant gratification in exchange for stronger hands later.
Now think back to the rules you’ve followed and actions you’ve taken throughout your life… did those build the stocks that will help you win the game you’re playing today? In my free time, I co-teach a class on failure at Harvard Business School (call it exposure therapy). The entrepreneurship department has a great trick in one of their classes—they put a page of around 20 actions up on a screen, including things like:
Broke curfew
Drank underage
Smoked weed
Stole money from parents
Failed a class
Regularly broke the speed limit
etc.
etc.
The first time I saw this, as a student, I was sitting there all smug, mentally checking off all the terrible things I had never done…4 And then the punchline: these were all features that successful entrepreneurs dramatically over-indexed on. Welp… there went that dream. Entrepreneurs were more likely to have thrown out externally imposed rulebooks and figured out their own optimization functions earlier. They built stockpiles that mattered to them in the long run—authentic relationships, passion, perspective, funny stories—and rejected the ones that didn’t (grades, short term parental/teacher pride). The longer we spend collecting gold stars for following someone else’s rules, the longer it takes us to question which rules we should be following in the first place.
Psychopaths
A short, but related, aside: I recently had a debate with a VC friend on whether extremely successful CEOs (and in particular, founder-CEOs) had to be psychopaths in order to be successful.5 Their take: yes - it’s inherent to disruption, the cost of doing business, the way to move fast, etc. My take: well, yeah, I’ve seen a lot of evidence that it’s the way things have generally evolved even in companies we admire, but we’ve all also seen the very direct and obvious costs. Does it really have to be that way?? It’s like a cheat code that only a few folks are entitled to use6 and makes everyone else want to stop playing. Maybe the answer is that we’re optimizing for the wrong thing. Could these be alternatives:
Playing to win well: At the crux of good sportsmanship is the ultimate objective to host another game. It requires people to want to keep playing. If we win poorly, the universe of players who are willing to play our game (or employees who are willing to work for us) dwindles. If we win well, we maintain trust, we maintain relationships, and while there may be different outcomes, everyone enjoys the process.
Playing to win together: I’ll admit, I’m somewhat famous for not enjoying cooperative games (think: Pandemic). Does that mean I’m a psychopath? But in the real world, it’s simply awesome to be on a team with a bunch of rockstars, solving hard problems, and beating the competition. And it stinks trying to accomplish something you believe in with a bunch of egomaniacs who care more about their own glory than the mission.
What’s better than cheating and winning? Beating a cheater.
Helping re-balance the deck
I was inspired to write this post because the other day I was on a long call with a first time founder/CEO who has actually done the hard thing: built a complex technical product that customers are willing to pay real money for (gasp!). They were following all the rules: Product market fit? Check. Lean team? Check! Good names on the cap table? Check!! The problem? The rule books, the ones handed out by the VCs, lawyers, bankers, board members - each just a little bit colored by their own incentives. This founder was so focused on doing the “right thing” for their investors, working more than overtime to prioritize VC wants and needs, that they now risked putting their own judgement to the side, losing sight of the real value they had created.
What motivates me these days is helping re-balance the deck for these amazing founders - opening doors, occasionally calling bullshit, and trying to help them write their own rules. The deck is still stacked in many ways that I find infuriating and, at times, demoralizing but then I remember that most games have loopholes and strategies that the game designers never thought up. The fun is in finding those and handing the underdogs a cheat code.
More hard things coming soon…
Postscript: Sometimes the rules change
As I was getting ready to publish this, I was catching up with a friend who sent me Arthur Brooks’ latest piece, How the Ivy League Broke America, in the Atlantic (incidentally Brooks also wrote the book I recommend in the footnotes about figuring out what the hell you value in life). In the piece, Brooks highlights two very different rulebooks for America’s “elite” - from the WASP-y “Well-Bred Man” to the progeny of tiger moms - and challenges the rulebook we have today.
Every coherent society has a social ideal—an image of what the superior person looks like. In America, from the late 19th century until sometime in the 1950s, the superior person was the Well-Bred Man…In those days, you didn’t have to be brilliant or hardworking to get into Harvard, but it really helped if you were “clubbable”—good-looking, athletic, graceful, casually elegant, Episcopalian, and white. It really helped, too, if your dad had gone there.
Once on campus, studying was frowned upon. Those who cared about academics—the “grinds”—were social outcasts. But students competed ferociously to get into the elite social clubs: Ivy at Princeton, Skull and Bones at Yale, the Porcellian at Harvard. These clubs provided the well-placed few with the connections that would help them ascend to white-shoe law firms, to prestigious banks, to the State Department, perhaps even to the White House.
…And then a small group of college administrators…set out to get rid of admissions criteria based on bloodlines and breeding and replace them with criteria centered on brainpower…
When universities like Harvard shifted their definition of ability, large segments of society adjusted to meet that definition. The effect was transformative.
And yet it’s not obvious that we have produced either a better leadership class or a healthier relationship between our society and its elites. Generations of young geniuses were given the most lavish education in the history of the world, and then decided to take their talents to finance and consulting…In short, under the leadership of our current meritocratic class, trust in institutions has plummeted to the point where, three times since 2016, a large mass of voters has shoved a big middle finger in the elites’ faces by voting for Donald Trump.
-David Brooks, How the Ivy League Broke America
If there is only one rule, it is that the rules will continue to evolve. A few of us will have the gumption to change the rules ourselves. For the rest, we must, at a minimum, pay close attention to when the rulebook we’ve been following no longer applies.
For more on this, I particularly enjoyed From Strength to Strength by Arthur Brooks. It can be corny at times but it’s a good wake up call for those of us who are addicted to winning but don’t even know what game we really want to play.
Men: read this book. Everyone else: I’d probably suggest NOT reading it, it risks pissing you off and demoralizing you, I had to put it down after a few chapters. A preview is available on Google Books.
Well, let’s be honest, I did a couple of those things but they really weren’t a big deal and I never got caught or hurt myself or anyone else, so do they really count? ;)
To be blunt: it’s generally considered ok to be an asshole (and almost always considered ok to be a highly competent asshole), it’s almost never ok to be a bitch.
