Board Game Theory: Winning at the Games of Life

Before we had children and lost all control over our lives, my wife and I enjoyed playing board games together. Our personal philosophies on those games, however, differs somewhat. While she plays to have a pleasant evening with friends and loved ones, I play in order to lay waste to the competition. There are moments when if Machiavelli happened to be playing Catan with us, he’d sit back and say, “Dude.”

Thinking about that side of me led to my own personal game theory. Every situation you find yourself in can be treated like a game—there are rules, objectives, and strategies. Knowing what those are gives you an advantage. Failing to see them means you do not pass go, you do not collect two hundred dollars. 

Most importantly, recognizing your circumstances as a game means you have a goal: to win. Not to dominate for its own sake, but because if you want to better yourself and learn, you need to put forth your best effort. Winning means growth, victory over stagnation. 

And if you’re not playing to win, why are you even in the game?

The Games We Play Every Day

Every action you take is a move on multiple game boards. Working on a project in the office, reading a book for pleasure, convincing your partner you’re not quite as dumb as the evidence suggests—these all have rules to understand if you plan to get the most out of them. They all have objectives to achieve for the best outcome. And they all have an incredible number of strategies you can apply to them. 

Knowing the game you’re playing is a prerequisite for enduring success. Luck and tap dancing only get one so far—eventually, the wolves come to play. And when you find yourself across the board from someone who understands the rules better than you and is there to win, every move you make will come up snake eyes. 

Thankfully, there’s an easy formula anyone can apply to the games of their life:

Assessment → Strategy → Action → Growth

It’s simple, but not easy. Though if it was easy, where would be the fun in winning?

Assessing Your Position on the Board

We start with assessment because it’s hard to get anywhere if you don’t know where you are. The number of games you could be playing is infinite, so take the time to figure out which ones you’re in. 

One accomplishes this in the most terrifying of ways: thinking. I know, I’m clutching my pearls at the horror of it as well. Modern society has done its absolute best to ensure that you never have to think again, and our new AI overlords make the threat more pressing than ever before. 

Thinking, however, is somewhat important to understanding. And that’s what we’re doing in this step: understanding our situation and recognizing its rules. Here’s how I recommend you break it down:

1. Categorize your situation into one of four buckets: Craft (work, hobbies, etc), Community (relationships, friendships, etc), Constitution (mental and physical health), or Contemplation (spiritual wellbeing) [special thanks to Cal Newport for that framework]
2. Define your ideal end state for each bucket
3. Identify how your situation aligns with those end states (these are the game objectives)
4. Map the systematic obstacles blocking your path (these are the game rules)

Couldn’t be simpler! This leaves you in an excellent space for the next phase: strategizing. 

Strategizing Your Next Moves

Strategy is a word that gets tossed around more than a Caesar salad, and with far less satisfying results. If you think that you’ve got a strategy because you underlined “go big or go home” on a whiteboard, the ghosts of Clausewitz and Sun Tzu both say you have brought dishonor on your dojo. 

Let’s break down what strategy is, then apply it to our games of life theory. First and foremost, a strategy is a theory of success. Theory because it hasn’t been proven yet but is backed by evidence, and success because obviously. That’s what strategy is, but what does strategy do? Three things: create advantages, develop new sources of power, and exploit weaknesses in the competition. 

Strategies in board games are a good example. When someone who knows what they’re doing moves a chess piece, they’re doing it to set themselves up for success down the road, establish positions of strength on the board, and prevent their opponent from doing the same. When I move pieces on the chessboard, it’s usually because I blacked out and panicked. We can’t all be Bobby Fischer. 

Now let’s move it from the chessboard to the game of life. A position opened up at work that you want like I want Cinnabon—an unhealthy fixation that must be met at any cost. Boom, there’s your objective. Now you need a strategy to get at that gooey goodness, your theory of success. A quick brainstorm, and you’ve got a few ideas:

• Create advantages: build a relationship with the person who owns that position, highlight your relevant skills, lower your stress so you perform better
• Develop new sources of power: learn new skills that fit the role, practice your interviewing, look for alternative opportunities to leverage 
• Exploit weaknesses: identify process gaps you can work, understand where other applicants might fall short and learn from that  

Now your strategy has some meat. Obviously, each situation will differ with environment and context, but this step separates players from bystanders. Because once you have a theory of success, it makes the next step that much easier—taking action. 

Taking Action That Matters

The best strategy in the world is as useless as my once-held ability to quote Star Wars Episode One verbatim if it’s not backed up by action. This is where rubber meets road, birds take flight, and possums hiss at people throwing their trash away. But not all action is created equal. There are two types: performative and useful.

What do I mean by performative action? I mean busywork we use to pretend we’re actually accomplishing something. Reorganizing your desk, rereading the same “productivity hacks” that have been regurgitated by the internet ad nauseum, 99% of meetings—these performances convince us we’re advancing when we’re just treading water. 

We are excellent rationalizers. I can convince myself that yes, I need that fourth cinnamon roll because if I don’t eat it, it’ll go bad and we’ll have to throw it out. And that would be wasteful. Similarly, we dazzle ourselves with excuses as to why the performative actions we assign ourselves are just as important—if not more so—as useful actions. Why do we do this? Because useful action is hard. 

Useful actions are those that move the ball forward in your theory of success. By definition, they act against resistance because if there was no resistance to reaching your goal, you’d have already accomplished it. And as anyone who’s ever upped the weight on their squat can tell you, resistance doesn’t care about your goals or your feelings. Resistance is there to jack you up like a playground bully desperate for the love he or she is so clearly denied at home. 

Imagine you want to improve your relationship with your partner.  I say “imagine” because that doesn’t seem to be the norm these days, but I digress.  You’ve assessed the situation and determined the rules of the game.  For sake of argument, we’ll say they involve acknowledging your partner’s feelings, prioritizing mutually enjoyed activities, and sharing the load of household tasks.  You’ve also put together a strategy: studying your partner’s emotional responses to see what does and doesn’t work in your interactions (creating an advantage), creating shared goals that unite your efforts and provide motivation (a new source of power), and identifying what it is you do that most drives your partner up the wall for immediate correction (exploiting weaknesses).

Now it’s time for useful action.  To continue the example, you might develop a relationship dashboard to track your shared goals, with fun date night celebrations baked in when you hit milestones.  Or you could have weekly “highlight” conversations, where you share with each other what made you feel valued over the past seven days.  Or you could put on a shock collar your partner gets to trigger every time you reuse that pun they hate.  The options here are endless—what matters is that each action directly makes progress on the strategy.

This has echoes of deliberate practice, a concept that states the obvious because we need to be spoon fed these days. In brief, the only practice that counts is practice done with deliberate intent and focus. The evidence in favor of the concept is overwhelming, but my favorite tidbit is this: how many hours do you spend driving in a week? In a month? A year? Yet with all that, are you any better a driver now than you were a year ago? No, because you are not deliberately practicing—you’re coasting on instinct. As the saying goes, that dog don’t hunt. Also, if you don’t use your blinkers, you’re a bad person. 

If you’re ever in doubt that your action is useful and deliberate, ask yourself this: what tangible result will this action have that brings me closer to my goal? The further your answer strays from your desired end state, the more you’re lying to yourself. You’ll know the difference because deep down, you know what you need to do. 

Growing Beyond the Game

Assessment. Strategy. Action. These steps lead to the most important one—growth. It’s critical for two reasons. First, without growth we stagnate, and there are few things as disappointing as a life wasted on stagnation. Second, growth is what prevents us from becoming a hyper competitive jackwagon. 

We’ve all hit moments of stagnation in our lives. Maybe you struggle to find the energy to workout, or the effort of keeping up relationships seems too onerous, or you think maybe that fourth cinnamon roll is a step too far. It’s ok, we’ve all been there. 

Here’s what I’ve come to believe about stagnation: it’s like a little form of death. Not so immediately permanent, but the longer it goes on, the harder it is to tell the difference. It starts with a day, then a week, then you look up from the grave you slowly sunk into over decades, realizing the entire world has passed you by. Because if there’s one constant in our temporal existence, it’s that the world will keep moving, with or without you. 

Growth is a choice. The world will never stop throwing challenges at you, but whether you rise to meet them is entirely on you. Could I have passed on that fourth cinnamon roll? Absolutely. Should I have? Actually, probably. But my dear reader, mountains exist for one reason: to be summited. It is how we learn and how we improve. 

Growth has another side. By approaching these challenges with humility, you acknowledge you have something to learn and room for improvement. This is the anti-jackwagon tonic.

It’s entirely possible to this point you’ve assumed I’m a raging, hyper competitive tool that you’d hate dealing with. I like to think that’s not the case, but you have to ask my wife (just not after I’ve crushed her at Everdell). Instead, I’d propose that I’m committed to growth in every aspect of my life, and that growth only comes when we push ourselves past our current limits. That push is when we either fail or discover new strengths. Both are central components to being a better person tomorrow than you are today.

Recognizing the difference between ego-driven competition and growth-oriented excellence keeps you on the right path. Otherwise, good luck keeping any friends on the invite list for game night. 

Playing to Win Without Becoming a Sore Winner

Similar to the jackwagon sentiment above, you might also be thinking, “Hey man, isn’t focusing too much on winning unhealthy?” That depends on your reason for wanting to win. 

There’s a simple rule to determine if you’re in the right headspace on this. Are you focused on winning because a) you want to improve and become the best version of yourself for yourself, or b) you desperately need your ego stroked like needy chihuahua thirsting after undeserved love?

I’ll give you a hint: don’t be a chihuahua. 

“Isn’t this, I don’t know, manipulative?” you might follow up with. My response: an astute observation! Again, it depends on your reasons. If you approach every situation with an eye towards self-improvement and a commitment to humility, I’d say no. If you do it purely to crush others, yeah, that’s probably leading down a path that involves pulling the wings off of flies. 

Remember, no model is perfect, but most models have value if applied appropriately. This game theory is just another framework to view your life through, and how you choose to utilize it makes all the difference in the outcome. 

“You’re coming across pretty judgy—I’m already trying my best.” Are you? Are you really? If so, that’s great! I applaud your effort. But even then, we all inevitably fall short. To quote the immortal Captain Picard, “It is possible to commit no mistakes and still lose. That is not weakness, that is life.”

The great thing about this game theory, though, is even if we lose an individual game, we can still move our piece forward on the Big Game of Life. So long as you learn and grow from your failures, you are improving and overcoming stagnation. You, my friend, are winning.

Your Move

If there’s one thing I want you to take away from this Wandering, it’s that eating four cinnamon rolls in one day should be acceptable in polite society. If there’s a second, it’s that viewing your goals in life through a game lens—complete with objectives, rules, and strategies—is a tool to help navigate the white-water rapids of life. 

Next time I’m crushing my wife at a board game, I’ll have a good time. And next time she stomps me, I’ll sit there with a smile on my face. Winning means nothing if it doesn’t involve growth. Recognize the true adversary in your life as stagnation, and play to win.