This is obviously not possible in the entirety of reality. In reality, with real-world dollars and currency, you could buy anything, spend your money in nearly unlimited ways. In the board game Monopoly, there are only three things to do with your money: buy new property if you land on it, develop properties if you own enough of them, and barter and trade properties and cash with other players.
Games, thus, make it a lot easier to study and understand life. In the real world, you can’t possibly math your way through every option; there’s nearly infinite options in the real world.
I love this sort of applied mathematics and game theory, but the greatest lesson I got from games was not one of the mathematics lessons. Nor even the lessons about behavior and self-control that I wrote about in Roguelike. No, the greatest lesson I got from studying games and game design was about how other players act.
Dr. Lewis Pulsipher is a master of the craft. He’s both a crafter of some very famous and popular board games, and additionally, a wonderful theorist of games. I’d really recommend reading anything he’s written; he’s always incredibly insightful.
The single biggest takeaway I got from Dr. Pulsipher was that players play games in very different ways based on their outlook and orientation to life, and that these outlooks and orientations can be studied and understood.
Indeed, we always bring our worldview, biases, and impulses with us everywhere we go. The most interesting classification of players is into Classical Play and Romantic Play.
***
WHEN YOU BEGIN A GAME…
Dr. Pulsipher –
“When you begin a game, you must first learn something about each of your opponents. Sometimes you will know quite a bit to begin with, but you can also ask people who know the opponent better than you do. You want to know if your opponent is generally reliable or not, what his objective is, whether he is a classical or romantic player, and whether or not he is good at negotiation, strategy, and tactics…
”Whether a player’s style is “classical” or “romantic” is tricky to define. Briefly, the classical player carefully maximizes his minimum gain. He pays attention to detail and prefers to patiently let the other players lose by making mistakes, rather than trying to force them to make mistakes. He tends to like stable alliances and steady conflict in the game. He tends to be reliable and good at tactics. The romantic is more flamboyant, taking calculated risks to force his enemies into mistakes, trying to defeat them psychologically before they are defeated physically on the board. (Many players give up playable positions because they’re convinced that they’ve lost.) He [the romantic player] tries to maximize his maximum gain, at the cost of increasing potential loss.”
If you skimmed the above two paragraphs, please immediately go re-read them carefully. I say without exaggeration – this is one of the single most insightful and important lessons I ever learned, in all of life.
The classical player carefully maximizes his minimum gains.
The romantic player tries to maximize his maximum gain, at the cost of increasing potential loss.
***
UNDERSTANDING HOW CLASSICAL AND ROMANTIC PLAY OUT
My closest friend and most frequent colleague, Kai Zau, we discuss “Classical and Romantic” all the time.
Indeed, after learning and discussing this mental model together, I’ve found it so powerful that I often share it with anyone I have frequent close collaborations with.
We all have different natural inclinations towards certain conservative gains or risky bets for larger gains, as well as how much we’re willing to risk and how much certainty we need.
This can vary by domain – someone might be very classical in the gym, with a very careful and conservative training program, whereas they might be very romantic in investing, buying risky assets that they think can pay off large.
Dropping out of university after one’s sophomore year to do a startup, especially if you were studying in a field that has largely good career outcomes (say, engineering or computer science), is a very Romantic move. Most startups fail, but the ones that succeed, succeed big. Dropping out to get into entrepreneurship increases both your chances of large failure and large success.
Getting a degree in medicine or law, on the other end of the spectrum, would be highly Classical – you’re investing 7+ years of study to reasonably assure yourself of a good salary. It maximizes the minimum gain, nearly guaranteeing some floor of credibility, earning potential, and career outcomes.
You can be Romantic in one field and Classical in another – the startup founder is almost always playing at least somewhat Romantic, but by being conservative with cash management, expenses, and burn rate, they can play more Classically than the norm in that field.
It’s possible, through careful design, to make startups easily acquirable if they fail. This could be ensuring your team is the type a company would want to buy in an “acqui-hire” if the business doesn’t work, developing useful intellectual property like patents that a company would want to buy, and early-on cultivating good relationships with potential acquirers. This would be leaning towards Classical play.
When Mark Zuckerberg famously turned down an offer for a billion dollars from Yahoo to buy Facebook, that’s more Romantic than accepting that acquisition. Yes, he was correct – sure, but it’s more Romantic. When Facebook bought Instagram for $1 billion some years later, Zuckerberg found his role reversed – it protected Facebook’s downside, since they weren’t doing as well on mobile as Instagram. Thus, it was more Classical for Zuckerberg to buy – even though he turned out to be correct again (with hindsight), at the time people largely were saying that Facebook overpaid to remove that risk from the landscape before Facebook’s IPO. Meanwhile, the Instagram founders made the opposite decision as Zuckerberg – they took the Classical route, choosing to take the guaranteed $1B instead of the more Romantic move of staying independent.
***
TOYOTOMI FORWARD HEADQUARTERS, ODAWARA REGION
As he was entering Hideyoshi’s war tent, Kuroda Kanbei bumped into the man who had largely replaced him, Ishida Mitsunari.
Mitsunari scowled at Kanbei, said flippantly –
“Hey Kanbei! How’s your God doing?”
Now 43 years old, Kanbei had mentally slowed a little from his mental peak as grand strategist of the Toyotomi forces – but not so much that he would fall into this trap.
“I believe all the Gods and Kami are doing equally well, smiling at our Lord Hideyoshi’s work being done. How are your gods, Mitsunari?”
Mitsunari laughed derisively as he walked off past the man whom he had replaced as Hideyoshi’s most trusted retainer.
The last major expedition Kanbei led for Hideyoshi had been to heavily Christianized Kyushu. After seeing how the natural Japanese fortitude blended into a beautiful pious ferocity with Christianity, he had converted himself.
But that same year, Hideyoshi had come to fear the rising power of the Christians, and passed his famous anti-Christian laws. Rather than be executed, Kanbei had renounced his new religion and took on a Buddhist monk’s robes in deference.
Nevertheless, Kanbei and Hideyoshi had their relationship strained and grew further apart. Meanwhile, Mitsunari had similar talents as Kanbei – he did not have the talent for master strategy nor the diplomatic skill, but with the Japanese Nation already under Hideyoshi’s banner, his skills as a treasurer and attention to detail – traits Kanbei also possessed – had caused Mitsunari to supplant Kanbei.
But never mind Ishida Mitsunari now – we’ll catch up with him in the next two chapters when he’s leading the Toyotomi Western Army once the Civil War reignites; he will get his due with time. Now, instead, Kanbei walks past the spiteful treasurer into Hideyoshi’s tent.
Hideyoshi is gleeful. “Kanbei!”
Relations had become strained between them, and they were less close than before, but on such a glorious occasion, these things were forgotten and the men embraced like the old
friends they once had been.
“Kanbei, I don’t have anyone else who has the mind you have; I want your advice about one very tricky thing.”
If Kanbei had felt any resentment internally, it melted away – at least for this moment, it was like old times between Grand Regent Hideyoshi and his former grand strategist.
“My Lord, it’s an honor. What’s on your mind?”
Hideyoshi nods to himself a few times before speaking, collecting himself.
“Well, we’ve – umm – we’ve won. The Hojo are beaten. There’s just one thing that’s gnawing at me…”
Despite the years apart, Kanbei could still finish Hideyoshi’s thoughts.
“Tokugawa?”
“Yes, that’s right.”
Kanbei asks, “What were you thinking of doing?”
Hideyoshi says, “Well, it’s a little crazy on a first look, but…”
As Hideyoshi explains his plan, Kanbei laughs and shakes his head, marveling a final time at Hideyoshi’s diplomatic ingenuity.
***
AN OFFER HE CAN’T REFUSE
Tokugawa Ieyasu was laughing.
“Well, this is something else, eh?”
He’d called only a few of his most stalwart retainers to initially discuss the proposal.
The famed ninja chief, Hattori Hanzo, had joined Ieyasu along with the fiercely loyal and stalwart Torii Mototada.
Ieyasu hands around the letter for his two close confidants to read, and then there’s silence for a moment. The room is tense, but would be far more tense if Ieyasu was not seemingly so unworried by this crazy new development.
General Mototada speaks first. “Frankly, I don’t like it at all.”
Hanzo concurs: “Yes, I don’t like it either. What if it’s a trap? If we had a few weeks, I could scout the provinces and assess the loyalties and morale and resources, but we know very little of the Hojo lands. This could be our ruin.”
Mototada pounds his fist into the ground. “Bastard Toyotomi!”
Ieyasu laughs. “Shikata ga nai, eh? It can’t be helped.”
Hanzo objects again, “Can we delay our answer? I can put scouts on the case immediately.”
Ieyasu nods. “Yes, it would be a good time to deploy your scouts. But no, I’m afraid we cannot delay. Hideyoshi controls the nation, and we’re outnumbered 6-to-1 here if fighting breaks out. We cannot give him the slightest pretext. Do start scouting though.”
Mototada stands and grabs his spear, “If your mind is set, I should depart immediately to the home castle in Mikawa to start transferring all the resources we can take.”
Ieyasu nods. “Yes, that’s the way.” He then calls for a messenger and dictates an answer in brief and friendly terms –
Your offer is accepted, Lord Toyotomi. Really, you do me too much honor. Thank you. – Ieyasu
***
A CLASSICAL OFFER; A ROMANTIC ACCEPTANCE
The Tokugawa’s native lands of Mikawa had two characteristics that were very disturbing to Hideyoshi Toyotomi: the first is that it was very close to the Imperial Capital of Kyoto, very close to the center of power in Japan of the day. The second is that sat at a crucial crossroads of Japan’s most important roadway, the Tokaido Road.
With Tokugawa being on his best behavior for five years, and known as a fierce fighter and excellent diplomat, any attempt of Hideyoshi to kill him risked his entire position.
Thus, he wanted to remove Tokugawa from near the seat of power – a very Classical move on Hideyoshi’s part. And thus, he offered Tokugawa a radical bargain.
Wikipedia: Tokugawa Ieyasu –
“In 1590, Hideyoshi attacked the last independent daimyo in Japan, Hojo Ujimasa. The Hojo clan ruled the eight provinces of the Kantō region in eastern Japan. Hideyoshi ordered them to submit to his authority and they refused. Ieyasu, though a friend and occasional ally of Ujimasa, joined his large force of 30,000 samurai with Hideyoshi's enormous army of some 160,000. Hideyoshi attacked several castles on the borders of the Hojo clan with most of his army laying siege to the castle at Odawara. […] During this siege, Hideyoshi offered Ieyasu a radical deal. He offered Ieyasu the eight Kantō provinces which they were about to take from the Hojo in return for the five provinces that Ieyasu currently controlled (including Ieyasu's home province of Mikawa). Ieyasu accepted this proposal. […] This was possibly the riskiest move Ieyasu ever made — to leave his home province and rely on the uncertain loyalty of the formerly Hojo samurai in Kanto.”
This was the last great Classical consolidationary move of Hideyoshi’s career – he maximized his minimum gain and removed the risk of Tokugawa Ieyasu near the center of power.
It was the most Romantic bargain Tokugawa Ieyasu was ever forced to accept – the Kanto provinces, including Edo (which became modern Tokyo), were of unknown quality. Potentially much richer, but not at all certain in quality.
Tokugawa accepted, and re-based himself far away from the center of power.
And thus, with the conquest of the Hojo, Hideyoshi Toyotomi had destroyed his last credible armed enemy, and placed the most dangerous potential insurgent far away from the sources of his power.
***
HOW THE ROMANTIC PLAYER GETS ADDICTED TO ROMANCE
I must confess – my natural inclinations were highly Romantic – my teens and 20’s were a set of unconsolidated rapid gains, bold actions, often spinning up one project before another completed.
I feel like many people take some risks early in life, and for the people whose risks pay off huge at a young age, there is a natural tendency to become Romantic and to love the excitement of it.
A great many of my young, potentially reckless moves paid off large – I became entrained thus, through osmosis and not necessarily intentionally, to love and embrace Romantic Play. I dropped out of a private high school my sophomore year, and spent my time learning computers and reading at the university. This didn’t stop me from getting into an excellent IB high school my junior year, and – really, with really not enough preparation – being part of the teams that won the Mock Trial and Model UN state championships. I dropped out of that high school, though, too, and yet was still able to – through a mix of a little cleverness and a lot of luck – rapidly take and pass my GED , and then convert that GED to a high school diploma at an adult school, and still get nearly a full scholarship to university, where, not surprisingly, I dropped out after three semesters.
When you keep making risky bets, and good things happen while nothing very bad happens, you can get addicted to the thrill of bold action, risk-taking, and Romantic Play – this is fine, perhaps, for getting started, but the danger is in not realizing when things have changed. Until the age of 28 years old, or so, nearly everything I did was done Romantically. There were a lot of successes, but a lot of backsliding and failures and aggravations.
Working with Kai began to change me – he’s hyper-classical. He has around a 99% success rate on his major projects… whereas my success rate had been around 30% when I took an honest look at it. To be sure, my 30% included some big successes, more than enough to keep going, but often I’d fail to consolidate the gains.
Dr. Pulsipher notes that Romantic Players are often sloppy tacticians who cannot endure and grind out decent games if their big bets fail to pay off early, and this was me. Kai and I wrote Gateless together in 2014, our first very large collaboration together after years of friendship, and I started to see the value of his Classical style. But even then, I ran GiveGetWin Tour I in a way that really could have disintegrated (and only didn’t through force of will, some luck, and multiple all-nighters to force things to succeed). GiveGetWin Summer Camp I the next year, likewise, was highly Romantically played – it really could have failed; without Kai stabilizing both Tour I and Camp I, both would have failed, actually.
To this point in my life, I’d had many abandoned – sometimes catastrophically failed – projects. My “mostly written books” in draft form that’ll stay forever unfinished list
crept up every two years or so; frankly, I didn’t know how to guarantee that successes would happen if the Romantic “big bets” didn’t pay off on and get past the finish line on momentum.
But these failures were a blessing for me, actually, forcing me to reexamine my premises. 12 years after starting university at age 17, I went back and took a couple boring classes to finish my undergraduate degree; after a severe illness and surgery, I sat down and slowly started focusing on one thing at a time. Laid up and recovering from surgery, Roguelike was the first book I fanatically hyper-focused on, and it was my first success running purely Classically from start to finish.
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