Lessons on Strategy, Self-Knowledge & Connection (via a Board Game)

Some of the most useful frameworks for living don't come from self-help books. They come from a board game, from noticing how you actually learn, and from a list of questions psychologists use to make strangers fall in love. Here's what those three taught me.

Life is a lot like Catan

I spent a long stretch playing Settlers of Catan — a game of resource management, trading, and tactics that's easy to pick up and hard to master. Mastering it sharpens negotiation and communication, but more than that, it's a startlingly good model for life. The lessons:

1. Early position matters enormously — and the early game is free. In Catan you place your first settlements for free, and the winning move is to put them on high-probability tiles (6, 8, 5, 9) rather than rare ones (2, 12). Life is the same: your first two decades are largely subsidised by your parents, and what you learn in that window determines how you play the rest. Pick a high-probability skill — one with a high chance of creating opportunity — and you've placed your settlement on a 6. Pick something that looks impressive but generates no opportunity, and you've placed it on a 2, then watched everyone race past.

2. Beat probability by widening your surface area. Even a settlement on a 6 sometimes never rolls. The defence is diversification — of skills and of investments. Early on, maximise your surface area: learn more than one thing, because you don't know which skill gets automated or which bet goes bust.

3. Then double down. After the initial spread, the great players stop expanding and deepen — converting settlements into cities that pay double. It's the venture-capital move: instead of grinding out new roads, pour resources into what's already working. With skills, once you have enough surface area, become genuinely expert in one or two things. Spreading across ten leaves you respected in none.

4. Big plays carry real risk. To make the biggest moves you have to hold more than seven cards — but there's a ~17% chance a roll of 7 wipes out half your hand. Cowards hoard nothing and stay safe but fall behind; some risks pay off and some hammer you. That asymmetry is just true.

5. Trying to ruin others is a waste. The biggest time-sink in Catan is spending resources to block someone else's game. Almost always you get nothing for it. The internet's favourite hobby — tearing down other people's work — is the same losing move.

6. Trust compounds, and so does its loss. Scam one trade and every player is watching; you lose future deals too. In the real world, word gets around — and sometimes you get painted unfair even when you weren't, which is all the more reason to guard the reputation fiercely.

7. Other people's needs matter more than yours. Novices try to offload their least-useful resource on people who don't want it. Good players study what others lack and trade on that. In life: don't push a product nobody wants — build the thing there's actual demand for.

8. Never underestimate anyone. I've lost from 7–7 to hidden development cards more times than I can count. Funded, multi-year companies lose to a few kids with something new constantly.

9. Don't show all your cards — and assume your competitors are hiding victory points too. Transparency makes you easy to attack.

10. There are many ways to win. Longest road, largest army, cities, development cards — no single path. Like life, there's luck involved, and you can't eliminate it. But the best players minimise luck's impact by spreading bets and going deep on what works.

Know your learning type

A second kind of self-knowledge: how you take in information. I read in a mode I'd call CASM — Constrained, Analytical, Skimming, Motivated. I'm driven by an analytical, goal-oriented approach but constrained by time, so I skim for the essential, actionable parts and move on. I read for problem-solving and application, not leisure — extracting just enough to use it.

The point isn't the label; it's that knowing your own reading and learning style lets you stop fighting it. If you're a skimmer who reads for action, structure your inputs for fast extraction (summaries, takeaways, checklists) instead of guiltily trying to read every page like someone who reads for pleasure. Match your method to your wiring and you learn far more per hour.

Deep connection is engineerable

The third lesson is the most surprising: closeness can be deliberately built. The famous "36 Questions" experiment shows that two people can generate remarkable intimacy by working through a set of questions that escalate in self-disclosure — starting light ("who would be your ideal dinner guest?") and deepening toward the vulnerable ("what would you most regret not having told someone?", "when did you last cry in front of another person?").

The mechanism is the real insight: intimacy is built through gradual, reciprocal vulnerability. You don't fall into closeness; you build it, one slightly braver disclosure at a time, each person matching the other. That's true for friendship, partnership, and even how you build trust with a team. If you want to be close to someone, stop waiting for it to happen — ask better questions, and be the first to answer honestly.

The throughline

Three different windows onto the same truth: position and patience beat raw effort (Catan), self-knowledge beats brute force (know your learning type), and connection is built deliberately, not stumbled into (the 36 questions). Spread your bets then go deep, work with your own wiring, and earn closeness through honest, escalating vulnerability. The game — whichever one you're playing — rewards it.