Friday Reflections: Whose Board Are You Playing On?

AI-generated image of a Risk board mid-game.

The Canary Compass podcast is live on Spotify and YouTube. Tuesday episodes explore the week’s note from a different angle. Saturday episodes companion the Friday Reflection. Bonus episodes on Thursday when two notes publish in the same week.

I had a losing record at chess.

There was a kid in our neighbourhood who played regularly, and I played against him whenever the board came out. I lost more than I won. I never kept exact count, but the record was clear enough. He was better than me. That much I knew.

What I did not know, because it never occurred to me to ask, was whether he was actually any good. He was the only person I ever played. My entire assessment of my own strategic ability was built on a sample size of two. For all I knew, he was also terrible. I just happened to be slightly more terrible. I accepted the verdict and carried it quietly for years: I am not a strategy person.

The trouble with childhood verdicts is the instrument, not the cruelty. You receive them at eight or twelve or fifteen, and they harden into facts about yourself that you stop examining. The losing record hardened into a conclusion I did not revisit.

My sister had a different kind of honesty.

I sang at church the way most children sing at church. Loudly and with conviction, without any evidence that the sound leaving my mouth was the sound I intended. My sister sat next to me, and by the second hymn she had reached her limit. She told me to keep quiet because I was embarrassing her. There was no room for interpretation.

That verdict travelled with me through secondary school, where I tried out for the boys’ choir. I did not get in on the first attempt. Or the second. On the third attempt, the teacher let me in, and I suspect it was mercy rather than range. When we performed, I was placed next to the microphone at the front. My tone was off. The mic did not help.

My sister was right. The choir teacher confirmed it by letting me in out of pity, and the microphone made the verdict public. I could not sing, and an honest woman had told me so early enough that I only lost a school term of dignity rather than a career. Someone loved me enough to say it plainly.

So one verdict was wrong and built on nothing. The other was right and built on proximity and honest love. The same person received both, in the same childhood, and could not tell the difference at the time. I did not know that verdicts needed auditing. I thought they were just things that were true about you.

The games I actually loved told a different story.

Scrabble came first. I was top of the boys’ club in our neighbourhood, and the feeling of placing a seven-letter word on a triple score was the closest thing to flight I had at fifteen. Every player looks at the same tiles and the same dictionary. What separates them is who can see the combinations nobody else is staring at. I did not know the phrase “pattern recognition” then. I just knew I could see the words the other kids could not.

Then there was Risk.

Risk was the one that mattered, though I did not know why at the time. Multi-front, with alliances forming and dissolving at the table, and no player telling you their real intentions. You absorb losses on one front to win on another. Timing matters as much as position.

And then there are the dice. You can read the board and position the armies well, and the numbers still fall against you. A campaign planned across three turns collapses because you rolled badly. The game is designed to break your plans. The skill is building a position where one bad roll does not end you. Fortify before you attack. Absorb the loss and wait for the next roll.

I loved it because it felt like the right shape. Multiple moving parts and no certainty, with your nerve being tested every time the dice went against you. Nobody explained any of this to me. I gravitated toward it the way you gravitate toward a room where the temperature feels right.

It took twenty years and a career in financial markets to understand that Risk had been teaching me my profession before I entered it. The kid with the losing chess record turned out to be built for multi-front positions under imperfect information, where resilience was the only currency that mattered. The chess record was accurate. The board was wrong.

The audit question I wish someone had handed me at fifteen is simple. Whose board am I playing on? Before you accept a conclusion you have carried for years, ask who set the test and whether the board matched the gift. My sister was right because the instrument was the right one for what she was measuring. Most of the verdicts we carry do not have that pedigree.

This weekend, pick one small old label. The thing someone said about you that you never revisited, the one you still introduce yourself with. Ask whose board you were playing on. Sometimes the verdict holds, and you just needed someone honest enough to say it. But occasionally you will find that the game you lost was never the game you were built to play, and the losing record was a story about the board, not about you.