I used to have a tendency to back off when I was winning.

Whether it was a board game or a bit of business success, some combination of guilt, laziness, or fatigue would lead me to coast a bit, leading to diminished results and even losses.

In order to curb this tendency, I took up tennis. I learned how to follow through on a swing and commit to a play. I practiced keeping up the intensity all the way to the end of a match, even when I was losing.

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I enjoy puzzles of all kinds, from Sudoku to crosswords to old-fashioned jigsaw puzzles.

What I appreciate most about them is the way they illuminate the unfathomable complexities of the mind.

Specifically, they show me how much is happening in my brain without my conscious awareness.

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My goal, in most assignments, is to get my students to think.

This runs counter to the goal that most of them have, which is to complete their work as quickly and easily as possible, without thinking.

It can’t blame them for this habit. Many of the assignments they’ve had over their school years don’t require any thinking. You do the work to prove that you were in class, paying attention, and that’s it.

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When I started designing a school curriculum, my intent was to make things fun whenever possible.

After all, learning is fun. Why shouldn’t school be fun?

I added brain teasers, puzzles, and games to the menu — and discovered that they did nothing to entice reluctant students. They felt just the same way about the supposedly “fun” activities as they did about the straightforward “read this chapter and answer the questions” assignments. They inspired dread, mostly.

I had overlooked a basic paradox of education: The puzzles designed to make learning fun are only fun for the learners who are already having fun.

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Monopoly is an awful game.

It takes forever to get going and forever to end. It involves too much luck, even without “Free Parking” jackpots.

And once someone starts winning, their victory is irreversible and soon makes the game miserable for everyone, even the winner. It feels icky to be the greedy landlord, riding high on your ill-gotten gains, relentlessly collecting rents in some dystopian Atlantic City where you’ve already bled your tenants dry and sent your own siblings to jail.

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