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Lesson 7 of 100 Goals & Games

Understanding Games

Now we talk about games. And before you decide this is going to be lightweight, “life is a game, man,” hold that reaction for a minute.

The word “game” doesn’t mean what you think it means. It doesn’t mean trivial. It doesn’t mean frivolous. It means something very specific. An activity with rules, moves, uncertainty, stakes, and an outcome that isn’t predetermined.

By that definition, almost everything important in your life is a game.

Games Are How Life Works

Your career is a game. There are rules. Some written, most unwritten. There are moves you can make. The stakes are real. And the outcome isn’t guaranteed.

Relationships are games. Not in the manipulative sense. In the structural sense. There are dynamics. There are things you do and things the other person does. The outcome, whether the relationship thrives, stagnates, or dies, depends on how both of you play.

Business is a game. Health is a game. Creative work is a game. Parenting is a game. Even your inner life, how you manage your mind, emotions, and energy, is a game with rules you’re still learning.

The people who resist this framing usually do so because they associate “game” with “not serious.” That’s backwards. Games are the most serious thing there is. They’re how we engage with uncertainty. And life is nothing if not uncertain.

Two Ways to Be Stuck

Just like with goals, there are two stuck shapes with games.

The avoider. This person won’t play. They sit on the sidelines of their own life, watching others engage while they stay safe. They don’t start the business, don’t enter the relationship, don’t take on the challenge. Not because they can’t. Because they’re afraid of losing.

Losing at a game you care about hurts. The avoider decided somewhere along the line that not playing hurts less than losing. They’re wrong, but the decision was made so long ago they don’t remember making it.

The compulsive player. This person can’t stop playing. Every area of life is a contest. Every interaction has a winner and a loser. They’re exhausted but they can’t step back. They can’t choose not to engage. They can’t walk away from a game even when walking away would be the smart move.

The compulsive player isn’t driven by love of the game. They’re driven by terror of what they’d feel if they stopped. Stopping means sitting with themselves, and sitting with themselves is the one game they refuse to play.

Free Play

A free relationship with games means you choose. You can look at a game, assess whether you want to play, and enter it with full engagement, or decline it without guilt. You can play hard and then stop. You can care about winning and still be fine if you lose. You can walk away from a game that’s no longer serving you.

Free play means the game serves you. You don’t serve the game.

This is what you’re after. Not avoiding games. Not compulsively playing them. Choosing which ones to play, how hard to play them, and when to walk away.

Today’s Practice

Take inventory. Write down the games in your life across these four categories:

Games you’re currently playing. What activities with uncertainty, stakes, and outcomes are you actively engaged in? Name them specifically. Career, relationships, health goals, creative projects, financial growth. All of it.

Games you’re avoiding. What games have you opted out of? What activities are you sitting on the sidelines for? What would you play if you weren’t afraid?

Games you’re compulsively playing. What can’t you stop? Where do you keep engaging even when it’s no longer serving you? Where is walking away not an option, and why?

Games you play freely. Where do you engage by genuine choice? Where can you play hard and also walk away? These are your models for how it should feel everywhere.

Look at the full inventory. What does it tell you about how you relate to games? That’s your starting point for the work we’ll do next.

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