The lessons we can learn from the game of Poker
Ask a poker player why he left a table and you will hear two kinds of answers. The first sounds like this: “The game turned bad. The rake was too high, the company was worse, and I was tired of losing.” The second sounds like this: “There’s a better game across the room, and I want a seat in it before it fills up.” Both players stood up from the same felt, chips in hand. They are not in the same condition at all. The first man is running from something, and wherever he lands, he will land empty-handed, with nothing but relief — and relief spends very fast. The second is walking toward something, and arrives with energy to spare. Retirement works exactly the same way, and which one you resemble will shape your next twenty years.
I spent decades as an attorney watching people retire, and the pattern was regular enough to call in advance. The clients and colleagues who retired from — from the commute, from the boss, from the billing, from the alarm clock — enjoyed a splendid six months. The golf was wonderful precisely because it was stolen time. Then the theft ended, the time became simply theirs, and a strange flatness set in. Tuesdays looked like Saturdays. More than a few of these people confessed to me quietly that they felt vaguely useless, and some of them drifted back to work they did not need, simply to have a reason to get dressed. They had planned their escape down to the last dollar. They had never planned an arrival.
The people who retired to something were playing a different game from the first day. They were often less wealthy, and their plans were rarely grand. One man I knew retired to a woodworking shop he had been imagining for fifteen years; another retired to the grandchildren, on purpose, with a calendar full of school plays and fishing trips; a woman retired to the literacy program she had long admired; a couple retired to a small town, a church, and forty acres they meant to know well. What united them was not the size of the ambition but its direction. They were not fleeing a life; they were beginning one, and they spoke of retirement as the most interesting part of the story, starting now.
The poker table explains why. A player who folds to escape a bad hand has made one decision; a player who folds for a better opportunity has made two, and the second is the one that decides what happens next. “From” is a complete sentence about the past. “To” is a plan for the future. Escaping something gives you a reason to stop; arriving somewhere gives you a reason to start every morning, and a standard by which a day can be called good or wasted. It changes how you weather the rough patches that come — the illness, the market drop, the loss — because a person with somewhere to go treats a setback as weather, while a person with nowhere to go treats it as the climate.
None of this requires a second career — but it cannot be left vague, either. “Spend more time with family” is a hope, not a plan; hopes do not fill a Tuesday. “Have dinner with the grandchildren every Sunday” is a plan. “Travel more” is a hope. “Drive the Pacific Coast Highway in September and be home for the holidays” is a plan. Specificity is not fussiness here. It is the whole mechanism. A written, particular list of what you are retiring to is the difference between drifting and dealing yourself in.
If you have not retired yet, you hold the advantage: write the list now, while the job still gives your days their shape, and even test items on it — a class taken, a volunteer shift tried — before the stakes are real. If you are already retired and recognize the flatness I described, take heart: the flatness is not a verdict on you or on retirement. It is information. It means the “to” list was never written, and it can be written this week, at any age. People begin the interesting part of their lives at sixty-seven and seventy-five as surely as Benjamin Franklin began his at forty-two.
Here is the takeaway. Get a sheet of paper — paper, not a phone — and finish this sentence as specifically as you can: “I am retiring to…” Name people, places, activities, contributions, and things to learn; put dates next to the ones you can; and mark the single item you could start this month. Then start it. The game you left is over. The game in front of you does not begin when you escape the old one. It begins when you can say what you are walking toward.
