Life

Play the long game

On patient accumulation, asymmetric bets, and winning Monopoly.

I played Monopoly (my favorite game) with some friends recently.

I got off to a slow start and was only able to purchase one property and two railroads.

One player got off to a fast start and quickly acquired the first monopoly.

Lacking enough capital to acquire new properties, I hunkered down and focused all my efforts on capital accumulation. 

Pass “Go”, collect $200.
Tax credit, collect $15.
Someone lands on my railroad, collect $50.

Turns out, the two railroads kept me in the game. People landed on them a couple dozen times.

The $50 payouts weren’t enormous, but I was able to accumulate some savings.

All the while, I resisted trade opportunities with other players. I didn’t want to give anyone a monopoly or obtain one via trade myself unless I had enough capital to build on it. While I was slowly accumulating, the player who got off to a fast start preceded to spend all his capital on expensive acquisitions that he couldn’t afford to develop.

It was at this point, about two hours into the game, that I negotiated a cash-and-property trade where we both got monopolies. Crucially, I received enough cash as part of the deal to immediately develop on my new monopoly.

It took more than two hours of grinding, but within a few short minutes, I was able to jump from 3rd place (out of 4) into the lead with a fully-developed monopoly in a great location.

I went on to win the game shortly after.

I was a two-hour “overnight success“.


Patient accumulation pared with asymmetric bets is the ideal strategy for both Monopoly and life.

Play the long game:

Accumulate, accumulate, accumulate then wait, wait, wait until you uncover an asymmetric opportunity with very limited downside and massive upside. Then boldly seize it.

It’s so much easier said than done.

Patience is difficult.

Saving and delaying gratification is difficult.
Identifying opportunities is difficult.
Having the courage to seize them is difficult.

It’s so easy…

To feel behind.
To feel stuck.
To feel disempowered.
To feel like life and others are passing us by.
To feel like opportunities will never come. 
To feel scared you’ll fail.

There will be times when all of those feel true.

Trust the process. Have fun playing the game.

One’s long-term strategy impacts the outcomes far more than one’s starting point (or current location).

Time is always working on our behalf.

Even when we can’t see it.


🤝 Stay in touch

I send an email several times a year with a handful of the most interesting things I’ve written or uncovered at home, abroad, and on the web.

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