“All I Want for Christmas Is You” is playing in a department store somewhere right now. Probably driving some cashier insane.
That was me once. December 2007, holiday job behind the register, waiting for exam results that would decide my future, listening to Mariah on repeat until I wanted to throw the speakers out the window.
Here’s something that surprises people about me:
- I’ve never owned a Monopoly board
- My friends never owned one either
I was a little jealous of kids who got one for ChristmasSo I’ve never played a single game in my life
Then I saw this recently:
I’ve never played Monopoly. But I’ve watched people live it.
Collecting their $200. Trying to stay out of trouble. Never buying a single asset.
Not really playing. Just going through the motions.
Like passing on a property because holding cash feels safer. A few laps later, you’re just paying rent to everyone who bought.
Some of them are in their fifties now. They tell me they wished they’d stopped playing it safe. Stopped living on autopilot.
By the time they realized, the options had quietly disappeared. Not just financial options. The freedom to choose how they live.
Palliative care nurse Bronnie Ware wrote a book called The Top Five Regrets of the Dying. Number one? “I wish I’d lived a life true to myself, not the life others expected of me.”
Living true to yourself takes freedom. And freedom takes intention. Planting seeds today that give you shade tomorrow.
That’s what steady compounding is really about. Not just wealth. Options. The option to stop playing someone else’s game and start building your own.
Funny thing about playing it safe. We can spend our whole life avoiding jail, only to realize we were sitting inside our cell all along.
Good news is, the board resets every year. In 2026, we get to choose. Keep going around the board and not do anything? Or start building something that’s actually yours.
Merry Christmas.