What to do when you can’t solve a big money challenge.


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Jan 09 2025 17 mins   1
Do you remember that scene in Lord of the Rings where Gandalf and Frodo and the whole fellowship of the ring crew were on a long, epic journey, and they were stuck at large stone doors, called The Doors of Durin, that had a riddle inscribed on it?

For hours and hours they sat before that stone door in the moonlight, trying to solve the riddle inscribed in stone in the elvish language. “Speak, friend, and enter,” was all the riddle said.

If they could solve it, the door would open and they’d be able to travel through the secret passageways that led through the mountain so they could finally destroy the ring of power once and for all.

In many ways, that scene is a perfect metaphor for the money riddles we all face from time to time.

We’re all trying to get somewhere on our epic journeys (a.k.a., our lives), and sometimes we end up blocked by an immovable stone door that has a seemingly unsolvable riddle about money etched on it.

The riddle might be something like “how can we afford to buy a house in this economic climate?,” or, “how can I bring in more money when I have a job where the salary is capped?,” or “how can we save enough money to send our kids to college with only a few years remaining?.”

Money riddles like this (which I also call “money koans,” like the koan questions you sit with in Zen Buddhist meditation practice), aren’t written in the elvish language on a big stone door, but they might as well be.

Just like Gandalf and Frodo and the whole crew sat there for hours trying to solve the riddle that would open the door, we often have to sit with our money riddles for days, or weeks, or months, or even sometimes years for the big ones.

Working with and solving these money riddles is the topic of today’s recording on the first volume of the Art of Money Mixtape I made for you.

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