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- Exploring the inner ring, uncertainty, and rest
Exploring the inner ring, uncertainty, and rest
Logan
October 09, 2025
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Exploring the inner ring, uncertainty, and rest
Happy Thursday! Thanks for reading Intentional Dollar — where we look at old money ideas through a new perspective.
What’s inside?
One idea to experiment with
Two quotes from others
Three questions to dig deeper
Four lines of poetry for the point
Disclaimer: This is not investment advice. These weekly posts represent my simple thoughts, a few quotes, and some questions — for educational purposes only.
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One idea to experiment with:
The Inner Ring:
In 1944, C.S. Lewis gave a lecture he called The Inner Ring. Over 80 years have passed since he voiced those words. Lewis is long gone, but his message remains as present and as true today as ever.
The Inner Ring is a goldmine, and I’ve linked it in the bonus reading today (below). It’s worth multiples of every second you invest in it.
I’ll point to Lewis’s lecture to do the heavy lifting, he makes a point far better than I could, and it applies poignantly to both our money and the way we’ve designed our lives. This isn’t new. The same status problems that have always plagued humanity continue to do so. They just wear different faces now.
The idea behind the Inner Ring is that we exist within a nested structure of rings, one inside the other, continuing indefinitely. At any given moment, your place in a ring means you are “in” that ring, but still outside a smaller, more exclusive one within. As novelty addicts, we endlessly pursue ring after ring until the final bell tolls.
Lewis put it this way:
“Once the first novelty is worn off, the members of this circle will be no more interesting than your old friends. Why should they be? You were not looking for virtue or kindness or loyalty or humour or learning or wit or any of the things that can really be enjoyed. You merely wanted to be ‘in.’ And that is a pleasure that cannot last. As soon as your new associates have been staled to you by custom, you will be looking for another Ring. The rainbow’s end will still be ahead of you. The old ring will now be only the drab background for your endeavor to enter the new one.”
Job titles, salaries, houses, cars, spouses, achievements, toys—anything you can name is vulnerable to this structure. There will always be something you cannot have. And the effort to grind your way into the next ring is the exact distraction that consumes your attention while the hands of time dance on.
Contentment is the only cure. And while contentment is immediately attainable, it’s slippery. We try to make peace with our lot, but slowly start to believe that the more exclusive lot must offer something better. We assume that once we break into the next ring, we’ll finally settle down, feel happy, exhale with relief, hang up our ambition, and experience lasting contentment.
But you and I both know that’s not what happens.
Our problem-solving brains start to ache for the next ring to join. So we march on.
I see two versions of this ring structure: the internal and the external.
The internal version is powerful and good for us. It’s the “inner scorecard” version. It’s the understanding that ambition and drive can make you better, but only when they’re applied to the rings that matter to you. In this version, you’re blind to society’s leaderboards.
The external version is destructive and it’s not easy to see. It’s an age-old, well-designed game that pulls us in. We begin working through the levels, the rings, but it’s someone else’s game, governed by an external scorecard. One where your worth is measured not by your own standards, but by someone else’s. And what good is that?
Maybe it’s simply human nature to want the next inner ring. If that’s true, then we must design a system of rings that make sense to us. A system where, when we reach the end, we don’t simply end up with more money, more toys, more status, more power, or more accolades than someone else.
what’s the next ring? Is it in your own game?
Two quotes on uncertainty:
Information mitigates uncertainty but never eliminates it.
“There will be very few occasions when you are absolutely certain about anything. You will consistently be called upon to make decisions with limited information. That being the case, your goal should not be to eliminate uncertainty. Instead, you must develop the art of being clear in the face of uncertainty.”
“Information is the resolution of uncertainty.”
Three questions on rest:
What does rest and recharge look like for you?
What happens if you don’t get adequate rest?
What cadence do you typically need this rest?
Which question stuck with you? Questions like these are spotlights for the mind. Reply to this email and let me know which one shined light on a previously dark cave.
Four lines of poetry for the point:
Contentment’s always under siege
There’s another level, no final prestige
We swipe hard at the pot of gold
But it’s an illusion we will never hold
Contact Me:
Content ideas, questions? Reply to this email or reach out to me at [email protected]
Disclaimer: This is not investment advice. These weekly posts represent my simple thoughts, a few quotes, and some questions — for educational purposes only.
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