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- Exploring some questions, the good times, and three risks
Exploring some questions, the good times, and three risks
Logan
August 21, 2025
In partnership with
Exploring some questions, the good times, and three risks
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:
Some Questions:
Where am I ignoring updates and running old operating systems, thinking that’s the best there is?
What would I work on if I were the only one to ever see the output?
If I went back to zero, how would I rebuild?
What would someone with unlimited agency do here?
What long-held habits might be compounding against me?
If I had to give all my money to charity, where would I give—and am I doing any of this now?
How many of my beliefs and behaviors are bound by personal conviction versus public conformity?
Do I need to change what I’m doing, or simply be more patient?
What’s my earliest money memory, and how has it shaped me all these years?
Where is my money trajectory taking me?
What financial thorns are stealing my sleep
What decisions am I making on financial grounds that should be made on non-financial grounds?
What’s the highest version of life I could see myself living?
What can I do (or stop) today so that 80-year-old me doesn’t live with regret?
What do I want to be remembered as?
it’s always good to ask some questions
Two quotes on the good times:
These are the good times. Extreme wealth in the past couldn’t afford the things we take for granted today.
“John D. Rockefeller was worth the equivalent of $400 billion, but he never had penicillin, sunscreen, or Advil. For most of his adult life he didn’t have electric lights, air conditioning, or sunglasses. Everything about wealth is circumstances in the context of expectations.”
“Nostalgia is a file that removes the rough edges from the good old days.”
Three questions on three risks:
in what areas of life am I over-leveraged?
Where might I be overconfident?
Where am I letting impatience drive my choices?
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:
A question or two
Might change what you do
Write them down
Think them through
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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