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Exploring the games, self-responsibility, and keystone habits
Logan
September 18, 2025
In partnership with
Exploring the games, self-responsibility, and keystone habits
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.
7 Actionable Ways to Achieve a Comfortable Retirement
Your dream retirement isn’t going to fund itself—that’s what your portfolio is for.
When generating income for a comfortable retirement, there are countless options to weigh. Muni bonds, dividends, REITs, Master Limited Partnerships—each comes with risk and oppor-tunity.
The Definitive Guide to Retirement Income from Fisher investments shows you ways you can position your portfolio to help you maintain or improve your lifestyle in retirement.
It also highlights common mistakes, such as tax mistakes, that can make a substantial differ-ence as you plan your well-deserved future.
One idea to experiment with:
The Games:
Morgan Housel hit on this in a recent podcast and it’s stuck with me.
We spend a lot of time looking over the fence at what other people have. Their house, their car, their job title, their vacations, and we internally grade ourselves against them. There’s a big problem with this; they’re playing a totally different game.
Housel used the comparison of a lifter and a runner to illustrate different games we play. Imagine two people at the gym. One is training for a marathon, the other for a bodybuilding competition. The runner logs endless miles, staying lean and light. The lifter spends hours under progressively heavier loads, chasing muscle mass. If the runner looked in the mirror and envied the lifter’s biceps, they’d feel inadequate. If the lifter compared pace times or tried a 20 mile run, they’d feel unfit. Both would be missing the point. Both are playing different games.
We do this financially all the time. Someone sacrifices weekends and evenings to climb the corporate ladder and buys the lake house. We see the lake house but not the missed dinners, the late nights, the constant travel. We think, I should have that by now, without ever asking whether we’re willing to play the same game they are.
The goal isn’t to win every game. It’s to choose the right game for you. Your values, your trade-offs, your version of enough. The worst thing you can do is borrow someone else’s scoreboard, then feel like you’re losing.
So next time you feel the comparison itch, pause and ask: What game am I playing? If you’re playing for financial freedom, don’t get upset that you don’t have the flashiest car in the neighborhood. If you’re prioritizing time with your kids, don’t destroy yourself for not hitting every career milestone.
Pick your game and let others play theirs.
know what game you’re playing
Two quotes on self-responsibility:
It’s our responsibility to unlock the doors we want opened. No one’s coming with the keys.
“Man is nothing else but what he makes of himself. Such is the first principle of existentialism. This means that man is responsible for what he is. Thus, the first effect of existentialism is that it puts every man in possession of himself as he is, and places the entire responsibility for his existence squarely upon his own shoulders.”
“People with a low agency mindset tend to be passive, reactive, and fatalistic. They see life as something that happens to them over which they have little control or responsibility. They frequently feel like a victim of circumstances and tend to see themselves as a supporting character in other people’s stories.
People with a high agency mindset are active, enthusiastic, and optimistic. They view life as something they do over which they have great control and responsibility. They view themselves as the hero and author of their own story.”
Three questions on keystone habits:
What single habit, if done consistently, would make the rest of my life easier or better?
Where am I fighting downstream battles that a single upstream habit could solve?
Which of my current habits quietly sets the tone, better or worse, for everything else I do?
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:
The games we play may look the same
But different are they ever
The strategy that works for you
For me is hardly clever
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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