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_{Exploring the contrarian, satisfaction, and choosing difficulty}

Happy Sunday! 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 Contrarian:

Most people think being contrarian means standing opposite the crowd. Not always, most times that’s just reaction. True contrarianism is having the patience to stand still while everyone else rushes past you.

The world rewards speed and certainty. Opinions travel so much faster than understanding. Beliefs are adopted not because they’re examined, but because they’re available, and the perceived, or real, social cost of not adopting those beliefs is painful. When enough people repeat something, it starts to feel true. That feeling can be dangerous, as a crowd walking toward the edge of a cliff is no less at risk than a single individual walking the same path.

Being contrarian begins with restraint. It’s the decision to pause when momentum is loud. As Mark Twain warned, “Whenever you find yourself on the side of the majority, it is time to pause and reflect.” Pause doesn’t mean reject. It means slow down long enough to think for yourself.

Independent thinking is quiet work. It rarely announces itself and almost never feels confident at the start. You don’t get immediate validation for it. Often you don’t get any. Nietzsche captured the cost well: “The individual has always had to struggle to keep from being overwhelmed by the tribe.” That struggle is daily. It’s choosing not to outsource your judgment. Nearly anyone with anything of consequence has faced the crowd and decided for themselves, left or right. And as Sam Zell put it, “If everyone is going left, look right.” Maybe there’s something over there, maybe not. But you thought about it, you set course and conviction from logic not largeness.

Contrarian thinking isn’t about being right in public. It’s about being right in private and patient in the meantime. It’s the willingness to sit with uncertainty while others borrow confidence from numbers.

The crowd offers reassurance. Independent thought offers clarity. You have to choose which one you want more.

_{Two quotes on satisfaction:}

As we head through the holiday season, into the new year, keeping the meaning of satisfaction in pocket will help us navigate the inevitable snares that snag us.

_{Three questions on choosing difficulty:}

1. What daily forks do I typically take the easy path instead of the difficult one?

2. What if I intentionally took the hard path for a month?

3. How can I gamify and make the hard thing fun?

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:}

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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.

Last Time the Market Was This Expensive, Investors Waited 14 Years to Break Even

In 1999, the S&P 500 peaked. Then it took 14 years to gradually recover by 2013.

Today? Goldman Sachs sounds crazy forecasting 3% returns for 2024 to 2034.

But we’re currently seeing the highest price for the S&P 500 compared to earnings since the dot-com boom.

So, maybe that’s why they’re not alone; Vanguard projects about 5%.

In fact, now just about everything seems priced near all time highs. Equities, gold, crypto, etc.

But billionaires have long diversified a slice of their portfolios with one asset class that is poised to rebound.

It’s post war and contemporary art.

Sounds crazy, but over 70,000 investors have followed suit since 2019—with Masterworks.

You can invest in shares of artworks featuring Banksy, Basquiat, Picasso, and more.

24 exits later, results speak for themselves: net annualized returns like 14.6%, 17.6%, and 17.8%.*

My subscribers can skip the waitlist.

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_{*Investing involves risk. Past performance is not indicative of future returns. Important Reg A disclosures: masterworks.com/cd.}