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The Sunday Letter · #168

Weekly Mix #168 - The Psychology of Money, Thinking For Yourself & Community

Weekly Mix #168 - The Psychology of Money, Thinking For Yourself & Community

Happy Monday!

This week I continued the 30 mini essays in 30 days project. You can read them in this Twitter thread.

After writing for ~5 years on my blog, and another few years of the newsletter, this week I think I finally figured out what it was about: living a better life.

It sounds trivial, and obvious, but it wasn't for me.

I started the blog in 2015/16 to write about the experiences I was going through as a founder, and working at Techstars Boston, and the newsletter has been mostly a way to share some of the stuff I found interesting each week.

Many blogs have a very focused theme—they write about personal finance, or tech startups, or product management—and I've always wanted to write about everything.

The unifying theme, I think, is living a better life.

Eating better, becoming more fit, being better at your job, mastering your own psychology, building positive habits, expanding your mental models, reading and organizing book notes on all these topics—all these things fit with building a better life.

So, I hope that fits with you, because ultimately you're the one who's giving me permission to be in your inbox every week, and sharing and reading what I produce.

The benefit of nailing this down is that I believe it will help improve both the blog, and this newsletter, as I'll always be able to circle back to the question: how does this help someone live a better life?

With that, on to the newsletter!

In this week’s newsletter:

Book Notes: The Psychology of Money by Morgan Housel​

Article: How to Think for Yourself - Paul Graham​

Product: Road-Haus by Wheelhaus​

What I'm Watching: Dave Chappelle Interview with David Letterman​

Have a wonderful week!

Graham

Book Notes: The Psychology of Money by Morgan Housel​

The most valuable part of this book is that it explicitly links personal finance with psychology.

Saving, investment strategies, decision-making—these have all been known as key parts of personal finance, but the psychological side is rarely explored, and that's what this book is about.

Reading this plus another book on the operational side of personal finance—I Will Teach You To Be Rich, for example—will put you ahead of 99% of the population on managing your money.

Financial success is far more about how you behave than what you know.

Luck and risk play a role in almost all outcomes. Individual effort can only get you so far.

Be careful about looking at specific examples of outcomes, and look more for general patterns.

The hardest financial skill is getting the goalpost to stop moving. And to do that, you have to stop comparing yourself to others, and start determining what is “enough” for yourself.

One of the single most important things you can do as an investor is wait, or extend your time horizon.

Staying wealthy requires some combination of paranoia and frugality.

Always plan for something to go wrong, and for some large, unexpected expense.

Controlling your time is the highest dividend money pays.

No one is impressed by your possessions as much as you are.

Building wealth has little to do with your income or investment returns, and lots to do with your savings rate.

Past a certain level of income, what you need depends only on your ego.

Aim to be reasonable with your finances, not completely rational. This will be more realistic long-term.

We can’t predict future outlier events. That’s what makes them outliers. So factor it into your plan.

You need to add room for error, and avoid financial ruin. Leverage—going into debt—pushes routine risk into potential for ruin.

Assume your priorities will change in the future, and avoid the extremes of financial planning. Examples include assuming you’ll be happy with very low income, or willing to work very long hours for higher income.

Everything has a price. The price of immediate consumption is much more visible than the price of neglecting long-term investment.

Know what game you are playing, and avoid taking financial cues from people playing a different game.

Stories are the most powerful force in the economy. Beware the stories you tell yourself.

Short takes:

Article: How to Think for Yourself - Paul Graham​

Paul Graham's essays are always thought-provoking and useful. This essay describes how to think independently:

Be less aware of conventional beliefs.

Cultivate friends of different types.

Treat idea exploration as a puzzle: there is always something to discover that you don't know.

Develop the habit of asking yourself "Is that true?" when you hear a new idea.

Develop the three individual muscles for thinking independently:Be fastidious about the truth: ask yourself to what degree something is true.

Resist being told what to believe: take delight (something positive) in finding ideas that subvert the common opinion.

Increase curiosity: indulge it by investigating things you're interested in.

Product: Road-Haus by Wheelhaus​

I've included lots of cabins or tiny homes in newsletters this year, mostly because I've been looking at various designs and thinking about building myself.

What I think is special about tiny homes and home design is they all ask the question: what does our living space really need?

This is a particularly beautiful one in my opinion, incorporating a lot of light and high-end finishes in just 250 square feet, while still keeping a queen-size bed and a beautiful shower.

What I'm Watching: Dave Chappelle Interview with David Letterman​

I've watched some of the Letterman interviews on Netflix, and I've watched lots of Dave Chappelle's work. I was still really impressed by this one.

Perhaps it's because Dave discusses some issues in more detail, and a different style, than usual, but I was blown away. I'm now rewatching some of his standup.

Here are some of the topics covered in the interview:

The benefits of small communities:Your days are more predictable

The faces are more familiar

Fostering trust and kindness is foremost in everyone’s minds

Lessons his father taught him: All politics are local

Community is everything

You can’t change the world, but you can make a corner of it pretty nice

How he needed to make his own decisions: he would help him sort through the pieces, but he wouldn’t put the puzzle together

Fame evaporates with regularity

Knowing that somebody loves you and cares inspires others to be courageous

Much of art is on the viewer to do the work to interpret it

So many people and groups act like suffering is mutually exclusive, or that one group is suffering more than another; this isn’t the case

Photo: Saturday sunset surfing

Finding ways to escape being online are becoming harder and harder, but few things are more relaxing than being able to head to the beach and get in the water on a weekend. After starting gray and rainy, the day ended with a beautiful sunset.

Thank you for being part of the newsletter every week.

It means so much that you let me be part of your inbox, and I love building a community of like-minded people with you.

If I could ask one thing: could you forward this to one person you think would enjoy it? They can sign up directly for the newsletter here.​

If you haven’t yet, feel free to follow me on Instagram and Twitter, and say hi!

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