The Philosophical Investor's Blog

Little Bets -Should Highest Cost Debt Be Repaid First?

debt

I recently read a summary of an interesting piece of research that is somewhat counterintuitive at first glance but upon deeper reflection makes more sense and it’s the cornerstone for one of life’s great metaphors, you’ll see what I mean.

Little Bets -What We Can Afford to Lose vs.

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An Embarrassment of Success

struggle Tennis

Steve Magness To get better, you have to struggle June 13, 2025

Free will can be quite challenging. We have so many choices and endless options. And like so many things, it can be a double edged sword. We can make choices which improve our lives and those of others or we can make choices that can negatively impact our health and well being as well as others.

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Roland Garros and Fathering

Fathers

I’m still mesmerized by the nearly five and a half hour final at Roland Garros between Carlos Alcaraz and Jannik Sinner. Sinner was up two sets and only needed one more to win the tournament, but Alcaraz never gave up and fought back with incredible ferocity.

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To Claim or Not To Claim. That Is the Question

Social Security Benefits

I saw a lot of coverage last week about people taking their Social Security benefits as soon as they become eligible at age 62. This is a typical headline.

Americans are filing for Social Security at record rates June 5, 2025

The thinking is that the much larger than expected number of people filing for their Social Security benefits at the earliest age is due to concerns that program benefits will be cut in the future as a result of DOGE and President Trump’s lack of regard for legacy institutions.

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The Insecurity of Perfectionism

Perfectionism

Besides following news on X, every so often, I am exposed to some real gems when reading threads on that platform. I have learned a lot from some great writers there who are able to take important and complex subjects and break them down into coherent and well thought out threads.

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From Procrastination to Perfectionism - The Art of Play

Procrastination

This week’s blog post continues with the second half of the summary of Free Play: Improvisation in Life and Art by Stephen Nachmanovich. Every creative person is constantly faced with obstacles that get in the way of their productivity. And these can be brutal.

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New - Debt Worries - Then and Now

Debt Worries
A blog for the curious skeptic –
There’s nothing new under the sun
(or at least very little)

I’m a big fan of newspaperarchive.com. I have a rather anti-social hobby of often going back and reading old newspaper articles. Occasionally I come across some worth sharing. The following is one written on March 18,

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Jacob's Incredible 30-Year Milestone

Jacob Stroke May 23, 1995

In 1995, I had been working at CWS for nearly eight years and had been married for six. One day, while I was in the office, I was interrupted from a meeting and told that my wife needed to talk to me.

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A Jenga Life

A Jenga Life

A little while back there was a tennis tournament in the Palm Springs area where we have a second home. A number of people were playing in the tournament who we knew and we had some of them over during one of the evenings.

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The Intelligent Ignoramus

The Intelligent Ignoramous

With this week’s blog, I will inevitably get drawn into the morass of politics by reposting this tweet from X.

Colby Badhwar @ColbyBadhwar vance is intelligent buy profoundly ignorant

Ignoring the typo in which “is” should have been “his” the post made me wonder about the paradoxical intersection between intelligence and ignorance.

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