Insecurity Analysis – A Wealth of Common Sense

Writing is a useful process for me. It’s how I organize my thoughts and learn what it is I really think.

It can also be a lonely endeavor.

You’re in your own head a lot. I sometimes forget someone is on the other end reading my words.

A number of years ago, I received an email from a very well-known investor who read one of my blog posts. Some would call this person a legend in the investment business. I didn’t really believe it at first. I thought it might be a prank so I had to verify with a reporter friend who knows things. It was the correct email address. Verified.

This giant of investing had a Google alert set up for his name. It popped up on my blog from something I wrote about him. He shared with me that sometimes the media is too critical so it was nice to see a more fair and balanced take.

The email was kind and respectful. We exchanged a few replies about the business, but that was the end of our communication.

What stood out most from this interaction was the unexpected insecurity. This person is ridiculously wealthy. He has an extraordinary investing track record. He is widely respected — some would say famous — in financial circles.¹

Yet he still had to search up his name to see what people were saying about him. It really put the whole idea of success into perspective for me. It’s a good reminder that you never really know what’s going on in other people’s lives or thoughts.

I was reminded of this story while re-reading Born Standing Up by Steve Martin. I love this book.²

Martin shares his story about coming up in the entertainment business. By the late-1970s, Martin became the biggest stand-up comic act in the world, selling out arenas all over the country. By 1981, he walked away from stand-up for good.

Here’s his explanation from the book:

Once he became the most popular comic in the nation the backlash began. So did the anxiety attacks. His personal life suffered. Seeing a smattering of empty seats caused far more pain than the pleasure he got from a sold-out show.

Martin has enough self-awareness to recognize how silly this might seem to people from the outside:

I fell into a depression that might be called self-indulgent but was real just the same.

I have heard the argument that celebrities want fame when it’s useful and don’t when it’s not. That argument is absolutely true.

Sometimes getting everything you want in life can be the biggest let-down when you realize it doesn’t automatically make you happier. Martin seemed to find more joy in the journey to stardom when he was broke and unknown and trying to work his way up.

Obviously, there are many ways in which wealth and fame can make your life considerably more comfortable. But money alone doesn’t guarantee happiness.

I don’t know if these stories are meant to make you feel better or worse about yourself.

In some ways, it’s good to know that no one has life completely figured out. Everyone has their struggles.

In other ways, it’s a letdown to know that getting everything you ever wanted in life and more might not be as fulfilling as you expect.

The Wall Street Journal asked The White Lotus star Jason Isaacs if he is happy financially-speaking. I like his answer:

I don’t do the jobs that would bring me money. I haven’t over the years taken the detective shows that are on forever. So I guess money can’t be that important to me. I read somewhere that if you ask people what the happiest day they’ve ever spent was, they almost always look back at something in nature: the day they were swinging across a river on a rope, or the day they went on a hike. It’s never, “The day I bought my plane.” 

Money can buy you things that make you happier, but your level of wealth alone is not going to move the needle.

There’s more to life than a few extra zeros in your bank account.

Further Reading:
Everyone Struggles

¹Finance famous is funny to me. There are a lot of people I respect in this industry but I can’t see myself getting worked up from meeting famous investors or business people. It just doesn’t move the needle in terms of excitement.

²The Steve Martin documentary on Apple TV+ is fantastic as well.