Responding to one of Dave’s old entries, where he talked about how he feels ashamed compared to what his classmates have accomplished.

That’s one thing I hate about having gone to Stanford and reading the Stanford magazine class notes. It’s not really about keeping in touch. It’s mostly about bragging, the notes being dominated by high achievers sharing their high achievements. Even the marriage / child announcements are kind of life achievements. Reading through it, you can’t help but feel outclassed.

But you know what I’ve realized? There’s no threshold of success after which you feel like you’ve “made it.” In fact, the biggest gunners I know are frequently the most insecure, because they’re even more prone to comparing themselves with their peers, and there are always people who have accomplished more than you. People that have become execs are insecure because they haven’t become CEOs. Rich people (by any reasonable standard) are insecure that they’re not more rich. It never ends, no matter how successful or rich you become. That to me is the saddest part about gunners. They accomplish a ton, but never feel satisfied.

People escape that, but it’s completely independent of how much you’ve accomplished or acquired. It’s purely a state of mind. A decision that what you have, what you’ve done is sufficient. And once you’ve made that choice, you’re not cowed by anyone else’s status anymore.

One could say it’s easy for me to say since I’ve “made it” in several facets of life, but I’m telling you, when I look at my coworkers and ex-coworkers, the vast majority of whom have achieved and acquired much, there’s just no relationship with how much they’ve done and how satisfied they are with their place in life.

Anyway, my favorite story from John Bogle, which I’ve shared before: “At a party given by a billionaire on Shelter Island, the late Kurt Vonnegut informs his pal, the author Joseph Heller, that their host, a hedge fund manager, had made more money in a single day than Heller had earned from his wildly popular novel Catch 22 over its whole history. Heller responds, ‘Yes, but I have something he will never have… Enough.'”

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