Risk Aversion

This quote pretty much sums up what happens to successful people as they grow older. They lose the ability to risk it all. The more successful they are, the more they want to protect what they have. You go from being a creator to a protector/hoarder.

One doesn’t have to look too far — those making headlines these days are too worried about the future, instead of trying to build a better one. It is not just individuals — even companies become a bit more complacent and take fewer chances. And nowhere is it more on display than it is in Silicon Valley, where companies are starting to age and are hampered by their valuations. The former risk-takers have become risk-averse.

For me, the hardest challenge is to unlearn, and be willing to embrace change, however scary it might appear to be. I try and do this every day — whether it is in foods I try, clothing trends I embrace or simply just jumping headfirst into new technologies. And then stress test them against the “meta data” of life, which can also be labeled as “knowledge.”

For whatever it is worth, “The Silent Season of a Hero” is perhaps one of my favorite stories by Gay Talese. It is as much about Joe DiMaggio as it is about all of us who know that someday, the lights will dim, the applause will end, and an eerie quiet will begin.

February 9, 2025. San Francisco

PS: I accidentally published a draft version of this piece, and it got emailed to those who have subscribed to get my posts as emails. My deepest apologies — teaches me a lesson to not use the WP mobile app!=

14 thoughts on this post

  1. I think that mirrors are physical decline as we age. We see that we can’t do what we wanna stick, or at least as well, so we hold on more tightly to what was.

  2. Sorry that got sent before editing.

    It should read:

    I think that mirrors our physical decline as we age. We see that we can’t do what we once did, or at least as well, so we hold on more tightly to what was.

    1. Rich

      Do you want me to delete the other comment?

      Also to your point, as I get older, I am getting a little bit more open to living on the edge.

  3. I agree with the sentiment but it’s more complex as the risk aversion is an also a function of having family and kids directly depending on you.

    It’s a lot easier to risk it all when it’s just you and significantly more challenging when your home, kids’ school and family lifestyle are on the line.

    There’s still an ability to take risk but it is much more measured and starts to feel increasingly feasible with a larger safety net in place. But even then, the goal posts tend to shift on new lifestyle normals.

    This quote resonates with me a lot as I feel so far from being able to risk it all to do another startup as I’ve gotten older. Maybe when kids are a bit older…

    1. Josh,

      While I understand the obligations, and responsibilities make you think different, especially when you are not economically privileged. But this is something what impacts everyone. I would argue that even the richest of them all become even more risk averse. I am seeing this play out in Silicon Valley right now.

  4. For so many (me included) there were no lights, there was only applause from kids below 10 years of age during a birthday. But everyone experiences the eerie silence.

  5. That sentiment is often expressed with regard to musicians and many examples in the pop world exist. The early stuff is what gets remembered. The later stuff is tame. But it is not a given. I think of Donald Fagan’s later work, Beethoven’s final string quartets and Ri char’s Strauss’ Indian Summer. Risk takers to the end!

    1. Amen to that. Thank you for that wonderful reference to Beethoven and Strauss. To be candid, I didn’t know much about their lives so this is very educational.

  6. I’m at a place where the kids have flown the nest and I’m eyeing retirement. It’s important to protect what I have — funds, health — because I need it to last!

    1. That is a fair way to think, but you can take risks intellectually, if not financially. I think risk aversion is often conflated with fiscal needs too much.

  7. This is why the Cloud Czars are vulnerable in the AI age. They’re defending territory and becoming AT&T, when they should be focused on writing better, faster AI SOFTWARE . Only the paranoid survive means you need to constantly make others paranoid, not go crazy yourself

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