Dirt off your shoulder (Ricky Weekly #87)

This is where I share 3 things every week with my friends and anyone else interested.
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A picture from my life:

Went to the mountains by Los Gatos last weekend for a retreat with my co-founder David. I had such a good time! We’re close like brothers, but as we’ve gotten older and life’s gotten busier, we don’t really get to connect much anymore. Our conversations are usually all business and to the point so we can get to our lives. Highly recommend just disconnecting (slow wi-fi) in order to connect.

A thing on my mind:

I was re-reading Sam Altman’s “How To Be Successful,” which is great but this tiny part caught my attention (emphasis mine):

Self-belief must be balanced with self-awareness. I used to hate criticism of any sort and actively avoided it. Now I try to always listen to it with the assumption that it’s true, and then decide if I want to act on it or not. Truth-seeking is hard and often painful, but it is what separates self-belief from self-delusion.

Hate criticism? Actively avoid them? I might’ve been a masochist for too long because I was surprised to read that.

I remember in college meeting a lot of brilliant, confident and often delusional characters. One time, one of them had a big public fall from grace. My friends and I were talking about it (admittedly in a moment of schadenfreude) and we made up this idea of the “bullshit-to-substance ratio.” Basically, you gotta walk the walk, otherwise at some point the BS-to-substance ratio becomes too high that it becomes plenty obvious to everyone you are full of it. The person who fell from grace seemed to have tripped over the line and got burned for it. But it was interesting to me how someone’s BS-to-substance ratio can even get that high to begin with? Then I got into the startup game, and this story seems to be playing out all the time. See SBF and Liz Holmes for the most prominent examples.

I used to be kind of judge-y about this, but over the years I’ve come to see that maybe it’s necessary, and a lot more necessary for some? Believing in yourself is hard and just like everything it takes practice and looking for positive feedback loops. Obviously, we all should strive for healthier confidence that incorporates criticism, but criticism is not easily digested as part of a positive feedback loop. Also, the more ambitious you are, the more confidence you need. The Miami Heat is playing out of their minds right now, and they talk about how Jimmy Butler is fully trusting role players like Gabe Vincent and Caleb Martin to make them feel like they’re the best in the world. I’m guessing there’s not a lot of criticism going on in that locker room right now.

I’ve met people over the years who are very good at protecting their egos for whatever reason. I know this guy who is great at noticing whenever he feels even slightly bad, and would make it a point to do self-care or take time off to restore the ego. I used to think that’s low pain tolerance or a lack of courage, but now I think I can see the wisdom in it. If you know you need your confidence to be at a certain level in order to operate, you need to actively shield yourself from being derailed. I can’t imagine there weren’t people around SBF telling him he’s flying too close to the sun, but I think I can understand why he’d want to tune that out and only look for positive reinforcement. I’ve written in the past about how I want to run my startup like I play basketball, and it’s the same idea of doing everything you can to feel like you’re the best when you step on the court.

Obviously this is a very generous take, and I’m not saying I’m gonna go delude myself. I’m too grounded for that. I’m just saying maybe all of this is a lot more deliberate and necessary if you are Gabe Vincent and you have to think that you are the best option on your team in order to make the game-sealing shot.

A piece of content I recommend:

Staring into the abyss as a core life skill - Ben Kuhn

If you read what I wrote and you’re like wtf Ricky 🙄, then go read Ben Kuhn for an actual smart take. I think it’s a much more grounded perspective. He says to be successful is to have no delusions and ample amount of courage to stare into the abyss, face the music, or whatever you want to call it, and then make bold changes on schedule that are not delayed by your ego.

🤗

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As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My primary focus (and where I focus) is on Flow Club.