Author Topic: Patrick OShaughnessy  (Read 154 times)

galumay

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Patrick OShaughnessy
« on: November 23, 2023, 06:46:55 AM »
The most powerful thing I am aware of is to spend your time doing what you want to do.

I've been on a multi-year mission to make as much of my calendar filled with things I actually want to do as possible. This has been SHOCKINGLY hard.

I've learned there's actually only one thing that I really love, that I'll do until I die: spending long periods of time with extraordinarily talented people (usually founders, investors, and teachers--people with really high leverage).

I like to learn from them (nothing energizes me like someone doing what they are supposed to be doing with their life), and I like to try and help them by unlocking something productive: a podcast that exposes them to the world's best audience, an introduction or two that accelerates some part of what they are doing, a distillation of their narrative or core message, maybe even an idea they hadn't considered before.

There are many days now where I have 2-3 long conversations and that's it. Those are the best days. "conversationalist" isn't a job you imagine as a kid, and its not one that'd "make your parents proud."

The bizarre part is that if you just do what you love, incredible but unpredictable things will happen. I run a private equity/venture capital business and a media company, and both were an unforeseen consequence of being a conversationalist. About every 100 or so conversations, an amazingly interesting investing opportunity spontaneously appears (I'm very rarely explicitly hunting for some specific investment, and I've found the best ones come from some strange source).

Kevin Kelly has this great idea that you need your own distinct definition of success. For me, success would be cultivating a very specific reputation. I'd like my reputation to be "talk to that guy and you'll leave energized, thinking about something new. Good things will happen, and it'll generally cost you nothing."

I sometimes feel guilty that my "work" doesn't feel like a grind. People think great accomplishment requires "grit" and "grinding," and I have nothing against those things, and surely tons of the great outcomes were just made possible by extreme grinders...but, I never feel like I'm grinding when I do the thing I like doing.

Maybe I'd offer an alternative to "grit." Great long term outcomes require an unusual fuel source. Chips on shoulders is one, but I tried that and it almost killed me. The best long term fuel source is some repeated act that energizes you in a way that then lets you become a generative person, who uses the energy to make things for others. A great question is "what is your renewable fuel source?" While its not perfect, I think the best answer is "do what you want."

Joseph Campbell wrote "the privilege of a lifetime is being who you are." Being who you are, or doing what you want, sounds selfish, but its the opposite. My experience with countless people doing what they want is that they do THE MOST for others.

What I've learned watching others try to do more of what they want is that the transition from a life of "I should" to "I want" requires extreme conviction, courage, and a leap of faith. It should be telling that while you sometimes see people make this transition, you never see someone transition back the other direction.

I sincerely hope more people take this leap.

"A bit of advice given to a young Native American at the time of his initiation: 'as you go the way of life, you will see a great chasm. Jump. It is not as wide as you think.'