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Scenes from a Steeplechase: The Winner (ca. 1845) | Henry Thomas Alken (English, 1785 – 1851)

1. Barry Ritholtz | Let Your Opponent Beat Themselves

Tennis is two different games. The winner's game is the game that the professionals play. You score by hitting aces, by just kissing the line, by slicing, by hitting with power, by putting the ball in all sorts of challenging places with all sorts of swings that require a lot of technique and expertise. Professionals win tennis by scoring points.
The rest of us, the 99 point whatever percent of us amateurs, that's not how we win a tennis game. We actually lose by making unforced errors. We double fault on a serve, we hit it into the net, we hit it wide, we hit it long, we hit it with not enough spin so it just bounces right up to the sweet spot of our opponent's swing. And so, if you just make fewer of these unforced errors […] if you just stay within your own skill set and don't try and do much, let the other person beat themselves, that's how amateurs win games.

More from Barry: Make Fewer Errors, Make More Money (Ep.261)

2. Joe Hudson | Weaponize Shame

Uber successful folks. They at the same time feel like they're better than most people and they hold a deep shame inside of them. So both of those two things are happening at once. They're subtly putting themselves above folks and at the same time they're trying to prove to the world that they're good enough. And so that, that component is there for a lot of hyper successful.

More from Joe: The Art of Accomplishment (Ep.280)

3. Billy Oppenheimer | Make the Work the Win

David Senra, I think, is a great example […] He just loves doing the thing that he does, and getting to do it is the win for him. And the things like the external recognition, the people reaching out to him, the cool conversations he gets to have, the cool dinners he gets to go to are a nice cherry on top. But for him, the best part of it is sitting down in his room and recording a podcast. And that, I think, is the common trait that I see across the people I write about and read about and look up to. For them, it doesn't seem like they have to get themselves motivated to go do to put in the persistent work. It's the thing they just are compelled to do.

More from Billy: On Curiosity, Creativity & Conceptual Ancestors (Ep.158)

4. Derek Sivers | Just Show Up

When we live in a place like New York City or LA, you can see this happen firsthand, even the pedestal of Hollywood. There's some people that, oh my God, when you see them on a big movie screen, you go in person to a theater, and their face is huge. Then, you get to know them as people, and you go, ‘Oh, wow, that's just somebody applied for the gig. That producer hired a director, the director needed an actor, and the casting person just needed somebody to play that role to say those lines with a certain look on the stage to make this vision happen, and this person that I know just went for the audition and got it.’ Suddenly, their face is huge on the screen, but they're not a special person in a... They're not a special breed. They're not a different type. They are just like you. They just took the chance and showed up to the gig. 90% of success is just showing up […] They just went and did it. They did the thing instead of watching TV, and that's all the difference it took.

More from Derek: How to Become a Picasso (Ep.185) | Just Do the Thing (Ep.186)

5. Anne-Laure Le Cunff | Replace the Ladder with the Loop

It really requires changing your mental model of success, and going from that linear model we've been talking about, which I visualize as a ladder. And the reason why I visualize it as a ladder is because it implies that you have a certain order in which you need to do things […] And the problem with this linear model, the ladder that we're supposed to climb, is that first it assumes that you know where you're going, which in many cases, as we've been talking about, is not the case. It also assumes that you know what you want, which there's tons of research showing that we're actually absolutely terrible at predicting what we will want in one year from now, two years from now, five years from now. And it also assumes that you as a person, you are this monolithic, static person, and then that the world is not changing as well. So it just assumes that whatever variables you're working with right now are going to be the same in the future. […]
So it's really about letting go of this linear approach and replacing it with a more cyclical approach, which you see that in so many philosophies, in particular Eastern philosophies, but a more cyclical vision of what growth looks like. And this is really replacing the ladder with the loop, where you don't try to climb and go to a specific destination. You just try to go through one cycle of growth, where you don't know where you're going. You're just trying to learn to grow, to try something.
It starts with that word that you used earlier. Maybe. Maybe if I do this, this will happen, but I'm not quite sure. Let's go through the cycle and let's see what happens. And that means that it becomes really impossible to compare yourself to other people because you're going through your own cycle. And it also means that you can grow without this illusion of knowing where you're going.

More from Anne-Laure: Experiment Your Way to a Better Life (Ep.259)

6. Ben Reinhardt | If You’re Successful, Pay it Forward

An idea I'd love to inculcate in culture is this idea of paying it forward. Many people in tech made a lot of money because someone in the past did really important research. And that person is not going to be able to capture the value of their research, because often there'll be someone who tried something, it failed, but it gave someone else the idea. And it's just like, you can't propagate it back. The time scales are long enough that they might be dead. So we can't really pay it back, but we can pay it forward and enable to do the research that will then enable someone in the future to make a fortune off of some new technology. That is a thing that I would love to incept in culture.

More from Ben: Speculative Technologies (Ep.248)

7. Danielle Strachman | The Success is Doing the Thing, Not Getting the Badge

We're constantly reminding Thiel fellows, ‘Hey, it's cool to be building and doing what you're doing out in the world. It's not cool to be a Thiel Fellow.’ Having a badge isn't the cool thing, it's what you're doing.

More from Danielle: The 1517 Rebellion (Ep.279)

8. Morgan Housel | Tell the Best Story

A thing that I really believe is true for all, everything in the world is that the best story wins. It's not the best ideas, it's not the right ideas, it's not the complex ideas. It's just the best story wins. I've used this example before of Ken Burns, the documentarian. His documentary on the civil war came out in 1990. When it came out in 1990, it was such a success. More people watched the civil war documentary in 1990 than much the Super Bowl that year. It was just like a ridiculous blowout success. This is a documentary on the civil war, which is like one of the most documented. How many books are there on the civil war? Thousands and thousands. There is nothing new in Ken Burns’ documentary, nothing new. This is not like he was the guy to uncover Gettysburg. There's nothing new in there, he just told a really good story about it. An amazing story with captivating music and amazing editing. Because of that, he took an event that everyone had known about, and everyone has known the detail about. He got more Americans to tune in than watch the Super Bowl that year.
I think there's so many examples of that, of things that everyone knows, have been discovered for centuries. Nothing's new but if you can tell a good story about it, you'll get people's attention. That is what I think a lot of academics, in particular, miss. Is that they have all the right answers but they are the worst storytellers. I think a lot of the times they go out of their way to be bad storytellers. They want to use big words to fit in with their colleagues, to fit in with the academic tribe. I think there's so much room to take what academics know and explain it to a layperson in a story that they're likely to remember and likely to hook onto. There's so much room doing that.

More from Morgan: The Best Story Wins (Ep.100)

9. Dan Shipper | It Takes 10 Years to Have an Overnight Success

People think that progress is linear and it actually does not feel linear at the time. It happens in jumps, it happens, you see a clear beaker, and then you drop a crystal of salt in it and it suddenly all just turns into salt. It's a similar feeling. And I think that's why there's that sort of adage about it takes 10 years to have an overnight success. That is actually what it looks like from the outside is an overnight success or an overnight whatever. But that's sort of the crystallization of all the salt that's been boiled in the water happening because of one little thing. That little thing doesn't matter. It's the years of adding salt to the water and boiling it that matters.

More from Dan: How I Learned To Stop Worrying and Love The Allocation Economy (Ep.237)

Explore previous instalments of our ‘Guide To’ series: Decision-Making, Money, Agency, Getting Sh*t Done, Leadership, Failure, Communication, Creativity, and Happiness.

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