Kevin Kelly's "103 Bits of Advice," Expanded
Kevin Kelly, who arguably has written one of the most influential essays regarding the internet and the creator economy, "1,000 True Fans", published "103 Bits of Advice I Wish I Had Known" on his 70th birthday. In the simple article, he gives practical advice, philosophical quips, and everything in between. I thoroughly enjoyed reading it when it came out. So much so, I printed it out and annotated bits I loved and wanted to go deeper on. To my luck, Freakonomics published an interview with him asking about that specific essay. Kelly was able to provide more context on his answers and share a few stories. The following comes from that interview. One of the pieces of advice observe, very factually, that "ninety percent of everything, is crap." Kelly goes on to encourage the reader to, if they find something they don't like, just try finding the ten percent that is actually good. But how to find that ten percent was left as a mystery, until now. Stephen Dubner, the host of Freakonomics asked him for his advice on finding the "'non-crap' 10 percent": > I have to say, this one I’m talking to myself because I often get very impatient. So, the only bit of advice for me is to keep returning to it with as much grace and open-mindedness as possible because nine times out of ten you’re going to be very disappointed. So why are you going to go back the tenth time? Of course, life is limited. We can’t try all the stuff that we don’t like. But when I have a chance and it’s not too difficult, I’ll give things a second or third or fourth chance. And occasionally, I do change my mind and it’s like, “Wow, I’m glad that I pursued that because I didn’t see it in the beginning.” Dubner cited research that showed when people approach the ages of 30 or 40, they typically are set in the ways of the food they eat and the things they do. Trying new things just isn't much of an idea as you get older. Fortunately, Kelly had some simple advice t

I think this is exactly what I was looking for, but couldn't put it quite so eloquently. Thank you.
I put Player X on a game show and imagined they had the choice to keep the $30,000 they have, or risk it for double or nothing. As you mentioned, if that player went on the game show because they had a $30,000 debt to pay before they lost their house, they're going to keep the money and pay off that debt.