Ryan hits a major turning point in his life and makes the decision to rapidly and dramatically change the direction of his career. We talk how he feels about his life now, what he’s thinking about doing next, and I coach him through the process, as well as help him realize the potential emotional issues that may be holding him back, or preventing him from being completely honest with himself. We also talk about some specifics of my learning philosophy/process including: how to balance learning new skills with practicing old skills, why I’ve been progressing so rapidly in skateboarding recently, and how I use goal-setting to motivate myself to improve. This is an exciting episode if you’ve been following the growth of Ryan, either personally, or through the lens of the last 11 episodes of the podcast. It will be interesting to hear in the next few episodes how Ryan’s plans work out, and how well he sticks to what he states is his goal at the end of this episode.
Selected Links for the Interview:
- The Art of Learning: An Inner Journey to Optimal Performance by Josh Waitzkin (in my top 4 books, it’s a great audiobook too)
- Antifragile: Things That Gain from Disorder by Nassim Taleb (in my top 4 books)
- WKND “Finger Skater Owned and Operated”
- My As a Man Thinketh Article
- Raymond’s Blog
- Jamil’s Blog
- Ryan Holiday on Rich Roll’s Podcast
- Show Your Work!: 10 Ways to Share Creativity and Get Discovered by Austin Kleon
- The Paleomodern Polymaths Facebook Group. If you listen to the podcast, you SHOULD join this!
A my #newtrickeveryday skateboard updates:
I try my hardest to learn a new trick everyday, but until recently I never really talked much about it. Skateboarding drives me crazy for the same reasons I love it: it isn't linearized, it isn't straightforward, there aren't check marked lists or objectives, and there isn't a clear path of how to become a better skateboarder, or what it even means to be a "good skateboarder". Some days you learn new tricks, and on others you forget old tricks. There are so many things I "used to be able to do" but can't anymore, and that's why I can never really tell if I'm improving as a skater. Part of this is living in my own head, and understanding how quickly the mind normalizes satisfaction and happiness. 2 years ago I would feel like I had a good session if I landed a single kickflip, and now I regularly defend kickflips in games of S.K.A.T.E. and end up thinking about how disgusting my kickflips look. I actually feel like a BAD skater when I land them because I don't like the way they look or feel anymore. I'm not one to rely heavily on external validation, which is one way of getting a more objective opinion on your progress, so I built two systems into my skateboarding practice that I've been consistent with, and have noticed a substantial acceleration in my learning process since implementing. 1. Learn a new trick, that I've never landed before, every single day 2. Film a trick everyday (ideally the new trick) and post it somewhere public where I can scroll back and see my skills develop as I continue to practice and experiment. New tricks look ugly and awkward, but they feel the best and make me the happiest to land. So while I might look "cooler" or "better" posting perfectly clean skateboard tricks everyday, I'm more interested in 1. The progression and 2. The authentic emotions behind the tricks. I'd much rather be happy than cool. Here's my daily skateboard practice in action. #nollie and #fakie #halfcab line inspired by @prod84 @bobbydekeyzer. It doesn't look pretty, but look at the expression on my face when I roll away. That's exactly the type of skateboarding I'm chasing, and what I want to capture on film. |📹 @tedfilmsskate
I mentioned that I try to land a new trick everyday, but how long does it take me to land a new trick. An hour? A week? Months? Three years ago I saw Keenan Milton's switch kickflip over a picnic table, became obsessed with the trick and started trying the trick every time I skated. Two and a half years ago I broke my foot, couldn't skate for 12 weeks, and could only skate switch for a month after. I thought I was getting close so I made a bet with my friend about when I would land it to motivate me to get it sooner. Two years ago friends at the skatepark would tell me "you can land this today" whenever I tried the trick. A year ago those same friends were landing it regularly. I did one on carpet and posted a promise that I'd roll away from one within a week on my wall. Nine months ago I thought I finally "figured it out" after I learned how to keep my shoulders and weight over the board. Seven months ago I decided to ban myself from doing flip tricks because it was stressing me out too much. Four months ago I wrote a note on my phone of my bucket list of flatground skateboard tricks, switchflip was at the top. A week ago I landed my first Nollie flip. Later that week @tedfilmsskate said "hey you know switch flip is easier than Nollie flip", and I reluctantly gave it a few attempts. 100 tries later I rolled away from one. Excited, surprised, and emotionally exhausted I convinced myself that I'd be happy with one, and I should leave before I get frustrated again. Ted said he'd give me 10 tries to land it on tape, and on the 9th try I rolled my ankle hard. I closed my eyes and remembered how it felt to watch Keenan Milton switch flip for the first time, looked up, and did this. A trick a day doesn't mean it takes a day to learn a trick. I spent 3 years taking ~10,000 attempts to land two switch kickflips. The hard part about skateboarding isn't trying when you get tired, it's continuing to try when you've failed for months, when it doesn't look like you're making progress, when you feel crazy for even thinking it's possible anymore. Sure tons of people can do this, but now I can too 🙂 #thankyouskateboarding