June 21, 2022 #176 Derek Sivers (Sort of). Three Questions to and Answers from a Modern Sage

Derek Sivers Derek Sivers is a modern sage. He’s been wildly successful by all the typical measures, but that’s not why I like him and his work. Nope. It’s because Derek seems to have beaten the game of life. He lives on his terms. Just because everyone thinks you should sell your company and make millions and then live the FU money life, Derek does not. He keeps things simple. He doesn’t waste time, words or seemingly any aspect of life. He appears to live one of the most contented and thoughtful lives of anyone I’ve witnessed. So naturally when read his book, “Anything You Want,” and saw his invitation to email him I jumped at the opportunity. Where one of my other virtual mentors and close friend of Derek’s Tim Ferriss erects walls and fortresses to keep everyone not in his inner circle out (and I don’t blame him) Derek says, come on in. I’ll talk to you. So I emailed him. Eventually, he responded and then multiple emails back and forth later we had some digital dialogue. I’m grateful to say the least. I like that this episode stretched me a little. I had to find a way to make it worthy of an episode, and I think I pulled it off. I hope you enjoy learning more about Derek. One day, I hope to have him on for a lengthier conversation. Until then, I’m truly honored to have at least got a personal touch for the Jason Wright Show. Here’s one of my favorite Derek TED Talks on goals. I’ve adopted this discipline. I actually learned if from Steven Kotler, but Derek drove home the point for me. More About Derek: I always write for my audience, not for myself, so this feels indulgent. When I think of expressing this kind of “about me” stuff in an article, I stop myself because it’s not directly useful to you. So this is just one big page where I can write all about myself, without feeling the need for it to be useful. And some day this site will be all that’s left of me, so I might as well write my own mini autobiography. Time line for context: 1969: born in California1976: started playing piano, viola, and clarinet1979: got a TRS-80 computer and dove deep into programming in BASIC1983: started playing guitar, decided I wanted to be a successful musician1987: started Berklee College of Music in Boston1988: joined a circus, as ringleader/MC musician1990: graduated college, moved to New York City, got a job at Warner/Chappell Music1992: quit my job, and toured Japan as Ryuichi Sakamoto’s guitarist1993: lived alone on the Oregon coast for 7 months, writing and recording music full-time, in a town with a population of 21994: played around New York and universities with my band “Hit Me”, and the Professional Pests1995: started a record label, booking agency, and recording studio1996: recorded and released my album1997: started CD Baby1998: quit the circus, after 10 years and about 1000 shows1999: started HostBaby2000: moved to Portland, Oregon2002: moved to Santa Monica, California2007: rough year, moved to London, decided to quit my company2008: moved to San Francisco, sold CD Baby and HostBaby2009: moved to New York City, started writing and speaking more2010: spoke at TED three times in a year, moved to Singapore2011: published “Anything You Want” book about my CD Baby days, started Wood Egg2012: had a baby2013: moved to New Zealand to raise him in nature and be a mostly-full-time dad2014 to 2018: sabbatical, but answered 92,354 emails from 33,776 people2017: started writing “How to Live”2019: moved to Oxford, England2020: moved back New Zealand, released “Your Music and People” and “Hell Yeah or No”2021: finished and released the best thing I’ve ever written: “How to Live” About me: I’m ambitiously focused on creating More than anything, I want to make lots of stuff. I want to make articles, books, websites, music, companies, systems, apps, and especially new ideas. This shapes most of my life decisions. Saying no to almost everything, so I can have lots of time for making. At the age of 14, I decided I wanted to be a successful musician. Knowing it’s something that millions want, but only one-in-a-million achieve, I knew I’d have to be fiercely focused, persistent, savvy, and work like an Olympic athlete in training. In other words, not casual. I was single-focused obsessed with being a successful musician from age 14 to 29 — crucial years when many of my friends were feeling lost. It had me waking up early to practice, staying up late to write, saying no to all distractions, and reading whatever I could to improve. Then, at age 29, I accidentally started a company, so I was narrow-focused on creating that for 10 years, through the age of 39. I also want to learn lots of stuff, especially different approaches to thinking and living. That’s why I read so much non-fiction, and want to keep moving around the world. I connect with those who stretch, strive, and grow. I can’t relate to those who chill, hang out, watch TV, party, etc. I’ve optimized my life for creating and learning. I’ve cut out most things from my life that most normal people do — (like hanging out or media consumption) — in pursuit of my bigger goal. My life philosophy I’ve always had an uncommon approach to life, mostly shaped by my ambition. But when I read a book on Stoicism I realized I wasn’t so unique. My own self-created philosophy lined up almost exactly with this ancient philosophy. So, if you want to know my approach to life, go read these book notes. Especially the biggest point about strengthening yourself for a more difficult future. But I’m also very skeptical, and was surprised to find that’s also a philosophy. Meaning: for almost anything on this page, the opposite may also be true. I don’t trust what I tell myself. It’s not a lie — it’s my truth at the time. But an opposite point of view can replace it when I shift my perspective. (I sometimes do this intentionally: do the opposite of my beliefs, just for a different perspective.) I don’t work for money Some might say I’m retired, because I haven’t earned (hardly) any money since 2008. And in some sense it’s true: I don’t want any more money than I’ve already got. And I don’t want more fame, recognition, or anything external. So in that sense, I’m done. Retired. No longer working for money. Now my ambitions are entirely intrinsic and intellectual. I work as hard as ever, but just for my own learning, creating, and giving. I love to work alone 12 hours a day I use the term “work”, because it’s more understood, but really it’s “me time” — doing what I love. Writing, learning, improving, and creating. Whether it’s creating music, websites, books, or companies, it’s all just creating. The word “workaholic” would apply, except it’s play, not work. It’s completely intrinsic — just following my own interests. I’ve found what I love, and do it as much as possible. I prefer this as a solo pursuit. Being around other people drains me, and I don’t want to compromise this side of my life. It’s a very personal pursuit. It’s not business — it’s more like art. The rewards are internal. Nobody gives a novelist shit...