What advice would you give your twenty-year-old self, and what should they ignore?
Recorded Derek Sivers said elsewhere, not written here
Yeah, anybody asks me about it, my advice was always, do not do it. In fact, it still is. Somebody just asked me last week, I was like, do not do it.

Tim Ferriss, The Tim Ferriss Show podcast, 23 April 2023 source ↗

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Willem Kolff Physician and inventor; builder of the first practical artificial kidney
By the way, the guys with very high grades are not necessarily the people that are the most successful in later life. They may be the ones that can regurgitate gracefully, and they get very high grades. But if the guys that have to work for it and do not have such good grades can do something extra, and prove that they can perform, they may have a chance.
Recorded Academy of Achievement recorded interview, American Academy of Achievement source ↗
Rosa Parks Civil-rights activist
The advice I would give any young person is, first of all, to rid themselves of prejudice against other people and to be concerned about what they can do to help others. And of course, to get a good education, and take advantage of the opportunities that they have. In fact, there are more opportunities today than when I was young.
Recorded Academy of Achievement recorded interview, American Academy of Achievement, 2 June 1995 source ↗
Amy Tan Novelist; author of The Joy Luck Club
I go back to this idea that I only discovered when I was older. I wish I had known it when I was younger, because I think I missed a lot of observations in life. That is to develop your own philosophy. I always thought philosophy was one of the most useless subjects in the world.
Recorded Academy of Achievement interview, 28 June 1996 source ↗
Frank M. Johnson Jr. United States district judge, Middle District of Alabama, 1955–1979; judge of the Eleventh Circuit
Study. Be honest. Don’t violate the laws and get in trouble. Get you a good spouse that will support you, because you never stop working and studying. The fact that you get the place just means you’ve started as far as the work and the pressure is concerned. That’s the only advice I’d know to give.
Recorded Academy of Achievement recorded interview, American Academy of Achievement, 16 March 1991 source ↗

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Question What is your favourite side project? Craft & work
The proudest achievement of my life at that time was that software. Wonderfully organized, extensible, and efficient: the culmination of everything I’d learned about programming in ten years. After a successful relaunch and Christmas rush, I was looking at my plan for 2008 and beyond. All my plans needed a huge effort for little reward, but were required for future growth. I had broken it into about 20 projects, each taking 2 to 12 weeks. But I wasn’t excited about any of them.
Recorded Essay on sive.rs, Derek Sivers, 13 October 2009 source ↗
Question What are you unwilling to optimise? Values & belief
Do you have a big visionary master plan for how the world will work in twenty years? Do you have massive ambitions to revolutionize your industry? Don’t feel bad if you don’t. I never did. A year and a half after starting CD Baby, it was just me and John, my first employee, running it out of my house. One night, I decided I should think more about the long-term future of this thing. I sat with my diary for a few hours of introspection. Afterwards, I wrote John an email that went like this: “I think there’s a chance that this thing might be huge one day, so we better start preparing for that now. I mean some day, we might have a thousand artists. We might need a third employee! We’d need three computers, and need to figure out how to network them together. We might even need to start moving CDs into the garage, since eventually they might fill up the living room. Yes, I know it sounds grandiose, but I think things are headed that way.” Years later, after I had 100,000 artists and 85 employees, John would often get a good laugh out of this letter I sent him in 1999. Journalists would ask, “What’s your long-term goal?” I’d say, “I don’t have one. I surpassed my goals long ago. I’m just trying to help musicians with whatever they need today.” So please don’t think you need a huge vision. Just stay focused on helping people today.
Recorded Essay on sive.rs, Derek Sivers, 14 July 2011 source ↗
Question What made you decide to stop something you were known for, and how did you know it was time? Time & hindsight
I read that at a key fork in the road moment for me where I just sold CD Baby and had a ton of money. I was like, “What to do now?” And I read this book from this filthy rich old man being entirely honest, and I thought I should just learn from his experience. ... So if what I’m doing seems weird, it’s because I took his advice to heart and I’ve quit the game.
Recorded Tim Ferriss, The Tim Ferriss Show podcast, 23 April 2023 source ↗

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