What are bad recommendations you hear in your profession or area of expertise?
Recorded Derek Sivers said elsewhere, not written here
The worst advice was to start a record label when I wanted to be a musician. It was smart advice. It could have made me more money, but it did not inspire me.

Lydia Chen, podcast transcript, Escape 9 to 5, 2 April 2025 source ↗

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Óscar Arias Sánchez President of Costa Rica, 1986–1990 and 2006–2010
Seeing that the past dictatorships were only capable of creating misery and crippling hope, how absurd to pretend to cure the evils of one extreme dictatorship by means of its opposite! No one in Central America has the right to fear freedom, no one is entitled to preach absolute truths. The evils of one dogma are the evils of any dogma. They are all the enemies of human creativity.
Recorded Oslo City Hall, The Nobel Foundation, 11 December 1987 source ↗
Ngozi Okonjo-Iweala Director-General of the World Trade Organization from 2021; Finance Minister of Nigeria, 2003–2006 and 2011–2015
And it brings us to the debate that has been going on here: aid versus private sector, aid versus trade, etc. And someone stood up to say that one of the frustrating things is that it's been a simplistic debate. And that's not what the debate should be about. That's engaging in the wrong debate. The issue here is how do we get a partnership that involves government donors, the private sector and ordinary African people taking charge of their own lives? How do we combine all this?
Recorded TEDGlobal 2007, Arusha, 7 June 2007 source ↗
Reid Hoffman Co-founder of LinkedIn; partner at Greylock Partners
Our culture lionizes entrepreneurs who navigate daring switchbacks in their career. Steve Jobs was admired not just for Apple, but also his detour to found Pixar. Elon Musk is revered for helming Tesla AND SpaceX. But don't be distracted by other people's winding paths. I believe you should celebrate your single-mindedness, and stick to your own overarching idea — for as long as it holds your own fascination. In my experience, that could last your entire career.
Recorded Hoffman's own Medium publication, Reid Hoffman on Medium source ↗
Zadie Smith Novelist and essayist
Don’t romanticise your “vocation”. You can either write good sentences or you can’t. There is no “writer’s lifestyle”. All that matters is what you leave on the page.
Recorded The Guardian Review, 20 February 2010 source ↗

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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 ↗
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 is one of the best or most worthwhile investments you have ever made — of money, time, or energy? Money & investment
When I decided to sell my company, I already had enough. I live simply. I don’t own a house, a car, or even a TV. The less I own, the happier I am. The lack of stuff gives me the priceless freedom to live anywhere anytime. So I didn’t need or even want the money from the sale of the company. I just wanted to make sure I had enough for a simple comfortable life. The rest should go to music education, since that’s what made such a difference in my life.
Recorded Essay on sive.rs, Derek Sivers, 4 December 2009 source ↗

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