My most important rule is one that sums up the 10: if it sounds like writing, I rewrite it.
What is the thing you are best at that nobody watching can see?
Question
What do you value most in your friends?
Relationships
Question
What is the most rewarding part of being a parent?
Relationships
Question
Who do you turn to when you need advice?
Relationships
Question
What is one of the best or most worthwhile investments you have ever made — of money, time, or energy?
Money & investment
Question
In the last five years, what new belief, behaviour, or habit has most improved your life?
Daily life
Question
What are you unwilling to optimise?
Values & belief
Sometimes you don't even need your friend to say yay or nay, you just have to hear yourself expressing it out loud to another person that's never heard it before. And I particularly like doing the out loud bit. I like my sentences to sound good.
Kelly Irving, community interview transcript, Expert Author Community, 29 August 2025 source ↗
Others on this question
View all 33 →
Elmore Leonard
Novelist and screenwriter
Ruth Bader Ginsburg
Associate Justice of the Supreme Court of the United States, 1993–2020; Judge, U.S. Court of Appeals for the D.C. Circuit 1980–1993
I have followed that advice - with, I confess, occasional lapses not only at home, but in the places I have worked, even in relating to my colleagues at the Supreme Court. It is important to be a good listener if you are to work with others effectively, but it also pays, sometimes, to be a little deaf - for example, in my current position, when a colleague, academic commentator, or journalist writes that an opinion on which I labored endless hours, worrying over every word, is "sloppy," "smug," "strange," or "profoundly misguided." I am making none of those up.
Recorded
New York Law School Law Review dinner, New York Law School Law Review (digitalcommons.nyls.edu), 12 February 1999
source ↗
Eliud Kipchoge
Kenyan marathon runner
When I have a lot of pain, I try to confuse my mind to forget about the pain and think about the distance. I don't want pain to be in my mind, because I'd really lose focus on running. After winning, you won't have that pain, but it comes later. The marathon is hard; the second day, you don't go up or down stairs.
Recorded
Address and Q&A at the Oxford Union Society, November 2017, Outside, 10 February 2018
source ↗
Athol Fugard
Playwright, director and actor
That is true. That one little corner of South Africa, Port Elizabeth and its immediate surroundings, is a region that I know like the back of the hand that holds my pen as I write about it. I can stand on a street corner in Port Elizabeth, look at anybody and put together some sort of biography. I know where they come from, where they’re going. I have a feel of the textures of their life. If I stand on a street corner in New Haven, which is a place I’ve gotten to know as well as any place outside of South Africa, I am still at a total loss to identify the people passing me on that street.
Recorded
Lloyd Richards, Interview conducted in front of an audience at the Poetry Center of the 92nd Street YMHA, New York, The Paris Review, Issue 111, Summer 1989, 13 October 1985
source ↗
More from Derek Sivers
View profile →Vulnerability. Mutual admiration. Wide open communication. Yeah. Those are my big three.
I’ve never been this close with anyone, or spent this much time with any other person in my life. We talk talk talk so openly about everything, and do everything together. He’s definitely the love of my life.
I literally just call my five or ten best friends around the world. Sometimes I just go through the list. I call Aly. Ah, no answer. Okay, let me try Mitra. Ah, no answer. Okay, let me try Zita. "Hey, I got an idea. Let me run it by you? Okay? You got a minute?"
Recorded
Kelly Irving, community interview transcript, Expert Author Community, 29 August 2025
source ↗
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.
In one month, two of my old prejudices were reversed. Two things that I was prejudiced against. I am now prejudiced towards, in favor of.
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.
More on craft & work
- What is the worst job you have done? 236 answers
- What do you consider your greatest achievement? 204 answers
- How does a new work begin for you? 82 answers
- What do you do when you feel creatively blocked or stuck? 80 answers
- How do you know when a piece of work is finished? 75 answers
- How much rewriting or revision do you do? 58 answers
Also answered this
Jensen Huang, Jamie Dimon, Jacqueline Novogratz, Simone Biles, Keith Black, Athol Fugard
Search the directory for somebody in particular.
Explore further
- All craft & work questions
- Explore the archive — by field, age, era, and subject