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Another great one, David, thank you! I appreciate your deep dives with living authors as much as your deep dives on deceased ones. With regards to quitting, I may be misremembering, but I think you make a similar point in chapter 6 of Range right? That before starting something, everyone should enumerate the things that must happen for them to quit? I don't have the book with me so I can't check, but I have that jotted down in my notes. Needless to say, I thought this was fascinating. A question for you: between these author chats and your journalist background, it's really clear you're very skilled and well trained at asking strong questions. As a teacher, I've been reading and thinking quite a bit about question asking as a skill, since it is crucial to ask the right questions to push student thinking and learning. Do you have any advice, thoughts, or principles on how to ask better questions? Asking the right questions is so important in so many walks of life.

Also, is there anything you're ready to share as a little hint as to what this potential book proposal might be? No pressure whatsoever, but I was so curious that I couldn't help but ask.

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I actually finally just realized what I'm good at—never had a word for it before or the right language to explain the framework for evaluating choices at each point with new information and the various odds moving forward: I'm good at quitting!

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I found you thru Barking Up t by e Wrong Tree and when Eric mentioned your "Substack" I had to Google the word having no idea what it meant.

I don't use Twitter, linked in or Instagram and I rarely look at FB but I enjoy reading good content that is well written. So I'll be back. Thank you.

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This is fascinating! I would not have seen it except for your blog. Thank you!!

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This is incredible. It is timely for me now regarding relationships. I think I am overly influenced by "sunk costs" My brain says quit, but I do not know if I can. In my career I analyze insurance risk. so that adds to the irony.

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I not only like the kill criteria but I have been using it - not aware of a term for it. As an ultralight pilot and motorcyclist, my personal kill criteria are - IF I imagine lying in a hospital bed after an accident and someone asks me - did you think it was a good idea to fly / ride and I can't give an immediate and definitive yes - I should stay home

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Nov 25, 2022·edited Nov 25, 2022

Thanks for this -- definitely struck a chord. It also reminded me of Astro Tellers "passionately dispassionate" at Google X, and how they try to cultivate a mindset open to quitting early:

"#6 Cultivate the ability to be passionately dispassionate.

While we can’t predict the future, we’re trying to invent it efficiently, to maximize the impact of our effort and resources. So it’s absolutely necessary to be intellectually honest and kill things that are pretty good (even if we love them!) so we can move on to even better opportunities." (from https://x.company/blog/posts/tips-for-unleashing-radical-creativity/)

While it's arguably not exactly the same, I see some complementarities and also analogies to what Anne so beautifully describes in the interview. I haven't read the book (yet) so I was wondering if she writes about being "passionately dispassionate" and the example of Google X in it?

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Can staying be quitting? For example, in your article the ER doctor who took the promotion to an administrative position based on her being identified as a good candidate. Could she have a kill criteria established to evaluate staying versus taking a promotion?

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Hi David, what really resonates is the suggestion that the quitting criteria is set in advance. What a great way to not only avoid sunk cost fallacies, but also when combined with a deadline, is a great way to bring choices to a head. Undone and incomplete projects seem to take quite a cognitive load. Really looking forward to reading the book. Thank you for these great newsletter essays.

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A really timely book and interview for a lot of us who should be taking an honest measure of our circumstances. The equations that lead to a good quit are a complex calculus. Thanks for the attempt to find a more unifying framework. Will add “Quit” to my future reading list for sure.

Also enjoyed your TED talks as an introduction... so much talent out here in the world it’s hard to keep up with everyone who deserves to be heard. Will keep collecting and focusing on the good shells I find, and realize I can’t comb all life’s beaches!

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Welcome to Substack! Excited to have you here - reading Range led to a significant reframing of my patchwork career to date, and now I view my diverse experience with gratitude.

Loved this interview and will check out the book. I quit a job in a toxic org at the end of 2021. Six months in to my new job there was a lot of chaos in the org and leadership was being careless with employees’ time and talent. I surprised myself by quitting and getting out quickly (I tend to be loyal to a fault). I’ve been much happier unemployed and just landed a new role starting in January. What a year!

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Glad to see ya on Substack, David! I always enjoy when you do interviews like this one. I still remember your interview with Fonda — which inspired me to pick up her incredible trilogy. :)

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A terrific read and as someone who's got some big decisions to make in the months ahead, this was just what I needed to read. Thank you.

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I found this helpful. I had already dropped out of two bachelor's degrees, the first time was slow deciding it, but the second time, I took the decision faster. Now I'm a little happier, learning the things I like or need when I need or can. I still struggle to find a job and decide when to decline an application for a job I may not like compared with other job applications where I feel more at ease.

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Great post! Thank you so much.

When faced with difficult decisions I often ask myself - If this wouldn't be the status quo, would I actively pursue it? If the answer is no then its time to quit or change the situation.

I think it was Steven Levitt (freakonomics) who ran an experiment. Indecisive people looking for advice and came to their website, were told either to stay with the status quo or change it. After a while they followed up on the same people and the ones getting the advice to change where significantly happier. So when in doubt opt for change. We don't quit enough apparently ;-)

Oh btw. welcome to the substack family David. :D - Great to have you

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