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“I would say the single most powerful technique that I have found is when you start your day, rather than checking email or or anything, start by pulling out a blank sheet of paper, whether that's literal paper or whether, like me, you use an electronic note-taking system, and just think on paper about your day. How's it going? What's up? What am I going to do today? What are my priorities and so forth?” – Jason Crawford

Jason Crawford (@jasoncrawford) is Founder and CEO of The Roots of Progress, a nonprofit dedicated to establishing a new philosophy of progress for the 21st century. He created Progress Studies for Young Scholars and is a technical consultant and adviser to Our World in Data. He previously co-founded Fieldbook and Kima Labs, and was an engineering manager at Flexport, Amazon and Groupon.

To hear Jason Crawford's full interview on progress studies, click here.

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Chapters

00:00:00 – Introduction
00:01:24 – Research on the Gutenberg press
00:03:51 – Learning, planning the day, and improving sleep
00:10:09 – Recommended apps, including Bear, Readwise, and Anki
00:12:27 – Startup failures, sci-fi books, and success on your own terms

Books Recommended by Jason Crawford

The Diamond Age: Or, a Young Lady's Illustrated Primer by Neal Stephenson‍
Ready Player One by Ernest Cline

Transcript

Daniel Scrivner:

Jason, I am thrilled to have you on 20 Minute Playbook. Thanks so much for the time.

Jason Crawford:

Certainly. Thanks for having me.

Daniel Scrivner:

So this should be a lot of fun. We try to ask around 10 questions, keep this episode under 20 minutes. The goal here is just to give people a little bit of a behind the scenes peek into you. We've obviously covered all your work with Roots and Progress in depth in the Infinite Games episode. And I'm super excited about this because I think you'll have some amazing answers. So the place that we always like to start is just to ask if there's something you've been excited or fascinated about recently, something you can't get out of your head, something you're thinking about all the time, for whatever reason?

Jason Crawford:

Yeah, sure. Well, I always have a large number of these topics within my work. I got going on my work with the Roots of Progress because I was just fascinated with stories of invention. Right now, one thing I am trying to understand, and these things get super detailed, but what was the exact alloy of metal used by Gutenberg to make the type for his printing press? So it was an alloy of lead, tin, and antimony, I think. Each of those metals is doing something specific in order to make it easier to cast the type or for it to work better. So I'm really trying to get clear on like, "Well, why couldn't it have been pure lead? Why couldn't it have been lead and tin?" or whatever. So these are the weirdly specific questions I dive into.

Daniel Scrivner:

Amazing, though. Amazing. Best answer so far. Just in terms of that, is part of the interest that there was something different with that press than previous incarnations of it?

Jason Crawford:

Yeah, definitely. Well, printing as such had been around for a long time in the form of woodblock printing, where you would carve out in a block of wood the thing that you wanted to print, and then you would press the paper against it and then rub the back of the paper with a brush or something. So Gutenberg didn't invent printing, but what he did come up with was a system of, A), movable type. So you had individual letters that you could arrange that were pre-made, precast, that you could arrange to make any page of type. He actually used a new and different ink based on oil or fatty-based ink rather than water-based. And I don't yet understand the full significance of that, but I think maybe it just didn't run as much.

Jason Crawford:

Then the third thing was that he used, rather than a rubbing mechanism, he used the press. So a screw press had been used for pressing olives to get olive oil and so forth. He adapted that. So it was those three things put together. Apparently the casting of the type was the biggest core problem, but those three things together made for his system. Like a lot of other inventors, all the components had already existed before him, but he was the one who put them all together and integrated them into a working practical system. And that's why we say he invented the moveable type printing press.

Daniel Scrivner:

I have more questions I would like to ask, but I'll stop myself. I'm really curious to hear your answer here. One question that I always like asking people is what their superpower is. Clearly, even just in your last answer, you just have a very unique ability to deconstruct things and just ask the why behind the why behind the why, until you get to just a really interesting answer. Maybe that's your superpower. Maybe it's not. How do you think about what your superpower is and how do you think about how you harness that to do the work that you do?

Jason Crawford:

I think definitely learning is a superpower. I feel confident that I can dive into any area and learn it just as fast as anybody else. I'm not necessarily the expert in any particular area, but I can go ramp up extremely quickly. Part of the reason for that is that I have a very finely tuned sense of when I really understand something and when I don't. I'm pretty much always able to pinpoint my confusion or my ignorance.

Jason Crawford:

So like I just said, I can tell you what alloy Gutenberg used, but I don't fully understand what each of those elements is doing. So I always know what is the next question to ask. I can ask questions like, "Well, what would happen if you tried to use 100% lead type rather than that alloy?" and that kind of thing.

Jason Crawford:

Just more broadly, I would say my strength is bringing clarity to any intellectual situation and bringing structure to ideas when, as so often happens in the study of history, you just have an enormous laundry list or a grab-bag collection of facts, and it's unclear how to put these all together into a structure such that they make sense as a big picture and can be retained and communicated. And I think that's why I do well as a storyteller in this area.

Daniel Scrivner:

Yeah. Those are true superpowers, especially for what you do. On the flip side, what do you find that you struggle with? And how have you improved or just worked around those things over time?

Jason Crawford:

Yeah. Wow. So many things. It is a real struggle to try to be a researcher and also be starting a new nonprofit at the same time, let me tell you. If you're familiar with, I think it was Paul Graham who had the maker schedule versus manager schedule. Those aren't just schedules, those are really mental sets.

Daniel Scrivner:

Can you do both? I don't think-

Jason Crawford:

You cannot do both in the same day, I don't think. It's very difficult for me. I can maybe do them on alternating days, definitely in alternating weeks, but sometimes I feel like I really just need to block out an entire week to go make progress on my book.

Daniel Scrivner:

On the habit and routine side... And I'm going to ask a separate question in a second about just writing process, research process, which hopefully, maybe a deep question, we'll find out. But separately from that, just in terms of daily routine, is there anything that you've learned about yourself, any routines or habits you've picked up that you try to input in your daily life? These can be things you strive for, or these can be things you're like, "Every single day, I've got to do this." Anything there that you find improves your performance?

Jason Crawford:

Yeah. Well, I'm a new dad, so my daily routine has been completely discombobulated and I'm still getting back to it. But I would say the single most powerful technique that I have found is that when you start your day, just certainly when you start your productive day, literally even if you can do this from the moment you wake up, rather than checking email or any communications or anything, start by pulling out a blank sheet of paper, whether that's literal paper if you like to write on literal paper or whether, like me, you use an electronic note-taking system, and just think on paper about your day. How's it going? What's up? What am I going to do today? What are my priorities and so forth?

Jason Crawford:

I learned this technique from a good friend of mine who I've been studying with for a couple of decades. Her name is Jean Moroney, and she has a consulting business called Thinking Directions. She taught me this technique when I was in college, and I've been using it almost daily ever since. I use this technique when I'm facing a difficult question or something I don't know how to make a decision on or something I'm confused about. I also like to use it just as a way to get the day started as just this technique of journaling.

Jason Crawford:

The counterintuitive key is you got to do it in full sentences and paragraphs, but do it completely without censoring or editing yourself. No one else is ever going to see this. It's completely for your own eyes only, but don't just make bullet points or jot down words. Write it in full sentences and paragraphs and get your thoughts out. It slows you down a bit, but that's actually part of the goal and part of the benefit, is it slows your thinking down so that you can capture all of your thoughts, and even the fleeting thoughts and emotions, which are sometimes the key to deeper insights.

Daniel Scrivner:

I have not heard her name. So I'm going to look her up and potentially try to get her on the show as a guest. This question may be a wash, because I know what it's like to have a newborn at home. We've got almost a 12-month-old. You may not have an answer here and we can just move on, but do you have an approach to diet, exercise, and sleep that you typically try to follow? Is that an area you've spent much time in? Obviously, I'm sure the answer today is "Just trying to survive."

Jason Crawford:

Yeah. So I'll tell you about my previous routine, maybe, rather than current.

Daniel Scrivner:

There we go. There we go.

Jason Crawford:

I don't know if I have any special secret answers here. Sleep, I used to have major problems with sleep, getting to sleep at night. I felt I was a night owl, and an insomniac, and so forth. I fixed that. The meta answer about how I fixed it is I just went and researched all the things that might be wrong and I tried them all until something worked. People seem to be highly variable here. So if you're having any problems with sleep, I recommend just experiment with everything.

Jason Crawford:

It turned out for me, the key was light management. So I'm very sensitive to blue light at night. Staring into a screen late into the night was keeping me up, but even just having the lights in the room on too brightly. So I installed this app on my laptop called flux, which makes my screen dim and orange in the evening. On my phone, I use night shift or night mode, whatever it's called. And then, literally, just all the lights around the house, I dim progressively throughout the evening. Now, my wife thinks this is hilarious and bizarre because she does not have this problem at all. She's completely insensitive to light. She can fall asleep with the light on, which is bizarre to me. Again, that just speaks to the point of your particular physiology is something you have to discover.

Jason Crawford:

Exercise, before the baby, I was on a pretty consistent three times a week. It helps me a lot to sign up for a bootcamp or something where I've got a time and a place that I have to show up and don't have any question about it. The key is do not question it. When you wake up in the morning, if you're asking yourself, "Should I go work out today?" just don't even allow yourself to consider that question. Just pretend that it's already locked in and you already made that decision, as if you have some commitment. You can trick yourself into thinking, "Oh, I don't have this choice." Just go do it.

Daniel Scrivner:

On the software and tool side, and maybe we can take this in the direction of talking about your note-taking system, but the question we generally broadly ask people is just anything interesting on the software side or on the physical tool side that people use to manage work tasks in time? And so for you, that could be really broad. Is there anything that you enjoy using? Is there anything you've picked up that you really love? Or we could just use this as a chance to dive into that note-taking system, because I'm sure you've got some interesting insights there.

Jason Crawford:

I don't have a fancy note-taking system or anything very special. I use an app called Bear Notes that I like. It allows me to take notes on all sorts of things and tag them. It has a hierarchical tagging system, which is nice, and it supports markdown and so forth. Another tool that I will plug because it is such a great tool, it's called Readwise. So Readwise is a highlighting system. If you have Kindle, which I do, and I read everything that I can on Kindle, I only read paper books when I have to, but it will suck in all of your Kindle highlights into a system. Then it does this great thing. It just emails you every day with five of them, random highlights, and lets you review them. I really like that. It's good to remember passages that I enjoyed. It's also great for Twitter because whenever I see a passage that would make a great tweet, I'll just share out the quote. And so it helps me kind of share all that stuff with my audience.

Jason Crawford:

The other great thing that Readwise does, it makes all of this searchable, and I've used that over and over when I'm trying to remember some quote that I read. It also integrates with pretty much everything else. So if you are reading a paper book, they have an iPhone app and you can just snap a picture, and it'll OCR it and then get the highlight into the system that way. So it lets you integrate everything. They are currently testing in beta a read-later app that integrates with all of this as well. I really like that team. I've been following them since early days and I've been a happy user of the app.

Daniel Scrivner:

I've heard people talk about that email that you'll receive. It feels like people are overly focused on what new information can I get in and not spending enough time on how can I remember, re-experience, and get reminded of all this great stuff that I've read. And it seems like a great tool at that.

Jason Crawford:

Speaking of which, I do also use Anki as a spaced repetition, flashcard system to remember facts, names, and dates, and so forth. So that's, I guess, another part of my system.

Daniel Scrivner:

And is that an app?

Jason Crawford:

Anki is an app. A-N-K-I. It is an app for doing spaced repetition flashcards, basically.

Daniel Scrivner:

I've not spent enough time there. So I will research that and we'll link to that. One thing that I'm always curious about is asking people for a favorite failure. And I think what we're really trying to get at there is we're all ambitious, we set goals for ourselves. Often, there are obviously goals that we don't attain. Sometimes we realize, at the end of the day, that was actually a great thing. It propelled us in a better direction. We learned something from it. Do you have any favorite failure that you're grateful for that you think about?

Jason Crawford:

The first thing that comes to mind is the last startup that I founded. It was called Fieldbook and it was basically a hybrid spreadsheet database, a lot like Airtable, but not nearly as successful. We never really got to profitability. We ended up shutting down the product and did a talent acquisition. Sold the team to a larger startup. I poured five years of my life into that, but it's one of those things where I am deeply glad that I tried. I was absolutely obsessed with the vision for Fieldbook for years before I started the company, just the same way I've now gotten obsessed with studying the history of progress. It's one of those things where if I'd never tried, I would always be wondering what if and why didn't I go for that thing that I couldn't stop thinking about?

Daniel Scrivner:

On the book side, in the previous interview we did, we talked about Where's My Flying Car?, the old book that's about to be re-released through Stripe Press and we'll link to that here. So I want to take this in a slightly different direction. And things that I was curious to ask you is, obviously, you're someone that thinks a lot about progress. Are there any sci-fi books or futuristic books that you think are really interesting? These could be older ones, these could be newer ones. And then alternatively, as a writer, are there any writers whose work you admire?

Jason Crawford:

Sci-fi, I've read some sci-fi. I wouldn't say I've read deeply in the genre. Probably the writer I've read the most of is Neil Stephenson. You can definitely find in a number of his novels inspiration for things that people could create. Diamond Age, for instance, famously. Essentially it's a book with an AI behind it that trains and provides education for young people. I won't say more than that to avoid giving away too much, but I've heard Stephenson say in interviews that that has inspired many people over the 25 years since that book came out.

Jason Crawford:

Every once in a while, someone will come to Stephenson and say, "I'm doing a startup based on Diamond Age," and they're trying to bring some aspect of it into reality. The funny thing is they're all doing something a little bit different, so everybody has their own different interpretation on what it should be. I thought Ready Player One did a good idea of envisioning what a virtual reality future could look like. I particularly enjoyed the dance club scene in the zero-gravity environment, which was just a cool idea. And then, sorry, what was the second part of this?

Daniel Scrivner:

Just any writers whose work you admire?

Jason Crawford:

Yeah, that's a good question. There's a small number of authors whose work I feel like I just want to read all of. So one who comes to mind, probably my favorite blogger today, is Scott Alexander and his blog previously Slate Star Codex, now Astral Codex Ten. He dives so deep into subjects. He covers them so thoroughly and yet in a way that just really pulls you along, is very easy to read, in my opinion. I think about comparing my own writing to his, and I think I'm pretty good at conveying the big picture, explaining deep concepts, at being really clear about subtle distinctions. Scott does all of that and he's really funny on top of it. I just envy that. I feel like I can't even quite match that. I can maybe be as clear as him, but I can't do it while also just being really funny at the same time.

Daniel Scrivner:

If it makes you feel any better, I can't do what either you or he can do. There is an order of hierarchy there. Last two questions. First is just if you have a definition of success. And this can be in your work specifically, in the impact you want to have there. This can also just be the way that you look at life and the way that you look at how you want that to unfold or what you want your life to stand for.

Jason Crawford:

I think the most important thing and the broadest level about success is that whatever it is, it has to be success on your own terms. And I think about this a lot, again, as a new parent and thinking about where I want my children's lives to go. And I might have a lot of aspirations for them, but I think it's far, far more important that they achieve whatever their aspirations are for themselves, and that they actually learn to choose that for themselves, which is a much more difficult thing than it might seem. I think, to really, truly choose for yourself and to pick something because it's what you want and not because it's what you think other people will approve of you for, or the thing that you think you're supposed to do, or even because it's just an old idea that got stuck in your head when you were young but isn't authentically you anymore, that can be really difficult. So just being true to yourself in that way.

Daniel Scrivner:

Yeah, really well said. Last question. What are you most grateful for in this phase of life?

Jason Crawford:

So many things. It's cliche to say my family, but I do have to say that. My wife is amazing and has been amazingly supportive as I've made this career transition and gone off on this. "Wait, so you're going to write your blog full time. What is this?" And the whole broader extended family has been very supportive. And just more broadly, the fact that there have been a number of people who have liked my work enough to just give me money to keep doing it, and people who've seen that potential and believed in me and made it possible for me to take this weird eccentric intellectual obsession of mine and just go deep on it and go it full time, I'm deeply grateful for that.

Daniel Scrivner:

Yeah, I am one of, I'm sure, many, many people that thinks the work you're doing is really important, thinks that you're a really important voice that I think the world needs right now. So I am thrilled to have you on just to give people a few links. You obviously write full time. This is now a nonprofit. You're starting to hire. You're starting to build more of a team. And people can find that work at rootsofprogress.org. They can also follow that on Twitter @rootsofprogress. Can people find you on Twitter?

Jason Crawford:

Yeah, sure. So I tweet even more than the Roots of Progress account. The Roots of Progress account is more of a feed of all of our posts and announcements, but I tweet all sorts of stuff. My handle is just my full name, Jason Crawford.

Daniel Scrivner:

Awesome. Well, thank you so much. This has been an incredible conversation. I highly encourage anyone listening to this that enjoyed this conversation to listen to the full episode, Infinite Games, where we go really deep in your work. Thank you so much again for the time, Jason.

Jason Crawford:

Been great talking to you.

On Outlier Academy, Daniel Scrivner explores the tactics, routines, and habits of world-class performers working at the edge—in business, investing, entertainment, and more. In each episode, he decodes what they've mastered and what they've learned along the way. Start learning from the world’s best today.

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