As I watch my kids learn, it sits with me how much we learn by copying. Imitation isn’t the enemy of originality — it’s the foundation of it. We learn
by copying, refine through practice, and ultimately create something uniquely ours. My latest post on Res Extensa:
In our rush to be original, we often dismiss copying as somehow lesser than “true” learning. But mimicry isn’t just a shortcut — it’s fundamental to how we master skills. We see it in my daughter’s creative reproductions, in my son’s workbench discoveries, and in every artist who’s traced the footsteps of masters before them.
The path to originality paradoxically begins with imitation. First, we copy to build competence. Then we understand. Finally, we create.
I ran back across this quote today, from one of Jonah Goldberg’s G-Files from a few years ago:
In Suicide of the West, I argued that our biggest cultural problem is that entitlement has eclipsed gratitude. This seems to be a variation of that. We all want to know stuff, but we increasingly resent the idea of having to learn it. It’s like wanting to be in great shape but not wanting to exercise. And when we discover something—like, say, the colonial divisions of Africa—that is actually important and useful to us, our sense of entitlement leads us to think it must have been hidden from us on purpose. Even our own ignorance is someone else’s fault. The proper (and healthier) response to learning something interesting that you didn’t know is gratitude. “Hey, thanks! I didn’t know that.”
In the piece ($) he’s making the argument that just because you didn’t know something doesn’t mean you were slighted, or that someone that does know the thing was advantaged against you. They may have had an advantage of some sort. But most often that person went out of their way to earn said knowledge.
It reminds me of something I used to hear earlier in my career from colleagues. When I’d advocate learning or reading up on a particular skill (one I enjoyed having invested in), I’d hear variants of “well that’s easy for you to say, you already know X”, or “yeah of course you’d be in favor of that, you got to learn Y already”. It used to piss me off royally, the entitled lack of respect.
That I knew how to use Linux or the command line or how to write coherently — these weren’t gifts from above. And at the time I had no explicit understanding that these things would become valuable skills to me later in life. I spent countless hours in college building and rebuilding computers, reading books, and writing on the internet because I enjoyed them and saw some value in them for myself — all while the critics were partying or watching TV instead.
I talk all the time about trial and error. The freedom to let yourself make mistakes, and the skill to make sure they’re not too destructive, are superpowers. With every interesting innovation, company, or product, you’re seeing the late stage of a long chain of missteps and failure. As long as you have the right mindset, mistakes are learning.
We talk about this as a product team — short cycles, iteration, feedback loops — ways to navigate toward broader visions while surviving and building something increasingly useful along the way. I also talk about it with the kids. The more you practice hitting off the tee the better you’ll get at hitting the ball. The more you draw pictures the better you get at it. Practice through the frustration. I try to reinforce with them that everyone that’s great at something got their through an incredible volume of failure and shortcoming before the skill you see today.
If you’ve ever built anything physical, like woodworking, crafting, or DIY stuff around the house, you’ll be familiar with making mistakes, often costly ones. There’s no frustration quite like taking a furniture workpiece you’ve glued up from other parts, honed, mortised, and sanded and making a miter in the wrong place, or cutting it down to length too short. Hours and hours of work can vaporize in a second. I’ve made project mistakes like this so many times, and each time there’s a part of you that wants to put it all down and just go turn on Netflix. But great creators are made by their ability to recover from these mistakes — both in the tactical methods to fix them and the mental drive to “just fix it” and power through.
Mistakes are where most of the learning is in the creative process. It’s not only through the feedback loop of trial and error either. The more mistakes you make and navigate through, the better you get at accommodating and recovering from them.
My grandfather was a hobbyist woodworker for much of his life, cranking out hundreds of heirloom pieces over the years. If you ever asked him about making mistakes, he used to say “making mistakes means you’re doing things.” No person is immune from error. By definition, if you aren’t making mistakes, you aren’t really doing anything. Or maybe nothing interesting or challenging.
In his piece “Why Books Don’t Work,” Andy Matuschak made a strong case that books are a poor medium for knowledge transfer. Even with the most advanced book experiences today (like digital ebook downloads to a Kindle), if you took away the digital e-ink screen, a reader from the 16th century would still recognize books as no different than what they had. We’ve added digital on-demand access, dictionary lookups, and the ability to have a library in your pocket1, but the fundamental model for conveying the knowledge is still what Gutenberg would recognize, based on the “transmissionism” mode of teaching.
Matuschak quotes this great passage from Carl Sagan in Cosmos:
What an astonishing thing a book is. It’s a flat object made from a tree with flexible parts on which are imprinted lots of funny dark squiggles. But one glance at it and you’re inside the mind of another person, maybe somebody dead for thousands of years. Across the millennia, an author is speaking clearly and silently inside your head, directly to you. Writing is perhaps the greatest of human inventions, binding together people who never knew each other, citizens of distant epochs. Books break the shackles of time. A book is proof that humans are capable of working magic.
Knowledge is transmitted, as if by magic, across the decades and centuries. This makes it all-the-more unfortunate how bad our brains are at retaining all that information. We have a mechanism for cheap, reliable knowledge transfer, yet are still bad at hanging onto that knowledge.
One can also be reading books for enjoyment. The act of reading itself can be fun, even if the signal strength of retention is less than perfect. Fiction is like this, of course, where the primary goal is entertainment, not education. Not that there’s no wisdom embedded in fiction — in fact, I would make a case that fiction offers deep insights worthy of remembering2. But I even see nonfiction works on my shelf that I remember enjoying years ago that I’ve mostly forgotten about, certainly in any conscious way that’s useful to me.
The defining purpose of nonfiction, though, is to educate, to convey ideas in a way that disseminates them to a wide audience and allows wisdom to compound over years by connecting dots in readers’ minds. Writers spend hundreds of hours distilling their ideas into works of a few hundred pages that we blaze through in a couple of weeks, retaining little.
Spaced repetition
Purely linear transmission is not the best model for understanding, but it’s the best that we have available to us today, cheaply and readily accessible. People like Andy Matuschak and his collaborator Michael Nielsen are busy behind the scenes working on this problem of how to build tools for thought that can harness the novel advantages of today’s technology. They experimented with this idea in their quantum.country project, using the complex subject of quantum computing combined with a “mnemonic medium” that integrated spaced repetition testing. The results they’ve shown from this experiment are promising evidence for the technique to increase retention. It’s a simple approach — interspersing simple questions within the text — but the problem is one of medium. Our existing reading and teaching tools don’t have affordances for this today.
Until we make headway in those new areas, what can we do to get more out of reading? How can we extract and retain the right ideas from what we read without having to reinvent the nature of books themselves?
Enter Readwise
One of the most useful tools I’ve discovered in the past year is Readwise, a service that’s working to solve this problem and enhance reading retention through a simple workflow:
Readwise syncs your highlighted passages from Kindle, web articles, and even tweets
See a sampling of those highlights in your inbox each day for review, through email or their mobile app (what they call your “Daily Readwise”)
Highlights are selected randomly from your archive, and can be resurfaced with whatever regularity you prefer
It’s such a simple idea that, like all great innovations, makes the most of the pre-existing infrastructure around it. The goal is to help readers retain what they read. I love it because of how simple it is. Readers like me aren’t looking for something scientific or complex; even an incremental improvement in reading comprehension and recall is enough to enhance the overall nonfiction reading experience.
Because I read so much and highlight copiously, my Readwise has over a hundred books, each with dozens (if not hundreds) of highlighted passages. At last check I have around 5,000 highlights in the archive. As they come through in each day’s review, I regularly get to see things I highlighted years ago from books I sometimes barely remember reading. There have been numerous times where a passage has spurred me to go and re-download the book on my Kindle and skim back through. This trigger is exactly what I want out of a service like this: a reason to be more diligent in reading practice, highlighting, and regular review. Just in the past year or so of using it, I’ve been able to dredge quite a bit of fleeting knowledge back up into memory. Without a service like Readwise (even with highlighting), it’s highly unlikely I’d ever remember much more than a two-sentence synopsis of most books in my library.
Readwise follows a spaced repetition model for increasing recall. True spaced repetition systems use specific algorithms to extend the time between recall tests (like the Leitner system). For example, you might first get quizzed on an item a day after first being shown it, and if your answer is correct, then you’ll be asked again in 5 days, 10 days, et cetera. The correct/incorrect answer provides a feedback loop to the algorithm to best estimate the spacing for resurfacing it again.
Tuning your reviews
Since not all the books in your archive are of equal importance to you, you can tweak the frequency that highlights are resurfaced on a per-book basis. I only have a couple in my library that I’ve turned down. Usually the quantity of highlights in a book is a good proxy for how interested I am in retaining info from it, so books with very few highlights are already less likely to appear in the daily batch. You can also dial in the preferences for new versus old books. You can have it favor more recent reads to review information while the reading is fresh, or favor pulling up more items from farther back in time.
Integrations
The most commonly used integration is probably their Kindle sync service. It’s certainly the most high-volume for me. But in addition Readwise can sync from iBooks, and even has a slick camera-based OCR tool for clipping sections from physical books3. You can also pull in highlights articles through Pocket and Instapaper, and even save tweets or threads to include in your reviews. They’ve also got a super slick integration with Notion, if that’s something you’re interested in.
Active recall
A key feature related to the native concept of spaced repetition is Mastery mode, which allows you to generate flashcard-like questions from specific highlights. On each highlight shown in review, you can add it to your Mastery catalog, either generating a question & answer flashcard or a fill-in-the-blank version of the quote (a technique known as cloze deletion). I only do this for concrete statistics and facts that I find notable enough to want to remember. Depending on the types of works you read most frequently, though, this could be incredibly helpful, especially for content like digital textbooks.
In my now-hundreds of Daily Readwise reviews, there have been countless times that a highlight pulled up from the archives has prompted a thought or idea that I jotted down in my notes. Occasionally they’ve even spurred such deep thinking (usually because I see it in a moment of already thinking about a similar idea) that I haul off and write a blog post from it. This for me is the one of Readwise’s core values. Since writing is a medium for learning, a tool in the belt that helps you synthesize ideas for writing is a powerful one.
Readwise has been in everyday usage around here. I recently had a 110 day streak that I broke a week ago, but still I make it a point to pop it open every day when I get the morning push alert and flip through the clips it assembles.
Future Ideas
One unsolved (and maybe unsolvable) area is a way to address audiobooks. Certainly the technologies exist to do playback, capture, and speech-to-text transcription, but it’s a question of integrating these all together in a system that would work. Audible is the largest player by far, but it generally has poor support for integrations of any type, and also generally innovates at a snail’s pace. I’m not familiar with other audiobook players, but maybe one day there’ll be a way for a new entrant to encroach on Amazon’s monopoly in this space.
For podcasts there’s a new player called Airr that’s doing something interesting with this, using a feature they call “AirrQuotes.” It allows you to clip a segment of audio from a podcast, along with the text transcript to send to another app. I could see a future integration here where you could have podcast clips automatically transcribed and added to your Readwise archive. (Update: Airr integration is now live within the Airr app, like they’re reading my mind)
I’ve added a post-processing step to my reading to collect the noteworthy ideas, forcing myself to write a concise summary and bulleted list of the salient takeaways that resonated. I’ve done this now with my last few books and it’s been a fantastic way to parse through the content a second time — sort of like the first “active recall” review. This extra passthrough to aggregate thoughts into a system helps drive compound interest on the ideas.
It’s rare for new productivity tools to stick with me this long. All of the tools in my daily routines are ones I’ve relied on regularly, and it takes a while for new ones to really click. Readwise clicked for me early and earned its staying power right away. If you’re an avid reader, you’ll love it.
Okay, let’s be honest: this is a phenomenal innovation. ↩
Science fiction especially isn’t just my favorite fiction genre for entertainment value, I also believe there’s a lot to be learned about invention, creativity, human behavior, psychology, and more from good speculative works. Check out Dan Wang’s comments on this topic. ↩
I’ve been using this a lot lately and it’s fantastic. Works great for any books you can’t (or don’t want to) read in e-reader format. ↩
A new piece from Andy Matuschak and Michael Nielsen (beautifully illustrated by Maggie Appleton). Can we make reading a more engaging and interactive learning experience? This builds on previous ideas from the authors on spaced repetition.
Interesting take from one of Byrne Hobart’s recent newsletters. Contrasting a typical “full-stack” model of company-building and VC funding to a “sumo” model:
The amount of VC funding has been rising steadily, and returns are skewed by a few positive outliers, so any fund that doesn’t have a specific size mandate is actively looking for companies that can absorb a lot of capital as they grow. The best way to get more capital is to move from a capital-efficient business to a capital-inefficient one, so there’s a strong incentive to pivot in this direction.
The incentive is sometimes too strong. Some companies go beyond the “full-stack” model to what I think of as the “sumo” model: raising an intimidating amount of money just to scare off everyone else. The sumo model does prevent one failure mode for startups: the situation where every time Company A raises a round, it validates the model and lets Company B raise more, which forces Company A to burn through their marketing budget faster and raise an even bigger round, and so on until the entire space is over-capitalized and everyone’s assumptions about long-term unit economics are implausibly optimistic. It’s an easier strategy to try when capital is abundant, but it’s a harder strategy to pull off; the bar for “an absurd amount to invest in a company that just does X” keeps going up.
In the arena of geeky digital marketing, this is a great deconstruction of organic optimization tactics in play at Canva, one of the best out there at enabling discovery through search and backlink traffic. I love how thoughtful and intentional their page architecture is; it enables so much adaptive targeting to sweep up long-tail keyword spaces.
Books are one purchase I don’t restrict my spending on. I’m not a big buyer of “stuff” in general, but I don’t hesitate at all about my money going to reading. I do try to be circumspect to not overwhelm myself, and to limit that spending to ones that I’m highly interested in and likely to read. I tend to think along the same lines as Shane Parrish here (and, by extension, Charlie Munger):
Books contain a vast amount of knowledge and knowing what most other people don’t know is how I make a living. While books can be expensive, ignorance is costlier.
This is why books are necessary. Charlie Munger loved to quote a line from an old machine tool ad: “The man who needs a new machine tool and hasn’t purchased it yet is already paying for it.” You’re already paying for the knowledge you need but don’t have yet.
(I’ll admit, this may be a way to self-justify the expense, but hey, you can waste a lot more money a lot more frivolously than on books.)
In recent years I’ve tried to keep the diet of books diverse between fiction and nonfiction, quick high-level stuff and deeper, richer ones. Since my interests are so varied already, covering a healthy swath of subjects isn’t a challenge. Over the years I’ve discovered my interests leaning toward “first principles” and classics. My very-occasional haulsfromused bookstores show my preference for a lot of original sources and old standards for the library.
I’m also an avid user of Audible and read more (by volume) via audio than print. It’s become so second-nature to me to listen to books, I’ve become much more adept at retention of information from listening than I was before. I still avoid reading deep stuff or books with heavy visuals in audio form if I can. People think I’m crazy when I say I always listen to books while running, but I’ve gotten so used to it that music while exercising sounds weird to me.
Now you might ask: why not support the local library instead of buying? I wholeheartedly support libraries and want them to continue to thrive, but the process of searching for, checking out, and returning books adds overhead to the process of reading that I’d rather not bother with. Not to mention the selection may not even contain half the books I’m looking for. Again, it’s a personal thing. Part of that is due to my own patterns of reading sometimes 4 to 6 books simultaneously, with 1 or 2 in there that might take 6 months to finish. Once my kids get older and start spending time at the library, it may tip my behavior in that direction, as well.
It’s not a shocker that American schools don’t produce the level of output we expect. I’ve written here before about this topic, and one of the largest failings I see (even dating back to when I myself was in high school, though not to the same extreme) is the rigorous constraint and hyper-measurement culture that’s pervaded education. It seems intuitive that measuring an outcome would help you to identify shortcomings to fix1, but measuring without a deep understanding of the means and ends can lead to blindness to what’s really happening, not to mention bad incentives to “increase the number” regardless of cost.
Because educating a diverse group of students is extremely non-trivial, expecting some consistent output with basic non-creative input is madness. This article discusses research by a group out of Harvard that analyzes the most effective high schools in the country to try and figure out what makes them tick. Teachers? Students? Parents? Process? It turns out that reducing constraints and enabling creativity from teachers can have a profound impact:
This is at least part of the reason so little creative experimentation occurs in U.S. high schools, the researchers believe. Teachers feel hamstrung by an “ecosystem of constraint”: externally imposed curricular requirements, standardized testing benchmarks, and metrics that colleges use in admissions processes. These external forces are extremely normative, explains Fine; teaching well within that context, as within any context, requires skill, mentorship, and practice.
“Every teacher we talked to, to a person,” she says, “expressed a desire to have their classroom be a place where powerful learning was happening, regardless of what kind of kids they were teaching. They all wanted it.” The challenge, she says, is that often “the system responds to perceived threats by asserting more control, rather than allowing for a natural release that empowers kids to make more choices and to take ownership of their education.”
Much of this stems from the assumption that a classroom or school is like an engine we can “fix.” Even if that were true, it’s a long game. Student engagement and learning aren’t going to skyrocket with a new policy or standardized test implementation. It’s by no means an easy task to marshal support in a diverse, politically motivated community of administrators, parents, and teachers, but hopefully research like this can shine the spotlight on what’s working.
Since I’m big on self-improvement and always looking for ways to get better at my professional craft, I was intrigued by this post from Marty Cagan from several years back. A post with a title the same as mine got me interested. Over the last few years I’ve occasionally read other companies’ job descriptions for that role to understand what they look for in skillsets and orientation.
It certainly matches broadly with my perception of the proper focus areas. I do think we’re particularly strong in what he terms “product culture”:
A strong product culture means that the team understands the importance of continuous and rapid testing and learning. They understand that they need to make mistakes in order to learn, but they need to make them quickly and mitigate the risks. They understand the need for continuous innovation. They know that great products are the result of true collaboration. They respect and value their designers and engineers. They understand the power of a motivated product team.
The makeup of our team is such that we don’t have to harp on these things much at all. It’s sort of the default mode for our crew how to approach developing product, not just code or software. Our team is comfortable with the core product development approaches of assessing pros/cons, opportunity cost, future technical debt implications, long-term support strategy, and creating a balance of small, medium, and large muscle movements to create the best end result1.
Versus focusing too heavily on only minor enhancements to existing capability, or only working on Giant New Features. ↩
The Khan Academy’s Long-term Research group studies new strategies for teaching and learning. This paper presents a method for freeform response and feedback on open-ended The dynamism and interactivity of these tools for teaching are fantastic. I haven’t seen some of these modern e-learning platforms in a long time, things like Blackboard or Canvas. I have used Khan Academy extensively and am always impressed. My childhood self would’ve really taken to the engaging presentation style of the content.
Students shouldn’t have to wait until their adulthood to pursue open-ended problems and improve their ideas through discourse with others. Indeed, as we’ve discussed, contemporary learning standards insist that students develop these skills earlier than ever. Skillfully-orchestrated classroom activities can successfully build these practices, but teachers across the country have lamented to us about how challenging and time-consuming these sessions are to facilitate.
What if online learning platforms could deliver rapid, reliable, and relevant feedback to students on complex open-ended activities, the way they already do on simpler multiple-choice exercises? What if these activities could facilitate thoughtful and energetic discourse between students and their differing ideas?
They have an interesting take on harnessing students’ skills to teach one another, through methods like peer review and feedback. Putting teachers in a position of being a “facilitator” much of the time would allow them the space to more effectively focus on students that need more help.
