In Praise of Readwise

This may come as a surprise to those who’ve read my earlier posts, but I’m not a big fan of subscriptions. :wink: Still, there are exceptions—and Readwise is one of them.

One of the great losses over a lifetime of reading is how much we forget. While PKM systems can help, I suspect most of us aren’t as consistent in using them as we would like. That’s where Readwise proves invaluable. Its ability to sync digital content, import PDFs, and resurface our highlights and annotations—daily, in my case—is a powerful tool for remembering what we’ve read and seeing new connections over time.

More recently, Readwise added an AI feature that is genuinely impressive. This morning, a highlight from a book I read many years ago appeared in my daily review. I copied the text and activated Readwise’s AI feature. It immediately surfaced other content from other books I’ve read related to my original highlight.

Certainly! Here are conceptually similar highlights to your Kotter text about why transformation cannot be forced and requires participation, sacrifice, and creativity rather than top-down coercion:

  1. From Rowland and Higgs’ Sustaining Change: the most effective leaders “enable organisational leaders to create the conditions for moving large systems towards improved performance - without them having to personally shape and control the outcomes”—which aligns with the idea of facilitating rather than forcing change (see full context).
  1. Their work also notes, “they can only create the conditions; that it is process and connections that create change, not predetermined plans and projects…change is ever present - if we so wish to see it. When leaders can create an organisation that holds the balance between stability and change…the organisation can continually evolve, learn and adapt without the need to impose change on it” (connection here).
  1. Additionally, the same authors point out, “Emergent change assumes complexity and that change should be self-organised, and therefore the leader can only create the conditions within which change will naturally occur” (relevant highlight).
  1. Jim Collins’ Good to Great simplifies this further: “Engage in dialogue and debate, not coercion” (see context), underscoring that lasting change comes through engagement, not demands.
  1. The book The Conviction to Lead by R. Albert Mohler Jr. notes that “power can be associated with coercion and oppression, it should also be linked to influence and guidance,” emphasizing the importance of influence over force (see highlight).
  1. In Sustaining Change, there is a specific warning: “In order to influence the conditions that enable the change to be successful, rather than attempt to directly control its outcomes, a leader therefore needs to avoid the temptation to…issue prescribed directives—but rather set out the overall framework and guiding principles behind what needs to be done so that people can get committed rather than compliant” (explanation here).

All of these highlights echo the central message of your original text: genuine, sustainable organizational transformation arises from leaders who facilitate conditions for change, foster commitment and creativity, engage in dialogue, and avoid relying on pure top-down authority or coercion.

This is a meaningful use of AI—very helpful for lifelong learning and writing.

I’m genuinely impressed. Readwise is one subscription I’m glad to pay for, and I highly recommend it to anyone who hasn’t tried it.

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+1 for Readwise and its companion Reader app. It’s one of the few services that extracts highlights from Apple Books, which is one of the reasons I use it.

Thank you for highlighting the AI feature. I haven’t tried it yet, but it seems like a good way to resurface your highlights across books. I will check it out.

For anyone who wants to try it, the service offers a 30-day free trial. I have a link that increases the trial period to 60 days.

P.S. If this link comes under promotion, please let me know, and I will remove it.

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I’m warming up to Readwise. I’ve got many book in queue to read and remember the stuff that stands out is crucial.

+1. For me, Readwise & Readwise Reader deliver a huge consumer surplus.

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Readwise is definitely one subscription that I will keep. My biggest complaint is that the reader isn’t very device friendly and rather clunky to use - so for RSS I generally revert to Reeder/Feedly

A caution about the Readwise Reader: it is still clunky (at least on iPad) after years of development. When I tried earlier this month, I was appalled that it couldn’t even open large PDFs (100k+ words and 10+MB) on my M1 iPad. Smaller bugs are everywhere. The web-ish UI feels awkward.


I can certainly see the appeal of resurfacing highlights. Readwise reportedly does an excellent job at just that. But let me argue that Readwise is not addressing the real problem, which is that we are not making use of our highlights. Forgetting is not the problem. Sealing the highlights in a dust-free, rotating display cabinet is. Even if the cabinet is as polished as Readwise is.

Starting last year, my notebook contained only content written by myself. I made an effort to rewrite every highlight in my own words after finishing a book, chapter or article.

This has been a highly enlightening process. I often found unexpected connection between a highlight and a prior idea of my own. As I weighed on word options for a rewrite, I realized I had seen similar choices before. A search query then brought about a two-year-old note, which took a different approach to the same topic. Such a discovery rarely occurs during reading. It always takes place when I write, presumably because I’m much more familiar with my own writing than with others’.

Another good thing about this approach: I don’t need to export Apple Books highlights anymore.

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Yes, the iPad app is subpar and in need of significant improvement. I primarily read books using Apple Books and take notes on the highlighted sections. Since the notes are synced along with highlights, I get my notes along with the context in Readwise.

I mostly read web articles either on Mac or iPhone, so its clunky iPad app doesn’t pose a big problem for me. That said, I would prefer that Readwise focus on creating, if not native apps, then at least high-quality apps that are on par with the platform’s standards.

(GoodLinks is an excellent app if you are looking for a good iPad experience.)

For reading and marking up my PDFs, LiquidText is my go-to app.

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Tried Readwise and dumped it after the trial. The team is great, but the product is just not me.

$5 inoreader pro sub, on the other hand, is legit worth it and tremendous value.

This is actually the reason I cancelled my subscription. The iPad app just wasn’t making progress like their web app. When I reached out to them I basically got told that it’s not a priority for them and pushing the iPad app along wasn’t high on their roadmap (if I recall I was asking about keyboard shortcuts like their web app has).

Your approach is ideal. The problem is that I suspect most of us are not consistent in following that process. At least, I know that I am not.

I’m curious, what apps do you use for taking those notes, resurfacing them, and writing? I’m always on the lookout for the best workflow when it comes to research, notetaking, and writing.

I signed up way back when and got some kind of discount. It holds in place as long as I don’t cancel, so I figured why jump to another app for the same price without all the fancy highlighting/Readwise stuff?

Honestly though, between us on this forum. I save 4 articles per week and read 1 per month. I just find the bar for me to want to save something to be really high and the bar to read it, even higher.

I have a Kobo though and I love that it syncs highlights to Readwise.

Only thing I’m trying to figure out is – and I could just ask ChatGPT I suppose but here I am; I find the differences in my highlights to be vast. Like, self help guru quotes beside a Pillars of the Earth quote. They don’t really jive. I almost need to break them up into categories. I’m sure this can be done, I just haven’t tried hard enough yet LOL.

One more confession. I never use keyboard shortcuts unless I am taking a screenshot – and I can barely remember that one. I don’t know how people rely so much on the shortcuts. I wish I had that skill.

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I think you might be the perfect customer for this app: https://ergonis.com/keycue

Thanks. I use Windows at work and use Windows/Shft/S (screenshot) which is burned in my memory – or is it ALT/Shift/S? My fingers know, my brain doesn’t LOL.

But on my Mac, other than cmd+q to quit apps and copy paste, I’m a power-user with newb shortcut skills. :upside_down_face:

I use Readwise Reader every day, but I will be the first to tell you that it is excessively fiddly to set up and maintain. I wouldn’t recommend it as a casual read-it-later tool or RSS reader. There are better, cheaper options for both of those things.

Here’s why I continue use it:

  1. I can upload, highlight, and annotate PDFs, ePubs, web articles, and newsletters. I haven’t found another tool that handles both PDFs and ePubs. (And if anyone knows of one, please let me know.)

  2. It will port my highlights to Obsidian automatically.

  3. It gives me a place to segregate my intentional reading. As long as I can afford a walled garden for what I have committed to read and nothing else, I will pay for one. Stuff I might want to read or RSS feeds I can safely ignore go somewhere else. If it’s not on my (admittedly elaborate) TBR (To Be Read list), it doesn’t go into Reader.

  4. All of the newsletters I subscribe to go to Readwise Reader so I can delete them from my email inbox and read them in a dedicated space when it’s time to do so.

I know my habits of mind: I’m a digital hoarder and usually find myself down one rabbit hole or another on a daily basis. Readwise Reader helps me fight my worst instincts.

There are a ton of things I’d change about Readwise Reader if I could—I’d love to be able to opt out of having it automatically segregate “seen” from “unseen” items, for instance, or to make the process of setting up filters more straightforward. (“Seen” doesn’t mean “you’ve read this”; it really just means you happened to click on it in the user interface, which is too easy to do by accident.) But for now it’s the best tool for what I need.

Do you happen to know if there is a way to do the same thing but have the highlights sent automatically to DEVONthink instead of Obsidian?

I use the free Feedly every day and I just have a hard time with the idea of paying more than 50 dollars a year for RSS. What Inoreader features have you hooked?

I’ve decided i’m just never going to expend the effort to memorize a bunch of key commands. If I can attach the important ones to something like a streamdeck button then that’s what I’ll do.

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Brett Terpstra has published a script that saves Readwise highlights in DEVONthink as annotated Markdown files: Readwise highlights to DEVONthink - BrettTerpstra.com

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Thanks! I’ll check it out.

This may come as a surprise to those who’ve read my earlier posts, but I’m not a big fan of subscriptions. :wink: Still, there are exceptions—and Readwise is one of them.

I’m teasing you just a little bit here Barrat, but I wonder if you like subscriptions that you find valuable, and maybe you dislike subscriptions that you don’t find valuable?

That would be sensible!