Tech is better when it kinda sucks

My e-reader is a Kobo Touch, released in 2011. It’s still getting feature updates after all these years, a minor miracle given how quickly other tech companies abandon their products. When Pocket shut down last year, for example, an Instapaper integration showed up almost immediately, which I deeply appreciate. 

So this decade-and-a-half old device is well supported in some ways. But not all ways. For example: there’s no simple way to get library books onto it. 

From the official Kobo documentation I know that some Kobo devices support transferring Libby books over WiFi, but the Touch isn’t one of them. Fine. Instead I need to use Adobe Digital Editions, desktop software that can transfer the book using a USB cable. Fine. 

But when I first tried that, it didn’t work. At some point in the past ten years—I don’t remember when—I learned that the Kobo Touch only works with Adobe Digital Editions 3.0. That version of the software cannot run on modern Macs, though—it’s 32-bit. So I have to transfer ebooks from a desktop PC running Windows. 

So generally I find the library book I want, download the EPUB file, send it over the network to my Windows PC, then use VNC to open it in Adobe Digital Editions. Then I plug in the Kobo and complete the transfer. 

It’s a lot of extra steps, and I can’t add library books to my e-reader if I’m away from my house. But it works, and I’ve been doing it for so long it’s become reflexive. I’m a little jealous of my wife, who has a newer device that can receive books wirelessly. But I’m not jealous enough to replace my e-reader, which is still working fine. I don’t mind putting in a little bit of work in order to keep using this still-functioning hardware. And to be honest, I get to feel a little smug about figuring out how to make it work.

Earlier this week I asked you about your most elaborate workarounds. One person mentioned digitizing old home videos using four different devices. Another mentioned learning formatting languages instead of paying for Microsoft Office back in grad school. 

I love stories like these. I am a big fan of how easy it is to use modern tech—it makes tools available to more people. But there’s real value to digging in, learning how these systems work, and finding workarounds. 

Figuring out how to make something work is satisfying, and the feeling of satisfaction you get from accomplishing something is one of the better parts of being alive. The tech industry’s obsession with removing friction is robbing people of that. 

I’m not proposing that tech be harder to use on purpose—that would be dumb. But I do think it’s worth pushing past what you think you can accomplish. If something’s not working, don’t give up—try to figure out why. You might just fix it. Worst case: you don’t fix it, but you learn a few things while researching. There’s no downside to trying. 

5 comments
  1. In 2009 I was the graphics guy in a printshop. I wanted a Wacom-style monitor/tablet, but it wasn’t in the budget. I bought this goofy thing that clipped 2 microphones to the side of a monitor, and listened to the audio of a buzzing stylus to triangulate its position for input. Janky. Glorious.

    1. What a beautiful mess. Could you use it for anything productive?

      1. In the sense that saying “look how hi-tech we are, we’ve got a drawing tablet” to the manager produced a positive review, yeah!

        In terms of actually producing any work…doodling on copy paper and scanning it in was more helpful.

  2. @JustinPot I'd be curious if calibre could handle Adobe DE books. I used it back in the day but still bought my books on amazon at the time.

    1. Justin Pot July 30, 2026

      So far as I know this isn’t possible, and it certainly wouldn’t be within the terms of service. Ic could be another very interesting rabbit hole, though…

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