My impossible quest for the best, most powerful and most personal journaling app ever

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By Webdesk


I wrote in my diary for 86 days in a row. It was my New Year’s resolution to really commit to keeping a journal of my days, and every day since January 2, I’ve sat down and done just that. This is the longest I’ve ever kept a journal – and almost certainly the longest I’ve ever held onto a resolution of any kind. I’m probably more proud of myself than I should be.

I used the Day One app, the giant of the digital magazine space. Day One works on almost any platform, is quick and easy, and lets me write text as well as save photos, audio, and links to my journal. It’s a great app!

But I had this moment, about a month into pouring my heart and soul (and hundreds of photos of my newborn son) into day one, where I started to worry about it. This app is a repository of my most private thoughts; I also gave it access to my location history, my calendar, and my camera roll. All that information is beautifully organized, collected and very problematic in the wrong hands. It’s also synced to the cloud, meaning it’s stored on a bunch of mysterious machines that other people control who knows where. Everything that makes Day One a great account of my life also makes it feel risky. Many people trust Day One, and I trust it every day for 86 days in a row. But should I? How should I know that?

You can also hear a version of this story on this week’s episode of The Vergecast.

This isn’t just a question about journaling apps, either. As more of life takes place online, we are being asked to devote more and more time, attention and information to digital services. In return, we get a wealth of convenience: access to our stuff from anywhere, tools to organize and use that stuff, easy collaboration with friends and family and colleagues. But almost all of these apps need access: to your data, your activity, your interests. Historically, the apps that ask for your most sensitive data often have the worst privacy records.

Are there still places in this digital world that are just? mine? Can I have all those modern conveniences without being constantly asked to share, socialize, upgrade to the enterprise plan? I started trying to figure out if I could trust my diary app, but eventually I started looking for a place of my own on the internet.

I started trying to figure out if I could trust my diary app, but ended up looking for a place of my own on the web

Paul Mayne, the creator of Day One, tells me he built the app after a similar crisis of confidence as mine. It required doing two big things right. “I wanted something that I entrusted myself with to capture and store all these memories that would last beyond me,” he says. That’s the first thing. The second was “the comfort of knowing that I could put whatever I wanted there, and it’s unlikely or impossible for anyone else to even see.” That meant a different approach to building the app: Instead of storing information in a central location and then building local apps that ping that server, Mayne built Day One on top of the Mac’s file system. “By default, only anyone who has access to your computer sees it,” says Mayne. “The downside is if you lose that computer, you lose all those memories.”

Now Day One syncs across a wide variety of platforms: iOS, Android, Windows, Mac, and recently even the web. That’s a big part of why I use it. I can write one item on my laptop at the office and the next from my phone in bed, and all my data will still be there even if my laptop goes up in smoke. But there is a risk involved; more data in more places means more things can go wrong. Mayne, of course, says Day One has done its best to mitigate the risks. The first sync Day One built was through Dropbox, but he didn’t like that setup: “the stuff stored on Dropbox was unencrypted and someone at Dropbox could definitely read it.” After a few years, Day One rolled out its own end-to-end encrypted sync service, which it still uses today.

However, encrypted synchronization comes at a cost. It’s hard for third-party services to access encrypted data – that’s the whole point – making Day One difficult to connect to other apps. Encrypted data and shared folders usually don’t work very well together. It can be more difficult to recover your data if something is lost. The list goes on and on. From a usability point of view, end-to-end encryption is an objectively bad feature. But for the way I think about Day One and want to use it, it’s also a totally essential one.

This is the fundamental tension on day one and basically in everything I would call “personal apps.” You can have cool, modern, useful features integrated and managed in user-friendly ways. Or you can have a system that goes out of its way to ensure that your data is treated in a personal and understandable way and that it protects against even your own mistakes and security flaws. You can kind of have a middle ground. But there’s no such thing as having it all.

There are a million examples of this trade-off, but the simplest is probably passwords. The most privacy-protective thing a developer can do is encrypt your data and make sure only you have the key. They don’t see it, they don’t store it, and there’s no way for an employee or hacker or secret government agent to get their hands on it. But that also means that if you lose that key, you’re screwed. (Just ask all the landfill hunters about the USB stick that contains all their Bitcoin.) On the other hand, having a customer service team that can recover your password is great – and a security risk.

The Day One team has always prioritized privacy, Mayne says, even when it made it more difficult or impossible to build features. (There’s a reason it took Day One 12 years to get a web app.) It just feels like good practice. “I hear scary stories about how much private information people put on platforms like Evernote that isn’t encrypted — all their passwords and stuff. And they just drop them right there in the browser! He thinks most people don’t know the risks, so it’s Day One’s job to mitigate them on behalf of the users.

Obsidian starts out very simple, asking you to enable the features you really want.
Image: Obsidian/David Pierce

The note-taking app Obsidian, another personal app I’ve come to like, takes a slightly different approach to the issue. Stephan Ango, the CEO of Obsidian, tells me that he also thinks a lot about privacy, but also tries to build an app that is extremely powerful and extensible. So Obsidian has become something of an app for your own adventure: when you first install it, it’s really just a simple text editor on top of a folder of files on your device. But you can enable some “Core plugins” such as multi-device syncing or the ability to share a note publicly. And if you’re really inclined, you can enable and install third-party plugins that change the look and feel of Obsidian, or add all sorts of new features.

The idea is that Obsidian can do almost anything, but only if you explicitly allow it. “Because we’re giving you so much freedom,” says Ango, “it means the user has to make their own choices about what they’re willing to give up in terms of privacy or longevity.” He’s particularly intrigued by a few new plugins that bring ChatGPT features to Obsidian. “You have to decide for yourself how you want to entrust OpenAI with your data.”

In the future, many of us will have to make that decision about generative AI. Tools like ChatGPT can be a huge boon to your life, making it easier to synthesize information, retrieve things you’ve previously saved, and even create new things. But that requires uploading data to someone else’s servers and letting large language models ingest and process all of your most sensitive and private information. Maybe the tradeoffs are worth it to you; maybe not. There is no wrong answer.

I’m not generally an online privacy fanatic. I don’t think you need a VPN all the time or ditch your Gmail account and switch to Proton. But I’ve gotten a little maniac about ensuring the longevity of my stuff. Breaking servers; products pivot; companies are taken over or go bankrupt or kill their less-loved stuff. No app is forever, and my diary entries and notes have to survive day one and Obsidian. That’s why any good Personal App should also have great export tools. I don’t care what app or service you use, if there’s no easy way to move your data – to another app, to a text file, to a PDF, whatever – you’re at more risk than I’m comfortable with at feel.

After asking around for a few months, I found a helpful section on how to think about personal apps. The best start with private spaces and add features instead of starting with a mountain of collaboration features and integrations and then following a privacy policy. They are usually subscription-based, which can help tailor their business to their customers. Many also tend not to be backed by venture capital: several developers I spoke to went out of their way to mention that they refused to take VC money, because taking that money means growing fast and growing fast means growing fast. to make compromises. It’s hard to make a good personal app when it’s mainly marketed to IT executives.

My Mind’s site makes it very clear how it feels about the state of most apps.
Image: My Mind/David Pierce

But the easiest way to know is to just look at the app’s website. It usually only takes three seconds to see how these developers feel about the state of affairs. The bookmarking app My Mind, for example, goes against the way platforms work now. “Our minds have been captured: by social approval systems, by news feeds and timelines, by advertisements and corporate calendars,” the site says. My Mind then promises to never (never!) have ads, tracking, social features or collaboration. Most personal apps have a value statement that’s just as aggressive.

But you might want social features and collaboration, and that’s fine too. There is no perfect answer to this, and ultimately you just have to decide what compromises you can live with. Personally, over the past few months I’ve found a few apps that get the job done that I can trust. (Anyway, as far as you can trust anything.) I use Day One for my daily diary. I use Obsidian for all my projects and notes. I use 1Password to store not only my passwords, but also my account numbers and personal documents. Everything is encrypted, everything can be exported, everything is in a place where no one can reach but me. As long as I don’t lose my passwords.

Most of my day-to-day life I’m still in Google Docs and Gmail and the like – using full privacy is more work than it’s worth, at least for me, at least for now. But I’ve found that having a few trusted digital spaces has improved my life. It’s online, it’s everywhere, and it’s mine and mine alone.



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