A journal has been open for 86 consecutive days. My New Year’s resolution was to keep a journal of my daily life. I have sat down every day since January 2nd to do so. This is my longest journal entry and probably the longest time I have kept a diary. I probably feel prouder than I should about myself.
I have been using Day One’s app which is the king of digital journal space. Day One is available on almost every platform. It’s fast and easy to use, lets you write text, save audio and photos, and allows me to link into my journal. It’s an amazing app!
After pouring my heart, soul, and hundreds of photos of my newborn son into Day One for a month, I noticed that I was starting to worry. This app stores my most private thoughts. I have also given it access my calendar, location history, and camera roll. It’s a beautiful, well-organized, and collated collection that can be very problematic if it gets in the wrong hands. It’s synced with the cloud, which means that it’s stored on mysterious machines controlled by other people who don’t know where. Day One is a wonderful record of my life, but it also feels risky. Many people trust Day One. I have trusted it for 86 consecutive days. But should I? But how do I find out?
This isn’t just about journaling apps. We are being asked to devote more of our attention, time, and information to digital services as more of our lives move online. We get a lot of convenience in return: easy access to our stuff anywhere, tools for organizing that stuff, and collaboration with family, friends, and co-workers. Access to your data, activity, and interests is required for almost all these apps. The apps that request your most sensitive data have the worst privacy records.
Are there spaces that I can use in this digital world? Are there any spaces that allow me to have all the modern conveniences I want without being constantly asked to share, socialize, or upgrade my enterprise plan? I began to wonder if my journaling app was trustworthy, but ended up searching for my own place on the internet.
I began by trying to find out if my journaling app was trustworthy, but ended up searching for my own place on the internet.
Paul Mayne, Day One’s creator, told me that he created the app after experiencing a similar crisis in confidence to mine. Two things were necessary to make it work. He says, “I wanted something I could trust to store and capture all these memories. That would be there even after I’m gone.” This is the first. Second was the “comfort of knowing I could put anything I wanted there and that it would be impossible for anyone else even to see it.” Mayne created Day One by placing information on top of the Mac’s file system. Mayne states that by default, anyone who has access to your computer will see it. “The downside is that if your computer goes down, all of those memories will be lost.”
Day One now syncs across many platforms, including iOS, Android and Windows as well as Mac. And, of course, the web. This is a major reason why I use it. My data is safe, even if the laptop goes up in flames. I can write one entry at work and another from my phone at home. There is a risk in this; there are more data points than one person can see, and that means more problems. Mayne claims Day One has done its best to minimize the risks. Day One’s first sync was via Dropbox. But he didn’t like that setup. “The things that were stored on Dropbox were unencrypted and anybody at Dropbox could certainly read them.” Day One eventually developed its own encrypted syncing service that it continues to use today.
However, encrypted sync is not free. External services can’t access encrypted data, which is the whole point of encryption. This makes it difficult to connect Day One with other apps. Shared folders and encrypted data don’t always work well together. If your data is lost, it can be difficult to retrieve it. The list continues. End-to-end encryption is a bad feature from a user-friendliness standpoint. It’s essential for Day One.
This is the core tension of Day One, and all of my “Personal Apps”. You can have modern, useful features that are integrated and managed in a user-friendly way. You can also have a system that makes sure that your data is kept private and easily understood, and protects it against your mistakes and security flaws. There is a middle ground. There’s no way to have it all.
This tradeoff can be made in many ways, but passwords are the most common. Developers can encrypt data and ensure that only the key is available to them. This will protect your privacy. They don’t have access to it, they don’t keep it, and any hacker, employee, or covert agent can’t get it. However, if that key is lost, it can cause serious problems. Ask all those people who have spent hours searching through garbage dumps looking for their thumb drives containing all their Bitcoin. However, having a customer support team that can retrieve your password is a good thing.
Mayne states that privacy has been a priority for Day One, even though it made it difficult or impossible to create features. It took Day One 12 years to create a web application. It feels good. I hear horror stories about the amount of private information that people store on Evernote platforms, which aren’t encrypted — their passwords, etc. They just put them there in the web browser!” He believes most people don’t know about the risks so Day One’s job is to mitigate those risks for its users.
Another Personal App I like is the Obsidian note-taking app Obsidian . It tackles this problem in a different way. Stephan Ango, Obsidian CEO, told me that he is concerned about privacy and trying to create an app that is both powerful and extensible. So Obsidian has become kind of a choose-your-own-adventure app: when you first install it, it’s really just a simple text editor on top of a folder of files on your device. You can also turn on “Core plugins”, such as multi-device sync and the ability to publicly share a note. If you are really interested, you can also enable and install third party plug-ins which change Obsidian’s appearance and work or add new features.
Obsidian is capable of doing almost anything, but only if you allow it to. Ango states that because we allow you so much freedom, it means that the user must make their own decisions about how long they want to keep private or what privacy they would like to preserve. He is particularly interested in a few plug-ins that integrate ChatGPT into Obsidian. OpenAI is your choice.
Many of us will have to make the decision about generative AI in the future. ChatGPT is a great tool that can make your life easier. It makes it easy to synthesize information and recall things you have saved. You can even create new items. However, this requires you to upload your data to another server and allow large language models to ingest and process all of your personal and sensitive information. You might find the tradeoffs worth it. There is no right or wrong answer.
I am not an avid online privacy advocate. I don’t believe you need a VPN 24/7. However, I have become a bit obsessed with ensuring that my stuff is kept alive. Servers fail; products change; companies go out of business, acquire or kill less-loved items. My journal entries and notes must last beyond Day One and Obsidian. No app can be forever. Every personal app must have excellent export tools. It doesn’t matter what app you use, if there is no way to transfer your data to another app, a text file or a PDF, you are taking more risk than you can handle.
After months of searching, I have a useful rubric that helps me think about Personal Apps. Instead of creating a mountain of integrations and collaborative features, the best Personal Apps start with private spaces. Then they add features. They are often subscription-based which helps align their business with customers. Many are not venture capital-backed. I have spoken to many developers who refused to accept VC money. Growing fast is a compromise. When the Personal App is mainly being sold to IT managers, it can be difficult to create a quality app.
The best way to find out is by simply looking at the website of the app. It takes only three seconds to find out how developers feel about the current state of affairs. My Mind, a bookmarking app, is a stark example of how platforms are currently set up. The site states that “Our minds were taken captive by social approval systems and newsfeeds and timelines.” My Mind promises that it will never (never!) repeat this promise. Tracking, collaboration, and ads are all prohibited in My Mind. Personal Apps are almost always as aggressive in their value statements.
You might want to collaborate and have social features. There is no one right answer. You just need to make the best compromises. Over the past few months, I have found several apps that do the job and I trust. You can trust everything, but you shouldn’t be able to trust anything. For my daily journaling, I use Day One. Obsidian is my preferred tool for keeping track of all my projects and notes. I use 1Password for all my passwords, as well as my account numbers and documents. Everything is encrypted and exportable. So long as I don’t lose my passwords.
My day-to-day activities are dominated by Google Docs and Gmail. I find that going Full Privacy is too difficult for me. However, I have found that having a few trusted digital spaces has made life easier. It’s online, everywhere and it’s mine, mine alone.