Digital notes are supposed to make life easier. Instead, I’ve wasted what is surely half of my life on trying to put the right system into place.

There was a time when I thought Evernote was great. And it was! You could collect stuff on a computer, and then that same stuff would be right there on your phone. There were a thousand ways to get stuff into Evernote, and Evernote was available on just about anything that plugged into a wall.

I jammed Evernote full of stuff. Everything from hospital discharge paperwork to weird things my kids said to my portfolio work.

But it was a little frumpy. All the green and brown made it feel like the menu at a Rainforest Cafe. It’s a terrible writing experience, and I never actually liked using it. I didn’t mind it. But I didn’t like it.

It also turned into a bit of a black hole. There are documents in there that will only be found by trained archeologists in the future. When I look through it, I am surprised by the sheer amount of things that I saved and forgot about. And I also wonder about why I decided to put half of it in there in the first place.

Then I was introduced to the wonders of plain text and Dropbox syncing. Compared to Evernote, it was like piloting a rocketship. I liked the freedom of being able to write in any text editor that synced with Dropbox. NVAlt on OS X is fantastic for plain text notes. Nothing is faster.

But it’s difficult to combine images and text in plain text. That left me scratching my head when I came across images or webpages or rich text that I wanted to save. This is how random stuff started to find its way into every nook and cranny of my file system.

Then Apple announced that they were revamping Apple Notes. I was sure that this would be the answer. The new version has a rich feature set, it’s available across devices, and it’s really easy to get stuff into it from the share sheet. Also, I was tired of thinking about which apps to use for notes. The idea of just sucking it up and using the default solution was incredibly appealing.

But I’m finally ready to admit that Apple Notes hasn’t been working for me. I caught myself hesitating to put some kinds of information into it. I can’t explain why, but it just doesn’t seem like the kind of app that wants to be jammed full of random thoughts and images and whatever else. It’s not really an information database in the sense that I’d like it to be.

It’s also a bit slow to load on my phone, and it drives me crazy that you can’t specify a folder for a new note from the share sheet. Oh, and you can only create subfolders on a Mac. iOS doesn’t offer the full feature set. Which seems completely bananas, and it has resulted in a giant mess of notes that aren’t easily searched.

Meanwhile, finding something that I knew I captured was becoming a chore. Was it in Apple Notes? Was it still in my dormant Evernote account? Did I capture it in plain text? Maybe it’s sitting in my Drafts.app inbox. Of course it could also be on Pinboard.in, or maybe I saved it to Instapaper.

This was a problem. It would’ve been better to just keep using Evernote in the first place. So I started to think about moving back in.

I swore Evernote off last year. It seemed like a dying company. The constant nagging in the app about whether or not I had heard about Work Chat was getting under my skin. And I still wasn’t enjoying the experience of using it.

But I also never found a way to replace it.

Evernote is bloated with features, and it sucks at most of them. But the things it does well, like really well, also happen to be really hard to find in other apps.

So I worked to come to terms with the reality of the situation over a couple months, and I set off to reactivate my subscription.

But then, riding over the hill, wearing shining white robes and flanked by reinforcements, came DEVONthink and the new DEVONthink To Go iOS app. They were either coming to the rescue or dooming me to another few months of fiddling.¹

I’ve known about DEVONthink for years, but I had never tried it. It’s costly, and it didn’t do mobile very well.

Gabe Weatherhead’s blog post about DEVONthink To Go 2 completely sold me on the app. It seems like it changed DEVONthink’s game, and it stands a chance of changing mine.

People really like the way DEVONthink works because it is more secure than other apps. And it doesn’t change what you put into it into some other kind of file the way Evernote does.

That stuff is all fine and good, but what gets me excited is the chance to use something with similar functionality to Evernote, but with a higher ceiling for organization than Evernote. It works with folders and tags, but you can also work with multiple databases. And I think there is unlimited nesting of folders and tags.

That means you can have more than one database. You can have a database for work projects and a database for your kid’s art and another database for cataloging the mustaches of the world.

It’s also much easier to search within the right context. Your search results for work projects won’t involve having to wade through pictures of the right yogurt to buy for your wife or your kid’s shoe size.

You can selectively sync each database with your devices. If you don’t need your party dip database on your work laptop, it doesn’t have to be there. But you can sure as shit have it on your phone to show off at parties.

Each database has its own unique collection of tags, so there’s no need to use characters like brackets to signify different kinds of tags.²

Want to keep your documents in the regular file system on your Mac? DEVONthink can take files into its database, and it can index files stored in your Mac’s filesystem to include in your database without actually having to move the files anywhere. Rad.

Oh, and the desktop version has AI that can help to autoclassify new additions to the database and help to find related items to your search. I’ve heard amazing things about this stuff, but I don’t have enough files in DEVONthink yet to try out the AI.

So now I have two choices. I can go back into Evernote, reupping my subscription at their increased yearly rate, or I can buy DEVONthink outright, at a fairly high price, but without any need for a yearly subscription.

I think I know which way I’m leaning.

Wow, if you made it this far, remind me to buy you a coffee sometime.