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Databases on the Mac

Our complex lives mean that we all live in some form of a database on our computers. Whether it’s email, a folder system, your home folder, Evernote, or the desktop, we all use some sort of system for our files. We need a way to store and then later find things in “an organized collection.”

Databases are tricky. They are easy and great at first when there’s not much information in them, but they rapidly balloon into something unworkable. You have to decide whether to use a file folder or a tagging system (gatherers versus hunters, in the nerdy lingo), but you don’t really know what sort of folders or tags you need. Only as the database grows with time do you really see how to organize things, and then you are left with cleaning up the database and the system (which no one really wants to do).

What really moved the ball forward in terms of a home database usage is the power of computer indexing and a google style search. I still remember how jaw-dropping gmail was when it premiered – seemingly unlimited storage for your email, the power to archive everything, and a lightning fast and accurate search. Google and gmail work so well because they are how people work – we remember some scraps of detail, a name or a word, where we were, when we search for something, and that’s all google needs. All home databases should work this way. The search field is one of the best bits of modern computers.

The challenge for databases is to make them fast, easily accessible, and secure. It’s easy enough to create a folder structure or even encrypted disk image, but how do you make that usable with multiple devices?

Nested folders are always an option, but they don’t allow for easy searching, indexing, or security. You can throw everything on Dropbox, for example, but you will probably want something more robust, that can handle weblinks, searching in files, and so on. This immediately leads us beyond nested folders.

Another issue is the endless problem with technology: just because we can keep a file doesn’t mean we should. I really don’t need last year’s utility bill. In the words of Marie Kondo, throw most all papers away. Banks can retrieve statements, and manuals are available online (at least most of the time). My thermostat is online but I don’t really care, I just want it to keep things around 74º F as efficiently as possible. Like task managers, databases get really kludged up by things we really don’t need.

One of the real problems with experimenting with different databases is that databases are inherently difficult to try out. Every database program is fun to start with, as it has little information in it, and you can tinker and imagine what your files will be like in the database, but the problem is, you don’t really know. You have to use it for 6 months, and put a lot of information in there, before you know if you really like it or not. You can’t experiment with a database application like you can with a word processor. They are long term applications that require a large investment, which is probably why people don’t change database apps very often.


I really liked Evernote for a long time. It was great to have an everything bucket where files could go. This bucket was available across most all devices and platforms, synced, was searchable, and could most anything. There were a few times I needed a manual, and it was great to pull it on immediately instead of going through a file drawer. But do you deal with financial information that you don’t want stored on Evernote’s servers? Further, text files were clunky and weird, there were annoying ads popping up, and there was a painful lock-in in that it was hard to export out of Evernote. Evernote was such a leader for a long time, but it’s been feeling a bit abandoned as of late. So I began searching for an alternative.

Plain text editors

Plain text editors are great. I play with them too much, probably, especially since many of them wall things off so that I can’t remember where I put a particular note. I still really like Simplenote, but Apple’s built-in Notes is great too, especially since Notes can store images, checkboxes, rich text, and so on. Simplenote and Notes pair well together. I also like Notefile a lot, it’s very pretty and syncs well. Vesper was great but seems abandoned. But Plain text editors can’t store files or get real fancy in terms of tagging.
I like a Plain text editor a lot, and would rather use such a system than one of the database managers. These database programs all pre-date the advent of plain text editors, so they have a built-in system of notes. But I’d rather have a fast, easy, and lightweight system of plain text notes alongside a database, than having a large database that brings up too many search results. If it’s a plain text note, it goes in Simplenote; if it’s a file of some sort, it goes in EagleFiler.


DEVONthink, despite its inexplicable name, is very likable. It looks and feels very Mac-like, it’s been around a long time, and it has its own artificial intelligence sorting mechanism. Many people rave about the AI searching, but I find it awkward to invoke (the command is buried) and not always reliable; if I have to confirm where you filed it, I might as well file it myself. You can create multiple databases and even encrypt them, which is great if you are storing financial information. It has a lot of powerful features.
But the application feels a bit aged in a cloud-based world. It's fiddly in a time when applications are more lightweight and cloud-based, and the features feel bloated. It feels overly difficult somehow, sort of like Microsoft Office did years ago, and is slow to boot up. There is no real sync possibility.


Pinboard is fantastic. It’s a super fast database of your saved weblinks, accessible from any browser. You can tag, search, and it’s wicked fast. It only does webpages – you can’t save documents or files. But Pinboard has really replaced this functionality in other applications, because it’s so fast and easy. It’s the gmail of your website bookmarks. There’s also great third party apps that you can use to interface with Pinboard (but this is optional). The one catch is that, unless you pay extra for bookmark archiving, your saved pages are dependent on those websites still existing. If you saved a great site to Shakespeare and the site goes down, it’s gone, unless you paid for archiving. Archiving actually saves the page to Pinboard.


Yojimbo is really great. It’s beautiful, despite its age. The developer is one of the most respected in the business, having written seminal applications like BBEdit. TextWranger is a great little free app that shows Bare Bones Software’s ability to make powerful and fast software.

Yojimbo does feel dated in some ways, despite its terrific design. The real problems are sync and security. There’s not an easy way to sync your database between devices (there are solutions, as with DEVONthink, but they are unsatisfying). Nor is there an easy way to encrypt a database. There is only one database, actually, so you can’t have multiple databases as in DEVONthink. In this respect, Yojimbo does the best job fulfilling a shoebox type of database, in that you are forced to shove everything in there. The tagging system is great, though, the search is terrific, and the fonts are design are splendid. It doesn’t do folders at all, which makes sense in many ways; if you want folders, you should just use nested folders. If you don’t need sync or encryption for your data, then Yojimbo is the best choice.


EagleFiler is a bit depressing to launch, as it looks and feels kind of weird (what is the eagle doing to the file cabinet, exactly?). It’s much more industrial in design. But don’t be fooled, because EagleFiler is really terrific. It is super speedy once it is launched, can handle multiple databases easily, and can even import and index email addresses. I downloaded about 5 years worth of gmail messages and imported them into Eaglefiler (messages in the hundreds of thousands of range, with attachments), and it did the job WITHOUT CRASHING. (You might want to re-read that last sentence again, as it’s amazing). The application is modestly priced considering its power, especially the ability to archive email from Apple Mail. (BTW, this is a great workflow – you should, on a regular basis, download email older than 2 years and throw it into an EagleFiler database.)
The killer feature of EagleFiler, though, is you can put your database on Dropbox or another cloud service, and the folder structure is completely transparent. As long as you only run 1 instance of the Eaglefiler database file at any time, it doesn’t really care what you do. You can put files in the “To Import” folder and it will import them automatically. You can open text files up in other applications and edit them, save them, and EagleFiler looks the other way. EagleFiler is pretty unique in having an open database where you can alter files (to some degree – you can’t rename files or move them, or edit the main EagleFiler database file itself). Most databases are locked down. This is EagleFiler’s real killer feature, in that it creates a built-in sync feature for users storing a database in the cloud. EagleFiler doesn’t offer encryption, though.

My favorite? EagleFiler, with a long look at Yojimbo.

Good luck.

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