Friday, April 15, 2016

Digital Declutter: Email Archives!


Virtual John Hodgman wants you to reach inbox zero.

While I have my paper mail decluttering down (I follow the KonMari rule of thumb: "get rid of all of it"), I don't follow the same rules when it comes to my digital clutter, especially my email inbox. I follow opposite rules, actually--I save everything. And I think I need to stop.

When I first got Gmail, it was a revelation to be able to archive old messages instead of deleting them. I had so much space. It was comforting and freeing: I could keep all my messages, and I didn't have to organize them, because if I ever wanted one, I could just search for it. It made clearing my inbox both simple and unnecessary. Any time I wanted "inbox zero," I just archived everything--kind of like sweeping everything under the bed. A bed with infinite space and search capabilities.

This practice has served me well for nearly ten years, but I have finally discovered a downside. My wife's family has had to go through the email account of a relative who died recently. It's hard to tell if any of the messages are emotionally, financially, or otherwise meaningful because they're so buried in the usual mess of newsletters, automated emails, and mundane exchanges. My wife also has backups of her own email inbox from pre-Gmail, and she just moves them from one hard drive to another because she can't be bothered to look at them. I've lost all my old inboxes long ago--I'm much less meticulous about backups--and while I'm sure I've lost some nice mementos and things, I'm glad I don't have an enormous old inbox to go through. It would be best to have, say, a few key entertaining or informative emails from the past. If you have everything, you might as well have nothing, because it's so much work to find the highlights.

The easiest way to preserve the highlights for Future Me is to adapt my email habits now. Instead of hitting the "archive" button when I'm done with an email, I'm training myself to hit the "delete" button. This doesn't just benefit the future self that needs to decide whether to port old messages to a new technology, or whoever has to deal with my inbox after I die; it benefits me now, because my searches are suddenly more helpful! For example, when searching for "library advanced search," an email in which I'd sent myself a URL that's kind of hard to find on the library website, I immediately found the relevant email at the top of the list, not buried under hundreds of "your library book is due in 3 days" emails.

What to Delete & What To Keep

It's easiest for me to decide what to keep and what to delete if I have clear guidelines, so here are mine:
  • Delete automated emails, particularly those that alert me of time-based information (your dentist appointment is tomorrow) or activity on another platform (someone endorsed you on LinkedIn). Ideally, I'll turn off any automated messages that I don't even care about in the present moment! Even for those messages that are informative or gratifying when I receive them, I don't need to preserve them for the ages. The email has done its job when I read it, and I can then delete it.

  • Delete marketing and/or charity promotions. Of course, as I've discussed before, I'll ideally unsubscribe from all these lists. Even for messages that I want--say, a coupon for a restaurant I love--I should delete it if I'm not going to use it. I can definitely delete the email after the offer expires.

  • Keep email receipts for products I may still want to return, but delete all others, just as I would discard a paper receipt for any item I don't plan to return or that is no longer in returnable condition. (Not that it's not mildly interesting to learn that in July 2010, I ordered a 2GB thumb drive and a copy of a book called Naked Men, Too: Liberating the Male Nude.) Even I, a personal finance blogger, don't look back at previous purchases or transactions all that often, and when I do, I use the website itself, or my bank statements, not my email.

  • Keep direct emails from human beings I personally know. Possible exceptions: forwards, mass emails I was CC'd on, invites to events that have already occurred.

  • When in doubt, keep. This is the opposite of my real-stuff strategy, but digital clutter is so easy to ignore that I was able to sit comfortably on ten years' worth of eBay auto-replies, so it's clearly not a big deal. If I get more stringent later, I can always declutter my keep folder.
Right now, in an effort to declutter my inbox, I am not just deleting messages after reading, but I'm using them as reminders to search for all similar types of emails and batch delete them. I'm hoping this will allow me to slowly chip away at my massive chunk of email without devoting a lot of time to it on any given day. After all, in ten years, I've amassed 40,000 kept emails, and I have no desire to sit down and go through them! Still, I was able to delete 5,000 emails in about 15 minutes just now. 35,000 to go. (Gmail hint: after clicking the checkbox at the top of the column to select all visible emails, watch for a little link to "select all emails that match this search." This will appear at the top of the page if you have more than 50 emails that match your search criteria. Clicking that link prevents you from having to go through the emails 50 at a time.)

How to Avoid Deleting What You Want To Keep

The biggest risk here is accidentally deleting emails I actually want to keep. Here's what I do to mitigate that risk:
  • I search by sender whenever possible. If I search for "amazon," I'll not only get automated emails from Amazon.com but my friends and I discussing Amazon.com, or the Amazon. Instead, it's safer to search for messages from auto-confirm@amazon.com. In Gmail, you can use a wildcard: "from:*.ebay.com"

  • I created a "keep" label. I realized I needed a way to tag emails I'd already marked as keepers, so I didn't have to re-decide on them each time they showed up in a search. This makes it easy to see at a glance which emails I've already deemed important.

    One important note -- your mileage may vary, but one key to making this work, for me, was not to have more than one label. I used to meticulously label each email I received based on content or sender, but it was impossible to keep up, and would be too time-consuming to apply to back emails. And I kept running into judgment calls that froze me: I want to keep this, but it doesn't fall into one of my preset categories! Is this email about a job from a friend a "friends" email or a "work" email? Hmmm.

    Just a simple keep or not keep decision is about all I can handle, and it's also the only thing that's relevant to me, since I don't tend to use content-based labels to find old emails (I only use keyword search).

  • I created a filter which automatically marks emails from friends and family as "keep." If Gmail sees any of their email addresses in the "from" field, it automatically applies my "keep" label. I can tweak it by hand by unmarking or marking specific emails, but this is a good starting place.

  • When searching for emails to delete, I exclude emails already marked as "keep." I still have to keep an eye out for keepers I haven't decided on yet, but this keeps me from deleting something I've already decided to keep. This is easy in gmail; for example, if I'm searching for "linkedin," I'd enter as the search term: "linkedin -label:keep"

  • After a big delete purge, I do a cursory search in my trash folder for anything that looks keepworthy. I note anything that slipped through the cracks, to help make my "keep" filter more robust.
At the very least, even if I don't stay on top of this, the automated filter should keep the "keep" label fairly relevant, so Future Me can safely delete/ignore/not port any email not marked as "keep."

The same rule applies to digital clutter as to physical clutter: either consciously and enthusiastically decide to keep something, or get rid of it. There's no middle ground.

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