How Gmail’s Archive and Search Model Made Me An OverDeleter

I remember the days pre-Gmail. Outlook search was horrible and so at every new job I started by setting up dozens of file folders to classify important emails. After several years the folders almost always became unmanageable. They contained too many emails to browse and, particularly for the oldest emails that could be classified several ways, I would sometimes forget which folder I had put critical messages into.

Enter Gmail. The mantra was to never delete anything, just archive it and use search to find old stuff. I loved it. When we started Backupify, we used Google Apps as our corporate IT infrastructure, so having everything in Gmail worked out great. That is, it worked out great until we were 2 years and 30,000 emails into it.

At that point, I started to have problems with Gmail search. The problem wasn’t that Google didn’t return good results; the problem was that for simple searches, there were tons of junk or irrelevant emails. I got around this problem by using labels. For the next year, I could search or browse by label and it worked well, but eventually that broke down too. It turns out that browsing and searching both fail once you get to massive amounts of content.

From there, I adopted the new strategy of using all kinds of complicated search queries to filter out messages that I didn’t want to show up in my Gmail searches. Finally I was on to something… for about six months. At that point, in frustration, I began deleting emails that showed up in search queries if I felt they were emails I would never ever need.

It didn’t stop there though. After a few weeks of that behavior, I started deleting emails directly from my inbox if I was pretty sure I would never need them again. And then, over time, “pretty sure” moved to “possibly sure” and the bar just kept moving from there. Eventually I was (and still am) deleting a ton of stuff.

The good news is, all this deleting worked. It is now much easier to find the old emails I am looking for, whether I search or browse, because I don’t have to wade through all the entirely useless stuff. The bad news is, all this deleting has turned me into an overdeleter. What is an overdeleter? It is someone who is so intent on deleting things that he or she sometimes deletes important items that were actually needed. And sure enough, after a few months as an overdeleter I deleted an email I turned out to need later. Luckily, we “eat our own dogfood” and I had Backupify to recover it.