my transition from apple mail to the gmail cloud, part 1
Posted by Steve Woolf

I decided to write a series of blog posts about moving the tens of thousands of emails from years of life online in my local email into Google's cloud. This is Part 1. Read Part 2.

Quick Background

I've been working on the web since 1994. In that time, I've used just about every major email client available for the Mac at one point or another, as well as a few for Windows when needed. I can't posit an accurate guess as to how many emails I've received and sent over the years, but it is certainly in the tens of thousands. For a long time I tried to keep an organized archive of all of it, but time simply doesn't allow that kind of indulgence anymore.

For the past few weeks I've been considering making the break from a local application and moving everything to Gmail's cloud. We're paying customers of Google Apps, so I have plenty of room, and the Gmail web application is very mature at this point and it has a great mobile version that was just updated yesterday.

The Challenge

The real hitch is that I have been using Apple Mail with a plug-in called MailTags for the past four years or so. MailTags is an outstanding tool that allows you to add meta-data to individual email messages in the form of tags, projects, to-dos, and lots more. It came out a few years ago and it really saved my life. At the time I was dealing with dozens of simultaneous projects from beginning to end, and setting up smart mailboxes with MailTags changed the entire way I managed my email. I could finally have granular control over the way I categorized my email without dragging messages to folders.

The flip side of this is that I basically became married to Apple Mail. I have literally tens of thousands of messages that were downloaded via POP, tagged, and categorized that are no longer relevant to my daily life, but are great resources to have on-call when I need to refer back to something. Without MailTags, all the work I put into adding meta-data to my email goes to waste. I want to find a way to preserve my meta-data, but transition to a tool that doesn't suffer from performance issues when dealing with tens of thousands of messages. I also didn't want to have to ever think about archiving my mail and backing up to a hard drive or DVD ever again. It's 2009, and that just seems ridiculous now.

Analyzing My Email Habits

My email habits are pretty organized considering the volume. Incoming email isn't a good measure of usage; I get dozens of notes each day from all kinds of social networks that aren't really pertinent to daily life, dozens of Google alerts, and so on. I have always looked at my true email volume by messages that I send, since that's a real measure of the time I spend thinking about the email I get.

On a typical day I send out somewhere around 100 emails. That's far less than it was three years ago, when I averaged about 300 daily emails sent.

These days email is an increasingly less important way of communicating for just about everyone. In many ways, it's a legacy app. Text messages, instant messaging, direct Twitters, Facebook messages, and that thing called the telephone all have a greater sense of immediacy, and therefore tend to get priority. Email still has an important role in managing my communication, but it tends to be more of a place for gathering and storing information to act upon later, as opposed to things that need immediate attention. I won't get into all the various methods out there for managing modern communication, it's a topic that has been covered ad nauseum by dozens of very awesome blogs.

The Plan

The main parts of this challenge are:

  1. Getting the thousands of emails stored on my local hard drive uploaded into Google's system
  2. Preserving the categories, tags, projects, and other meta-data in some manner, most likely through the use of Gmail's labels
  3. Preserving the dates of all the messages to maintain a proper chronology
  4. Preserving the attachments of all the messages to maintain completeness

As I go through the process of researching and testing, I'll update the blog with links to everything I find and a writeup of my results. I'm hoping to be pleasantly surprised by finding an easy way to make this happen, but I am a realist. :)

Since I'm far from the first person to deal with this kind of transition, there are lots of blog posts and articles online with good information. But I have already noticed that there is very little consistency with how each author recommends approaching the problem, and there have been a variety of disastrous results, too.

I have backed everything up and burned my email archives to two DVD's, so I should be able to handle any disaster. In the meantime I'm turning off my POP accounts and using Gmail for daily communication of new messages. Wish me luck, and please post questions, suggestions, or links to resources in the comments so that we create a resource for people!