Organizing Sent Email

I’m having a really tough time finding a useful tool or system to easily organize sent email. Every “organizing your email” tutorial out there seems to focus on the deluge of inbound email and how to handle, process, and organize it.

An overlooked problem, it seems, is organizing your sent email. Typically, most of us, when we need to find an email we sent previously, just search through our email Sent folder. Thunderbird and Outlook are more than capable of doing this.

What if I just want to easily browse through the last 20 emails I sent someone?

What if I just want to find the very first email I sent someone?

I have over 3,000 sent emails - and I’ve actually missing a two-year chunk of emails and have gone through and deleted a lot of emails I sent that I no longer need to keep. So these are 3,000 emails I want to keep and possibly refer to someday. Doubtful that I will, but I like to live under the illusion that, at the least, my children could read through them someday to get a sense of what kind of person I was, became, or was growing toward. Sort of like the way we go back and read the letters and writings of great men like Theodore Roosevelt and C.S. Lewis - except that I’m not great, my emails are rambling and monotonous, and I doubt there is even six words of wisdom among all of them. If they were written letters, I’d have to throw them out just to declutter. But in an age where Western Digital is pushing 1.5 Terabyte drives as “portable storage” (although it’s really a NAS), it’s hard to justify deleting them. You never know, I suppose. Keep everything. It’s all about preserving your digital life. That’s what society is pushing us toward, right? Maybe that’s content for a different entry some other time.

Of course, like most people, I keep my Sent email folder sorted by recipient. This still poses problems, as many people have different email addressees - either currently (work, home, etc) or different ones they’ve used over the years. Thunderbird, my preferred email client, puts some recipient names in quotes, some not. This naturally means that, at the least, I have to look in two sections - the “with quotes” section and the no quotes section. Even for a person with only 1 email address. Have two? Then that’s four places to look… and so on.

In thinking about this, I think I’ve seen why creators of these tools have avoided tackling this problem. It gets messy.

Think about this: Every email you receive is addressed to you. Maybe not only you, but it got to your email box somehow. It was sent to one of your email addresses. I have over 30 different email addresses - some for obscure websites, some business, some personal, some I just watch for clients. But no matter which email address someone sent the email to, it winds up in my main Inbox. They could have copied 50 other recipients, but I don’t need to worry or care about that - at least in terms of sorting it. Once I’ve replied to it or handled it, the copy of the email goes into the folder in which I store received items for that person or business. Easy. Some folks even pre-sort their email by Sender into folders and then later process or handle action items from within those folders. This is probably better for many because it saves you from dragging or moving each processed email. However, for me, I generally receive a wide variety of emails each week, on a wide variety of subjects, from a wide variety of people. So I prefer to see them all in once place because I tend to handle them using the FIFO method (first in, first out). In other words, I would spend a lot of time clicking and browsing through multiple folders to process my inbound email.

I digress.

The point is this: organizing inbound email is easy.

Now think about your outbound email. Let’s say I send an email to a typical group of friends: Matt, Jay, Graham, and Deke. I send it TO: Matt, but CC: Jay, Graham, and Deke. The next day, only Deke replies with a question or comment. So, I reply only TO: Deke. Two weeks later, Graham sends a long response to my original email - from his work address - and copies two other people (whom I don’t know - let’s call them Jim and Bob), but for some reason didn’t copy Deke, probably because he was at work and didn’t have the original email at hand. I hit “Reply To All” to defend my original assertion, not realizing that two new people are on the list and that Deke has been removed.

Now, here’s what I would like: I would like each person to automatically have a folder with a copy of the email I have sent to them. Thus, for the above example, my very first email should not only be in my general Sent folder, but also copies placed in respective folders for Matt, Graham, Jay, and Deke. Each of those folders, when viewed, should have look like a regular list of emails, except it should have a column that indicates the person’s Recipient Status on each email I’ve sent them. Thus, it should show TO, CC, or BCC, next to the subject line of each email. Therefore, I could easily sort Matt’s folder by Recipient Status so that his emails I’ve sent TO him would appear grouped above those emails where I’ve only CC’d him or BCC’d him.

Next, a copy of my singular reply to Deke should be in his folder.

Finally, a copy of my “Reply To All” in response to Graham should be in Graham’s folder, even though he sent it from work, and appropriate copies in Jay and Matt’s folders. None would go in Deke’s, of course, since he didn’t receive that “Reply To All” email. The CC’s to Bob and Jim should just be copies as individual emails in an “Unknown” folder. Thus, I could easily pore through my Unknown folder by Recipient and/or Recipient Status.

Now, here’s what I’d really like as well: If at any time in the future I add Bob or Jim to my email address book (because they become such good friends for defending my position to Graham), a folder is automatically created that also automatically moves the emails I previously sent to them into that folder.

Now, none of this is particularly high-tech. It just needs to be scripted and written as a plug-in or extension for Thunderbird, Outlook, and other email clients.

What puzzles me is that I seem to be able to find no other interest or indication that anyone else is even thinking about this. Am I the only one?

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I have an interest in this as well. You are not alone! Another concern - how do I store and maintain blog comments? My email files are extensive but I don’t know how to save this message I’m sending to you right now. It’s a vicious circle.

Matt: Excellent point. However, at least on the blogs, I may have a solution. Or more accurately, other companies have some free solutions. See some of Lifehacker’s reviews of some of the commenting systems out there. I haven’t used one yet, although it is getting to the point that I probably should.

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