You know the email system wasn’t designed for what you’re doing, don’t you? It’s a nice system for a few messages each day. But you can’t control yourself! Hundreds of messages every day, huge file attachments, a complete inability to hit the “Delete” key – look, it’s time for a little refresher course.


If you want to send files to someone that are bigger than 10Mb total, don’t use email. You’ll clog up your Internet connection and slow down your computer and the files won’t arrive and I won’t help you. Maybe your mail program will crash and burn, maybe your company mail server or ISP or mail host blocks bigger file attachments, maybe there are similar blocks at the recipient’s end. Just don’t do it! And especially don’t tell me anecdotes about how your friend Charlie sends 5Gb movies by email all the time and how come I can’t make it work. I’ll get irritable and put ugly wallpaper on your desktop.

Look, there’s no shortage of ways to send files to people.

It doesn’t matter which one you choose. There’s a learning curve for each one. But if you’re trying to mail 50Mb of photos to your mom, or trying to send huge PDFs to opposing counsel, or trying to send pirated movies to your friends – give up on email and figure something out!


We’re allowed to have big mailboxes now. The online services now allow virtually unlimited mailboxes. Outlook 2007 can handle bigger mailboxes than Outlook 2003. That’s not an excuse to let things pile up!

You can check the size of your Outlook mailbox by clicking on Tools / Mailbox Cleanup / View Mailbox Size.  At 2Gb, Outlook 2003 starts to fall apart. At 3Gb, all operations in all versions of Outlook start to drag. At 4Gb and above, you’re still technically within the limits of what Outlook 2007 can handle but problems will start to show up, I just guarantee it. The program will run slowly, backups get to be a headache, it’s much more difficult and time-consuming to recover from a problem, it takes forever to rebuild the mailbox on a new computer – really, it’s just not worth it.

I know, it’s all terribly valuable work-related stuff. Except it’s not. For goodness’ sake, will you delete the stupid movies and the funny pictures after they’ve gotten the 3 seconds of attention they deserve? (And by the way, don’t send movies or forward them. If they’re truly irresistible, find them on YouTube and send a link to them.) Delete the spam and advertisements. Delete the messages that say, “OK” and “See you Tuesday,” and “The meeting has been cancelled.”

An inbox with 20,000 messages in it is not much more useful than an inbox with 0 messages in it.

If you’ve been sending large email attachments, go into the Sent Items folder every so often and sort the messages by size. (In Outlook, click at the top of the message list where it says “Arranged by:”.) Get rid of all the messages with attachments that are 5Mb or larger. You almost certainly have those files somewhere else. Save the attachments if you need to but get them out of your mailbox.

Oh, and one more thing – the Deleted Items folder is a wastebasket. It’s not a filing cabinet. It will be emptied. You should empty it occasionally. Do not use Deleted Items as a place to store things you want to keep. It’s the trash and I will not feel guilty if I empty it while I’m working on your computer. I see Deleted Items folders with thousands of messages in them and it makes me wonder what those people’s houses are like.


Many of you don’t need a scolding about these things. This is for the people who never learned good manners.

  • Don’t hit “Reply to All” unless every person on the list needs to see your contribution. It’s lazy and inconsiderate.
  • If you’re sending a message to a group of people who don’t know each other, don’t put all their email addresses on the “TO:” line. Address the message to yourself and put their addresses on the “BCC:” line. Some people want their email addresses to be private. (In a new message in Outlook 2007, click on Options to find the “Show BCC:” button. In a new message in Outlook 2003, click on View / BCC: Field.)
  • Don’t send messages to more than 25 people at a time. It will be trapped as spam and most of them won’t receive it.

I know people who are so overloaded with work e-mail that it has become the least effective way to communicate. Too many business mailboxes are effectively useless because the volume so far exceeds what people can absorb. There are more and more nervous jokes about declaring email bankruptcy and starting over with an empty inbox, or giving up email altogether. Start managing your own mailbox more carefully, and be considerate of other people’s mailboxes, ok?

(Thanks to friend and colleague Brian Dent, who suggested this post after struggling with oversized mailboxes until he felt like his head would explode.)

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