The problem with your email Inbox
If you're like most people, you probably use your Inbox as a combination "to-do" list and archive. You tell yourself, "I need to keep this message, so I'll just leave it here and deal with it later." Unfortunately, with new messages arriving every day, any single important message will move farther and farther back in the list. Over time, your Inbox can grow to hundreds or thousands of messages.

Why bother?
This is not about capacity. Most people think having a lot of email messages somehow slows down or overburdens their computer. While that's technically possible, most of the time it makes no difference at all to the computer. Yes, including yours.

The real issue here is clutter. Having too much email can mean that:

• You can't find the important messages because there are so many unimportant ones.
• Related messages aren't together because they arrived on different dates, perhaps from different people or email addresses.
• Related messages also aren't together because some are in your Inbox and others are in your Sent folder.

So, if you're finally fed up with the enormous number of messages that have been piling up, if you're really serious about cleaning them out and organizing them, then read on for my advice on how to tackle this.

Overview
Here's a summary of my recommended techniques:

• Sort your Inbox by From (Sender) or Subject, look for themes, create folders, move messages into those folders. Be specific, avoid "Miscellaneous." Create subfolders (or use specific adjectives) as appropriate.
• Delete unwanted or obsolete messages as you go.
• For important information that no longer makes sense to keep in email, transfer it to a regular document, then delete the email.
• Unsubscribe from legitimate vendors.
• Repeat for your Sent folder!
• If you mix incoming and sent messages in the same folder, turn on both "From" and "To" columns.
• Delete all messages older than a given date.
• Use Rules or Filters to route incoming messages directly into folders.
• If you use the www.gmail.com web site you won't be able to sort, so this will take more work.

How to get started
Like any cleaning and organizing project, keep your expectations reasonable. You didn't receive all this email in a day, you're not going to conquer it that quickly. For each of the techniques below, set aside some uninterrupted time. As little as 10-15 minutes can get you off to a decent start.

Technique #1, Part A: Sort by "From" or "Subject" instead of "Date" (Can't do this on www.gmail.com)
Whether you use a "regular" email program (like Outlook, Outlook Express, or Apple Mail) or you use webmail (accessing your email on a web site like www.yahoo.com, www.aol.com, or www.comcast.net), when you work with your email you will see your messages in a list, with information about each message arranged in columns, including From (Sender), Subject, Date, Attachments (a "paper clip" icon), and more.

Most people keep their Inbox sorted by Date. Some prefer to see their newest messages first, some prefer newest last. Either way, sorting by Date is very inefficient for cleaning out your email. Reading down a list of messages in date order will have you mentally jumping around among all different topics, e.g., lunch with Uncle Joe vs. Staples orders vs. movie tickets. If there are 20 separate messages from Uncle Joe scattered over 20 separate dates in your Inbox, you'll waste time and effort thinking about (and moving or deleting) those messages 20 separate times.

To efficiently review a long list of messages, sort them by "From" instead. This will group together messages from each sender, so you can see all of Uncle Joe's messages in a group, putting them in context and enabling you to decide whether to keep or delete them much more quickly and efficiently. And if you're keeping them, you can more effectively and consistently see themes among those messages, and move them as a group.

How do you sort? In most email systems, you click on the title at the top of a column to sort the messages by that column. To sort by the "From" column, click once on the word "From" at the top of that column. This will sort the list of messages alphabetically by sender from A to Z. (If instead the list sorts by sender from Z to A, click once more on the column title to reverse the sort order to be A to Z.) In a similar way, if you'd prefer to sort by Subject, click once on the word "Subject" at the top of that column.

When you're done, put the list back in Date order by clicking once on the word "Date" (or "Received" or "Sent") at the top of that column. (If the resulting Date order is the reverse of what you prefer, click once more on the word "Date.")

Technique #1, Part B: Look for themes, create Folders, move messages, delete unwanted messages
Once you've sorted your Inbox by "From," scroll through it and look for themes or categories.

• For a personal email account, common themes include Family, Investing, Volunteering, Taxes, Bills to Pay, Receipts, Reunions, and Vacation.
• For a business, common themes include Urgent Projects, Clients, Prospects, Marketing, Orders, Receipts, and Newsletters.
• Once you see some themes, create email Folders (sometimes called Mailboxes) for your themes. Be specific. Try to avoid "Miscellaneous" for now.
• Then, select one or more messages and move them from your Inbox into the appropriate Folder. In some systems you can drag-and-drop selected messages into a Folder, in others you click a "Move" function and then pick the Folder from a list.
• You may find so many messages to put into a given folder that it soon makes sense to separate it into more than one folder. If your email system supports subfolders (creating a folder inside another folder), that's one option, e.g., creating Smith and Jones subfolders inside your Clients folder. If that's not an option (or if it doesn't appeal to you), I suggest adding adjectives to the end of your folder names, e.g., Clients vs. Clients-Smith vs. Clients-Jones, Orders vs. Orders-Software vs. Orders-Hardware, etc.
• Your folders will probably be listed in alphabetical order (which is why I prefer "Clients-Smith" over "Smith Client."). You can use clever prefixing to force a folder higher in the list, e.g., "aaaClients" or "111Hot Projects."
• Your list of folders won't be perfect, it will evolve over time.
• You will also see obsolete messages that can be deleted now, like lunch with Uncle Joe back in January, Staples orders from two years ago, expired coupons from last Christmas, etc.
• You may also see messages with information worth keeping but that no longer make sense to keep in your email system, like finished projects or interesting tidbits. In these cases, I recommend transferring the information to a regular word processing document or text file (using Copy and Paste or Save As), placing it into an appropriate folder on your hard drive, and then deleting the email.
• Periodically "empty" your Deleted messages (or "Trash") folder if appropriate.
• Sort your Inbox by Date when you're done.

Urgent email needs special handling
Since you'll be moving messages out of your Inbox, you won't see them at a glance anymore, so come up with a plan for how to handle important or urgent messages. Will you put them in a "Hot" (or "aaaHot") folder? Leave them in your Inbox? Move the information into a "to-do" document (or print them out) and then delete from your email? What's best for you?

Technique #2: Unsubscribe from legitimate vendors
You'll probably also find some messages you regularly receive from vendors because you (explicitly or implicitly) signed up for their newsletters, offers, or other email notices. If these are from legitimate companies with whom you have a relationship but you no longer want to receive them, don't report them as spam (not fair to the vendor)! Don't just delete them (doesn't stop them)! Instead, open them, scroll to the bottom, click on their "unsubscribe" or "opt-out" links, then delete them from your email. A few minutes spent unsubscribing can eliminate hundreds of unwanted messages in the future.

Technique #3: Now tackle your Sent folder!
The other place where lots of email messages accumulate is your Sent folder. You may even find that you send much more email than you receive! However, similar techniques apply:

• Sort by From or Subject (can't do this on www.gmail.com).
• Look for themes, create corresponding folders, be specific.
• Select and move messages from the Sent folder to those more-specific folders.
• If you mix together messages from your Inbox and your Sent folder, the sensible approach is to turn on both the "From" and "To" columns to minimize your confusion about which messages are which. However you can't do this on many webmail sites, including www.gmail.com, www.comcast.net, www.rcn.com, www.verizon.net, www.aol.com, etc., so investigate this first before you spend a lot of time moving messages out of your Sent folder. If you can't turn on the "To" column, all your Sent messages will only show "From (your email address)" in your folders.
• Delete messages you no longer need.
• Save messages worth keeping (but no longer need to be in your email system) as regular documents, then delete from email.
• Sort your Sent folder by Date when you're done.

Technique #4: Delete all messages older than...
Another simple cleanout method is to delete all messages in your Inbox or Sent folders older than a certain date, say a year ago or the start of this year. I'm not fond of this method because you may lose some important messages by arbitrarily deleting based on date. However, it is quick and expedient and it may make sense in some cases.

Technique #5: Use Rules or Filters to route incoming messages directly into folders
If you get regular emails from certain senders that you find yourself always moving into the same corresponding folders (e.g., newsletters, offers and discounts, your chatty Uncle Joe), most email systems will let you create Rules or Filters to "automatically" move those messages into those folders as soon as they arrive, so they won't accumulate in your Inbox. Doing this will save you the effort of moving those messages manually, but weigh that against the possibility that you won't notice new messages arriving in those folders, plus the possibility that some of the time those mechanical Rules may not do what you intended, especially if something changes about those incoming messages. ("How did that email from Al Gore end up in my Weird Al Yankovic folder?")

Stick with it!
These techniques may sound quick and easy, but they take time and thought. Depending on how much email you've accumulated, your initial cleanout may take days, even weeks.

Going forward, you would maintain this organizational system by taking the time to periodically review your Inbox and Sent folders, and then moving messages into folders (or deleting them) as appropriate.

The www.gmail.com web site only sorts by Date!
The Gmail web site is one of the most innovative, clever webmail systems I've ever seen. However, while other webmail systems let you sort your messages by Date, From, Subject, Size, and other columns, despite years of user requests, as of this writing Gmail only sorts your messages by Date (newest first). This severely limits your ability to review your messages efficiently. However, there are two alternate techniques you can use.

Gmail cleanout technique #1: Use IMAP and email software to sort
This method involves accessing your Gmail account without using the web site:

• You can use a "regular" email program (including Outlook Express, Thunderbird, Windows Mail or Outlook on Windows, Apple Mail or Thunderbird on Macintosh) and temporarily set up access to your Gmail account using the IMAP protocol.
• Then you would follow my method for cleaning out and organizing your email, using your email program to sort, examine, move, and delete your messages.
• However, in order to create or rename your Gmail Labels (which act like folders, except that any given message can have multiple Labels), you will have to quit your email program, go back to the Gmail website, create or change your Labels, close gmail.com, then reopen your email program.

Gmail cleanout technique #2: Use search as a poor substitute for sort
If the IMAP technique above is not practical for you, try this:

• Look over your Inbox or Sent Mail, choose someone whose email you want to clean out.
• Search your messages for their name or email address (or key words from the Subject).
• Using the search results, create Labels as appropriate, then select and move messages into those Labels (or archive or delete those messages).
• Remember that by default, Search does not include your All Mail (archive), Trash, or Spam folders, but Gmail's advanced search lets you do that and more.

This somewhat-laborious technique will help you clean out messages to or from specific people, so I recommend starting with people with whom you email more than just a little.

Conclusions

• Cleaning out and organizing years of accumulated email isn't easy, but if you're ready to tackle it, there are reasonable ways to accomplish it.
• If you use the www.gmail.com web site, your cleanout will take more work, but you can still make it happen.
• Once you've got a reasonable system in place, maintaining it won't be as much work going forward.

Where to go from here

• Look at your current email system and learn how to: sort messages, create folders, move messages into folders, turn on additional columns, and "empty" your email trash.
• See "After you delete something, is it really gone?" (http://www.kadansky.com/files/newsletters/2007_09_19.html)
• See "How can I stop email spam?" (http://www.kadansky.com/files/newsletters/2011/2011_03_30.html)
• If you use Gmail, tell them you want to be able to Sort your email, maybe they'll add it someday: http://support.google.com/mail/bin/static.py?hl=en&page=suggestions.cs 

How to contact me:
email: martin@kadansky.com
phone: (617) 484-6657
web: http://www.kadansky.com

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I love helping people learn how to use their computers better! Like a "computer driving instructor," I work 1-on-1 with small business owners and individuals to help them find a more productive and successful relationship with their computers and other high-tech gadgets.