Google’s rolled out a new option to turn off “conversation view” in Gmail. I’m dumbfounded that I’ve seen two different people now question why anyone would want to do this. OK, I’ll bite.

But Conversation View Is So Great!

Let’s do the critics first. Here’s Google’s Matt Cutts about the crazy people who don’t want conversations:

But ability 2 turn off Gmail conversation view is like ability 2 hit head against wall. Why would you do it? #notefficient

Here’s Christopher Dawson over at ZDNet:

Google announced today that it would allow users to disable what, in my opinion, is the single best feature of Gmail and one of the most touted new features of Outlook 2010…

This sounds to me, however, like it is really about attracting enterprise-types who have become accustomed to Outlook and Exchange, where a conversation view only became available with the launch of Outlook 2010. Conversation view, for non-Gmail users, is a real switch

Heck, even Google itself, in announcing the change, makes me feel like I’m an insane pariah for wanting it:

It turns out not everyone feels the same way. And just as an outspoken minority has banded together in unison to declare their distaste of one of nature’s most delicious herbs, some of you have been very vocal about your dislike of conversation threading.

Let Me Count The Reasons To Opt-Out

So why am I so crazy as to want this off? For one, because I want to, OK?

I don’t care if you love Gmail’s conversation view and think it’s the best thing since sliced bread. Not everyone does. So having a choice to disable it is nice. Choices are good. I’m glad it’s here now, and I’d prefer that you didn’t question my decision to use it.

Conversations Aren’t Perfect

Other reasons. You know what? Gmail’s not perfect. Sometimes it puts things into a conversation that aren’t actually part of it. Sometimes it misses other things On the odd occasion, I’ve got some spam or off-topic message that I don’t want in the middle of everything else.

Here’s an example right now, in my inbox:

That’s the latest comment on a blog post that I have about sneaked versus snuck. That post has over 100 comments. I’ve got over 100 notifications of each comment. However, Gmail thinks for whatever reason that only 4 of them today are part of the “conversation.”

OK, that makes sense if you’re talking the most recent conversation. But I thought Gmail was all about keeping track of conversations over time? Where’s the rest?

It’s also frigging annoying. I’m one of those people who likes to deal with an email individually and have it done. So in my inbox, I have what feels to me four different messages coming back, when I really only want to deal with the latest one.

Deleting Is Easier

I also get a lot of crap email, stuff I want to delete. But I never feel safe using the delete feature from the inbox because it will wipe out a bunch of messages that may have been wrapped into a conversation. Instead, I have to click into the conversation, then delete what I might want to kill.

I know, I know. Unlimited storage! Never need to delete. Yeah, that’s not really true, as my Pondering “Email Conservation” After Hitting Gmail’s Storage Limit post gets into. Hey, I solved my storage issues for $50 per year, and it’s well spent. With 60% of my quota still free, I don’t need to delete. But if I want to, I want to, OK? And a non-conversation view makes it easier.

Focusing Can Be Easier

Another reason is sometimes, I have long emails that in turn are shoved into long conversation views. This is another case when I might more easily want to deal with just a single email, in a non-conversation view.

How About An Easier Toggle?

So thanks, Gmail, for allowing me the option. Want to make it better? Allow me to easily toggle it on or off, like Outlook 2010 does. This having to dig into settings and switch it on and off as a global option is crazy. It should be a view option from my inbox or “all mail” summary. Hey, showing snippets ought to be, too.

For related views, also see here on Techmeme.

Periodically, I shrink my Outlook PST file. For one reason, it’s easier to back it up manually from time to time when it’s smaller. For another, I guess I feel things just run better when it’s small and tidy.

Today, I shrank my file from over 1.1 GB to 80MB, a pretty drastic reduction. Being excited about such things, I tweeted it, which resulted in a bunch of people asking how. So here are my how make your Outlook PST files smaller tips!

1) Delete sent mail. But wait, you want to save that sent mail? Two options:

1A) Archive via Gmail or another hosted email system, so that you have a permanent online archive of anything you’ve emailed. See my Moving From SpamCop To Gmail & Loving POP Download With Archiving for more about this.

1B) Make additional PST files and move mail into these. For example, I have two PST files active. One is my main file called Danny, which is where my current mail resides. The other is called Archive, where I have a 2008 folder within it:

Over the course of 2009, I’ve periodically taken email that I want to have a local backup of and copied from the “Sent Items” folder in my Danny PST file over to the 2008 Mail folder within the Archive PST file.

Down the line, I’ll make another PST file called 2008. My 2008 Mail folder will get moved into into that. I’ll then detach the 2008 PST file and save in case I ever need it. I have a series of these for each year. Meanwhile, my Archive PST file remains as an active holding place for mail. It’ll gain a new 2009 Mail folder.

2) Empty Deleted Items Folder. Yes, even though you deleted that email, it’s still sitting around in your Deleted Items folder making your PST file bigger until you really delete it. Do that by right clicking on the folder, then selecting the Empty option:

I usually only keep about 1 month’s worth of deleted mail at a time, just in case I need to go back and find something locally (such as when I’m on a airplane).

3) Compress! Right click on your PST file (not the folders within it, but the main file itself as listed in the navigation pane. Then select Properties:

A new window will appear, your Outlook Today window. Select Advanced, which makes your Personal Folders window appear:

Choose Compact Now. Sit back and get something to drink. In about 10 minutes or so, depending on the size of your PST file, it will be dramatically reduced in size.

Why go through all this hassle. Why not just use Gmail directly? Short story is that Outlook’s a fantastic email management program. Long story is for a future post, where I detail why I like using both Outlook and Gmail together.

Back in April, I became one of the rare people to run out of Gmail space. Due to a glitch with Google, I was also unable to purchase more space for several weeks. As a result, I became hyperaware of how much email space gets eaten up each day routinely. Newsletters, product offers, Facebook and Twitter notifications, that person you don’t know who emails you a 7MB file. It adds up. And Gmail’s supposedly “endless” space might not be keeping pace.

None of this is a crisis for the vast majority of people out there. You rarely hear people talking about running out of Gmail space. Those like myself who rely on email so much for business work as to run out of space probably wouldn’t think twice about buying more. I certainly would have done so, if I could have, at the time.

Still, I feel like all this crud going into our email boxes is wasteful. That in the era of cheap disk space and fast bandwidth, we don’t think twice about what we send, what we receive. But all that stuff is consuming disk space, server space, energy. Is there a case for email conservation?

Maybe. People far more knowledgeable than I might perhaps weigh in, and I’d love to hear from them. To kick things off, I’ll serve as a case study. Here’s how I’ve grappled with trying to stay under my Gmail quota over the past few weeks.

Out Of Space!

It was on April 30 of this year that my Gmail account started sending out this message to people who emailed me:

The email account that you tried to reach is over quota.

It surprised me. In the back of my mind, I remembered Google saying something like you’d never run out of space in Gmail. The percentage of my quota used, shown at the bottom of any page in Gmail, had been stuck on 97% for as long as I could remember. I kind of thought that was part of the gimmick — that somehow, Google kept upping the quota in each individual account to always keep it above water. Not so. Despite the promises on the Gmail home page, I needed to delete mail in order to have space for more.

The Gmail Infinity Space Promise

When Gmail launched on April 1, 2004 (yes, it was on an April Fool’s Day), the suggestions of unlimited storage were there at the beginning. From the press release:

Unlike other free webmail services, Gmail is built on the idea that users should never have to file or delete a message, or struggle to find an email they’ve sent or received….

Storage: Google believes people should be able to hold onto their mail forever. That’s why Gmail comes with 1,000 megabytes (1 gigabyte) of free storage – more than 100 times what most other free webmail services offer.

A year later, Google rolled out the “Infinity+1″ storage promise, giving everyone an extra 1GB of space (taking the total to 2GB at the time) and promising to keep increasing this.

By October 2007, Google increased the amount of free storage space it was providing, writing on the Gmail blog:

In April 2005, we started increasing Gmail storage as part of our “Infinity+1″ storage plan. At that time, we realized we’d never reach infinity, but we promised to keep giving Gmail users more space as we were able. That said, a few of you are using Gmail so much that you’re running out of space, so to make good on our promise, today we’re announcing we are speeding up our counter and giving out more free storage.

And, just in case you are like my friend Miriam, whose sister sends minute to minute photo updates of her kids in RAW format, then we still have a paid storage program where you can get your fix, and we’re giving you more space than before for the same price.

By the way, businesses, schools and organizations using Google Apps to get Gmail on their own custom addresses (like Google does for our @google.com accounts) will get a storage boost in the coming days, too. Standard and Education Edition storage (now at 2GB) will begin matching Gmail’s counter, and Premier Edition users get a whopping 25 GB (up from 10 GB).

As you can see, at that point, Google had also offered paid storage options. I thought that was great, because some people might need more than even the huge amount Google was providing for free. But “Infinity+1″ implies that buying space shouldn’t be needed. And if you go to the Gmail home page today, you’ll see this message:

Lots of space
Over 7369.392583 megabytes (and counting) of free storage so you’ll never need to delete another message.

The number is constantly counting up (more on this in a bit). The claim is pretty straight-forward. You’ll never need to delete anything. And yet, that’s exactly what I needed to do. Certainly some others have to do the same. So that claim ought to go.

How Much Do They Give You? Not Much!

It’s also easy to assume, with that number constantly ticking up on the Gmail home page, that tons of extra space is constantly being allocated to your account. In reality, it’s about 1MB every three days (Google Operating System said 0.33MB per day back in 2007, and that still seems to be the case). Those in Gmail are constantly being increased. Those using Gmail through Google Apps get a boost to match Gmail whenever there’s a 10MB gap between the two services, it seems. Here’s a chart illustrating this, the maximum space offered by both versions of Gmail over the past few weeks:

For some people, that may seem like plenty. But as I was forced to stay under my quota, I discovered the daily increase in space wasn’t that much. Moreover, while I may have hit my quota this year because of how long I’ve had a Gmail account, it’s possible that if space isn’t increased more than now, many more might hit theirs in years to come.

The Fight To Stay Tight

Let me share a bit more about my situation, then I’ll go more into my observation about how much email junk may be “wasting” space for everyone.

I’m fairly unique in having had a Gmail account since the day it launched. I used that account as a backup to my regular email account, sending a copy of anything I received to it. Last year, I merged all that mail into a Gmail account that runs using my own domain name as part of the Google Apps program. When I was done, I’d pretty much stuffed my main Gmail / Google Apps account full. That’s the account that ran out of space this year.

My immediate thought was to upgrade and add more storage. However, I couldn’t. When I tried, I got a “We are unable to process your request” message from Google. This continued for about two or three weeks, a bug for a small number of users, to my understanding, that Google eventually solved.

I had no choice to conserve space. My first reaction was to sort my mail by size, so that I could find any email with big PowerPoint files or other large attachments. However, Gmail has no sort by size feature. It’s an oversight that’s long due to end. Yes, the Mail Goggles feature to keep you from drunk emailing is funny. But a sort by size feature has been standard in my Outlook email program for as long as I can remember and Pegasus Mail before that. Gmail lacks this? Want to lobby for it? Join this thread at Google Groups.

How about searching for files with attachments, specifically anything with PPT (PowerPoint) files. Sure, I did that. Unfortunately, it still didn’t sort them by size. It was a painful, time consuming process to try and free space up this way.

Another reaction was to search for any email not in English. Unless you want to converse with me in really, really bad German, English is all I speak. Virtually anything in my inbox not in English is spam that’s gotten through the filters in some way. I don’t need it. I blogged about wanting a feature like this back in 2006. It still doesn’t exist.

Among other things, I searched for any Twitter notifications that I’d received. I had thousands of these. Wiping these out saved much more space than I was expecting. That got me thinking about all the other “useless” mail I’ve got stored from over the years, things I really don’t need to save. How much do they consume?

The Useless Mail

While I can pay for more space and probably will soon, I’ve kept to a free account over the past few weeks so that I could study the situation more. Every few days, I’ve looked at my mail to understand how much has come in, what I could free up and figure if I’m staying ahead of the space I’ve been given or falling behind.

For example, let’s take today. When I logged in, my account had used 7,240 MB of space used, out of a total 7,365 MB allowed — 98% of it. That means since I last went in, I’d picked up 74MB in new email.

74MB! In that same period, Gmail had given me 4MB of new space — just 5% of what I’d gained. So much for infinity plus one.

OK, I’m just unusual, right? Maybe, but maybe not so much. To clear space, here’s what I did:

• Killed about 300 Twitter & FriendFeed notifications (message about people following me or taking my feed). That freed 4MB of space.
• Cleared 2,250 spam messages, freeing up 45MB of space.
• Deleted 100 email reports from Google Analytics for five different web sites I watch going back to mid-July, freeing 8MB of space.

Doing these things still left me using 20MB of space more than I was on Sept. 9, a net loss versus the 4MB of space Google had given me in that same time period.

Every few days, I’ve gone through this type of routine, sometimes aggressively. Here are a few more stats to illustrate some of the “dumb” or “useless” email, as I call it, that has taken up space:

• Facebook/Twitter/FriendFeed/LinkedIn Notifications: Virtually none of these are useful a few days after they’re received. Searching for common words would often find hundred of these messages over the years the first time I’d look. Even after clearing them out, I’d find plenty more new ones had been received. Very roughly, 100 of these can equal about 1MB of space.
• WordPress Backups: I watch over two blogs on WordPress and each week get emailed a backup. Handy! But two weeks worth of these for me equaled 7MB of space. Once a new one comes in, I really don’t need the old one — much less one from weeks ago. They just eat space, but because I have (or thought I had) so much space, I didn’t think much about receiving them.
• Google Analytics Reports: Getting regular reports by email are awesome, but as noted above, they take up space. Since I have access to Google Analytics itself, I really don’t need these in the long term.
• Business Newsletters: Killing 150 “Inside Apple” newsletters since 2005 saved 4MB of space. Wiping out 200 Amazon Store newsletters saved 10MB of space. Build-A-Bear has sent me 110 offer emails since 2007. Major League Baseball has sent me 80 in the same period. I had 100 notifications that my credit card statement was ready from my credit card company going back to 2006. 30 message from Tickets Now back to March of this year. I could go on, and some of these counts are low (because the initial count Gmail returns for a search often rises as you go to the second page). The bottom line is virtually none of this email is useful to me in the long-term, yet it takes up more space than you’d imagine.
• Inbox Busters: A PR person sent me a pitch with a 1MB attachment, worth 3 days of “new” space from Gmail. No warning, and not relevant to what I cover. The same person sent me a 0.5MB logo attachment a few weeks before. Someone sent me a bug report with a 7MB screenshot attached. 7MB! Someone I don’t know, who somehow put me on some email list I’m not interested in, which sent me a 4.5MB image. Someone pitching to speak at a conference sent me a 7MB presentation with their email. Wipe out all “dumb” email you want — things like these dwarf those savings.

What To Do?

Like I said, this isn’t a crisis for most people. I also know I’m an usual case. But I think things will get worse for more people over time, largely because we just don’t think much about what we email.

In the bad old days of dial-up, you’d never send someone a 1MB file out of the blue. Just shoving it down the pipes would take forever. Now we don’t think twice. We certainly don’t think that this file is eating up 3 days worth of Gmail quota.

Email messages themselves have increased in size, as HTML email has become more common. All those business emails can add up.

Notifications that are so handy can get out of control. They’re like hundreds of little cuts to your quota. They serve no use in the long term, but they sure consume space collectively.

I know I can just pay to get more email on Google. Yahoo says it has unlimited email, announced in 2007, so I could move over there, if I really wanted to be cheap.

But it’s not about being cheap. It’s just more amazement, I guess, at how when you open things up with seemingly no limits, suddenly conservation gets lost. Maybe there’s no reason for email conservation. Perhaps storage will keep getting cheaper, and none of this will matter especially versus the time it takes to conserve. But it still nags at me. I’m just that way, I guess.

Gmail Suggestions

Meanwhile for Google, some suggestions:

Don’t say you’ll never need to delete on the Gmail home page, since that’s clearly not true. Modify it, advertise it accurately.

Sort By Size. It’s overdue. Offer it now.

Filter By Language. Why are we still waiting for this?

Consider an option that might understand all those “dumb” emails that we get, those special offers from stores, those Twitter notifications, pingback notifications and so on. Maybe sense when we have a lot of these from one particular source and ask us if we want to delete them.

Related, if we unsubscribe using your new auto-unsubscribe feature, perhaps search for related emails when we do this and ask if we want them deleted. And let us unsubscribe without having to use the spam button to do this. That makes no sense at all.

Finally, don’t get me wrong. I love Gmail. It’s a great service, and I’m very happy with it. It’s just through an accident of being unable to upgrade, I got a close-up view of how much storage all those emails I get consume.

Twitter’s all buzzing with the news that Gmail and Google-hosted mail through Google Apps has gone down. The Google Apps status page also confirms it. The thing is, it’s not down if you use an email client that pulls information in via POP or IMAP protocols. I’m happily still getting my mail — and you can too. Tips below.

Personally, I use Outlook 2007 to download my email from a Google Apps account. This allows me to have full, dependable offline access. It allows me to periodically backup and archive my mail, protection against the rare case where Google might somehow delete my mail on their servers. It allows me to have easy access to search mail back for half a decade. To understand more, I recommend these posts I’ve written:

• Moving From SpamCop To Gmail & Loving POP Download With Archiving
• 8 Tips For Dealing With Email Overload

At the moment, Gmail has gone down for those trying to reach it via the web. But anyone trying to get their email through a client — a software program that automatically talks to the Gmail servers — seems to be fine. I’ve had people on Twitter report getting access through their iPhones, BlackBerries, instant messaging and even Google’s iGoogle personalized home page. So you can, too!

Gmail provides full instructions on how to configure a number of email clients here. Some of these programs are completely free to use. You can also try Yahoo’s Zimbra Desktop, which can handle multiple email accounts. Even though that’s not listed with explicit instructions from Google, use the “Other” option for advice on how to configure it. The same is true for any email client that’s not listed. Pegasus Mail, anyone?

Downloading a client too much work? I liked Josh Finkelstein’s suggestion that if you have an iGoogle page, you can get your mail that way. You’ll find the Gmail gadget to that here. With one click, I had access to my Gmail account. However, this won’t give access to those who use Gmail through Google Apps (I have both, a Gmail account from before Google Apps accounts were offered. Merging Gmail & Google Apps Mail Accounts explains this more).

Remember, some free web-based email systems like Yahoo’s can import from other web programs (though you might have to pay for this). That’s also an option. Still, it’s why I ideally would like Google to offer its own lightweight email client, as I covered in my Google Needs To Learn Browser Isn’t Best post. Sometimes the web goes down, but the web is only part of the internet. A client provides a nice backup.

Got your own tips? Please add them below!

Postscript: Google’s just blogged about the issue — and look there, advice that POP/IMAP access works just fine!

We know many of you are having trouble accessing Gmail right now — we are too, and we definitely feel your pain. We don’t usually post about minor issues here (the Apps status dashboard and the Gmail Help Center are usually where this kind of information goes). Because this is impacting so many of you, we wanted to let you know we’re currently looking into the issue and hope to have more info to share here shortly. If you have IMAP or POP set up already, you should be able to access your mail that way in the meantime. We’re terribly sorry for the inconvenience and will get Gmail back up and running as soon as possible.

Also see related discussion on Techmeme.

A few weeks ago, my computer crashed. Suddenly, I was fully living in the cloud, depending on Gmail for my email, Google Calendar for my calendar, until I could get Outlook up and running again. And I realized that despite Google wanting the browser to be the interface to everything, software applications still have a place — with Twitter being a case in point.

Plenty of people start off using Twitter on the web. But as you get into it, you realize how much better your experience is when you use a dedicated application like Twhirl or Tweetdeck. Light and easy to install, they provide many features that Twitter on the web does not. They also provide a better user experience for those who want to interact with Twitter.

That brings me back to Gmail. I love Outlook. It’s an outstanding email / contact manager / calendar client. But it’s heavy, and it’s a pain when you need to reinstall it. It doesn’t remember all those account settings you have, how you want your email to display, signatures for your email, what “day of the week” you want your calendar to start on and so forth.

So why not shift fully to Gmail, which remembers everything? The “client” in the browser is still clunky. Sometimes I want to open several “email windows.” Or with Google Calendar, I want to see a month at-a-time with that meaning four weeks, not literally a particular month. Most important, I use multiple Google accounts. If I sign into Gmail with one, I’m stuck with that, having to sign-out into another. (Moving From SpamCop To Gmail & Loving POP Download With Archiving explains more about why I like Outlook as a client to Gmail).

A Gmail client would solve this. I’d be able to log into my main Gmail account without worrying about whatever else was going on with my browser. Those who worry about Google tracking them when logged in would be especially reassured by a client. Plus, I suspect a better user interface could be crafted. (I could use Yahoo’s Zimbra, I suppose, but I found it also kind of heavy).

With few exceptions, Google doesn’t provide apps for its software (Picasa and Google Earth are examples of those exceptions). Google pushes the Chrome browser because it fully believes that the browser is the way forward when it comes to software applications — those applications will live in the cloud, and the browser will be the universal user interface.

I hope Google thinks beyond the browser, Chrome or another. Using Adobe AIR or anything that can give me and others a lightweight, multi-platform application that can access our cloud data (and our preferred user settings). The browser can remain a universal backup, but for many, I think custom applications still can enhance the user experience.

I keep my inbox pretty clean, and Gmail does an excellent job at prevent spam from even reaching it. That’s why I was stunned about a half-hour ago to discover that suddenly, Outlook was downloading over 1,000 new messages that fortunately were then being routed to my spam folder.

What was going on? I did a quick search and discovered that today’s malware incident that hit Google web search also impacted Gmail accounts (including, I’d assume, those using Gmail through Google Apps, like me).

Google says that by mistake, some legit messages might have gone into your spam folder, so to look closely and make sure nothing important is there. They added that an automated fix was being rolled out.

I suspect what just hit me was that Google took everything that was in my spam folder (typically I might have 2,000 messages or more here accumulate in a few days), rolled it into my inbox and then planned to reprocess my inbox according to the new spam filter. Just guesswork here. But it resulted in spam that normally I’d never download starting to flow into Outlook.

My quick solution was to filter my Gmail inbox to find unread messages, since it was pretty much only spam that wasn’t previously read. Then I deleted all those, refiltered by unread, deleted and kept rinsing and repeating. Eventually, after about 20 cycles of this, I caught back up to only “read” mail — which matches probably the last time I used the “Delete all spam messages now” option.

Hard to say what’s best. Personally, I’d say review your spam folder right now, make sure there’s no spam in it, then use the “Delete all” option to clear it out and avoid Google perhaps moving all that spam into your inbox, assuming this is indeed something that they’re rolling across accounts.

A few years ago, I remember having like 400 email messages in my inbox and feeling completely overwhelmed. I wanted to get through them all but then did the math. If I spent only one minute answering each email, that was going to take an entire day. And more would come in, plus I knew many of them were going to take much longer than a minute to deal with.

Email can still be overwhelming, at times. But usually I keep my inbox in the 50 to 75 messages range (it’s 53 right now). Over the years, I’ve tried a variety of strategies that have seemed to help. I thought I’d share some of them.

1) Deal With It Immediately: When I get an email, I try to answer it as fast as I can. That doesn’t mean I’m constantly checking and trying to deal with the newest stuff. Instead, it’s more a “touch it once” strategy. Try to respond when you see an email for the first time, whenever you get to it, and it’s done. If you save it for later, you’re wasting time twice. Or three times. And so on and so on.

2) Let It Sit: You can’t deal with everything immediately. You can’t deal with all the email and requests you receive at all, in many cases. So some stuff you’ll pass by. A day goes by. Two, three and more. Eventually, that email is so old that either (A) whatever was so important turned out not to be or (B) if it was that important, you’ll get a new email about it. Let go. Allow time to deal with some of your current email woes.

Of course, I still try to get through everything. It’s kind of sucky when I get to some question that may have taken me a month to finally answer, only to find that the person who sent it didn’t use a working address or has since found a solution to their problem.

3) Don’t Send Unless You Have To: This is sort of a corollary to Let It Sit, and it’s more a plea to anyone who sends email than those who trying to deal with it. Did you really need to ask someone something? I love feedback, and I really love to help people and answer questions as best I can. But it’s a timesuck if someone sends out the same question to 5 or 10 different people. You make time to respond, only to get back “Oh, so and so answered me.” Or worse, “Oh, I did a search and found what I was looking for.”

4) Pick Up The Damn Phone: Got yourself in an email conversation that’s now going into its fourth or fifth round? There’s this thing called the phone. It’s over 100 years old, and it really works well at this concept of two-way conversation. There’s no need to have an Earth-Mars timelag in our conversations. At some point, email ceases to be the best way to communicate. Call people.

5) Clear The Clutter: One nice thing about Outlook is how it will group things by date. Of the 53 messages currently in my inbox, 14 are grouped as “Today.” I’ll try to work on those tomorrow, and get through as many as I can. Another 5 are flagged as “Yesterday,” then 2 as “Last Week,” then 6 as “Two Weeks Ago” and so on. At the bottom of my inbox, there are about another 16 tagged as “Older.”

Chances are, I won’t catch up to those older things. Some of them have just gotten too dusty. My oldest message is from June 2007, from Matt Cutts, about some Google issue I still mean to catch-up on. That’s nearly a year-and-a-half old now. I’ll probably never get to it, and if I do, it probably won’t still be relevant. I really should just delete the dang thing — along with some of the others. Save me some time; saves Matt some time (he’s got his own email issues and tips)

Outlook effectively clears the clutter for me by shoving everything like this automatically into the “Older” group. But if you’re using Gmail, try an alternative I used to use with Outlook. Make a folder for each month. Go on, right now, make these:

• December 2008
• November 2008
• October 2008
• September 2008 & Older

Now go to your inbox. Anything from December 2008? Shove it into the December folder. November to November, October to October and all the rest — shove it into September 2008 & Older.

Now look at your inbox. Feeling a bit better, seeing less there? Hopefully, at least, you feel less overwhelmed. I know, I know — but there’s all that email you have to answer, that you’re just hiding!

Yes, you are. But remember the Let It Sit rule. If it’s crucial, you’ll get fresh message about it. Meanwhile, in the back of your mind, you can subconsciously relax that you really do expect to get into those various month folders and deal with the older email. You won’t! But let yourself believe it, and you’ll can hopefully get more functional with the stuff you really can deal with.

6) Pray For A Virus: Not for you, of course. For others. Seriously, email viruses are great. When they go around, folks stop sending an email, and it’s catch-up time! Or email holiday time.

7) Categorize: I used to be a big categorized folder nut. I’d have folders for all different types of projects (and in Gmail, you can label stuff to do the same). I’m not so big on that now, mainly because I’ve gotten a better handle on my inbox over the years. I realized shoving stuff in a particular project folder meant I probably wouldn’t get to it. But in a few cases, it can be helpful.

8 ) Use Gmail For Searching: Merging Gmail & Google Apps Mail Accounts and The Great Gmail Import & My Short Life With Web-Based Mail have some background on what I do with Gmail (now with offline support! — and more here). But the short story is this. All my mail runs through Gmail (actually, through Google Apps, which has the benefit of solving what I covered in my Gmail’s “Custom From” System Messed Up By “On Behalf Of” Headers post).

From Gmail, I download into Outlook (which automatically archives a copy in Gmail). That gives me a backup in case Google from some reason loses all my mail. It also gives me a tool that I find handles my email needs much better. But if I need to find a particular message? I fire up my browser, hit Gmail, and within seconds can locate whatever I want in the 155,000 archived emails I have stretching back to 2004.

Being able to search like this has greatly reduced my need to file and store email within Outlook. I just don’t worry about that, any longer. And if you’re not spending time trying to find email, you have a bit more time to deal with it.

Happy emailing. Or not emailing!

About two weeks ago, I dived in to merge two years worth of mail from one Gmail account to my existing Google Apps mail account. I wanted to cover how it went and how it caused me inadvertently to abandon my cherished desktop client, Outlook, for two weeks. No, it didn’t make me a web-based email convert. But perhaps it might down the line.

Merging Gmail & Google Apps Mail Accounts is my previous post covering some of the discoveries I made when combining the two accounts. I had no idea it would ultimately take 12 days to complete. During that time, I had to shift to using only web mail because any attempt to download only “new” mail caused hundreds — thousands! — of imported messages to be seen as new by Outlook.

Coincidentally, the Gmail blog just posted Tips for importing old email to Gmail noting, “It might take a while for Gmail to fetch everything from your old account….” Indeed, 12 days? I know, I had over two years worth of mail. But both accounts are hosted by Google. There should be a much easier, efficient way to combine two accounts without having to go through POP downloads.

I covered some of the glitches already, but here are some additional ones:

Watch spam carefully! All new mail brought in is reassessed through Gmail’s spam filters. This is kind of odd. If you didn’t tag it as spam the first time, why reevaluate it and risk false positives?

Surely there wouldn’t be many false positives. After all, I extensively tested Gmail spam filtering when I switched over to it back in 2006. Part of the reason I moved was that false positives were minor. These days, when I get several hundred spam messages per day, I routinely hit that “Delete all spam messages now” link to wipe out thousands of spam mail without a second glance. I trust Gmail that much.

Don’t. Don’t trust it that much with imported email. I found it was nabbing hundreds of messages that I myself sent as spam, stuff that by no means was. I found many other important messages from others being nabbed by the filters. I wish I’d more closely reviewed the spam messages earlier as they came in. I only realized so many false positives were happening about midway through the process.

FYI, of the 90,000 messages I imported, it looks like about 20,000 of them were indeed spam that didn’t get caught the first time they were seen by Gmail. So there is a plus to the second run in spam filtering. But it has its downsides.

As part of this, I found myself amazed again that over two years since I last complained about it, you apparently still cannot whitelist people in Gmail. Insane. C’mon, Gmail, get with it. How hard is it to allow people to create whilelists for mail that shouldn’t be filtered. Did I miss this somewhere? And how about an option to simply filter out any email in non-Latin languages. Trust me — anything sent to me in Chinese is spam or something I don’t need to see. I don’t speak Chinese. Let me filter it out. You know, like I asked for two years ago. And still no ability to see more than 100 items at a time? Sigh.

The mail that won’t die. For some reason, I had about 300 messages that refused to be archived or go away. I ended up downloading them to Outlook yet they continued to stay on the server as if they were new. Well, 300 messages out of 90,000 imported ain’t bad. Ultimately, I deleted them. It was the only way forward.

Moving on, I wanted to talk a bit about using web-based email. It’s weird to me, OK? I live in Outlook. Like if you don’t email me so that it reached Outlook, you don’t exist. I do everything through Outlook in terms of my scheduling, action items and so on. FYI, if you send me Facebook mail, there’s a very good chance I’ll never, ever get back to you. Hey, I’m swamped with regular email. Facebook mail is like a second disaster zone for me. Send me real email! But you know, don’t. Nah, it’s OK, — I’m actually pretty good at managing a heavy email load. Expect a future post later.

So I know people who swear by web-based email, seem to fly along with it just fine, and more power to them. But for me, it just felt strange. Suddenly, I found myself stuck in the world of web-based email, since it was impossible to download into Outlook. How’d I like it?

Better than I thought. OK, it was kind of nice being able to archive messages, assign multiple labels to them instead of having them exist in only one folder and so on. I did get used to it.

Give me offline functionality! Still, I’m not a convert. Most important, I need my email portable. I just did an eleven hour flight. I had 25 messages in my Gmail inbox. I couldn’t get them into Outlook. I couldn’t access them on the plane. And the fast save I did of a few messages in HTML turned out to not save anything at all. No offline email, no conversion for me. End of story.

Yes, lots of Google products are going to offline functionality. But Google Gears doesn’t seem to have given that to Gmail yet. Way back, there was a mention that you could read your most recent Gmail messages using Google Gears, but I haven’t played with that nor seen many talking about it as a serious way to use Gmail offline.

IMAP’s Kind Of Cool. I’ve used POP to get my email for years. When Gmail announced IMAP support, well, yawn. I didn’t get it. Just before I started the merge process, I enabled IMAP thinking it was time to grow up. Instead, I freaked out. I had all these folders I didn’t understand, each corresponding I learned later to a label on the server. I hit the root folder out of habit and was told it wasn’t accessible. Overall, things just didn’t feel right. I went back to POP.

Tonight, I really need to get those 30 or so messages in my Inbox in Gmail into Outlook. Another flight, you see — this time a 16 hour jump from LA to Sydney tomorrow for SMX Sydney. The problem is, after the mega import, Outlook won’t download them through POP. It thinks they’ve already been downloaded. Time to see if this whole IMAP two way thing works.

Cool, it did! Enabling it let me get those messages that were trapped on the server. But the problem it, it also wants to bring over all the messages associated with them in a conversation. Hey, I don’t need all those other messages, and bringing them explodes my nice neat Inbox from 30 messages to over 100. Argh!

Meanwhile, I added a number of labels as part of the import process I went through. One was called ME NOT SPAM, to list any email sent from myself in my old account. There’s nearly 3,000 messages tagged like this in Gmail. And now I have a folder matching it in Outlook. And if I dare click on that folder, Outlook tries to download all of them. Gads, imagine what that will do to my PST file.

Overall, I kind of like what IMAP in Gmail might offer. I can learn to avoid clicking on labels that will bring up too many messages. And having labels that can correspond to the Outlook folders I use might be kind of nice. Plus, it offers a way to potentially get around the offline problem. But for now, I’m going back to POP. You know, the email POP, not POP goes my heart (Music & Lyrics, great movie, check out the clip below!)

NO BACKUP! I realized that over the past two weeks, I have no offline copy of what I’ve sent using Gmail. I’ve heard the rare horror story of someone that lost their hosted data (video, pictures, email, whatever). I’ve never worried much about such stories because I always have an offline copy of my data, most especially email. But for the first time, some of my email only resides with Google’s servers. Long may they wave. But the ability to download and backup on a regular basis is vital.

I’ve had a Gmail account since the day they were first offered, back in April 2004. Then at the end of 2006, I opened up a new Google-hosted mail account under my own domain name using Google Apps, which I highly recommend. It provided me with all the great archiving and spam filtering that made me move to Gmail, plus it solved the Gmail Custom From issue that I’ve written about before.

The only downside is that all my mail from 2004 through 2006 is in my old Gmail account, which is a pain if I need to look up some old software registration number (bringing up my repaired desktop today, I’ve been having to do a lot of this). First I’ll usually check my existing mail account, then I’ll go over and check my “old” mail in Gmail. Wouldn’t it be nice if I could move all the email from the old account to the new one?

Well, you can. It’s not even new, but it’s been on my mind since Matt Cutts reminded me of the option with his 11 Power Tips For Gmail blog post earlier this year. I explored a few more posts offering advice, and Google Operating System probably has the best write-up I found. So how did it go for me?

Slow would be the best description. But I’ve got a lot of mail. My old Gmail account has 3GB of mail, or 90,542 messages. On Saturday afternoon my time, I configured it to allow downloading all mail via POP, even mail that’s already been downloaded. And away it went, slowly pulling across 200 messages every two minutes.

Hmm. Whipping out the old calculator, that means about 450 “fetches” of 200 messages each to get all my mail. Two minutes per fetch, that’s 900 minutes or 15 hours. A long time, but it should be done by now, right?

Nope. Sometime last night, despite Google talking to Google, there was a timeout error. I had to restart the process today. How’s it stand?

To figure it out, first I’d go to my All Mail option in my new account, then click Oldest and click my way back on the Newer link until I saw the gap between old mail that came in (dated in 2004) and existing mail (which began at the end of 2006). To go faster, I’d just change the number after P in the URL to jump ahead, say from P511 to P475.

After a full day, I’ve gotten to June 2004. Two months. That’s it. That leaves me with 16 months or so to go. I sure hope it speeds up.

I also discovered a number of issues. First, despite the mail coming in under the old date and being immediately archived, my mail program thinks some of it is new and wants to download it. For example, if I try to POP download now, there are 305 messages that Outlook would pull across, if I let it — and all of these from April, May and June 2004.

This is a pain. To stop it, I have to go into Settings, then to Forwarding & POP/IMAP, then change to Enable POP for mail that arrives from now on. If I do that, voila! Those 305 messages are treated as old by Outlook, and it doesn’t try to download them. Unfortunately, more messages keep coming in. So it’s rinse and repeat — you have to keep going back and enabling that “arrives from now on” setting, since it will magically reset itself back to enable download of all mail since whatever is the oldest date it has fetched (at the moment, after just doing this, it has set itself to May 15, 2004).

The other problem is that any real “new” email you want won’t get pulled into your Outlook client, if you do this. Fortunately, the weekend has been quiet. I’ve mainly been getting messages about people subscribing to my Twitter feed. As a sidenote, there’s been such a rise in activity that I feel real pressure to be a more interesting Twitterer. I’ll try! Plus, with Jason Calacanis going all out to be a top Twitterer as rated by Twitterholic, I’m thinking hey — only 700 more people and I could crack the top 100. So tell a friend, at least if you want a search person up there. But sorry, I have no Macbook Air to give away.

I digress. So new mail has been slow, but at least I can see the “real” new mail showing up when I log into my account using the web interface. To be clear, if I do a POP download, some of the “old” mail shows up as “new” despite being dated from back in 2004 plus any real new mail shows up as well. But in the web interface, only that new mail is showing up in my Inbox, probably because the imported mail is set to automatically be archived.

So my workaround? It looks like I’m going to be using the web interface a lot over the next few days, until this import process completes.

Here’s another tip. A faster way to see how far things are along is to go to your old account, the one you’re importing from. Go to Forwarding & POP/IMAP, then look at the POP download section. The status line above the options should say that POP is enabled for all mail that has arrived from a particular date — and that date will get newer as the export process to your old account continues.

Postscript: One last observation. It’s amazing to watch how much Gmail’s spam filters have improved over the years. Hundreds of imported emails that previously came to my old Gmail account as not spam are not being nabbed by the spam filter as the import process reexamines each email. For the record, my current account had about 51,000 messages before the process began. When it’s over, I’ll be able to tell how much of that imported email turned out to be spam.

For whatever reason, I couldn’t get some of my messages from Outlook to
actually send through Gmail this weekend. I went through the
various things I’ve
tried when this has happened in the past and settled on the
solution of
deleting my Gmail account settings and entering them anew into Outlook. When I went to get
the right settings from Gmail help,
I came across a promo for a new
Gmail POP Troubleshooter utility that you can
download from Google. Hallelujah! Poking around, I found that it

rolled out earlier this month.

Firing up the software, it checked my settings and declared them OK. It then checked the connection with the Gmail server, then shut down
and disappeared. Along with this, my mail also
started to go out, as a result.

I kept having sending problems for about an hour or two. Each time I ran the
troubleshooter, they went away. I have no idea if the troubleshooter was
actually making some change or it was all a coincidence, with Gmail perhaps having a slow day. Regardless, the troubleshooter solved the problem, so
I’ll give it the credit.

Check it out, if you’re having an issue. I was disappointed that after it
runs, it just shuts down with no summary screen or report of what it found.