From Off the Hoof:

Let’s start with the premise that you have a 40 hour week. (If you just started crying you need a new job.) That’s 40 hours of time to do your job. Now look at your calendar. If your job is to spend a very large part of those 40 hours in meetings scheduled for you by other people then you’re fine. If your job is to produce things such as code, comps, analyses, flow documents, etc., then why isn’t the time to do THAT on your calendar? People rarely schedule working time. And when they do it’s viewed as second-tier time. It’s interruptible. Meetings trump working time. Why? And why so often are the same people who assign deadlines the same ones reassigning all of your time? Crazymaking. They should be securing work time for you and protecting it fiercely.

CloudMagic is a Google Chrome and Firefox extension which indexes your email locally on your computer, and provides ridiculously fast results when you search. The extension provides a CloudMagic search field right in Gmail with a shortcut key of Ctrl-/ (rather than just / for Gmail’s regular search field). It features search-as-you-type that seems to react instantly to your keystrokes, and uses many of the same search operators that Gmail already uses, so you don’t need to re-learn how to search.

On a large email archive it can take a few days to complete indexing, but the search speed it offers will be worth it for some people.

This five minute video describes the most interesting new email-related idea I’ve seen in a few years. Hilary Mason, a computer science professor, has created some shell scripts (very simple software programs) that help her deal with some of the more common ways that dealing with email wastes her time.

On her site she says that she is working on making the scripts generic so that she can release them as open-source projects anyone can use.

I’d love to see smarts like these bundled into popular email clients and web mail products.

[ via Gina Trapani ]

For example, have you ever gotten back from a holiday to find your inbox filled to the brim with unread messages? How do you tackle it? What do you do when you know there’s no way you can get it down to zero in one or even a few sittings?

When I find myself in this situation, I use the 10% rule. When I am sitting down to process my email, I know that I can get rid of at least 10% of the messages in the backlog. This means the 10% refers to messages that are not new ones that came in since the last time I processed my inbox – all the new ones will be dealt with as well.

Think about it; if you’re a typical user, probably half of the messages in your newly-overflowing inbox are bulk mail subscriptions that you only scan anyway. Someone tagged you on a photo in Facebook? It’ll take you 10 seconds to view the image, 20 if you comment, then delete the notification from your inbox. Do that a bunch of times, and you’ll have knocked off 10% of your backlog in no time.

The first few times you sit down to process your inbox, it should be pretty easy to get rid of 10% of your email backlog. And the beauty of this technique is that as you get rid of the low-hanging fruit and it becomes more difficult to get things out of your inbox, you will have already reduced the overall number of messages substantially. This means that the 10% you need to get rid of is constantly diminishing in size, as the likely difficulty of dealing with the emails increases. With a bit of work your backlog will get small enough that you can just knock the last few stragglers off, and voila: you have an empty inbox!

This technique can be of some benefit if you’re in that first category of people that has a full inbox of messages you’ve read, but still plan to do something about. But if you’re using your inbox as a task list, you probably won’t ever actually get your inbox completely emptied.

But there’s a better way.

The problem with Send & Archive is that it spits you back to your inbox after you send each message, meaning that you now have to decide which message to tackle next. And that encourages you to skim through all the email subjects again looking for the easiest or most appealing next one to deal with.

And let’s be honest here: what you’re actually doing is processing your email. You’re going to need to get through all of them anyway, so why not make that process as simple and straightforward as possible?

So instead of Send & Archive, I recommend that you turn on Gmail’s keyboard shortcuts on the General tab in Gmail’s settings, and get very comfortable with the ‘[’ and ‘]’ keys. These keys will archive the current message and immediately show you the previous or next message, depending on which one you press.

In practice this means you can start at either the first or last message in your inbox, read it, and reply if necessary (or not), but just press the appropriate of these two keys to archive that message and look at the next one. You can cruise right through your entire inbox without any time sitting there trying to decide which message you’re willing to tackle next.

Of course, eventually I learned that there are downsides to this strategy. I found that I was spending all of my time monitoring my inbox and batting away incoming messages like tennis balls shooting at me from machines on the other side of the net. Getting each ball over the net was more important to me than really considering my responses and sending the bestresponse back that I could. And while I was busy bouncing away the incoming messages, not much real work was getting done. I’d go home for the day feeling exhausted, but not able to think of anything productive that I accomplished during the day.

What was even worse was the fact that the incoming messages seemed to be getting more and more frequent – coming at me faster and faster. I was training people that I was someone who delivered fast responses, so they quickly learned that if they wanted something done, they should ask me first. A lot of the email I was getting was only marginally related to my job, and yet I was fielding all sorts of requests for my time because I’d cultivated a reputation as someone who was reliable and quick to respond. But my actual responsibilities were suffering, and my stress level was through the roof.

It’s fine to respond quickly if the answer is top of mind and you don’t need time to consider it. But don’t be afraid to sit on an email for a day or two if you need to decide the best way to respond. In many companies email has become almost real-time, and people expect you to have read and considered messages that they sent you only minutes before. That culture is toxic. Your instant messaging client doesn’t have an inbox because it’s a real-time tool. Email does, because it’s intended as a place for messages to gather while you’re not actually “doing email”. In other words, email was never intended to be real-time. It’s not unreasonable to let people learn that while you might not always answer immediately, your answers will be considered and of a high quality.

Another benefit of sitting on a message for a little while before replying is that the sender may actually be able to solve their own problem if they give it a bit more time. Or another recipient who is better suited might respond. This isn’t to say that you should be a jerk about it, but if you’re overwhelmed, remember that you control your time, not the people who send you email.

There’s definitely a balance to strike here, since you want to be a reliable correspondent, while protecting your time to give yourself the room to actually think, and do real work.

It’s easy to forget this, and I often do, but doing email isn’t doing work.

Okay, it’s time for a reality check here. You need to admit that you’re probably not going to get to those important messages buried somewhere in the pile. And if you do, it’s not going to be by accidentally seeing them in the list, but rather because you actually went looking for a specific message.

So, given that, what you’re going to do is take everything that is currently in your inbox, and move it into your new Archive folder. You can still search for messages in your archive, so it’s really no different from having them in your inbox, except you’ll now be able to easily see the new items that come into your inbox, and anything that is important enough to not archive it right away.

Some people struggle with this idea because it feels like you’re just cramming a bunch of unorganized stuff into a closet. The thing is, almost all modern email programs contain sophisticated search functionality that makes it easy to find a needle in the haystack. Your closet, on the other hand, does not. And even though you haven’t methodically organized this pile of messages, the truth is that you were never really going to anyway – you were just going to feel bad indefinitely about the fact that you hadn’t organized them.

By the way, this method of cleaning house works well for cluttered computer desktops or download folders too. Just burn a CD or DVD containing with everything that is sitting on your Desktop or in your Downloads folder, date the disc, and set it aside. I’m willing to bet you’ll never actually need it, but if you do it’s there.

The problem with this kind of thinking is that it doesn’t scale. If you are only receiving 5 email messages per day, then sure, you can probably keep everything in your inbox and find the items you need when you need them. But if you start receiving 50 email messages per day, that gets a lot harder, very quickly. I would argue that even if you only receive 5 emails per day, you should still empty your inbox as a habit, because your email volume will invariably increase over time. Good habits are just as hard to break as bad ones are, so instill good ones now.

Sure, but you haven’t answered the question: Why?

The thing is, you really don’t need most of those old messages, but having them hanging around is making it really hard to find the stuff that you actually do need. Don’t worry, I’m not going to suggest that you throw them out; in fact, I have every single email message that I have sent and received for the past almost 10 years. The point here is that you need to archive the non-actionable emails (anything that doesn’t require you to follow-up on it in some way), so that it’s not in your inbox. Don’t worry right now about where it goes, just make a folder called Archive. Gmail has a beautiful built-in system that allows you to press an Archive button to instantly remove a message from your inbox, but keep it forever in an easily searchable archive. If you’re not using Gmail, you can mimic this behaviour by simply creating an Archive folder and getting into the habit of moving any messages from your inbox into it once you’ve read them.

Okay, but is that it? This is just about making it easier to find things?

No, not exactly. It’s actually about helping you breathe easier when you look at your inbox. If you’ve been coping with an inbox that is crammed full of messages, it’s likely that some part of your brain cringes every time you look at it, or maybe you feel guilty about all of those messages buried somewhere in there that at one time felt important (and maybe still are). If you’re reading this site, it’s likely that you feel that you have a problem, but the idea of having an empty inbox as a goal seems too far-fetched, scary, or crazy. Truthfully, it takes some work to get there and stay there, but once you do it you will feel a level of relief, and you will even find that over time it takes less effort than living with the clutter of thousands of unimportant or unnecessary messages.

If you’re still not convinced, I’d invite you to read an essay I did five years ago at my personal blog. In it, I take a slightly less diplomatic approach, which can be seen right in the post’s title, If Your Inbox has More than a Screenful of Messages In It, You’re Rude.

Having worked in very email-centric organizations in the high-tech industry for the past 10+ years, I’ve become accustomed to dealing with a very high volume of email. For years I’ve tried to discuss my trials and tribulations with dealing with the onslaught of information coming at me via my inboxes with my friends and family, only to find them a little bewildered. They simply weren’t experiencing the same issues.

However, in the days leading up to 2010, if there’s one new year’s resolution I’ve heard from those same friends and family more than any other, it’s an intense desire to get their inboxes under control.

Maybe I’m getting a bit ahead of myself. I suppose you’re wondering just who the hell I am, and why you should listen to me when it comes to learning how to better manage your email?

My name is Jason Clarke. I’m a 34 (almost 35) year-old father of 3 young children, and devoted husband. I’ve been blogging for 7 years, including 5 years writing for the AOL-owned publications Download Squad and TUAW. My day jobs for the past 10+ years have all been in the software industry, as an Implementation and Support Technician, Software Test Engineer, Project Manager, and currently hold the positions of Manager of Technical Services and IT Manager for a Vancouver-based software company.

When dealing with software people, one thing quickly becomes clear: they like to communicate via email. And the only people who I know that like to communicate via email more than software people are technology bloggers. So, given that I’ve spent the better part of the past 10 years involved in both camps, I’ve become accustomed to managing an average of 100-200 new emails per day, per group. That’s 200-400 emails per day, typically. And sometimes it’s worse – much worse.

Just think what that means.

If I receive 200 email messages in the course of a notional 8-hour work day, that means that I get an average of 2.4 minutes to handle each email message. And that’s assuming I do nothing but deal with email all day! Of course, many of those emails are one-liners requiring no more than 30 seconds to read and file or delete, but that is balanced out by the multi-page screeds that must be truly studied.

Now consider that the blog-related email I receive is at the same volume, and must be dealt with in my own time. I certainly don’t have another 8 hours in my day for non-business email, never mind any personal messages I get.

I must be absolutely crushed under the weight of all of these incoming email messages, right? Well, if I’m honest, yes… sometimes I am. But, most weeks my inbox is completely emptied at some point, often many times during the week. That’s right – zero messages in any of my inboxes.

If this seems impossible, it’s not. And if you’re struggling to tame your inbox, I’d like to help you get it under control.

If you have a moment, I’d appreciate if you could drop by and have a quick look at Inbox Era. Kick the tires, metaphorically speaking. And let me know if this sounds like something you’re interested in learning more about.

Also, please feel free to send your questions my way. I can’t promise that I can answer them, but I’ll certainly give it a shot. Hopefully we can learn how to handle the era of the inbox together.

Here’s the section I contributed to:

Jason Clarke, who works in the technical sales and marketing department at Wenco International Mining Systems Ltd. in Richmond, British Columbia, receives about 100 e-mails daily. He said that on his PC, Outlook 2007 “hangs completely for three to seven seconds typically, and up to 20 seconds in worst cases when new mail is being downloaded.” Turning off Outlook add-ins that he has installed, such as ClearContext Corp.’s e-mail management software and Caelo Software Inc.’s Nelson Email Organizer, “does improve matters marginally, but not nearly as much as it should,” Clarke said. “The hesitation is still very noticeable — jarring even.” Clarke, who oversees Wenco’s e-mail system, has posted information about Outlook’s slow performance on his personal blog. He blames the problems on the new e-mail indexing engine that Outlook 2007 shares with Windows Vista. The indexing allows searches to be done almost instantly in Outlook 2007, a vast improvement over Outlook 2003. However, the process also appears to be CPU-intensive. Microsoft recommends that users put indexing on a regular schedule instead of letting it run constantly in the background.

Now, I just want to point out that I consider ClearContext and Nelson Email Organizer to be essential Outlook add-ins, and made the point in my email to the author, Eric Lai.

Also, between the first time I spoke with him back in November for an article that came out in December, and now, I have a completely new job, albeit at the same company. I can assume some blame for that, though, since there’s no reason to think that within a few months someone would change positions. But I feel weird about it nonetheless.

For what it’s worth, here is the content of my email to Eric. To preface it, Eric linked to a few complaints about Outlook 2007 performance on the web, and asked me whether I thought the complaints were legitimate. Here is my response:

I’m struggling with how to answer your question; I’ve read the links you provided below to some of the user complaints with Outlook 2007, and while I’m certainly frustrated with the product’s performance, I’m not having the same kind of trouble these users are complaining about. I actually wrote about my frustration with Outlook 2007 about a week ago on my personal blog in a post called Outlook Slowness. My complaint is weak compared to the others you referenced; I’m basically saying Outlook 2007 is mildly better than Outlook 2003, but that I’m using a faster PC so it’s not really a fair fight. The specific performance issue that I face is that Outlook hangs completely for 3 to 7 seconds typically, and up to 20 seconds in worst cases when new mail is being downloaded. Turning off the Outlook add-ins that I rely on (ClearContext and Nelson Email Organizer) does improve matters marginally, but not nearly as much as it should; the hesitation is still very noticeable, jarring even. After testing Microsoft’s desktop search product (the one that Outlook 2007 nags you to install), I came to the conclusion that it is inferior to many of the other similar free products that are available (like those from Google, X1 / Yahoo, and Colibri), and removed it from my system. But it’s worth noting that anyone that is using a desktop search product to index their email for faster searching is likely to see a noticeable performance hit. I’m still running Outlook 2007 on a Windows XP system. I should note that when I tested it using the exact same PST file (email catalog) on Windows Vista, I found it to be noticeably snappier. Some of the enhancements that have been made to Vista allow Outlook to load in a few seconds after a reboot, whereas on XP it can take Outlook up to 30 seconds to become usable on the exact same system. Unfortunately, I haven’t used it enough to comment reliably on the actual email download hesitation problem. In fact, I’m dying to do exactly that and see if I can ease my pain. For people that are frustrated with Outlook’s performance, Brad Meador at ClearContext posted a fantastic tutorial for ensuring the health of your Outlook mail (PST) file. At one point I was experiencing a significant overall Outlook slowdown, and following Brad’s advice helped matters greatly. I hope this helps!

One last point I should make. I’ve put a lot of time and energy into Outlook over the years, so it may come as a surprise to some of my readers, but I finally found the ultimate solution for it. A Mac.

That’s right; I had the opportunity to choose a new laptop at work, and decided to get one that would simply help me get things done, rather that having to muck around with every last little thing. For the moment I’m using separate Gmail accounts to manage both my personal and work related email, and finding the experience very enjoyable. Gmail excels at handling very long email threads, which is something that happens in my work email very frequently.

Beyond that, I may give Apple Mail a try as an offline email client. So far I haven’t felt the need to. And it would be disingenuous of me not to admit that although I’m operating most of the time in Mac’s OS X operating system, Intel-based Macs do run Windows fine, and I have a Windows instance available to me whenever I need it. In fact, that’s where I keep my archive of emails from before the point where I decided to switch to Gmail, and it works just fine.

So, I’ve given up on Outlook for day to day work. But if you want to or have to use it, do check out Clear Context and Nelson Email Organizer. They both have the capability to supercharge the way you deal with your email, and both work fine for me under Outlook 2007. And although I do have affiliate links for both of these software packages, you’ll note that I’m not using them here. I truly think that both of these software packages are worth your time, and I don’t want you thinking that I got paid to say so.

[tags] Computerworld, Eric Lai, Outlook, Outlook 2007, Outlook slowness, Clear Context, ClearContext, NEO, Nelson Email Organizer, Mac, OS X, Gmail [/tags]

This includes when I shut off the Outlook add-ons that I have come to rely on; I know that adding things on to an application that I find to be already somewhat slow isn’t all that smart, but there’s no way I’d live without ClearContext or NEO Pro, never mind Anagram.

And in terms of Gmail, it’s not like I don’t add functionality on there too; using greasemonkey, I’m able to add on saved searches, added hotkeys and even conversation previews. But the speed difference is still somewhat astounding.

Although I’m comparing Outlook 2007 to Outlook 2003, I have to keep in mind that I’m using 2007 on a faster computer that has a true dual-core processor. So in fact, it’s probably more than likely that Outlook hasn’t gotten any faster at all between the 2003 and 2007 versions.

The worst slow-down I experience is when Outlook is actually checking my POP mail account, which is the only way that I actually receive email into Outlook. The problem is FAR worse if I’m checking multiple accounts, but it’s really bad even with one, particularly when there are a lot of messages to download. I can’t for the life of me figure out why such a modern application can’t handle the rigors of checking mail, something that email clients have been doing forever.

Colour me frustrated.

Drop me a note if you also have trouble with Outlook slowness, and if you’ve had any success speeding it up I’m all ears!

[tags] Outlook, Microsoft Outlook, Outlook 2007, Outlook slowness, Outlook slow, MS Outlook, email [/tags]

The article that the reporter was writing was posted today at Computerworld’s website; here’s an excerpt:

December 21, 2006 (Computerworld) — His real desk may be a mess, but Jason Clarke’s virtual office is as neat as they come due to his assiduous answering, filing or deleting of the 400-plus e-mails he gets each day. “My feeling is that if you have more than a screenful of e-mails in your in-box, you’re being rude,” said Clarke, a technical sales and marketing manager at Wenco International Mining Systems Ltd. in Richmond, British Columbia. Clarke is an archetypal “filer,” spending hours a day managing his Microsoft Corp. Outlook e-mail program.

While the gist of the article is accurate, it seems a few liberties were taken with a couple of the details. I don’t know if this was for readability purposes (artistic license) or simply the result of having interviewed tons of people about the same topic, but I thought it would be worth clarifying a couple of points in the article.

The first is my current job title; although I am in technical sales and marketing these days, I’m not the manager of the department. The other point is the number of daily emails I receive; at one time in a previous position Project Manager (at a previous company) I was receiving well in excess of 400 emails per day. Mercifully, today that number is down around 100, and often dips to half of that. And although I’d like to say the comment about my desk being messy is untrue, that’s unfortunately completely accurate.

Those details aside, I think Eric has written a nicely put together overview of Outlook 2007 and what makes it interesting in contrast to earlier versions of the product. I also stand by the point that while Outlook 2007 is much better than previous versions, to really super-charge your email management you need the help of ClearContext’s IMS Outlook add-in. Considering how often I pimp that product, you’d think I’d be throwing an affiliate link around – and I probably should. But I’d simply rather that you understand how much ClearContext can positively impact your email management if you use Outlook. One day I’ll get around to posting my recipe for ultimate Outlook email productivity, using Outlook 2007 (although it works with other versions), ClearContext, and a competing Outlook add-on called Nelson Email Organizer, which I consider to be the best of breed email desktop search client available. I’ve touched on them both before, but I feel I’ve really found the sweet spot with these applications now.

Thanks to Eric Lai for choosing to speak with me for his piece.

[tags] Outlook, Microsoft Outlook, Computerworld, Eric Lai, ClearContext, NEO, email, email productivity [/tags]

Lifehacker has a wonderful post up called Hack Attack: Become a Gmail Master. In it, they describe all of the reasons I love Gmail, as well as some very useful tips on how to make it work even better for you. I highly recommend it.

If you don’t yet have a Gmail account, but are inspired to try it out from this post, drop me a line at jason at jasonclarke dot net. I’ve got many invitations available, and I’m happy to share.

[tags] email, Gmail [/tags]

The new software is called ClearContext Information Management System Professional, or IMS Pro for short. (If ever there was a product Microsoft should purchase, it’s this one; both for the awesome functionality and also the Microsoft-inspired mouthful of a name… )

I’ve been a ClearContext user since the 1.0 days, and had the good fortune to act as a beta tester for IMS Pro for the past few months. It’s clear that ClearContext have noticed the popularity of David Allen’s Getting Things Done system, in particular amongst technical people, and much of the functionality in IMS Pro is in service of supporting a GTD system. In fact, I used to use the official Getting Things Done Outlook Add-In, and found that after using IMS Pro for a short while I was able to remove the GTD Outlook Add-In and retain all of the functionality I needed (and more).

I should also mention that the team at ClearContext is one of the most approachable and easy-to-communicate-with teams I’ve ever dealt with for a consumer software product. In fact, one of the new views in IMS Pro is the direct result of a question I sent to them when trying to build a view in Outlook that it simply can’t do natively. That view (it’s called “Threaded” if you’re curious) is now of vital importance to me in my work-flow, and I bet you’ll like it too.

Let me put it this way: if you find your email difficult to manage, and don’t feel that Outlook does enough to help you, give ClearContext a try. There is a short adaptation period, but because it’s very cleverly designed to work within Outlook’s framework, you are free to use as many or as few of the new features and work-flows that ClearContext adds. Of course, I suspect you’ll find you like almost all of them.

IMS Pro will retail for $69.95 USD. Luckily, ClearContext will also soon be releasing a free offering based on the same technology: ClearContext Inbox Manager 2.0 Personal Edition (yet another mouthful). The free version doesn’t have the GTD work-flow functionality, but will still go a long way towards helping you get a handle on your inbox.

Heh – I just re-read this post, and I sound like a commercial. But I don’t mind; I really love this software and if you’re an Outlook user I think you should try it.

[tag] email, Outlook, ClearContext, ClearContext 2.0 [/tag]

Merlin has that unique ability to inform, entertain and inspire through his words – believe me, it’s time well spent.

[tags] email, email productivity, 43 Folders, Merlin Mann, Getting Things Done, Getting to Zero [/tags]

While I can definitely see the practicality in this, it’s important to consider how to apply it to your job, and what sort of responsiveness your job demands. If you’re in sales, this may simply not work for you, but if you’re in a more technical role it might be perfect. The 90 minute window seems arbitrary, and something that could be modified to fit your role.

My one concern in this situation is that you could very easily spend time and energy on emails threads that have already been resolved, and by the time you connect to sync up your incoming and outgoing emails, it’s too late to prevent your out-of-date response from going out. But this is a minor downside, and one worth risking.

The beauty of this concept is that it allows you to treat email processing like any other task you would set aside time for. It also gives you a clear finish line since no other mail will be coming in while you’re busy processing. I wonder how this could be achieved for someone that works directly connected to an Exchange server?

[tags] email, email productivity, offline, Outlook offline [/tags]