Still, it’s worth pausing to look into what BlackBerry brought to mobile email, and to point out how iPhone and Android users can replicate some of RIM’s best features.

The Core Difference Between BlackBerry and iPhone/Android: Email

In full disclosure, I began writing this post after a bunch of former BlackBerry users moved to AwayFind.  I started digging deeper into what AwayFind had to do with BlackBerry, and it all made sense: BlackBerry is a server-to-server enterprise email tool with a mobile device serving as the frontend.  Android and iPhone are mobile computers with email clients as one of their applications.

What these different architectures mean for smartphone users:

• The BlackBerry Enterprise Server (BES) sits behind a corporation’s firewall and talks directly to a mail server, in realtime.  It stores all the mobile device’s settings, and thus only communicates with the BlackBerry when there’s something it needs.  The BES is designed to make email on the BlackBerry as fast and efficient as possible, and utilizing the phone (and its battery) only when necessary.
• Android and iOS devices check the email on their corporation’s mail server directly, over the internet.  This happens in one of two ways, either the phone asks every few minutes, “is there any new mail?” or the phone does its best to maintain a connection with the mail server(s) directly, waiting for a change in the inbox.  In either case, it takes up battery life, and is neither as quick nor as reliable.  Without a server in the middle, the phone does the hard work.

The reason for this is simple: BlackBerry is an enterprise email device; Android and iPhone are consumer devices with software that checks email.  If you’ve ever traveled with a laptop, you know that email software sometimes works great and sometimes works unreliably—email isn’t at the center of the universe on laptops.  And the same is true on Android and iPhone.

Without a server-to-server mail environment, iPhones or Androids will never perform the same as BlackBerry devices, but the gap in capabilities is narrowing.  There are now both native and third-party ways to bring the worlds together.

In case you’re curious: the parallel to AwayFind is that the AwayFind server talks directly to the mail server and only notifies an iPhone or Android device when necessary, similar to BES.  Since AwayFind uses the push notification service provided by Apple/Google, it’s usually faster than SMS.

Features that BlackBerry Users Miss on iPhone and Android devices.  And how to replicate them…

AutoText / Word Substitution

BlackBerry has a robust shortcut-> common phrase tool, that even lets you insert variables like the current date/time.  For instance “lmk” can automatically turn into “let me know.”

With iOS5, this is now relatively easy…but Android still hasn’t quite caught up.

On iOS, go to Settings > General > Keyboard > Shortcuts.  Type the full phrase in the “Phrase” and the abbreviation in the “Shortcut.”  You can see some of my examples to the right…

On Android, you most likely won’t find Auto Text with the keyboard that comes pre-installed.  Even Swype (the most popular third-party keyboard) does not include it.  Auto Text Keyboard is one the most popular apps for this.  Just be aware that when installing a tool like this, you are changing the entire keyboard on your phone, and not just adding Auto Text.

Once you have Auto Text available, I’d recommend taking a couple minutes to insert common phrases.  As you can see in the image above, I have shortcuts for my email address and common phrases.  For instance, “afloc” transforms into “I’m at 169 11th St, SF — http://bit.ly/sfawayfind” (which is my office address).

Blinking Indicator for New Emails

BlackBerry is perhaps best remembered for its multi-colored blinking LED, which let you know of various states for the phone.  By default, red means “new message,” green means “low battery,” and blue means “bluetooth.”  People were particularly keen on the red display (more on this in the next section, in the video especially).

On Android, there are many applications that allow you to customize the color and behavior of the LED, however not all work on all phones.  One popular application is called Blink (pictured to the right), which can display a particular color indicator for an SMS or phone call.  While this won’t let you know about new emails, you could use a program (like AwayFind ;-) that converts an email into an SMS to accomplish this.

On iPhone, you can navigate to Settings > General > Accessibility > LED Flash for Alerts and turn it On.  If you place your phone face-down on your desk, you’ll see the LED flash light up once for any notification.  There isn’t a way to set a persistent blink (without jailbreaking it and using a program like FlashEnhancer).

Notification of Only Certain New Emails

On BlackBerry, one can even further customize their LED to only blink for emails from certain specific people.  This is one of the most popular BlackBerry features, since it can be distracting to see a blinking light every time an email arrives.  A quick story about why BlackBerry users love this this:

If you use Gmail and Android, you have the ability to send specific senders to specific labels.  Then on the Android Gmail app, you can set specific labels to trigger a notification.  (On the Android Gmail app, Go to Settings, click on your email account, and then click setup both Email Notifications and Labels to notify.

At present, iOS does not offer this.  However, on iOS6, they’re introducing an Email VIP feature where you can star specific people.  Then, when those people email you, a notification will appear with the context of the message.

Even with these features, this need is one of the main reasons people come to AwayFind.  AwayFind offers this for both iPhone and Android, integrates with Exchange, Outlook, Gmail, and Google Apps, and can be deployed throughout a company (even for non-smartphone users through SMS).  It’s also much faster than the push functionality built into the iPhone and Android OS because AwayFind talks directly to the mail server.

Keyboard Shortcuts for Compose

On the BlackBerry, it’s always quick to create a new email. From the Home screen, you need simply press C (since there’s a physical keyboard!) to create a new email or SMS. There are all kinds of shortcuts for similar things.

While this might be possible with iOS’s new AssistiveTouch, it’s definitely not designed for this, and I wouldn’t recommend trying. Fortunately, tapping the Home button, clicking Email, and pressing Compose shouldn’t take more than 2 seconds. The Compose button is available from every email display view (except when you’re already composing an email).

On Android, it can take a little longer to navigate to Compose (about twice as many clicks in some cases), but you can use a gesture to navigate straight to the Gmail application. My Gesture Shortcut Launcher is one application to try, which will at least cut a few steps.

BlackBerry vs iPhone and Android for Email

If you spend all day replying to emails on-the-go, BlackBerry will be faster.  But not because of the above features—it just comes down to the keyboard.  Swype for Android may help, and the iOS keyboard is pretty good, too…but nothing beats a physical keyboard.

On the other hand, if you spend more time reading and processing email, then the bigger screens and easier navigation will make the email experience more pleasant, and perhaps as productive.

And, it goes without saying that iPhone and Android have a much larger array of both productivity applications and games.  From multimedia to news to task management, and even just keeping the device in sync (with things other than Enterprise mail), BlackBerry still needs to catch up.

How Have You Found the Switch?

While many individuals made the switch a long time ago, a lot of enterprises are going through the jump just now.  If you’re running into difficulties getting your users moved over, I’d be curious what challenges you’re experiencing?  Maybe there’s something I can help answer in the comments or in a future article…  Feel free to respond below or email me at jared A technotheory.com.

While it was an interesting project, I don’t believe his experience or needs are indicative of what I see everyday with AwayFind customers and in my eight years of clients at SET. 

However, you too can reply to 0.3% of your email, read on… (on AwayFind blog)

Normally $50, I’m able to offer both mine and Joe’s analysis, along with the survey results, as a free PDF to Technotheory readers.  Read on for a couple snippets and a link to download the full article.

Creating the survey was fun, though I wasn’t surprised with the direct survey results, so I wanted to see if there were any correlations in the data.  Since I know little about regression analysis and sample sets, I contacted Zoë Thorkildsen (an economist/statistician who is looking for full-time or contract work right now—contact me for info on getting in touch, she’s in DC) and we discovered some fascinating correlations like this one from page one of the article:

Users with more than 100 messages in their inbox are…

• Less satisfied with the quality of their finished projects
• More behind on their projects
• Less likely to know what tasks they need to work on at the start of a workday

There were other interesting correlations about the way people prioritize their time, when they finish projects, and how much time they spend working after hours.  You can download the full article from Cutter Benchmark Review here (my article is pages 13-19 and all of the survey results are included.  Joe’s article, which really digs into the data, is also included).

                                  Download it here! – use code PERSPROD

While I think you’ll love the article (it’s amazing how much an editor can improve one’s writing!), here’s a snippet I wanted to make sure made it to Technotheory.  It’s my explanation of The Critical Path, a topic I’ve been meaning to explore here:

–The remainder of this post is from the article.  For much more, download it!

When analyzing the research data above, I touched on the urgent-versus-important prioritization.  A technique for visualizing and clarifying the most important items is plotting out the critical path.

Urgent tasks are ones that ought to be completed in the immediate future, like a memo due this afternoon. Important tasks are ones that will have a serious impact on your position or your company, like migrating staff to a new accounting system in which your company has already invested. There are times when an important task becomes urgent. There are times when an urgent task feels important. But to get my head past these nuances, I like to think of a third category called critical tasks.

My company has a software application, and if we don’t launch its next version, then we will go out of business. Thus, my critical objective — my most important goal as the company’s leader — is that we launch and that we do it in the fall. The tasks that get me much closer to launching our application are what I consider to be critical, as they’re on the critical path to the company’s (and my) success. It’s important to identify both your critical objective (or if you have two or three, what they all are) and the tasks that will get you there. Your critical objective is likely the accomplishment you’ll write down on your résumé some day as something you’ve done. It’s the item that takes a lot of work but will be transformative for you or your company. To determine your path to your most critical objective(s) follow these steps:

1. Grab a sheet of paper and spend five minutes brainstorming every task that you need to complete. List the small things and the big things, crucial tasks, and incidental tasks. List everything.
2. Grab another sheet of paper, this time lengthwise, and write out your most critical objective on the right side in the center (see Figure 1; while for ease of reading we’ve presented an example in a more formal way, yours may certainly be handwritten). If you have two critical objectives, write them both (one at a third up from the bottom of the page and one two-thirds up).
3. Draw an arrow (or arrows) from the left side of the paper pointing to the critical objective(s).
4. Using the list of tasks you brainstormed, plot the ones that will get you close to your critical objective on the line. Treat it like a loose timeline, with the tasks that must be completed first further to the left.

What you’ll likely find is that there’s a very small percentage of your responsibilities that are essential enough to be on your critical path. Every day you’ll want to make sure you make some progress on those responsibilities. They’re not just important, they’re necessary. What you’ll notice is that on the days where you address those critical tasks you’ll feel like you’ve made progress; you’ll feel like those are the best days at work. On the days where you get things done that aren’t on that path, you may actually feel worn out because, to some degree, you didn’t get the bigger project closer to the end point.

I’d suggest keeping that piece of paper near you at your desk. If necessary, you can draw up a new one every month as your responsibilities shift. You’ve probably heard of the concept of the “critical path,” but time and again I’ve seen people’s eyes light up when they actually grab a sheet of paper and go through this exercise. Visualizing your tasks and identifying those tasks that will truly move you forward can really change your perspective.

–

Do you have any thoughts or questions about identifying your critical path?  If you’re interested, there’s much more in the Cutter Benchmark Review article (with more awesome illustrations), download it here.

Flickr photo credit: CarbonNYC

It’s because the internet has no order, but we’d like to think we do.  Guess again: using an orderly approach to storing and retrieving is similar to paying full price for airline tickets: it made sense twenty year ago but is a costly decision today.

Here’s how to file and find things in the next decade.

Bottom Up vs Top Down

Storage and retrieval ultimately fit into two methods: top down and bottom up.  A top down approach is to come up with categories, and perhaps sub-categories, and sub-sub-categories…and then to place each item in exactly one place.  For instance, my residency might be classified as United States:Maryland:Prince George’s County:College Park.  From a legal perspective that’s the only place you’d find me today.  This is how file cabinets and hard drives have been setup forever.

However, in a bottom up system, one places all items into just one bucket—that means all residents aren’t classified into countries, they just get adjectives (or tags).  They have their name and their adjectives, some of which might conflict.  For instance, I could be a resident of both DC and Maryland in a bottom up system, of both the United States and Spain.

In the physical world it would be impossible to find anything if it were all lined up next to one another, but with fast servers and intelligent algorithms, you can search for “Jared Goralnick” without having to narrow your search to any geographic criteria.  This is helpful, because I identify first with DC, second with Baltimore, and not really at all with College Park.  So if you met me you might have trouble looking me up in and old-fashioned (top-down) phonebook—you might never look in the College Park edition.

There are numerous reasons why bottom up storage and retrieval are better than top down approaches when it comes to digital information:

• When filing something, there’s only one place to put it.  Tags are optional.  No choice means a heck of a lot less time filing
• When retrieving something, it’s better to use a (very fast) search tool…rather than guessing the right folder to look in first
• If an item relates to two projects, or is from an old friend but relates to business, etc…there are times when it’s tough to know where to file…or to retrieve it.  In a bottom up system, you just archive it in one place and search for it later.  End of story
• With tagging, one can tie one item to many categories.  So something can be tied to two projects without one having to copy it into both folders

Applying Bottom Up Approaches to Email

Not everything in the world of technology is ready for a flat, bottom-up architecture.  But email is, at least if you use Gmail, Outlook 2007, or Postbox.  I presume Mail is the same (feel free to verify in the comments).  The fewer folders you have, the faster your filing and retrieval will be.

That is because these modern email clients/web email sites use search indexing, the same technology that allows sites like Google to search the web so quickly.  With Outlook you can even search within the body of the files that are attached to your emails.  And it’s all instant.

That being said, you may still want to have folders for broad categories, but if you do, I’d suggest that you ensure that you can see all the folders on the screen at the same time.  That means that if you have more than a dozen you’d probably better rethink things.  Try to have fewer than five.

You may be thinking that having fewer folders feels less organized.  But in reality there’s less to deal with: fewer places to go, fewer places to look, and less time spent filing or retrieving.

Applying Bottom Up Approaches to the Rest of Your Technology

Data is becoming more bottom-up friendly every year.  The search features in Windows have been pretty good since Vista, and get some helpful improvements in Windows 7.  Same goes for Mac’s Finder—it gets faster in Snow Leopard.

For a long time you’ve probably paid attention to metadata (which is a fancy word for the tagging taking place inside a file) for your music collection—your artist, title, track, album, and other data have been associated with your music files.  That trend is going to be carried through to everything over the next ten years.

So I’d suggest that you think seriously about it the next time you do some reorganization on your computer.  We have more files than ever before (even if they’re online).  So labeling and tagging will be more relevant.  With photos, this is especially true.  But all documents deserve better labels, not better folders.

As we’re surrounded by more and more data, bottom up filing and sophisticated searching will be the only approach for us.  We need to start shifting our mindset and getting ready for it.

You can start now, with email.

Flickr photo credit: John Pannell

If you want to get yourself out of trouble and be more efficient in Gmail, installing these takes about 60 seconds.

To find these features, login to Gmail and then click Settings, Labs:

I’ve broken my list into three parts, those that just take one click and that everyone can save time with immediately, those that take a little more setup, and those that have less to do with productivity but I still wanted to mention.

Gmail Labs Time-Savers that Take Zero Time to Install/Use

Forgotten Attachment Detector – if Gmail detects language indicating you meant to include an attachment, and there are no files attached, it’ll warn you before sending the message.

Vacation Time! – We often forget to turn on or off our vacation auto response messages.  With this, you can now set start and end dates for your vacation message…so it’ll automatically turn on and off during the dates you select.

Send & Archive – When you respond to a message, the next thing to do is archive it.  But we usually forget to remove it from our inbox until much later.  This adds an option to both send a reply and archive the message thread at the same time, saving you the trouble to come back later and file it.  I LOVE THIS.

Undo Send – Did you ever press the send button and then realize right afterwards that you forgot something or that there was a typo in the subject or perhaps  something much worse?  Undo Send gives you a short amount of time (assume 5 seconds) to press a new Undo hyperlink before it mails out your  message.  So if you made a mistake, you can fix it before the message is delivered.

Title Tweaks – Sometimes I click over to the tab for my email just to see if I have new mail.  That’s because the count of messages often gets cut off by the number of browser windows I have open.  This fixes that by placing the message count earlier in the title.  If you use Google Apps for Your Domain this is a MUST feature.  Note the difference in the picture below (new result shown before old result):

Suggest More Recipients – When you start messaging a group of people, Google intelligently selects who else you frequently send to along with that group.  This is incredibly helpful.  For instance, in the message below, Melody and Tim are usually involved when I’m messaging Genie and Jessica.

Gmail Labs Timesavers that Take a Little Bit of Thought

Email Addict – Adds a link to your Gmail menu bar called Take a Break.  Clicking on it will force you away from email for 14 minutes.  Not for everybody, but it’s sure a great help for me!  (sadly you can get around this by opening the account in another tab. Shoot, I shouldn’t have said that!)

Offline – this is the only one that requires an installation, but it’s also pretty amazing to be able to read and respond to email while you’re offline.  If you find yourself on a train, plane, or generally without internet access, this can come in handy.

Tasks – For email to get out of your inbox, you either need to respond to it or save it for later.  To save it for later, you need a task list.  While Gmail’s task list is not the most robust in the world, it gets the job done.  Once enabled it will appear on the bottom right of your Gmail window.  When expanded, it appears like this:

Gmail Labs that I Use But You Might Not Need

Signature Tweaks – I don’t like my email signature going at the bottom of the email, I much prefer it just below the message I’m sending.  This takes care of that.

Advanced IMAP Controls – Since I use Postbox on my desktop I like to be able to control which labels (i.e., folders) are synchronized and which aren’t (I find the “All Mail” label to be redundant).  This lets me do that.

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Other Gmail Labs or Gmail tools you find to be particularly helpful?

Below I’ve indicated the timestamps for when AwayFind, email productivity, and Bootstrap Maryland are discussed…so you can dive right in.  After the videos are also some recent links, like being in Gartner’s 2009 Cool Vendor Report : ).

Robert Scoble Interview on Scobleizer TV

• 00:30: Continuous Partial Interruptions
• 1:31: Difference between AwayFind and the Vaynerchuk/Ferriss approach
• 5:30: What I’m working on for the future—understanding different channels
• 6:55: What sucks about Twitter and lack of chat, being used for support, etc
• 11:17 Bootstrap Maryland discussion

Note: After this interview, I was also on air for a longer discussion with Robert Scoble and Dave McClure.  It was an excellent discussion of the state of the venture market (mostly just Dave sharing, because Dave knows it better than anyone).  Robert’s blog post and video are here.

Greg Cangialosi Interview on Blue Sky Factory TV

• 11:30 My interview starts
• 16:20 How to better manage when we check email
• 21:00 I explain how I go through my day
• 30:45 Bootstrap Maryland discussion
• 48:15 My interview ends (stay on for email marketing tips)

AwayFind Around Town

• Gartner Research: Cool Vendors in Project and Program Management, 2009
• The Digital Marketer: Four Tools to Manage Your Calls
• Summit Daily News: Technology Solution of the Week: AwayFind
• Tokyo Beer & Blog Meetup with AwayFind
• San Francisco Meetup at House of Shields (Facebook)

Thank you to Robert, Greg, and the other folks who were kind enough to speak with me and review AwayFind.

–

We’ll soon be back with our regularly scheduled programming, like an upcoming post on “Action Tweeting” : ).  Cheers!

And I want to reiterate the point.

Have you ever gotten a call from someone asking you an important question, and while they’re explaining the problem to you, before you even get a word in, they solve it themselves?  If you had missed that phone call, it’s safe to say that without your involvement that person would have been just fine.

That kind of thing happens all the time when you’re available all the time.  It’s always more difficult and expensive to be on the bleeding edge, to stay current with the news, to solve problems before any of the dust has settled.

Seth Godin’s article today discusses this much more cogently, and one of his examples is email:

You can check your email twice a day pretty easily. Once every fifteen minutes has a disruption cost. Pinging it with your pocketphone every sixty seconds is an extremely expensive lifestyle/productivity choice.

I’d recommend you read his quick article and then think seriously what you decide to stay current with, and whether it would save you time, money, or energy if you waited a little longer for that information (or gadget, or software, etc).

The rest: an immediately practical, very readable, and quite beautiful 26-page guide that may not be available in 48 hours…

As I was working with beta testers of AwayFind, it became apparent to me that removing email interruptions and emptying our inboxes was not a technology problem.  It was one of education.  If you haven’t fully digested Getting Things Done or other time & email management systems, then it might be a challenge to really put AwayFind into practice.

Thus I wrote a guide to complement AwayFind’s technology…but the truth is that there are few mentions of AwayFind.  It’s an accessible summary of mine and many smarter people’s recommendations around email.  If you like what I write about here, this is the juiciest stuff, with pretty diagrams, too :-).

The catch?  It won’t be free after tomorrow (it may come back again, but not sure in what form…).  It’s downloadable as part of the Basic AwayFind setup process (the last step).  So if you want it, now’s your chance—just sign up for AwayFind here.

Along with getting the guide for free, the 30% discounts for being an early-adopter also end tomorrow.  So if you were considering the Professional version of AwayFind, now’s a good time to try it—after all, you won’t get charged for 30-days and can cancel anytime, so there’s nothing to lose.

I’m sorry for making what’s quite clearly a pitch here…but I feel like I’d be doing a disservice to you if I didn’t share this guide.  I’ve never been so proud of something I’ve written…and I want you to have a chance to benefit from it.  However, I don’t feel comfortable leaving it up for free indefinitely since I’ve put so much work into it.

Thanks for reading and I hope the guide helps.  You can grab it on the fifth step of the wizard here.

In the next post I promise to rant about something completely unrelated :-)!

Today we launch AwayFind.  It’s time for a little retrospective…

The Short Version

AwayFind began as a side project inspired by The Four Hour Workweek, but it quickly morphed into the primary focus with my team.  Our goal has always been to help people to use technology as a vehicle rather than an obstacle for getting things done…and this was an opportunity to help so many more people at once.  If you haven’t heard me go on and on about it for hours, this 90 second clip explains it, and includes a quick tour:

The Retrospective

Needless to say, we’re pretty ecstatic to launch today.  I don’t like the word “blessed” but I’m damn lucky to work with the team I do…

David, it’s been fun to grow up together these last five years.  You now know more about browsers, Visual Basic, and a whole host of random Microsoft Office stuff than you ever wanted to, and you probably know every keyboard shortcut known to man.  Not to mention your crazy Wii skills…

Keith, your ability to transition your design to the web never ceases to amaze me.  That both the SET Consulting and new AwayFind homepage were designed in PowerPoint 2007 both shocks and inspires me.  If I could only have half of your methodical creativity…

Wayne, I’ve never before met someone who could walk through walls, but that’s what it’s like to watch you navigate code.  Your energy and discipline are unstoppable.

Okay, enough of the sap story.  But I should at least mention that some other people really stepped up to the plate at the last minute here: Scott Stead rocked the instructional video, Andre Pennycooke blasted thru the intro piece (above), and my favorite dancer/bookkeeper/marketing guru Emily S proved once again that she can do anything and everything.

Thank you, too, to Emily P for her design ideas, Kate for her disciplined writing, Clay for countless suggestions, and the dozens of others who helped out.

The Anticlimax

So this is the anticlimactic part where I realize I need an insane number of users if I ever want to make a difference (and/or pay for this).  If you want to spread the word, here’s how (and thank you in advance!!):

1. Sign up for AwayFind.  It’s free and you’ll love it.  Don’t want to use an auto responder?  Just place AwayFind’s link in your email signature.  Don’t have time for that today, the remaining are quick hits…
2. Help us look good—join our Facebook fan page and follow us on Twitter
3. Spread the word: tweet, blog, or send a link to your favorite journalist about AwayFind.   Don’t send them here, since this post says little about the product, instead mention the homepage and the coverage we’ve gotten with…

People Who Have Been Kind Enough to Write About Us Today

• ReadWriteWeb: Escape Your Email At Last (Really!) With AwayFind
• Lifehacker: AwayFind Gets Urgent Email Through When You’re Offline
• DidIGetThingsDone.com: AwayFind – Increase your Email Productivity
• Chris Brogan: AwayFind Launches Big
• East Coast Blogging: AwayFind, Take Back Control From Your Email.
• Stepcase Lifehack: An Interview with Jared Goralnick — Founder of AwayFind

(I’ll try to keep this up to date)

Not only will this explain how I use Gmail and Outlook, but it’ll describe a fair amount of my workflow with email and social media.

Separating My Worlds

As a geek and business-owner who’s building a web product, my online activities overlap between personal and business worlds. Still, I’ve made distinctions between which email program and domain I use for each.

I use Outlook (and the setconsulting.com domain) for all correspondence related to work projects or with people where the role is generally work-related. That includes direct inquiries from this blog and any correspondence with people from a work setting.

I use Gmail (and dancingwithwords.com / goralnick.com) for all personal correspondence, social media activities, beta sign-ups, and purchases.

One caveat: even though it’s not particularly popular in the geek crowd, I use Outlook 2007 for reading and managing RSS. This offers me the benefit of having offline access to my feeds and takes little effort to flag articles in my regular task system. I mention this because to me it’s really all about convenience/workflow and not just about business vs. personal activities. The fewer places I have to check, the better for me.

Then why separate?

While part of my separation relates to identity and branding, that wouldn’t merit separate email applications—either program would let me send from multiple email addresses. It’s a matter of both convenience and the natural features of the products.

If you live in a top-down, things-have-their-place world then Outlook is for you. If you have a system for managing your data and tasks, then Outlook lets you do it that way (albeit, it may take some time to customize). Since Outlook has a task list (with many views for accessing it), it’s much better at managing things that need to be deferred or followed-up.

If you live in a bottom-up, let’s-jump-in-and-get-moving world then Gmail is your place. Gmail makes it easy to find things and work rapidly, especially for messages that can be quickly dealt with by short messages or archiving. They keep it simple so you can. For getting stuff out of the way fast, Gmail is great.

And perhaps as importantly, I can log into my “connected world” in Gmail or my mostly-work oriented world in Outlook. Outlook helps keep me safe: entering a web browser can be a dangerously distracting place for me.

My life has (at least) a couple modalities, so I have two email systems to go along with it.

Why I Use Outlook

Here are some things that I love about Outlook.

The Offline Experience

All my computers have a fully synchronized version of my Microsoft Exchange data that’s available online and off. With the exact same workflow I can process a lot of messages on a train, plane, or subway.

As I mentioned earlier, I use Outlook for my RSS, which means I can catch up on blogs while offline. I recognize that Google Gears offers most of the features for their Google Reader without an internet connection, but Outlook 2007 has the exact same experience online and off.

Tasks, ‘Nuf Said

Tasks can be intimidating in Outlook with so many options, but once you get going with them they’re darn amazing. I love the integration of the Task list into the calendar, which means that I can get the total picture of my day in one screen (the calendar).

I fully recognize that Remember the Milk has some pretty amazing integration with Gmail, but it still takes more steps and screens. And the fewer steps for me means the more likely it is to happen.

In addition, the fact that Outlook’s tasks are in sync with my handheld’s reminders, online or off, is a big help.

Message Flagging

One of my favorite features in Outlook is its ability to flag a message with a due date and then file it away. It’s the easiest way for me to make a task from a message and then plow through the rest of my Inbox. There is zero copying with all the benefits of a task. (Yes, I’m still caught up on the Tasks thing.)

Mobile Phone And ActiveSync Experience

As of now, Microsoft has a large chunk of the mobile phone market supporting both Windows Mobile and ActiveSync. Since they’re all designed to work with Exchange, things just play well. It’s an okay phone experience that stays in sync with my Outlook application on my desktop.

For BlackBerrys and iPhones there’s much better mobile integration available for Gmail, but sadly that doesn’t help me as it’s limited on Windows phones. However, both BlackBerry and the iPhone offer full Microsoft Exchange support.

Note: if you go through the trouble of installing a Java Virtual Machine on a Windows Smartphone then you can get Google Apps working on a Smartphone…but it’s an awful lot of trouble and not particularly speedy in the end.

Loving My Add-Ins

I’m actually not a big add-in guy, but I’ve been pretty happy with some of the tools I’ve installed in Outlook. At the moment I’m enjoying Anagram (which lets me turn an email signature into a contact in seconds, amongst other things), Xobni (which explains the relationships between contacts and offers a powerful search feature), and OneNote (a note taking and organizing application, and its Outlook add-in allows my notes to very quickly turn into tasks or other items).

Why I Use Gmail

Here are some things that I love about Gmail.

Gmail’s Rockin’ Filters

Gmail’s Filters just feel faster, safer, and more inviting. So I use them more. Thanks to filters I’m at the point where nearly everything that makes it to my inbox is a personal message. That makes my email processing so much faster.

Fast Search, and Stuff I Want To Hold Onto

I don’t have to worry where I put something in Gmail, because it’s so easy to find it, even if it’s stuff that’s years old. Yep, I actually moved all my personal email from 1995 onward into Gmail because it’s so lightning fast to find it there.

I can reliably search for a conversation, receipt, itinerary, login information…without any trouble. Outlook’s search is depressingly inaccurate sometimes and it still lends itself more to top-down than bottom-up searching.

Experimenting is Cheap

I love Google Apps for Your Domain because it gives me an inexpensive place to manage my family’s email accounts while offering decent spam filtering and pretty good administrator features. Sure, it’d be okay to get them on Exchange, but it’s not worth the money when they’re not going to use all those other features (like the ones I wrote about above).

It Just Works

Gmail to me is pretty simple. But not too simple that you can’t do stuff. It’s simple enough that if I don’t think too hard about workflow or organization, it’s easy to find messages, recall email addresses, and file things away. For the place where I put my less-urgent correspondence, it’s great that I don’t have to work too hard to manage it.

Where do you manage your email?

Do you use one place for all of your email and organizational activities? Two? Three? I’d be curious to hear what works for you.

Flickr credit: HarryArthur, rovlls