How I solved my Outlook-Google Calendar issues

How I solved my Outlook-Google Calendar issues

Summary: Working on a number of different PCs and connected devices introduces all sorts of complexity. A constant issue is how to keep all of the information I need access to at hand, regardless of the device I happen to be using. E-mail is pretty easy - between Gmail and IMAP I can access all of my e-mail from any device I use. Calendar info, contacts, task lists, and files all present tougher issues and, as I'm now in full-time platform switching mode using both the Tablet PC and the MacBook as well as the Treo 700P and the Nokia N93, the complexity has increased in a big way.

TOPICS: Google

Working on a number of different PCs and connected devices introduces all sorts of complexity. A constant issue is how to keep all of the information I need access to at hand, regardless of the device I happen to be using. E-mail is pretty easy - between Gmail and IMAP I can access all of my e-mail from any device I use. Calendar info, contacts, task lists, and files all present tougher issues and, as I'm now in  full-time platform switching mode using both the Tablet PC and the MacBook as well as the Treo 700P and the Nokia N93, the complexity has increased in a big way. I'm well on my way to having it all figured out though and thought I'd share some of what I've learned over the past couple of months as I've worked my way through all of this.

Like most GTD practitioners, I rely heavily on my calendar and my task list and reference both many times during the day as I'm working through my projects. Because so much of what is actionable in my life arrives via e-mail, I have developed techniques that make it fast and easy to transfer what is actionable from an incoming e-mail message onto my calendar or task list as it arrives. This is the essence of my ability to keep my Inbox empty (I'm averaging a zero Inbox state at least 4 days a week).

SpeedFiler Outlook add-inDoing this in Outlook is easy enough. I've written extensively about the "magic act" transformations that Outlook makes drag-and-drop simple and how they allow me to process much of my incoming e-mail in seconds. In essence, I drag a message to either my calendar or to my task list, depending on whether there's a hard date associated with the action required (calendar) or not (task list) and then file the e-mail away which I use the SpeedFiler utility from Claritude Software (shown at right) to make fast and easy from the keyboard or with the stylus. From the keyboard, I use the standard Move to Folder shortcut (Ctrl+Shift+V) and type the first few letters of the folder name I want the message filed in and SpeedFiler word wheels the list down as I type. With the stylus, I can select from a list of the folders I've most recently accessed or tap on the folder hierarchy to locate the right destination. Either of these is easier and more precise than dragging a message with the stylus across the screen. There's a lot more to Inbox triage than that but this simple explanation suffices for the current discussion.

In Mail on the Mac, I use Scott Morrison's MailTags to accomplish the same thing. In addition to tagging my email messages (assigning context in GTD terms) and associating them to a current project or activity, MailTags allows me to add either a calendar item or task to iCal while I'm viewing the message itself.  MailActOn allows me to file messages in appropriate folders with a keystroke by enhancing Mail's built-in Rules engine. Both are essential add-ons for the Mac's e-mail application.

Google calendar sync with iCalTo get the calendars on my two PCs in sync I rely on two utilities and Google Calendar as the "glue" to make all of this stick together. To sync the iCal calendar to Google, I use Spanning Sync which was officially released today after an intensive seven-month beta test. This utility matches calendars in iCal with corresponding calendars I've set up in Google Calendar and performs a very fast bidirectional synchronization on either a timed or manual basis. It's easy to set up, fast to sync, and has been trouble-free since the day I began using it. With the official release, Spanning Sync has announced their pricing model - $25 gets you a one-year subscription to the service and $65 gets you a permanent license. I like the options and consider either to be well worth the investment for the trouble-free way the utility helps me keep everything organized.

Charlie Wood first announced Spanning Sync during a panel on APIs and Feeds I moderated at the Office 2.0 Conference last Fall and I've been following the development ever since on his blog. I began using the utility when I picked up my MacBook at the beginning of this year and it has become one of the most heavily recommended utilities in my toolkit - especially for web-facing folks. There are two big advantages to keeping the iCal and Google calendars synchronized for me. The first is that my calendars are now accessible from either of my mobile devices as both the Treo 700P and the Nokia N93 can access the Google Calendar in their browsers with no problems. I also sync iCal with the Treo and Nokia built-in calendar applications using iSync as I tend to use my mobile devices for creating appointments more than just about anything else when I'm out and about with the possible exception of adding actions to my tasks list. I'll discuss how I've brought all of my tasks into a single accessible environment in an upcoming post.

SyncMyCal settingsThe second advantage to having all of my calendar events synced into Google Calendar is that, as I mentioned above, it acts as the "glue" between iCal and Outlook. To achieve the same bidirectional sync with Outlook's calendar, I've been using SyncMyCal. This Outlook add-in works in much the same way as Spanning Sync and allows me to associate one of the calendars in Google Calendar with a calendar in my Outlook PST file. In my case, I associate all of the calendars I'm actively using with the main calendar file in Outlook. SynMyCal can perfor either a one-way (Download Only) or bidirectional synch on demand or on a scheduled basis.

SyncMyCal is available in two versions. The free version lacks only the ability to perform automatic synchronization and to specify a date range to sync. It will sync only a seven-day range. To add these two features, the full version is a reasonable $25. PDA synchronization is promised for a future release which will add additional value to an already useful tool.

So there you have it. Using these tools I've created a pretty much foolproof system that guarantees that regardless of which of my devices I happen to be using, I'm able to access an up to date calendar and feel confident that any changes I make will be updated on all of other devices in a matter of minutes or on-demand, depending on the current context in which I'm working.

This is part of a larger effort I have underway to assemble a "unified field theory of productivity" to address my increasingly mobile work and inability to use just one device. In future posts, I'll address how I'm solving the same issues as they relate to my tasks lists and files. I welcome any suggestions about web services or Windows and Mac utilities you've found to be helpful in keeping your information in sync between your your devices. Feel free to chime in in TalkBack. 

Topic: Google

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  • GTD Outlook Add on

    Love your article, wish it would work for my situation. However, here is an Outlook Add on for GTD people that I find very useful.

    Here are a couple of links:
    • I've covered this in the past... and will again

      Rudy - I've written quite a bit about the GTD add-in from NetCentrics in the past and plan to again as soon as a Vista-compatible version becomes available in the near future. It's a good choice for GTD practitioners and accomplishes what SpeedFiler does an d a lot more.
  • Time zones, the dreaded time zones!

    Marc -

    I know you're a fairly mobile guy, and I'm sure you've got time zone challenges when scheduling meetings. Outlook 2007 goes a long way in addressing the ever changing time zone problem with a nice new time zone button. Those move over quite nicely to my 700p via Exchange. So far so good. But, when I try to get GCal into the mix, it all falls apart. In a given week I may be traveling across, or be scheduling conference calls based on several time zones. Doing this on Outlook 2007 works, but synchronizing it with GCal is still a challenge.

    So, what are you doing to handle time zone challenges when setting appointments (and synching with Google Calendar)?
    • There is no good solution for this AFAIK

      Nitin - it is a problem and as far as I know, there is not good solution to resolve these issues. I just use my excess cranial capacity to make adjustments when necessary and accep that this is an issue that not all software is yet designed to address. Fortunately, most of my travel is between Mountain and Pacific time zones so the calculations are pretty simple.
    • Buy a new watch.

      I'm not being facetious. Use a watch that displays two time zones. Make [i]all[/i] of your calendar entries in your home time zone. The other time zone displays the local time.

      If you're like me and no longer wear a watch, then it's easy enough to find an appropriate clock for your Palm or WinCE device. It's cheap and effective.
      • Got one!

        My trusty Timex Expedition ($39.99 at Target) has dual-time zones, dual alarms and works great. I switch to local time when I'm traveling and leave my calendar alone. When in situ, if I set an appointment, I know it's local time to where I am if the event falls in the time frame I will be in that time zone. I always set appointments to local time for wherever I will be on that date and at that time. Works fine for me.
  • Marc, if you used Lotus Notes, like David and I do...

    You would have had all of this functionality... 7 years ago.
    • That's nice

      But I don't use Notes and none of the organizations I've been associated with over the past seven years has either.
  • Spanning Sync

    Absolutely great post, Marc. Thank you.
    I am trying to implement with iMac and XP combo and Pocket PC and Palm TX, and
    have run into a glitch with Spanning Sync. Right now, changes to my Google
    calendar are not reflected in iCal. I use several calendars in iCal, matching pretty
    much the standard GTD categories, with a bit of customization of course. But, I
    am only using one calendar on Google Calendar. You mention that you have
    several calendars setup on Google (or at least I inferred that) ... do you have a
    Google calendar set up for each category? I'm a bit puzzled as this is my first dive
    into Google calendar and definitely my first dive into Spanning Sync.

    I especially look forward to your post on how you handle tasks across the different
    platforms. I am considering using Google Docs for this and just getting away from
    the task apps, but have use the task apps for so long that I wonder if the
    adjustment would work.
    • Here's what I've done

      I have a calendar defined in Google Calendar that matches each of the calendars I've defined in iCal. It's a 1:1 sync. On the other side (Google to Calendar to Outlook) I have all the Google calendars syncing with the standard calendar in my Personal Folders. I thought about maintaining separate calendars in Outlook to match the Mac and Google but there's a less compelling value in doing that on the PC as I use Categories in Outlook to code and filter events and appointments.
      • Thank you, but Spanning Sync still problem for me

        Thank you for getting back on this, Marc. Somehow I managed to overlook your
        reply for a while ... sorry.

        I have done as you suggested and was able to get iCal and Google Calendar to
        sync. However, some recurring appointments are showing up in the wrong month
        (birthdays and anniversaries in Google Calendar). I left a problem report on the
        author's site and will see what he proposes, but I noticed that there are a lot of
        other major problems reported there in addition to mine. Is Spanning Sync still
        working okay for you?

        On the Windows side, SyncMyCal seems to work okay, but Outlook locks it out half
        the time ... I generally have to go into Outlook options and re-add (check mark)
        the SyncMyCal add-in. Not sure if this is due to Outlook security settings or to
        ZoneAlarm or both, or neither. But, a bit frustrating.

        I've had some success using Missing Sync to sync iCal to my Pocket PC, and then
        ActiveSync and Outlook to sync it on the Windows side, but only after numerous
        iterations and a careful procedure. But, when I tried to add my new T-Mobile Dash
        into the mix, I am having to go through the iterations all over again.

        Enormously frustrating!

        Bruce Keener
  • Good Lord...

    I'm almost hesitant to comment, because what you describe is truly better than what Outlook provides, so in that sense it's a truly useful, informative post. Now, since I own my Domino server I've got no problem synching my multiple machines; I simply can use the Notes client on Windows or on Linux (I don't have Macs). Note that Notes has a built-in webmail client to access mail and calendar. So I'd guess that for many Notes users synching with Google isn't something that's proved necessary, though I might experiment now that you've mentioned it. I've got Google, of course... it's just that it hasn't proved better than what I use.

    Your post is useful and informative in another sense, too... [i](and here I'm going off-topic, since your post is about keeping your calendars synchronized and not about general productivity. So I'm not kvetching about your post OR your solution. I just want to make an admittedly verbose observation and illustrate it.)[/i]

    I [i]don't[/i] use Outlook, so I'm sometimes take the tools I have for granted. A quick for instance...

    [i]I never file anything.[/i] I don't need to. Every contact in my database has categories associated with their name. When email arrives in my Notes inbox, it's picked up automatically, uniquely identified by the sender's email address, and and is imported into my correspondence database (along with any emails where the subjects match certain key phrases) flagged as "unread". Everything else is held in the spam trap. This is a simple case of whitelisting... except that the import also applies the appropriate categories for me, and associates the incoming documents with the metadata in the organization and person profiles. Rather than manage a list of rules, this behavior is built-in and based on the correspondent's profile. This is all done with no human intervention. Again, I do no filing. That's what the program is for, and after having had this digital secretary as long as I have, I don't think I could tolerate a program (like Outlook or Evolution) that didn't do it for me. My inbox is ALWAYS empty, every hour of every day.

    The upshot is that, having expended zero energy in filing, my correspondence is instantly categorized and prioritized. If I want to view all the correspondence with Marc O., I can do that. If I want to view correspondence with anyone from his company, I can do that, too. All correspondence for all vendors that may have worked on "Project X" (or any other category)? Sure, I can do that. By date? Yep. In addition, I can do nearly instant full-text searches for criteria I haven't even considered... and I can combine views and full-text searches to find information during a phone call so fast you don't even know I'm looking it up.

    Since everything is related on receipt, I rarely have to look up a contact's record. Then it's usually for BI, and not interactive. The pertinent contact information is always displayed right there with the email, or fax, etc. I can read an email, and from the email click the "Dial" button to phone the sender. I don't even look up phone numbers.

    If anything proves to be actionable, I simply click "convert to JournalEntry" on the email's actionbar. I put a date on it, and tell it what type of action we're talking about (To-Do, appointment, etc.) Now, if I were using plain-vanilla Notes I'd be able to do the same sort of thing by changing the form from Memo to Appointment. My method is a little bit of improvement in that it preserves the original correspondence and hyperlinks it to the action item. If an action item is billable, then I simply click the "Billable" checkbox and at the end of the month the program knows to apply the properly hourly rates to the time calculated from the calendar entry itself when I'm building that customers' invoice (unpaid billable calendar entries show up as if they were inventory items).

    My purpose here isn't to push my system (I'm unusual in that I picked tools that allow me to empower myself, and most people stick with the market gorillas regardless of their options), but simply to point out that most people think that the dragging and filing they're forced to endure are easy simply because they haven't had real alternatives to it. And believe me, it takes a lot of development effort to make a system that does all this when that's what your computer should have been doing all along.

    Both Microsoft and Apple could stand to go back to school to figure out what usability and workflow are really about. IBM's closer, but they're delivering the path to a solution, and not the solution itself. Linux vendors are too often concerned with delivering the same **** that everyone else is since that's all people know. All of these vendors' thinking is anchored inside the box. By this I mean that because of their thinking, their users are concerned with what's going on in that box, when they should forget the bloody box and concentrate on the people outside of it. The box should be a facilitator for your job, not part of the job itself. Using it should feel like...thinking. And I think it's just plain sad that with billions of dollars spent in R&D and usability testing that absolutely [i]nobody[/i] delivers a truly satisfactory stock solution 40 YEARS after Doug Englebart described the goal.

    That's my rant. Thanks for the space.
    • Nice explanation

      Dave - your fondness for Notes and Domino is well known to regular readers here and it's apparently a good fit for you and the work you do. I've used Notes in the past but it's been quite a long time since I had the opportunity to spend any time using it. I don't have my own server (and don't want to), am in the position currently where I'm adding and dropping devices from my toolkit (especially in the PC and mobile categories) on a fairly regular basis, and am trying to create a solution that accomplishes two things (primarily:

      - make my data accessible in an up-to-date state from any of the devices I am using currently or may switch to as I continue evaluating new tools.

      - find the appropriate role for web services in my system so that even when my best option is to use someone else's PC, I can access all of my stuff.

      Understand that I've been using Outlook for a long time and it's been a great tool for me. It does everything I need it to do and I've learned to configure and use it in a very effective way. Like you, my e-mail Inbox is regularly empty (except when I'm traveling and in all-day-into-the-evening meetings like I have been this week).

      While your Notes setup sounds like it works for you, I'm guessing that this is the product of quite a bit of learning how to use the tools to best advantage and configure the client and server to meet your needs. It seems unlikely that someone less experienced and knowledgeable in using Notes and setting up Domino would have the same experience you do.

      I [i]do[/i] use a Mac, [i]don't[/] use Linux (and don't intend to) and am pretty sure based on the feedback I've gotten here in the comments and in direct e-mail in response to this post that there are a great number of people who use a similar (if less varietal) set of platforms, devices, and tools as I am.

      Take from this what you can and leave the rest. As always, I'm not trying to convince anyone to change what they're using or doing - just sharing my approach in the hopes it may provide a good idea or two or answer a nagging question.
      • Sorry for the extended italics in my last comment

        I shouldn't use tags late in the evening when my eyes are tired and my brain is medium well-done. ;^)
      • Oh, I agree 100%

        As I said up front, my rant was off-topic. It was in no way intended to be critical of your approach or solution. Your post was, as I said, informative and useful. My brother's a big Outlook user (and not likely to change); if he follows my advice he'll read your blog and do likewise.

        I also agree (and said) that my setup was the product of lots of development effort on my part (you have no idea how much). And it wasn't a sales pitch for Notes. The reason I [i]had[/i] to put all that development effort into it was because Notes, out of the box, doesn't do what I want. As a tool it's capable; as an end-user application it's not. Its main saving graces for individuals are that the necessary functionality (other than web services) is largely contained in the single Notes client rather than being spread around; and it's easier to modify than other packages. Most users are neither capable of nor inclined to do that.

        What I'm frustrated at is the fact that folks like you and I [i]have[/i] to jump through these kind of hoops to get our systems to work smoothly. Nobody... and I mean [i]nobody[/i]... offers a system for managing your information that's really effective and transparent and coherent and consistent. This is despite the fact that people have been studying and working on this sort of thing longer than most of your readers have been alive. Having read "Augmenting the Human Intellect" by Doug Engelbart, I'm continually surprised at how disjointed and frankly difficult are the systems we've built. (That's as compared to what they could be and were envisioned to be in the 60s.)

        I dunno... maybe the original work was too cerebral. Maybe the vision that applied to large central systems got lost in the PC revolution. But we're at the point now where "the network is the computer", and much of that old stuff is current and new again as applied to distributed, rather than centralized systems. Maybe it just needs to be restated for a modern audience. Or maybe I'm just barking up an empty tree.
        • Oh, one other thing.

          The reason I post this sort of thing [i]here[/i] as opposed to elsewhere is that of all the blogs on ZDNet, yours is the one where such things are most likely to be read intellectually and fairly rather than immediately descending into some platform-religious flame-fest. (though as soon as I say it...)

          Besides, if the title is "Office Evolution", isn't it fair to actually talk about the [i]evolution[/i] of our office systems (both past and prospective)?
        • As usual - we agree that there is no perfect solution

          Dave: No worries. I think you and I have gotten past explaining our motives - at least to each other ;^)

          I had a good talk with a new PM for OUtlook last night at dinner (I'm in Redmond for the MS MVP Global Summit right now) and we were both talking about how hard it is to get Outlook configured to do what you want. He's young, idealistic, and coming from an academic background so maybe hecan help them make good decisions about the next release.

          What can I say? I'm an optimist at heart ;^)

          I suspect you are too.
  • Tasks?

    Thanks for the tips on using Google Calendar. You talked about e-mail and calendar sync - what do you do about tasks? (The most important GTD component.) I'm currently trying to figure out how to keep things in sync when I have two Exchange e-mail accounts in different companies (my employer and my full-time client.)
  • What about Contacts?

    In your article you mention Contacts and Files being a part of the problem in syncing multiple computers. Any luck with syncing Outlook to Google Contacts? If so, what do you use? Thanks for the Calendar tips!
  • Similar Problem Outlook to Google Calendar

    I had a very similar problem to yours. My personal calendar was in Google and my professional calendar was in Outlook 2007. It was painful and frustrating and in the end I leveraged Outlook 2007's built in calendar publishing to syndicate my calendar to Google. I was so happy with it, we ended up wrapping it in a service. You can read about my experience here: