Share Your Thoughts and Tips on Data Syncing

One of the most visited pages on this blog is my March 2007 article on Keeping a Pocket PC, Outlook, Mac iCal, and a Palm in Sync. When I recently realized how popular that page is, I also realized a couple of other things:

• I have learned some things writing that article, and probably needed to revise the article to reflect that. So, over the holidays I rewrote it.
• Maybe a fresh new article on syncing might be of value.

This article is a result of the second bullet. This article repeats a good bit of what is in my updated March article, but the focus herein is different: I hope this article generates further discussion about the value of data syncing and the possible ways of keeping data in sync across multiple devices and multiple platforms. I think we can learn a lot from each other in this area. All I am trying to do is to get a discussion going by sharing some of my experiences and thoughts on data syncing.

My own experience has been in trying to sync data between a Mac, a couple of Windows installations, a few PDAs and Smartphones, and Google Calendar. My Ubuntu installation has been gathering dust for the past couple of months (haven’t made the time to do anything with it yet), so I am unable to personally share insights on syncing with Linux. Hopefully some of you can chime in with how to do this.

I do think one can become so absorbed in trying to keep data in sync so as to miss out on some better ways of managing data. In my case, my desire to sync PIM data across multiple platforms and devices has kept me from experimenting with some potentially useful Getting Things Done applications on my Mac. For example:

• A few months ago I was accepted into the private beta of OmniFocus but ultimately dropped out of it because I wanted to use only apps I could sync existing data with.
• For the same reason, I have missed out on experimenting with iGTD.

Given that I use my iMac far more than the other devices, perhaps I should change my philosophy about trying to keep data in sync.

Reflecting on my own situation brings me to a couple of key conclusions about data syncing:

• You need to decide what your data needs really are. I personally have wasted far too much trying to keep data in sync across platforms and various devices when I have no real need to do so.
• New applications and online tools are being made available all of the time. That’s good. And bad. We all appreciate competition: it results in better products for all of us, ultimately. It can also cause us to go from one application to another, looking for the perfect data solution. If we are not really, really careful, we can wind up chasing down a rabbit hole that has no bottom.

With these points in mind, I’ll now mention a few ways that one can approach the data syncing issue. Although the following is somewhat repetitive to my March post, it seems worthwhile to repeat some of its points herein:

• You can use a hosted exchange service with a suitable PDA (Smartphone, BlackBerry, a Pocket PC with Wireless connectivity), Outlook, and Entourage on the Mac.
• You can use an online syncing service that is designed to sync across multiple platforms. You can get a sense of one such service, Plaxo, by reading my interview with Plaxo VP John McCrea
• You can use software on your Mac to brute-force a syncing between iCal, Address Book, Outlook, and a Pocket PC. Software such as Missing Sync or SyncMate can be used to implement this approach. I discuss my use of Missing Sync in my sync article I mentioned earlier.
• You can decide to not waste time keeping everything in sync, and just keep your data on one platform and one handheld device. In my case, I run Windows on my iMac through VMware Fusion, so I can have Windows and my iMac operating simultaneously and can even copy and paste data between them. I describe this a bit in How VMware Fusion Eliminates Some of My Syncing Woes
• You can skip the syncing altogether and use online tools such as Google Calendar, Gmail, and Remember The Milk.

I discuss some advantages and disadvantages of each approach below. Again, this is not intended to be an “everything you wanted to know about syncing” discussion, but one that touches on key points and spawns further discussion.

Using a Hosted Exchange

I used this approach in the year preceding my retirement. Being tied to my corporate exchange server worked great.

Recently I experimented with setting it up for my personal use. I selected a hosted exchange service (there are many to choose from), and used it to tie into Outlook via the Windows partition on my Mac. Then I set it up on Entourage on my iMac. Lo and behold, my Outlook and Entourage were now synced.

But, when I got to the part of setting it up on my BlackBerry Curve, I found out that I need to have BES (BlackBerry Enterprise Service) instead of the BIS setup I have (BlackBerry Internet Service). Given that this could cost me up to $30/month extra, and given that the hosted exchange cost is about another $20/month, I decided against this path.

If I were consulting a lot, especially if I were on the road a lot, hosted exchange service would certainly appeal to me. But, with me having a fixed retirement income, I decided to not go this route and cancelled my hosted exchange service. This is a great option for you to look into, though, if the cost does not concern you and if you use Entourage on a Mac (hosted exchange does not work with iCal).

Update: What I originally had in this paragraph was wrong. I had noted that hosted exchange does not work with an iPhone. But, Thomas sent an email to me stating that you can use hosted exchange to sync data with Entourage and then use iSync on the Mac to sync that to iCal and Address Book. Of course he is right. I had overlooked that. Thomas will probably provide more detail in the comments when he gets time, but I thought it important to clarify this.

Using Plaxo

For a while, I thought Plaxo was a perfect solution for keeping my two platforms and several devices in sync. I can say that it does a very good job of syncing what it does sync. The only real downside I saw to it was that it does not sync your Outlook Tasks to iCal (or vice versa). And, it creates a new calendar in iCal that has all of your Outlook entries in it, rather than creating separate iCal calendars for each Outlook Appointment Category (such as Work, Home, Travel, …). If you want true syncing across Outlook and iCal, it does not really give it to you.

However, it does sync your tasks and calendar and contact and notes online, so you can access them anytime you are online:

Plaxo does have the added benefit of syncing your data to Google Calendar. For my situation Plaxo works well. I can forget about iCal and just use it in the online mode when I am using my iMac. I can change (or add or delete) tasks online, and they will sync back to Outlook when I boot into Windows. Plaxo is available as a free service, although I use its premium service so I can have access to its Pulse features (not related to syncing).

Using VMware Fusion

VMware Fusion lets you ignore iCal and Address Book in the Mac, so that you use Outlook exclusively, even when you are at your Mac. It does not populate your Outlook data into the Mac apps, so if you want to do that, this approach will not work for you. If you decide you don’t care that the data is in iCal as long as you can access it in Outlook from your Mac, this is a painless way to go.

Using Google Calendar and Other Online Data Services

A lot of people I know are just fed up with trying to keep data on different systems, and are using Google Calendar and Remember The Milk and Gmail and similar apps for just keeping their data online. If you can be connected all of the time, this is probably the most sensible approach. Software manufacturers will always stick with their own data formats, and there is virtually no hope that iCal and Outlook and any other PIM software will ever use a common format that makes it easy for you to sync your data between them. Going to an online approach overcomes this problem.

If you are tethered to Outlook in your office, though, this approach is not likely to work for you, unless you can get your IT department to find a tool to sync your Outlook data with Google Calendar and other online apps of interest. Few IT departments would be willing to take this on, though, as it would often involve supporting software by third-party vendors that do not have an established credibility with corporate IT departments.

Note, some online PIM applications are compatible with Google Gears (for example, Remember The Milk is), so you can have your data without even being online.

A couple of final thoughts on this approach:

• It should work well with the iPhone (or even with the iPod Touch, if you decide to use it is a PDA).
• My sense is that this is the approach being taken by a lot of entrepreneurs and small business managers. I have no data to back this up, but I do a heck of a lot of reading and and research, and that has led me to suspect that this is the case.

Your Turn

Well, I’ve overviewed data syncing based on my knowledge of it, and would love to hear your thoughts and tips on it. Let’s make this post a repository for good information on how to sync and on whether syncing is worth all of the effort.