The Mac and the Droid

The following off-topic article is written strictly as a service to Macintosh users who may be getting started with a new smartphone, and who I would hate to see making the needless mistakes I made with mine.

Can A Mac User Get Along With a Google Phone?
I travel a lot, my work involves a lot of project and document management, and much of what I do is dependent on the Internet. It’s the kind of work for which I have long thought a good smartphone could be very helpful. I’m locked in to Verizon as my cell phone provider (for reasons that don’t matter here), and for months I eagerly followed rumors that they would soon offer the iPhone. I held on to that hope as long as I could, but last month, reluctantly, I gave up. If the iPhone was ever going to come to Verizon, it wasn’t going to be soon enough to meet my needs.

That was a tough conclusion for me to come to, since I’ve been exclusively a Mac user since the mid-1980s, and I know how good Apple products can be. Verizon’s December introduction of two new Droid phones made it easier to take, though. These phones, with Google’s Android operating system, have virtually nothing on them that comes from the “evil empire” (as we Mac users lovingly call it) of Microsoft, and they looked very good in early reviews. So I went that direction, choosing the HTC Droid Eris model over the Motorola Droid because of its lower price ($99 versus $199, after rebates), and because its HTC Sense user interface was getting raves from its users.

Thus began my odyssey of marrying my Mac computer life to a Google phone operating system. After lots of trial and error (I’m an experimenter at heart), here’s my conclusion. The Eris is a really fine smartphone.* If you want to use it in conjunction with a Mac, you certainly can. You can do it wrong, or you can do it right. I’ve done both. I’m here to tell you what I learned by doing it wrong, and eventually getting it to where it’s right for me.

The story I’m about to tell has a happy ending: the phone can work very well for a Mac user. I’m sure it’s nowhere near as clean and easy to use as an iPhone. I have the advantage of never having actually used an iPhone, though, so I don’t have that superior experience to compare to my own. iPhone users who read this will undoubtedly shake their heads sadly at the story I’m about to tell. But at least the Droid is available from providers other than AT&T. And yes, it does work with a Mac.

The Droid Eris runs Google’s Android 1.5 operating system, while the Motorola Droid is already on Android 2.0. (The Eris is slated for an upgrade to 2.0 or 2.1 in first quarter 2010.) I have only used the Eris, but as far as I’ve been able to tell from spec sheets and reviews, what I have to say here applies to both phones, and probably also to other Android phones from other providers.

The first order of business with a new phone is to fill up its phone book. The salesperson where I bought the phone tried to transfer my contacts from my old phone, but there was an equipment problem at the store—no fault of the phone—and the transfer failed. “No problem,” I said. It will synchronize with my Google contacts, right?” She assured me I was right about that, and I went happily on my way, ready to solve my own problems my own way.

Android is a thoroughly Google-centric operating system. It has options for email through Exchange servers (which I have not tried, not having a need for it) and POP3 (which is satisfyingly simple to set up and easy to use); but you really have to have a Gmail account set up to unlock many of the phones features. One of those Google features is contact synchronization, which is intended for use only with a Gmail contact list.

I was ready. Or at least I thought so. My Mac is running Snow Leopard, which provides for Google-Address Book contact synchronization (Leopard does not have the same capability unless you’re using an iPhone or iPod touch with it—or if you want to try a terminal command to get around that limitation. I have no idea how well that works and I make no representations about its safety.) I knew all this in advance. I had already set up my Google contacts list, I had tested it, and I had confirmed it would stay in sync with my Address Book. “No problem,” I thought, “I’m on my way!”

And there was yet one more problem: In Address Book I had also combined some married couples’ first names: [First Name:] James and Sandra [Last Name:] Bailey. When that synced with Google, and then back again to Address Book, it became [First Name:] James and [Middle Name:] Sandra [Last Name:] Bailey. Worse yet, on another round of syncs some of them became something like [First Name:] James and [Middle Name:] Sandra [Last Name:] Sandra Bailey.

This was not going well. I did some web research and found a shareware utility that would bypass Google’s contact synchronization altogether: The MissingSync for Android by Mark/Space. I downloaded the free trial version and used it to replace all the contacts on my phone. It was slow. For my set of about 1,100 contacts, it took over an hour to read, compare, and update contacts. After that it only synchronized what changed, but it had to read everything from both devices, so even then its speed was nothing to brag about.

I did find other things to like about The Missing Sync, which I’ll return to later. But for Contacts I decided to re-establish the Google connection. Did I mention this article was about what not to do? I made the mistake of keeping both The Missing Sync and Google synchronizing at the same time for a couple of days. Theoretically, if all they’re doing is synchronizing, that could work. Theory falls before fact, however. I ended up with at least two, and in some cases four, copies of every contact on my phone.

In the end I disabled The Missing Sync entirely for contact management. I systematically removed every prefix and suffix from every contact in my address book. I cleaned up all the combined couples’ first names. I told iSync to do its synchronization thing, and before long my Google address list looked just the way it should.

It looked right. But it really wasn’t. There were still duplicate contacts galore in the phone. I had to discover and run one more step. I noticed that my Google contacts had a list called “My Contacts,” numbering about 1100 persons (which was correct), but at the bottom of the window was another link to “All Contacts” numbering about twice that many. There were duplicates hiding in there, which the phone was faithfully reproducing. I selected “All Contacts” and clicked the link instructing the page to find all the duplicates and merge them together. That worked fairly well, but some cleanup was still necessary. I went through and systematically (again) deleted all the contacts with prefixes and suffixes—they were duplicates of contacts without that extraneous information, so it was safe just to delete them. One more sync, and everything was finally just right.

That was a long story I could have avoided—and you could too—by knowing how to clean up my Address Book contacts to make them Google-friendly before my first sync with Google contacts. Here’s the right answer: Start before you get your phone. Remove the prefixes and suffixes in Address Book and make sure you only have one name in the first name field. You’ll be off and running and wondering how I could have had so much trouble. The Google contacts method is free, it’s easy, and it works. If you do it right, that is—which I was finally figuring out.

But contacts aren’t the only thing most users want to synchronize between their computer and their smartphone. The next most important thing to me was my calendar. I tried two different approaches to matching calendars on my phone and computer. I started by backing up my iCal information. (That proved to be a very good idea. Backups often are.) Then I created a CalDav link (available in Snow Leopard’s iCal Preferences) to my Google account. There was a problem with that from the start: I had several different calendars running on my computer: Work, Family, Church, etc., but I could only sync one Google calendar with iCal. For the sake of free synchronization with the phone I moved all my current and future calendar items to the Google calendar account. The process ran, and soon all my events showed up on my phone. It worked.

But I wasn’t happy about giving up my separate calendars. And appointments I had accepted by email from other persons’ iCal or Exchange calendars were stubborn: they wouldn’t move to the Google calendar. I did some more research and found BusySync from It promised to sync my information with Google the way I wanted it. So I restored the old iCal information I had backed up, ran BusySync in its free trial mode, and voilá, there on my Google calendar web page, all of my iCal calendars were there fully duplicated, right down to the color coding. Not only that, but after that synced with the phone, the same set of calendars showed up there, too! Syncing worked perfectly in all directions: an event entered on iCal, on Google Calendar, or on the phone would soon show up in all three places. For me that was easily worth the $25 BusySync license fee.

BusySync works on Tiger and Leopard, too. If all three of these are true: you’re running Snow Leopard, you don’t use multiple calendars, and you don’t get emailed appointment invitations, then you probably won’t have much interest in BusySync; you can just use a Google calendar connection on your Mac. Otherwise, though, I think you might agree with me that BusySync is worth the moderate expense.

To-Do Lists
The Droid’s Market (Android’s version of iPhone’s App Store) offers a number of highly rated to-do lists, but I wanted one that would sync to my Mac, and I wasn’t very impressed with the offerings I found there. None of them were free, for one thing. I settled on a lesser-known solution, Tasks, by Crowd Favorite. I have some history with Tasks; I had used it for a long time in the not-too-distant past, and though its interface takes some getting used, to, I liked its flexibility and its hierarchical structure. I quit using it some time ago when I started spending a lot of time on airplanes; Tasks is a web-only solution, unless you have the skill and daring to set up a MySQL server on your own Mac. Now that I have a smartphone, though, my priorities have changed. Having the same task list both on the phone and on the Mac has become valuable enough that I’m willing to be away from it for short periods once in a while, like on airplanes. And being a web-based solution, the exact same Tasks list is always immediately accessible both by computer and by the mobile device (it has a pretty decent mobile interface).

For $29.95 you can set up your own full version of Tasks on your own server, which is how I was using it previously and have now returned to doing. That takes a website and a minimal level of comfort with setting up a database. But you don’t need a website or special skills to use Tasks. You can use Crowd Favorite’s own hosting for just $3.95 per month instead. And here’s a nifty trick. Tasks allows you to attach tags to each item. Some of my to-do items are, of course, phone calls. I’ve marked all the phone calls I need to make with a Phone tag. On my Droid, I have a bookmark and shortcut set up to select just those tagged telephone tasks. That in itself is helpful: where will you find a more sensible place to gather your list of phone calls to make, than on your phone? But there’s more. When I create the task (normally on the computer, not on the phone), I can enter the phone number I need to call. When I open that same task on the phone, all I have to do is tap that pre-entered phone number and the phone dials it for me.

Not everyone will like the Tasks interface. Google itself has a to-do list function I’ve never tried. (I was already well-enough satisfied with Tasks, and I already had a licensed copy, so I didn’t need to look for another web-based solution.) Android’s Market includes to-do lists with cleaner interfaces, some of which are location aware: they’ll remind you what to do when you’re where you might need to do it. If some of them improve their synchronizing capabilities I may switch. But not yet.

Music And More
The Droid has file storage, music, podcast, and photo capabilities as well. You can connect the phone to the computer by USB and transfer your files manually from the Finder. But this is where The Missing Sync is really useful: it will keep all your chosen items synchronized and up to date for you automatically, every time you make that USB connection. I tried transferring a CD’s worth of music to the phone directly from the finder, without using The Missing Sync. It worked—sort of. The songs played in alphabetical order. And it was a musical—Les Misérables—I was trying to listen to. I can assure you the writers of that show did not sequence its scenes in alphabetical order.

The Droid really doesn’t specialize in music, and in my opinion it would be a mistake to treat it as if it did. I’m not giving up my iPod.

I haven’t even tried to use anything but The Missing Sync for my photos. Its price—$39.95—seems rather high to me, especially if one makes the $25 commitment for BusyCal, but it just might be worth it. I’m not quite sure yet—I’m approaching the end of the trial period for The Missing Sync, and I haven’t decided whether I can afford it. But I do recognize the value it offers. The Missing Sync will also keep a designated folder of documents synchronized with your Android, though that could be done about as easily through the Finder. It will also keep your videos and ringtones in sync. (Mark/Space says they will be adding Calendar synchronization to the package at some indefinite future time. Depending on how that works, it might render the $25 investment for BusySync unnecessary, which would make The Missing Sync that much more attractive.)

I suppose if there are any Mac/iPhone users who have followed this discussion to the end, you’re thinking, “All this could be so much easier.” I have the advantage of never having used an iPhone. I don’t know what I’m missing! And in the end, what I’ve found really isn’t hard to work with. With a properly prepared set of Address Book contacts and a Google contact list to sync it with, I’m happy with how contacts work. BusySync makes calendar synchronization just about perfect. The Missing Sync takes care of the rest; only music is seriously inferior on the Droid, in my experience.

The Bottom Line
In other words, iPhone users, you can still shake your head sadly. I know your Apple product is, well, an Apple product, which makes it hard to beat. But I still really like the Droid Eris. It has capabilities and features I haven’t mentioned here since they have nothing to do with connecting to a Mac, but which are proving to be both fun and productivity-enhancing.

I’ve found it can work successfully with the Mac. It’s not as clean a connection as the iPhone’s undoubtedly must be, yet it works. Mac user, chances are you’ll like an Android phone just fine. I hope the story of my mistakes will help keep you from making the same ones yourself.

*I have received no consideration or compensation of any kind with respect to any of the products or companies mentioned here (not that I would be opposed to it 😉 ). This is not intended as an exhaustive review of any product, but only as a description of my experience. Where I said I did not find some capability in some product, that should not be taken to mean anything more than that I did not find it. The capability might actually exist. Your experience with any of these products may be different than mine. The names I used here as sample contacts are all fictitious.

Tom Gilson

Vice President for Strategic Services, Ratio Christi Lead Blogger at Thinking Christian Editor, True Reason BreakPoint Columnist

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3 Responses

  1. Tom Gilson says:

    I just found out about DoubleTwist for syncing media. I’ll be giving it a try.

  2. Rachel says:

    I have been beating my head against a wall for about a month now trying to determine how to sync my work iCal to my Eris calendar for easy/quick access on the go. YOU HAVE SOLVED MY PROBLEM! Busysync is working beautifully as of about 5 minutes ago. Thank you for putting this discussion out there!

  3. John says:

    If you mount the USB connected storage to your mac and start up iPhoto, it will find the photos just like if you used a regular digital camera. So, downloading your photos to the mac is one step more than a digital camers (mounting the USB flash storage)

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