Migrating Palm to iPod: a dinosaur evolves

The Cretaceous era

I'm never the first to lunge for the bright and shiny. My apartment building dates from the 1920s. My car is a '91 Subaru.

I started using a Palm T|X a little more than halfway through the gadget's 3.5 year production run. I've been using it for about four years, until last week. What happened last week? I bought an iPod Touch 4G.

(Why not a smart phone -- an iPhone or an Android? Simple. I don't like to get sucked into screens when I'm out and about, and I hate talking on the phone. So why pay a monthly data plan fee only to suffer always-on internet and always-available phone service? Look, that's a plane ticket to Paris, each and every year. Think about it. Anyway, you can run Skype on the Touch 4G over a wireless connection, if you've got one. That's good enough for me.)

When I first got a Palm T|X I migrated the data from my Palm Tungsten T, a device I used for the previous four or five year. Mostly calendar, contacts, and a categorized pile of notes, everything from poems I like to carry in my pocket, to the battery type used in my desk clock, to New York restaurants that friends recommended, to my novel manuscript.

A novel manuscript, you ask? On a PDA? What ever for? Well, backup for one. Also, I have an infrared keyboard that works with the T|X, and software from DataViz called DocumentsToGo that lets me create and edit Word documents on the device. It's a handy way to work in a cafe, lighter than a laptop.

But I'm not selling Palm PDAs today, I'm talking about getting from point A to point B.

See, migrating from an old Palm to a new Palm is one thing. Palm had me covered, it was a cakewalk. Getting data from a Palm device into an iThing? That's another story altogether.

Warning to readers: this is going to get pretty geeky. More than anything it'll be useful to folks migrating from Palm to iPod themselves.


What to migrate?

With eight or nine years of accreted information in my latest Palm device, I was determined that before I made a switch I had to know I could get the important stuff moved over without undue pain. For me the important stuff included my old calendar data (which functions, essentially, as an electronic diary -- a record of what happened when); contact info that includes personal and work-related people and businesses; and all those notes, to which I've more-or-less outsourced long term memory.

A look around the web wasn't encouraging. I found little in the way of one-stop solutions. Those who claimed to have easy-to-use synch software that would migrate everything sold it at a cost (i.e., it wasn't freeware), which would have been fine ... but the fine print revealed that the products don't quite do everything after all.

Some of the solutions were cloud solutions. I wasn't looking for a cloud solution. The "P" in "PDA" stands for "Personal." Personal Digital Assistant. I didn't put information about who I met when, what I need to tell my doctor, and so on, into my P-as-in-personal D A only to upload it to some corporate-owned server and have Sergei Brin or Steve Jobs datamine it, or hand it over to the government. Nein danke.

What I really wanted was to use my new device's built-in synchronizing capability to migrate the big ticket items, and to keep a copy of that same data current on my home computer. If I could do that I'd be happy to let the little stuff go. Setting low expectations, in my experience, is the surest path when it comes to getting machines to do one's bidding. Did I mention that I work in Information Technology? Shoot yourself in the foot enough times, you learn a thing or two.

So what were the most likely options? Outlook. iCal. Address Book.

I'd never used any of these programs before. I've owned and worked on Microsoft computers since the early DOS days, but have avoided Outlook like the plague. I'd always figured the Mac's calendar and contact tools were for those who use Apple bit boxes as their primary machines. My Macbook is far from primary, it's a carry-to-meetings machine (a plague on meetings, with or without a sleek little laptop).

Nonetheless, Outlook, iCal, and Address Book looked like the most complete, ready-to-roll options for desktop synchronization of my new iPod Touch.

Since my main machine is a Windows 7 box, it looked like Outlook was going to have to replace Palm Desktop as my home computer's repository of the stuff I carry in my pocket device. I installed Outlook 2010 reluctantly -- I'd unchecked it when I first installed the MS-Office suite, because I had no interest in using the application. So it goes.


The pain

But neither the export capabilities of any one version of Palm Desktop, nor the iPod-friendly import and synch capabilities of any one desktop app or suite were up to the task. Not solo.

Palm Desktop 6.2.2 on my Win 7 machine would happily export all my notes, and keep the categories straight; and Outlook 2010 would happily import them. But that version of the Palm software wouldn't export all my old calendar data in a single go, or my contacts either. And one-at-a-time was a non-starter.

Palm Desktop 4.2.2 on the Mac, on the other hand, would export calendar data and contacts (as vCal and vCard data sets), which could be imported into iCal and Address Book on my MacOS 10.6 laptop ... but I didn't see a way to move the notes over using the Mac software.

I needed all the bit boxes I could get my hands on. And two versions of Palm Desktop. The migration was going to be a hack. Pity the schlub trying to juggle this stuff on one operating system.


How I migrated

First I exported my data from the desktop-synched copies of what I had on my Palm device, and into desktop software to which the iPod Touch 4G could synch:

• Calendar: From Palm Desktop 4.2.2 on MacOS 10.6, I exported all calendar items as vCal. Then I imported them into iCal (included w/ Mac OS 10.6).
• Contacts: From Palm Desktop 4.2.2 on MacOS 10.6, I exported all contact items as vCard. Then I imported them into Address Book (also included w/ Mac OS 10.6).
• Notes: From Palm Desktop 6.2.2 on Win 7, I exported all notes as Tab-separated values. Then I imported them into Outlook 2010. While I was there, I moved categories of notes into folders I created using the category names. This was a waste of time as far as the iPod is concerned, but it keeps the notes more organized on my desktop.

Next, I did a double-synch trick.

When I first started the new iPod Touch 4G I synched to iTunes on my Win 7 machine. That became my "home" iTunes instance, but the first synch was all about music, not about moving PDA data into the iPod.

Once I had all my Palm data exported and imported properly into iTunes-compatible desktop software, it was time to port it to the new device via synchs to iTunes on both my Mac and Win 7 computers:

• First I synched the iPod to iTunes on the Mac. I had to be sure to specify that I did not want to overwrite the iPod with the music in my Mac instance of iTunes -- I wanted to keep my Win 7 desktop as the machine to which I would normally and primarily synch. But on the "Info" tab of iTunes, I specified that I wanted to synch Contact and Calendar data between the Mac and the iPod. Voilà. Palm data migrated.
• Second, I synched again to iTunes on my Windows machine, this time specifying on the "Info" table that I wanted to sync Contact, Calendar, and Notes data with Outlook. Voila, Palm notes from Outlook to the iPod, iPod calendar and contacts from the (Mac synched) iPod to Outlook.

Then it was time to look at what got screwed up.


What I lost

Nothing worked perfectly. But, remember, I'd set my expectations low...

• Calendar: This was the most painful migration. A lot of repeating events didn't migrate at all, I can't say why. Others migrated ... weirdly (all day events that ended up spanning two calendar days). And notes associated on my Palm T|X with repeating events that did migrate were nowhere to be found in Outlook or the iPod (they'd made it only as far as iCal). I had a fair few repeating events, many of which had notes, so that was disappointing. Repeating events are handled weakly in the iOS calendar app, so it's not so surprising that the migration dropped data at the iCal-to-iPod step. Alas. On the other hand, much of my calendar data did migrate, including future events which are the ones that matter most, so I'm just sucking it up, copy-pasting the future-essentials from Palm Desktop to Outlook, and letting the past remain archived in my Palm Desktop software. For a few more years, anyway, then it'll be bye-bye forever.
  
• Contacts: So far I haven't found any lost data. On the other hand, custom fields are labeled in a pretty ugly way: X-Palm-Custom1: blah blah blah. Ditto for categories (X-Palm-Category1:...). Okay, I'll live with that. Over time, if I get really bored, I'll manually edit out the field names.
  
• Notes: Notes on the iPod are weak too. There are no tags or categories, it's just a big old pile of stuff. The good news is that iOS makes it easy to search through big piles of stuff. Still. Bummer.
  

I didn't mention ToDo lists. I used them on the Palm, but iOS doesn't have a native ToDo app (that'll change in the Fall, it is said, with the rollout of iOS 5's "Reminders" app). I'm planning to copy-paste the ones that matter manually, assuming I upgrade to iOS 5. Yeah, I could download an app and have it now ... one friend recommended Toodledo, which is practically free at $2.99. Maybe I'll try it as I settle into the new device.


What I gained

So far I like the iPod Touch well enough. The wireless works great, and the Safari Browser is a better web experience by leagues than what the Palm T|X had to offer. The calendar is underpowered compared to the Palm device, but I'm learning to live with it. Skype can call phone numbers from the Contacts app if you have Skype credit or a subscription that pays for calling land lines: I do, and that's convenient. Handling music, of course, is what the iPod is really built for even though it's not my main interest in the device -- for me that's a nice to have. Ditto for the camera, with which I'm not impressed, but maybe I'll get the hang of it and come to depend on that more over time. The display is awesome.

Maybe the most dramatic gain is among the most mundane: because the Palm T|X is essentially a dead device, I couldn't get an up-to-date app to keep a schedule for the BART system -- the Bay Area's regional rail -- to carry in my e-pocket. Problem solved, thanks to iBART, with a big shout-out to the Pandav team.


Anybody want to buy a used Palm T|X?




Related posts on One Finger Typing:
Rock, Paper, Digital Preservation
Safeguarding cloud ephemera Part I: the big picture






Thanks to Stefano Palazzo for the Palm T|X image on the Wikimedia Commons.