I was a big fan of the Palm Pilot in the 1990’s and 2000’s. As a corporate marketer, I lived by my 
Outlook Calendar, Contacts, Tasks and Notes, and all of my various email accounts were routed through Outlook. The Palm let me put all of that information in my shirt pocket when I wasn’t at my desk. Being afflicted with mild ADD, whenever I got totally immersed in what I was doing, my little Palm Pilot saved me a number of times by chiming to let me know that I was supposed to be somewhere in 5 minutes.
Time went by and Palm’s fortunes declined. They had a brief rebirth as the Treo smart-phone but, as in all things technical, the number of platforms in the market was destined to decline. Today there’s less than a handful of contenders; the ubiquitous iPhone from Apple, the popular Android from Google, and a possible resurgence by Microsoft with the well-regarded Phone 7. I’m not an expert in this space, but it looks to me like Blackberry is on life-support.
For years I resisted the call of the smart-phone. But when my last Palm died a few years ago, I bought an Apple iPod Touch to be my portable Outlook vessel (The Treo was off the market by then.) By installing Apple’s free iTunes on my PC, syncing the iPod to Outlook was a snap. If I made changes on the PC or the iPod, the next time I synced, each one updated the other. Just like the Palm, only it had a color screen, music, movies, and WiFi so I could surf the web.
Life was good, but I finally tired of looking up phone numbers on my iPod and typing them into my phone, especially while driving. Although this did not technically violate the no-texting-while-driving law in my state, it did take two hands and my full attention, and I began to wonder if it was just a matter of time before I hurt some poor innocent person, myself included.
On the advice of an industry expert, namely my teenage son, I traded my old flip for a Motorola Bionic, which runs the Android operating system from Google, though all young and cool people refer to the platform as “Droid.” I was amazed by the screen and the camera, loved the Google map with GPS and directions, and rejoiced when I discovered that I could now compose text via spoken dictation. Right off the bat, the phone demanded my Gmail account login, which I surrendered willingly enough. Then I tried to sync it with my calendar and contacts in Outlook on my laptop and things got ugly.
First, I connected the phone to my laptop using the supplied USB cable, but all I got was a pop-up video encouraging me to buy Verizon Backup Assistant Plus. (Note to Verizon: when you want to sell something, you have to tell people what it costs. Making them watch the same video each time they plug their phone into their computer isn’t as effective, and actually starts to get annoying after 6 or 7 times.)
I searched the phone for an appropriate app or setting, but found nothing suitable. So I did what everyone facing an insurmountable technical challenge does. I googled “sync android with outlook.” Up came a bunch of articles and blog posts about how it’s almost impossible to sync an Android phone with Outlook. Perhaps, they suggested, my IT department could sync my new Droid with Microsoft Exchange. Unfortunately, our company doesn’t use Exchange so no help there.
Why had Google not made it easy to sync Droid phones with Outlook? Instead, what I was reading (mostly on Google sites) was that I needed to put all of my personal data into Gmail, Google Contacts, Google Calendar, Picasa, etc. So I considered for a moment what Google would know about me and was hesitant to give Google that much information. And even after giving Google all of this information, I’m still not sure if the darn thing would sync with Outlook. Total elapsed time: about 4 hours. And I hadn’t even begun to tackle the issue of porting across my iTunes music and videos. Back to the store went the Droid.
I figured I’d have better luck with Microsoft. After all, they have a new smartphone OS called Phone 7 that’s getting positive reviews. And who better to build a portable platform that can sync with Microsoft Outlook than Microsoft, right? Wrong! Before investing myself in the same arduous trial and error, I visited the Microsoft website and discovered that Phone 7 can sync with Exchange (some IT support required) but not with Outlook. Are you kidding me?
Then it dawned. My iPod Touch works. And an iPhone is nothing but an iPod Touch with a cell phone and GPS built in. So, I bought an iPhone, plugged it in to my laptop, fired up iTunes and told it to move all my stuff over to the new iPhone.
It took half an hour to move about 25 GB of data to the phone. And it works like a charm. Who knew that you need an Apple product to carry your Outlook data around with you in your shirt pocket?
