Back yonder ’round about 1998, when I finally dove into the world of the PDA (Personal Digital Assistant, otherwise known as a PIM (Personal Information Manager)), I bought a new but discontinued Newton, the MessagePad 100. It was fairly inexpensive, as Newtons went, and I could not afford any of the newer models.

I loved the thing. The handwriting recognition wasn’t nearly as bad as people had made it out to be… though, granted, my 100 had an upgraded engine for that. The Newton was a study in delightful, fun, easy-to-use design and UI. It was an utter pleasure to use. It synced with my Mac, so I could keep all my data together. That data, free of photos, music, and video, could fit in the tiniest of storage spaces.

Yes, that’s a 2 MEGABYTE card. You would not even be able to store one song on that today.

Some time after I got my Newton, I got my first cell phone, a Qualcomm thing where you could slide the earpiece to answer and end calls. It was an amusing phone, looking back on it. But it had a mean streak. One day, I put my Qualcomm on the top of my cubicle storage shelf. I forgot it was there, and when I closed the door to the shelf, the phone came sliding off, and it smashed my Newton’s screen. It was a sad day.

The Newton being a “dead” platform by then (more on that later), I decided I should buy a Palm Pilot instead of another MessagePad. The “Pilot” part of the Palm name had already been sued out of existence by the Pilot pen company, so the device I bought was simply called a Palm III.

The Palm was nice. It was small, incredibly simple, sipped on battery power, and was perfectly suited for my needs. But it was not a Newton by any means. It had frustrating limitations based on OS design choices, and, worse, synced very poorly with my Mac. Thanks to that, my Palm became my one repository of all phone numbers and calendars. I could access the info via the Palm Desktop app for the Mac, but it was such a terrible program, I simply never bothered. My Mac was cut off from my information.

When the Palm III began to show its age, I upgraded to a Palm Tugsten T. The Tungsten had a color screen, a fast processor, Bluetooth, but was still limited by Palm’s unchanged app designs and inability to sync properly with my Mac.

By this time, the Mac had made a huge comeback. OS X kicked ass, and Mac hardware itself was becoming utterly sick, as the kids these days might say. The new OS improved and began to offer wonderful features combining integrated use of calendar and contact data. Because I wanted to use these features, I had to double up on locations for data. In the world of information, you should never do this. You should only ever have one place for personal information, otherwise confusion and mismatched data will ensue. However, technology was not allowing me to work this way, so I made a valiant and very successful effort at managing two contact lists.

In the meantime, I seemed to go through cell phones like water. I was definitely a Nokia fan, as you can see, because their interface was the most well thought-out, in my opinion. (Below are all my cell phones, minus the Qualcomm and my first 6230. From left to right are the 3360, 3560, 8290 (the greatest!), 3120, an unlocked 6230, and the Microsoft mPhone Vista Personal Ultimate Edition.)

The following is not one of my old phones, but I had to include the picture anyway. It’s a circa 1994 Motorola sitting next to the new Motorola WSHR. Thanks to Fuz for letting me have this brick.

A year or two ago, I was tired of keeping two sets of records, so I stopped using my Palm for contacts and moved everything to my Mac. My Palm was then only being used for my calendar and a list of all my passwords. The Mac stored my contact information so I could use it seamlessly for iChat and Mail. With .Mac syncing, I had my contact info on my home Mac and all of my work Macs, and if for some reason I needed the info on the road, I could look it up on my Nokia or iPod. iSync did an okay job of syncing a selection of my contacts to my Nokia cell phone, though again, there were limitations.

This was all a mess, but it worked somehow.

When rumors of an Apple phone started to surface years ago, you can understand why I was so intrigued. Many was the time I had been tempted to buy a used Newton 2100 and spend the time to hack it to work with OS X. Believe it or not, people out there still hack the Newton, and you can find solutions to make a now-ancient MessagePad sync with any modern Mac.

The temptation to buy another Newton never took solid form. I had become accustomed to a smaller device. Newtons were huge by modern standards. No, what I really, really, really wanted was a new Apple device. No one else was going to have the smarts or the business drive to make a really good phone/PIM gadget that worked seamlessly with the Mac.

This January, for the first time in maybe 14 years, I got to attend Macworld. I went on Disney’s dime, and so I bought the package that got me good seats for Steve Jobs’ keynote. I have never been to a Steve keynote before. His October appearance at a Studio work event was fantastic, but that was not a keynote. The January 2007 Macworld keynote will, of course, be the one that goes down in history, because it’s when Steve Jobs introduced the iPhone. (Download the “Macworld San Francisco 2007 Keynote Address” video if you follow that iTunes link.)

I wish I had a video of myself and Ben at that keynote, because the iPhone, as Steve was revealing its many wonders, turned out to be far more exciting and fantastic and brilliant than I had ever imagined it would be; Ben and I were excited beyond reason. My facial expressions alone would, I’m sure, be priceless YouTube fodder.

Here it is, over six months later, and I’ve had my iPhone for two weeks. I love the thing. The keyboard is much better than people—most of whom had never even used it— have made it out to be. The iPhone is a study in delightful, fun, easy-to-use design and UI. It is an utter pleasure to use. It syncs with my Mac, so I now, once again, keep all my data together.

Between the Newton and the iPhone, I had probably 8 years of simply passable PDA experiences. I am finally at the day I’ve thought about for so long.

Of course, there is another similarity between my old Newton and my new iPhone: both are early version products. Had I been able to own a newer Newton back in 1998, I’d have had a more refined product, with less quirks and a very mature feel. My iPhone, being on version 1.0, has plenty of things it could do better. However, the iPhone feels like it’s already been around for years. As someone else said, verison 1.0 of an Apple product is like version 7.0 of another company’s. What’s so fantastic about both the iPhone and the Newton is that Apple got the basics right from the very beginning. The concepts were sound, the designs were top-notch, and intelligence just oozes out of both products. As the iPhone gets updated over the next few years, I know Apple will fix some things, add others, and the iPhone will only get better.

For a great set of beautiful pics that inspired me to dig out my own Newton, go visit philcarrizzi at Flicker.