the holy trinity of palm pilot, flip phone, and ipod

Judging from that thousand-yard stare, you’ve been reading the news again. Stop that! You’re not going to fix anything, unless you’re Robert Mueller, in which case, stop procrastinating and get back to those indictments.

For the rest of you: While I can’t help you unsee any of the things you’ve seen, I can, however, distract you from the Desert of the Real. (Whether you think this is a reference to The Matrix or the work of French cultural theorist Jean Baudrillard, you’re a nerd.)  Settle in and keep reading.

I came of age on the Web with Jason Kottke. Reading this interview with him about the death of blogging makes me feel old and tired.

I got serious about my own blog back in 2003, according to the Internet Archive Wayback Machine. That’s when I appear to have moved it from Blogger to my own domain at

(Feel free to browse the archives at the Wayback Machine if you’re curious. Just don’t go to the actual I’m pretty sure it’s been porn ever since I let the domain lapse.)

Blogs were exciting in 2003. They didn’t really go mainstream until 2004 or so; it still felt like a secret club. Yet, somehow, people found what you wrote. It just kind of bubbled up. (Yes, even without Facebook’s brilliant algorithms.) I once likened the appearance of avant-garde theater director Richard Foreman to animated cartoon character Droopy Dog. Within a day, interns at his theater in New York had discovered the post and shared it amongst themselves. Delighted by the (apt) comparison, they offered me free tickets to Foreman’s next show, which I happily accepted. (I mean, he is a great director. Just droopy.)

The true magic of the early Web only becomes more apparent as it recedes further into civilization’s rear-view mirror. When I think of all the odd and interesting bits of serendipity I enjoyed thanks to my blog or, a couple of years later, my podcast, it’s hard not to feel like I took it all far too much for granted. (Is this how Boomers feel about rock and roll and the Man and all that?) I went to some of the very first flash mobs, and when I blogged about them, my posts went to the top of the search results like magic. I used to be the internet authority on Star Wars Kid, too. After I started podcasting, complete strangers recognized me from my voice. This is while I was reaching only a few thousand people. How bizarre is that? Yet I let both the blog and the podcast lapse after a certain point to focus on my “career.”

I guess I assumed that the Web would always be there for me when I chose to take advantage of it again. After all, technology always gets better with time, right? Blogs, podcasts, RSS readers: sure, they were good, but the best was yet to come.

Little did I know.

Cal Newport recently shared Joe Rogan’s interview with Perfect Storm author Sebastian Junger. Junger admits that he still uses a flip phone, that he in fact has always used a flip phone. Junger writes a lot of big, amazingly crafted books. This is not a coincidence.

The Junger piece dovetails nicely with what I was actually going to write about today, before I got derailed. (This should come as no surprise. I always get derailed. In fact, there are no rails. This is an all-terrain, four-wheel-drive newsletter.)

Tech does always improve in raw metrics like size, speed, and power, but I think it goes in cycles when it comes to how it feels. For example, people enjoyed their cars way more in the 50s than they did in the 90s. Every technology has its happy periods and its sad periods. And the internet was a happy technology in 2003. In 2017, to quote one of its prominent users: sad.

There’s a theory that every technology reaches the true peak of its development the moment after it becomes obsolete. Sailing ships, for instance, reached their design apotheosis only after the arrival of steamships. So maybe that’s part of it: when your technology suddenly becomes everything you’d always dreamed it could be, it’s a sign that it’s already been disrupted.

Personal technology was a happy technology in 1999. That was the year of the Palm V. The Motorola StarTAC came out a few years earlier and the iPod a couple years later, but I remember a distinct moment during this era when I had a perfect personal digital assistant, a perfect flip phone, and a perfect MP3 player in my pockets. (Cargo shorts?) Regardless, they all worked beautifully and made my life better. My only thought was: one day, I’ll have a device that does all three of these things, and then life will be perfect because I won’t have to wear cargo shorts anymore.

Compared to these marvelous devices, the Blackberry was just sad. Sure, it was a status symbol. A Blackberry meant power, at least at Penguin. It was still pathetic, though: the blinking light, the constant, fearful checking, the furious thumb-typing. To me, thumbing away at an “emergency” on a Blackberry looked like a grown-up version of the large-iced-coffee-and-pajama people theatrically stumbling into college lectures. “Oh my god, I was up studying all night.”

When the iPhone arrived, I scoffed. Sure, it seemed to fulfill my vision of One Device to Rule Them All, but it was comically slow and fussy. It couldn’t offer the crisp efficiency I enjoyed adding calendar events to my Palm with “Graffiti” or selecting a song on my iPod with the click wheel. I’d always have that.

Little did I know.

Ultimately, what I now hate about my iPhone is the very same synthesis I once craved: Palm Pilot + iPod + Flip Phone + GPS + Blackberry. So I’ve devised a solution that’s worked very well for me so far. I’ve subtracted the Blackberry, the sad little nougat at the iPhone’s center. Not only have I blocked every non-essential website, I’ve actually taken email off my iPhone entirely. No more thumbing away at “emergencies.” Now, I use my iPhone for calendar, tasks, phone, music, and maps. And I’m happier for it. I’m living the tech dream of 1999. Join me.

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