Article: The Ten-Year Challenge

by on February 20, 2019

While this site is celebrating its 20th birthday this year and there will be plenty of content about that, I’ve recently been thinking about how much has changed on a much smaller scale in the last ten years. The iPhone was just starting out. The iPad, a device this site is primary produced with, wasn’t more than an idea within Apple. The influence of Google, Facebook, and Amazon has grown exponentially. Microsoft has turned things around.

Although there’s a lot of things that are fundamentally the same, the technology world feels much darker, a bit slimier, and much more pessimistic. I was just out of college when the economy fell apart, but the notion that anything could be solved with the right technology and the capabilities were only getting better prevailed. Now, we can do much more, but sometimes the motives don’t feel as good.

This particular article is a bit of random thoughts on the last ten years and how my feelings of some of the large technology companies have evolved. I’ve been reflecting on some fond memories of a time when I was interested in technology, but not sure what I wanted to do when I actually got a job.


In early 2009, Apple was certainly in great financial shape, but also wasn’t as “bulletproof and invincible” as it is today. The iPhone was still exclusive to Cingular AT&T in the United States, and rather expensive for many, so the Mac and iPod were still Apple’s bread-and-butter products. The iPhone 3G would have been the device for sale exactly ten years ago—while it had great capabilities for its time, it felt out of reach for a graduate student who rarely needed cellular data (our campus was one of the few with excellent Wi-Fi almost everywhere) and was used to paying $20/month for a cheap cellular plan. My Mac and an iPod touch were my essential devices, while my phone typically fit in the AirPods coin pocket of my jeans when I’d be out.

Apple gets covered rather exhaustively here and while I’m generally pretty positive about most of their products, I think there are some neglected areas that need attention. As it stands, I really have no interest in buying a new Mac, between pricing, flaky keyboards, and other compromises. If my current Mac mini died tomorrow, I’d probably replace it with another Mac mini, but it’s a shame that the 12″ MacBook or MacBook Air couldn’t be a computer that replaces everything (maybe even my iPad?) On the iOS front, the iPad software could use some refinement, but I love that the $329 iPad exists. iPhones feel mature and stable and outside of notches and Face ID making their way across the lineup, a proper replacement for the SE would be interesting. Still, most things Apple does feels good and for the right reasons.

Unfortunately, as the iPhone and iPad product lines are mature, that leads to things feeling boring and iterative. Honestly, I’m fine with that personally, but it has led to less content opportunities for this site.


Back in 2009, Microsoft still sort of felt like a bit of an “evil empire” in that its products were pervasive, incompatible with quite a bit of Apple things (you couldn’t add an Exchange email account without IMAP/POP loopholes to Mac OS X until Snow Leopard, for example). Being a fan of Apple, I tried to use as little Microsoft products as possible because I felt that the quality was lacking. Windows Vista was still fresh in many people’s minds and supported this idea.

While I still prefer Apple products, my stance on Microsoft has changed quite a bit. They still make a lot of boring, corporate products, but they are doing some interesting things and generally play pretty clean. I use Office 365 at work and mostly interact with their iOS or web apps, which I find quite nice. Windows has gotten better, but there are little quirky, ugly moments behind the scenes that bring back memories of XP.

Microsoft’s hardware has been interesting because it feels like it should be from some parallel universe where they only controlled everything, like Apple, and the rest of the PC industry doesn’t matter. A few of the Surface products lack the polish of MacBooks, but they’re at least different (go look at how many vendors have made thin, PC laptops with black keycaps in an aluminum enclosure). It bugs me that Windows Phone never became a viable alternative to iOS and Android because it had the potential to be a hit, but never took off. I suspect a few of us who checked it out will remember it fondly as a “what could have been” like the Commodore Amiga.


If I was in college today, Amazon would be a godsend—anything you wanted in two days, video streaming, music streaming, and all sorts of other services. For some reason, I had an account since 2006 (I think to spend a gift card), but didn’t really use Amazon much until 2011. I think they weren’t as pervasive and most people still thought of visiting Walmart, Target, Best Buy, or Circuit City for most things.

I still haven’t gone all-in on Amazon with many services, but it complements the other retailers I use. Devices like the Echo don’t appeal to me and I find the Fire TV interface to be a bit cluttered. I stick to using Amazon for buying things I can’t easily or cheaply get elsewhere and Prime Video gets some use for certain series.

The size of the company gives me pause at times, but I find that no different than the anti-Walmart people in the 1990s or early 2000s. Plus, as long as viable competition exists, there’s always alternatives.


My feelings about Google have changed a bit in the past ten years, and have probably mirrored Apple’s. In 2009, Google was an interesting company that complemented Apple hardware nicely. They had an excellent search engine, some useful mapping technology, and YouTube was still relatively young. The overall product design was somewhat clean, but tended to place function over form.

Once Google released Android, it was an interesting competitor for the iPhone and provided another smartphone option. Chrome gave some value to anyone using Safari, as it was another product based around WebKit. While Google seemed to prefer you to use all their products, they were also okay with coexisting with Microsoft and Apple.

Today, Google has grown up and the “don’t be evil” mantra has been long-removed. While many of their things are quite satisfactory, some of the behaviors associated with running a business of free-with-ads have driven me away. Throw in their tendency to kill certain successful products (I loved Reader and used Hangouts) and my attitude towards Google has become to use their products as little as possible. It’s not an outright boycott or anything that ridiculous (I still watch things on YouTube), but they’ve certainly contributed to my tech pessimism.


Facebook launched when I was in college and I was quick to sign up. MySpace felt like it was on the decline and a new, popular service seemed like a great way to reinforce and build friendships on a platform that catered to a very specific group of people that I’d actually interact with in real life. As time went on, the interface got better, cleaner, and I really liked the overall designs of 2007-2009.

It made perfect business sense to open the site up to anyone, but that changed the feel of the site in many ways. From what I remember, there was a bit of agreed upon etiquette by a lot of users because we “grew up” with the technology in those first few years and it still was a bit of a novelty. I know my group of friends on Facebook were mostly comprised of those from where I was going to school and I typically saw many of them on a regular basis. That created a bit of accountability because it existed with real-life interaction. Once it became commonplace, everyone used it differently for good and bad. The company continued to try to find new revenue streams and tried to replace email and instant messaging.

Behind the scenes, the company grew and grew and hit a tipping point of sorts where it just felt exhausting (I still argue that algorithms for social media timelines are crap) and creepy at times. By playing fast and loose with privacy and trying to do everything for everyone, it just became something that didn’t appeal to me. Unfortunately, Facebook is such a big industry player that I still feel like some topics must be covered.

The Next Ten Years

I have a theory that social networks (and maybe some technologies as a whole) are best when they have a limited lifespan. Friendster gave way to MySpace, MySpace petered out in favor of Facebook, and Facebook is still around. Google replaced all the mid-’90s search engines, and SMS/iMessage/Facebook Messenger kind of took care of AOL Instant Messenger. Apple reinvented the Mac numerous times that what you can buy today is in no way like what you can buy in 2009, 1999, or 1989. I think moving on from something keeps companies fresh and competitive, but we haven’t had that in awhile.

If I didn’t believe that there was any good in the world of technology, I’d probably have shut this site down or at least stopped writing on it. Things feel a bit stagnant and I hope Apple and Microsoft continue to play their role of being industry players that generally do the right thing. As for the others (and some not mentioned here), I’d like to see some competition and newcomers to make things more exciting and offer choices. How have your views changed of the different industry players over the past ten years?

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