Generation Oregon Trail

Picture by Jesster79
Picture by Jesster79

Growing up, I never considered myself to be part of Generation X. To me, that generation involved Ben Stiller and Winona Rider in Reality Bites. All of them were a good 10 years older than me. But the generation below me is clearly different as well.

Then I came across this article.

I feel like this explains the middle ground of my life pretty well. I don’t remember when I first got my hands on a computer but the time was short. My school had a lab of Apple IIs where I remember some short time playing Carmen San Diego but what I loved was the in classroom Texas Instruments computers.

I have strong memories of staying in from recess in 5th grade to program a beating heart in TI Logo. That would have been Feb of 87. By Christmas of the same year I was playing my first computer game: King’s Quest 3. I would go on be be terribly addicted to the whole King’s Quest series. On the bright side of things, teaching yourself how to type so that you could activate your magic teleportation stone before the yeti got you was quite honestly a lot more fun than the traditional way of taking a typing course.

I had my first interaction with the Internet my senior year of high school. We had e-mail accounts and it was all text based. I remember getting my first look at a locally hosted web page my sophomore year of college as my roommate had created a webpage for his girlfriend. I remember it included a list of her allergies and included one picture from Ranma 1/2. By then I was chatting regularly with people on MUDs (even met my one day wife there) and stalking the Dungeon and Dragons Usenet groups.

So the story so far:

  • 0-10 years old: No internet or computers though we did have a VCR.
  • 10 – 20 years old: Computer games and then online text interaction

Let’s jump ahead now. I’m 40. While I spend most of my day sitting in front of a computer answering e-mail and/or coding… that’s what I do for work. The interesting technology is the one that I carry around in my pocket. My smart phone is my access to just Dailyabout everything that keeps me sane.

  • Books (Kindle for pulp novels, Google for D&D books)
  • Music (My entire CD collection in Google Music, plus an app for ‘Radio’ style play)
  • Movies (YouTube for fandom stuff, Netflix for binging, and Vudu for my DVD collection)
  • Pictures (Facebook and Instagram sure, but my Dropbox has every picture I’ve taken digitally going back to 1999)
  • Games (Currently it is Pokemon, both Go for my son and Emerald playing on an emulator)
  • Work (Daily e-mails, my Timesheet, calendar reminders for meetings)
  • Trivia (Aka. Using google to look up who the hell that guy in that movie was)
  • Communications (Phone, Text, and Social Media)


‘The Singularity’ is where some AI makes life as we know it completely different from what we knew before. The Oregon Trail generation has lived through a minor version of that. When I was born computers were giant machines that filled rooms and served as glorified calculators. In the course of my lifetime they have become second brains that we carry around with us. The difference between us and Millennials is that we remember the time before. The difference between us and Baby Boomers is that we aren’t wrapped up in the nostalgia of ‘simpler times’.

Philosophizing aside, this is something that comes up in my daily life at work. Part of my job is rolling out new software to my company, managing change and making sure people are trained on what it means to use this new software in their daily work lives. I find myself having to modify the messages that get sent out depending on the audience. Millennials know their technology. They aren’t Luddites and they get frustrated if we over explain what they need to be doing. They’ll figure it out. The Baby Boomers on the other hand tend to be scared that they’ll do something wrong but also are annoyed when the new system doesn’t check their work for them. Gen Xers can fall to either extreme depending on the individual.

My generation is a transitional one and a small minority within the greater Generation X community at that. The reality is that it is a small Sample and when future taxonomists start sorting groups, we’re going to get dropped from those historical discussions. So much of the technology we use is in its infancy. Computer businesses go out of business regularly, their servers dropping off the internet and ending up in dumpsters. The Amazons and Googles of the world will keep their records for future archivists (hopefully) but how much information from the DIY side of the web will make it into the hands of people 100 years from now? It can be scary to contemplate but for now, this is my classification.