Still Not Easy After 40 Years

My Tablet Setup Saga

In the early 1980s, we were introduced to a brand-new concept: the personal computer. IBM’s PC arrived in 1981, and the Apple Macintosh followed in 1984. By today’s standards, those machines were laughably clunky—limited in speed, memory, graphics, and the ability to do more than one thing at a time. But at the time? Absolute magic. We could compute, create, and communicate without waiting in line at a university lab or asking the guy down the hall who “knows mainframes.”

Fast forward more than four decades and the world has changed. Personal computers are in our pockets. Storage is measured in terabytes, not floppy disks. And setup? Well, surely that’s been streamlined into a plug-and-play breeze, right?

Apparently not.

A few weeks ago, I bought an Android tablet—a Microsoft Surface Pro—to prep for a summer trip to Alaska. It wasn’t a whim purchase. I wanted something lighter than my laptop but still capable of basic work: email, browsing, note-taking, and maybe a little blogging along the way. The Surface Pro looked like the ideal travel companion: sleek, portable, and allegedly “familiar.” After all, I’ve been using Windows since it needed a DOS boot disk.

What could possibly go wrong?

Plenty, as it turns out.

What should have taken a relaxing Saturday afternoon turned into a four-day slog through the tangled jungle of modern tech. I wasn’t trying to build a custom server or edit a feature film—I just wanted my apps: Word, Excel, Kindle, YouTube TV, and a couple of others like Libby and LinkedIn. The basics. And yet, each step felt like the tablet was throwing me a new puzzle, guarded by a troll who only speaks in system prompts and authentication codes.

Let’s start with the basics—accounts. Microsoft insists you activate the device with a Microsoft account. Google wants you to log into the Play Store using a Google account. (That is, if your device actually supports the Play Store, which Surface does… sort of.) Then there are individual apps like Kindle and Libby, which demand their own credentials and make you feel like a stranger for not remembering the name of your childhood pet or the street you grew up on—yes, that one with the potholes.

Even my password manager—normally my faithful digital companion—decided to go rogue. It either wouldn’t load, wouldn’t sync, or forgot to fill in fields altogether. It’s like hiring a personal assistant who shows up late, forgets your appointments, and takes frequent naps.

And then there’s Gmail. I have the same Gmail account across my laptop and iPhone, and it works flawlessly. But getting it to work consistently on the Surface? That was an adventure worthy of its own travel series. The default mail app kept pushing itself like a clingy ex. Only after I properly installed Google’s native apps did email finally start flowing—days later.

Add to that a potluck of browser quirks (Edge, Chrome, something else that showed up uninvited), mysterious permission pop-ups, and sneaky system updates running silently in the background—like raccoons rummaging in your garage at night—and suddenly, I’m not setting up a tablet. I’m project-managing a digital play with a cast of character straight out of Hollywood.

All this begs the question: after 40 years, shouldn’t this be easier?

I’m not denying today’s devices are more powerful. My Surface can process video, recognize my voice, connect to Bluetooth headphones, and probably launch a small drone if I knew the right app. The potential is astounding. But for everyday users—not coders, not influencers, not tech YouTubers—the process of getting started is still unnecessarily convoluted.

Let me ask a simple question: Why can’t I log into a new device and have it say, “Hey Terry! We see your existing setup—want us to load your apps and data from your laptop or phone?” Instead, I get a digital obstacle course: multiple sign-ins, code verifications, app re-downloads, and a setup assistant that feels like it’s training me, not the other way around.

And app compatibility? Don’t get me started. Technically, my Surface runs Windows—not Android—but I wanted to use it like a tablet, with touchscreen apps and all the mobile convenience. That turned out to be wishful thinking.

What happened is some apps behave differently—or worse, don’t work at all. It’s like being told your hotel has a pool, only to discover it’s decorative and filled with koi.

Apple has its walled garden, and Microsoft its fortress of solitude, but shouldn’t we at least agree on a few standards? You know, like email, calendars, contacts, and not hiding the Play Store behind a curtain like it’s Oz?

Now, imagine you’re not me –a seasoned user who’s spent a lifetime working in and around technology. Imagine you’re just starting out, maybe newly retired, trying to dip a toe into the digital world. That “toe” is going to get chewed up by pop-ups, drowned in conflicting instructions, and spit out by forums written in technobabble.

It’s not just frustrating—it’s discouraging.

When I first started using computers, it was a thrill. I still remember upgrading to Windows 95 and feeling like the future had arrived. When dial-up gave way to Wi-Fi, when floppies became flash drives, when “plug and play” actually worked—each milestone brought us closer to a more intuitive future.

Now, it feels like we’re heading in the opposite direction. The challenge isn’t hardware anymore. It’s ecosystems. It’s endless syncing, account juggling, and a baffling abundance of options that only confuse the core user experience.

And speaking of options, we now live in a world where everything is an app. Case in point: I recently lost my gas station discount card. When I tried to get a replacement, I was told they don’t do cards anymore—just an app. An app I didn’t ask for, didn’t want, and had to set up just to save a few cents per gallon.

This trend is everywhere. Medical records? App. Banking? App. Coupons? App. Want to order a sandwich? You guessed it—app. And if you don’t have the app? Sorry, you don’t exist.

Which brings me to a related rant: where did the manuals go? You used to open a box and find a nice little booklet that told you what button did what. Now you get a QR code (if you’re lucky), a two-page warranty disclaimer, and a smiley icon encouraging you to “explore the app.” The “manuals” we do get—when we can find them—read like they were written by 26-year-olds who’ve never had to explain anything to someone over 50. They’re jargon-packed, light on logic, and clearly not tested on actual humans.

Don’t get me wrong—I love innovation. I’m not afraid of change. But I do think we need to re-center technology around real people, not just the folks who live on Reddit and drink oat milk at coworking spaces.

So yes, I’ll take this new tablet to Alaska. I’ll answer email, jot down thoughts, and maybe even watch a movie or two. But the experience of getting here has made one thing clear: just because a device is smart doesn’t mean the setup is.

Next time, I may just pack a notebook, a pen, and a couple of extra gas station cards—just in case they haven’t been eaten by the app monster yet.

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