The Digital Age of Help: From DOS to Dummies

I want to address two items: "HELP". Customer service is on different sides of the same coin. Nowadays, but not at the inception of the rule. In the beginning of the computer age, and into the 2020s, these have helped us possibly, or catapulted us into swearing in front of our grandparents. On their anniversary. On Christmas morning. Imagine you get a gift...

This article breaks down into two categories—customer service and help manuals—both of which had their heyday in the early 2000s. And what we've got that's working (a star-system for how satisfied you were) or not working (It takes 13 minutes to reach the hold line for Revenue Canada, at its quickest).

How do I hook up my new computer? Why doesn't my purchase look like the one in the picture? Why did the screen freeze? How do I get my computer to recognize a wireless mouse? Can I do something over the phone so I don’t have to haul everything back to the store?

If you've ever used a Microsoft product, you've probably had one of these moments. And if you've ever clicked the 'HELP' button, you've likely marveled at how unhelpful it actually is. The information almost applies to your problem, but the solution is nowhere to be found. The Troubleshooter serves no real purpose except to spit out a cryptic error code like XYFJS-8236, offering no guidance on what to do with it or who to call. You’re left stranded, as if the system is patting itself on the back for a job well done.

It’s like looking up “car” in the dictionary and finding, “see auto,” then flipping to “auto” and being told, “see car.” That is Microsoft’s Help system.

Then came the war on customer service standards. Companies, in their infinite wisdom, decided they—not customers—were the best judges of service quality. Just as they were laying off customer support agents, they realized, oops, people still needed help. Robots took over phone lines, only for companies to scramble to bring human voices back. Before the 2000s, alternative manuals, troubleshooting guides, and decent customer service contacts were rare.

IKEA was a pioneer in the “how-to” world, its assembly images setting the gold standard. And if you were missing a screw, a toll-free number had your back. Computers, on the other hand, came with a growing list of peripherals—external drives, USBs, headphones, scanners, DVD drives—that all needed to “talk” to your system. Yet, actual help was elusive.

Finding the right driver without downloading a virus was a challenge. Well-meaning forum users tried their best, but what we really needed were official manufacturer pages—something companies were slow to grasp. Turns out, what happens in a boardroom doesn’t always align with what customers actually need.

Windows 95 (yes, I chose this relic deliberately) left users trapped in their problems, armed only with a useless 'help' button.

Customer service shouldn't just be a department, it should be the entire company. — Tony Hsieh

Enter the DIY revolution. DOS for Dummies was the first of its kind, bridging the gap between manufacturers and befuddled users. Packed with cartoons, footnotes, and easy-to-follow instructions, it launched a series that has since spawned 339 titles. That alone proves how little manufacturers were helping in the first place. Microsoft, unintentionally, helped create the modern self-help industry.

Car manuals? They’ll tell you where your brakes are, but not how to change them. Enter the Haynes Manuals in the 1960s. Computers? They came with a flimsy multilingual leaflet that barely explained setup. Private companies filled the knowledge gap between product and practical application.

Using Windows 95 felt like being stranded on an island. It was isolated, inhospitable, and utterly uncooperative.

I remember my 72-hour battle to get Microsoft Flight Simulator to recognize a Microsoft throttle. They were sold as a package, yet refused to acknowledge each other. The meager, staple-bound leaflet was useless when things went sideways. Microsoft, ever confident in its product, seemed to embrace caveat emptor—buyer beware. I clung to the hope that, any moment now, they would magically connect. They never did. In 1997, Windows 95 for Dummies was released, marking a win for the users.

DOS was the gatekeeper of that era—an intimidating, blinking cursor demanding unwavering attention and precision. Bookstore shelves were lined with dense, code-heavy tomes for techies, but nothing user-friendly existed—until the Dummies and Idiot’s Guide series arrived. And they begged the question: If these books could make things simple, why couldn’t Windows itself? The likely answer? Microsoft made a fortune on customer support calls.

Kind words can be short and easy to speak, but their echoes are truly endless. — Mother Teresa on customer service in Calcutta.

The 2000s changed everything. As computers became essential at home and work, customer service became a priority. Today, companies even survey you post-call to see how your support experience went. Personally, I only give feedback when I’ve had either a 1/10 or a 10/10 experience.

Zendesk puts it well: "The main difference between service today and service 10 years ago is that customers expect premium service to be built-in from the first sales or marketing interaction and carry through to the moment they ask for help, post-purchase, and back again."

Indeed, if you bought Windows 95, you had nowhere else to go. But now? Buy a printer and the company will bend over backward to ensure you 1) don’t return it, 2) buy their ink, 3) get all the setup help you need, and 4) consider them again for your next purchase.

In the world of Internet Customer Service, it’s important to remember your competitor is only one mouse click away.—Doug Warner

Customer service has become the face of every company. We battle phone robots, pressing numbers in secret combinations to reach an actual human. Websites now offer real help. Buying a new printer today carries a level of trust that didn’t exist 20 years ago. We have service centers, online communities, FAQs, podcasts, live chat, video tutorials, and even text-based support agents.

And warranties? They’re essentially a product’s “best before” date. If a company offers a five- or ten-year warranty, they’re betting their product will last at least that long. I respect that, but I always seem to get the lemon, the coconut, the package that doesn't recognize its peers.

I didn’t know any better back in the Windows 95 days. I just knew my Microsoft game and throttle—packaged together in a sealed box—would eventually work if I just stayed awake long enough.

What a Dummy.