I was reading this list of the 10 biggest web design mistakes in 1999, and it was a good read on what drove people crazy back then, and considering how those sins have changed over time. Let's take a look at a few choice quotes.

Don't pollute my screen with any more windows, thanks (particularly since current operating systems have miserable window management). If I want a new window, I will open it myself!

My modern brain of course thought about browser tabs here, but it's worth mentioning that no mainstream browser had tabs in 1999 when this article was written. Opera would introduce them in 2000, and Firefox, Chrome, and Safari would follow suit in the next couple years after that. This article calls out InternetWorks from the early 90s as being the first to have tabs, which I'd never even heard of, but yeah, those do seem to be a form of tabs!

Non-standard GUI controls were one of the biggest usability problems identified in our usability testing of 46 web-based applications in Flash.

Truly, I don't know if young people today appareciate how bad web UIs were in the Flash era. A nightmare for accessibility and absolutely zero consistency as each Flash app had to basically create its own UI from scratch.

Old information is often good information and can be useful to readers. Even when new information is more valuable than old information, there is almost always some value to the old stuff, and it is very cheap to keep it online. I estimate that having archives may add about 10% to the cost of running a site but increase its usefulness by about 50%.

Somebody tell CNET!

The web is awash in money and people who proclaim to have found the way to salvation for all the sites that continue to lose money. Push, community, chat, free email, 3D sitemaps, auctions — you know the drill.

Swap in some new buzzwords today (crypto, web3, NFT, AI) and the story is the same.

Selective attention is very powerful, and web users have learned to stop paying attention to any ads that get in the way of their goal-driven navigation. That's why click-through rates are being cut in half every year and why web advertisements don't work.

Ooh, okay now this one caught my eye because the modern web basically runs on advertising, so I clicked the link above, which took me to a 1997 article called, Why Advertising Doesn't Work on the Web. Let's go…

Because of the drastic differences in popularity between sites, only the top 0.01% of websites can generate sufficient revenues from advertising: in the larger picture, advertising is almost irrelevant for the success of the Web. Right now, Web advertising is attracting much media attention for two reasons: Advertising is currently the only way for sites to generate a direct revenue stream (except for sites that support direct sales). This situation will change once we get micropayments (pay-per-view at the page level) as well as alternative revenue models like the link commissions paid by Amazon.com for people directed to their site by other sites.

This is how the article starts, and it's a bit all over the place looking back 26 years later.

1. Ads still only make serious money once you get really big. I run ads on this site, and with about 20,000 page hits per month (my analytics are public if you wanted to check them out), I make about $10-20 per month on ads. That's not nothing, but it's also not exactly making me rich.
2. Micropayments have failed so many times it's kind of hilarious. People simply do not want to pay a small fee to read something on the web, and this model which gets carted out every time there's a new technology (last in 2021 when crypto was going to make micropayments a thing…okay crypto goons…) and people again and again show they don't care for that model at all.
3. Amazon commissions are indeed a real source of revenue, although I will not that over the years, those affiliate programs have gotten less generous or disappeared completely (looking at you, Apple).

This value is usually very small, which is why Web advertising works poorly and (while not completely useless) will be one of the smallest contributors to the future of the Web.

Kinda beating a dead horse here, but it's worth mentioning again that many of the biggest companies on the web (Google and Meta, specifically) are among the biggest companies in the world full stop and their businesses are almost entirely advertising.

The Web is very different from television: it is mainly a cognitive medium, whereas TV is mainly an emotional medium. This makes TV much more suited for the traditional type of advertising which is flashy and promotes superficial qualities of products.

I think it's fair to say that the social media revolution has lead to the web becoming a very emotional experience as well. I'd also argue that much of Instagram advertising could specifically be described as "advertising which is flashy and promotes superficial qualities of products."

I don't mean to shame the authors here by any means; I'm sure my takes on the future of the internet in 1997 and 1999 would be hilariously wrong as well. I was like 12 and didn't post anything online then…I wouldn't even have known how, so they would surely be even more hilariously wrong. I just think it's interesting to go back to what people were proclaiming confidently well into the past to get a better appreciation for how what seems clear at the time isn't always as clear as it seems.

This isn't an excuse to not make predictions or to have opinions in the first place, but to loosely hold those opinions and be willing to adjust as time moves on.