The web's evolution
– 90s Nostalgia
Growing up in Cupertino in the 90’s, I was surrounded by computers. Apple provided computers with color monitors to my elementary school, and I remember class activities creating reports on Alexander Graham Bell using HyperCard, a precursor to PowerPoint (and one could argue, Notion and other database based visual knowledge organization systems).
I was also lucky enough to grow up in a household with multiple computers. Although we had a 28kbps/sec dial-up modem that only allowed one computer to access the internet at a time, my childhood hobby was developing websites offline using Microsoft FrontPage and the Notepad app.
But the point of this article is not to reminisce on these early days of the web. Rather, it is to trace the current state of the web in 2021, analyze trends with a design theory lens, and propose a vision for how we can interact with each other online and evolve the web in the future.
Current status: Researching and documenting
Bracketed Navigation

https://www.webdesignmuseum.org/old-software/html-editors/microsoft-frontpage-97
Frontpage ’97
Reference CLI: https://carlalexander.ca/introduction-command-line-interface/
man man
shows that brackets are optional inputs


https://www.webdesignmuseum.org/exhibitions/search-engines-in-the-90s/magellan-1996
Choices separated by bars: https://www.ibm.com/docs/en/app-connect-pro/7.5.3?topic=app-connect-command-line-interface-reference
Add image: First website on CLI
Bullet Point Navigation

https://www.webdesignmuseum.org/gallery/yahoo-1994
Craigslist Aesthetic

Add image: First WYSIWYG editor
Tables
Although Craigslist today embodies the look of default design from the 90s, its 1995 design actually looked quite different. Notably, mixing Verdana and Times New Roman and using a sidebar (potentially an iFrame) similar to default FrontPage layouts.

https://stage.thehustle.co/proof-that-your-favorite-startup-started-out-awful

https://www.telegraph.co.uk/technology/6125914/How-20-popular-websites-looked-when-they-launched.html Apple’s 1996 website also used this sidebar/table/iFrame look.
Site Maps

https://www.researchgate.net/figure/Web-site-schema-in-Frontpage-98_fig1_44938655
If I didn’t learn how to hyperlink in FrontPage, I don’t think I would have understood site maps as well as I do today.