@vega Serendipity is the opposite of the filter bubble which leads to intellectual isolation.
Facinating thread. I think hyperlinking is the key here, it's free, low tech and we control it. I like the idea of adding curated but serendipitous links to newsletters, but I also like the old idea of link pages or surf pages: a public list of hyperlinks to things we like.
Remember those old Web 1.0 Top List voting sites? These were generally labeled "Top 50 Star Trek Sites" and ranking was by remote voting. I could sometimes dig up the most obscure pages via those - not in the top 10 but deeper down the list.
There are other ways: Boingboing.com serves links to odd stuff daily.
I tried to add some serendipity to my web directory, by adding a random link feature but I'm not sure how successful that is.
@kicks makes an awesome whimsical list of links at href:cool.
So yes I would encourage everyone to make time to link to things that are just fun. cc. @dancohen