https://www.joshuakennon.com
https://www.oaktreecapital.com/insights/howard-marks-memos
http://www.docbastard.net
https://meltingasphalt.com
http://paulgraham.com/
Rachel by the Bay https://rachelbythebay.com/
Jessie Frazelle https://blog.jessfraz.com/
The Grugq https://gru.gq/
Matt Green https://blog.cryptographyengineering.com/
Rob Graham https://blog.erratasec.com/
Cindy Otis: http://www.cindyotis.com/articles.html
Maciej Cegłowski (pinboard, idlewords) https://idlewords.com/
Julia Evans: https://jvns.ca [Systems | Linux | Networking | Core CS]
Joel Spolsky: https://www.joelonsoftware.com/ [Software | Product | Hiring | CEO of Stackoverflow]
www.waitbutwhy.com
www.moretothat.com
www.daedtech.com
www.kalzumeus.com
https://medium.com/the-year-of-the-looking-glass
https://www.collaborativefund.com/blog/authors/morgan/
https://nav.al/how-to-get-rich —- not personal blog per se but collection of all personal interviews. Excuse the clickbaitish title, it is not a pitch of any kind.