My relationship to the internet falls into a few distinct eras:

Down the rabbit hole (1994-1999)

• Connecting to other teenagers on Usenet and IRC
• Learning HTML and building my first websites
• Building a thriving local news website in 1994, complete with classified ads
• Writing small shareware games and setting them loose on the network
• Releasing an internet magazine about technology and interviewing celebrities who had literally no idea I was fifteen years old
• Starting to blog
• Choosing to study computer science at university purely because of my love of the internet

Building community (2000-2004)

• Maintaining my own website but mostly posting on Livejournal, multiple times a day
• Accidentally creating a very popular website that gets millions of pageviews a day, with no real idea what to do with it - but it’s real cool
• Letting the lines blur and meeting a bunch of people in real life that I’ve been speaking to online
• Graduating and going to work on edtech for the university because there’s no substantial internet industry in Edinburgh in 2002

Building a career (2004-2009)

• Realizing that all edtech absolutely stinks and everyone involved resents it at best, but people are learning from each other on the emerging social web, so maybe let’s use those same principles to help people really learn?
• Building a prototype, offering it to the university, getting laughed out of the office
• Quitting and starting my first startup
• Building an open source social networking platform that’s translated into multiple languages and used all over the world
• Developing my underlying principles of distributed ownership, un-predatory business models through open source, and avoiding centralized lock-in
• Raising money and having a terrible experience with investors, falling out with my co-founder in the process

Media (2010-2015)

• Leaving my startup to save my sanity
• Going to work as first employee of a tech company for the first time, in an industry I care about but have no experience in (news)
• Building a tool that NBC News (among others) uses to send video back to the newsroom, and learning a ton in the process
• Becoming part of the indieweb, a community that’s completely in line with the principles I developed in the previous era
• Going back to found my second startup - another open source communications platform
• Learning about design thinking and raising money for the startup
• Winning awards with our customers

Getting serious (2016-2018)

• Acquihired by Medium
• First time working in a big VC-backed startup with insane amounts of money, a whisky shelf, and kombucha on tap
• Wake up one day to realize I’ve lost my love for the internet without: without the scrappiness and the punk sensibility of building something better than what all those rich people can manage, the joy for me is gone
• But also, maybe it’s everything going on in the world - Brexit in particular hits me hard
• Become a VC at the firm that funded my last startup, end up teaching other startups and media companies how to approach problems using design thinking
• Re-codify my principles: I want to work on projects with the potential to create a more informed, more equal world
• Become first employee at a blockchain-related startup

Life happens (2019-2021)

• My mother’s terminal illness becomes the primary concern
• I don’t have time or mental energy to build interesting things on the internet anymore
• I take a job that is not really what I’m here in the world to do, but it’ll keep me going while everything else is happening (and I meet some lovely people while I'm there)

Reinvigorated (2022-)

• Hired by The 19th, fully in line with my principles!
• Experimenting with networked technology in new ways
• Building projects in my spare time
• Baby arrives! I get to think about what kind of world we’re building for him
• Excited for everything again
• Let’s see what happens?

How does your relationship to the internet break down? How do you feel about it today?