I turn 50 today.

I feel incredibly lucky to have experienced these particular 50 years.

I was born in 1976 — when Steve Jobs and Steve Wozniak founded Apple, the year after Bill Gates dropped out of Harvard to start Microsoft. But I grew up largely without technology. To me, technology came in waves, and it was always exciting and new.

I remember the Atari 2600, and later the Nintendo. The Commodore 64. The acoustic coupler in War Games. My first PC. The turbo button that made it fast (50 MHz). The sound of dial-up. I remember BBSes and MUDs. Archie, Gopher, Veronica, and the World Wide Web. I was there for all of it.

1994 was a big year for me. I graduated high school in the spring, and started college in the fall. Swamp Ophelia came out that year, and I’ve been an Indigo Girls fan ever since. (I just saw them on Tuesday.) It was a huge year for technology, too. Linux 1.0 was released, the World Wide Web went mainstream, and the W3C was founded. Netscape was released. Amazon was founded. Yahoo! came online. Rasmus created PHP. Even the QR code was invented in 1994.

I loved technology. I ended up switching my major to computer science, because it had the word computer in the name. I learned everything I could and exhausted the curriculum. The department chair told me I should learn HTML, because my C programs could output HTML, and that was the way to build the UIs of the future. I just had to print a couple of extra lines (HTTP headers, but I didn’t know that yet), and voila! I was a web developer. Perl made some things easier, and PHP made them easier still.

When I graduated, I got a job at the USPS in Memphis, and within a couple of years, I was leading one of the most important teams in the organization.

It didn’t start that way. Academia had given me a lot, but the job demanded more. I stopped by Borders every night on my way home to read books and decide which one I was going to buy. A lot of the good ones had animals on the front. (I would later write one of those.) My second bedroom had a dozen servers and half a dozen workstations, most of which were bought on eBay, some of which I built myself. I ran every OS imaginable — multiple flavors of Linux, BeOS, and even Windows. I was building with ColdFusion and Solaris during the day, PHP and Linux at night. I learned all about networking and routing tables. I built my own device drivers. I built Quake to run in ASCII, because Quake was open source. I wrote shell scripts (and had an especially fun time with Expect) and made web apps. I built APIs.

For a few years, I was learning faster than at any other time in my life. I don’t know exactly when it happened, but I went from feeling like I was in over my head to feeling incredibly competent.

I could do anything.

My team built a solution for providing every US citizen with a personal digital certificate. We also built a universal registration system for all USPS services. It was called eServices Registration. I was in a lot of meetings about it, including one with Microsoft, who wanted us to integrate Microsoft Passport. I asked some questions in that meeting, particularly regarding their use of cookies and a recent cookie vulnerability in Internet Explorer. I left that meeting having disclosed a security vulnerability to Microsoft that I discovered just by talking to them, and it led to my first article, published in 2600 Magazine.

This began a deep interest in HTTP and security. You couldn’t view source to see HTTP in the same way you could see HTML, so I made a proxy called Protoscope that would add HTTP request and response details to the HTML. This was years before Firebug. Protoscope taught me HTTP, and I knew it better than any spec, because I got to see how things were actually working. (For many years, the best reference for cookies was a spec published by Netscape, not the RFC.) I ended up writing one of the first books on HTTP.

We lived in Manhattan when we first moved to NYC, above the famous B&H Photo on 34th Street. I worked on 14th Street building eDonkey, which became the world’s largest P2P network. I handled everything server-side and called myself a webmaster. Being the largest P2P network in the world during the height of file sharing meant we were in the news almost daily. I bought server hardware (including two Cisco LocalDirectors) on eBay and learned a lot about networking security and scalability. It was estimated at one point that eDonkey traffic accounted for 40% of all internet traffic worldwide.

My RSS feed dates back to 2003, which is when I started calling my website a blog. I wrote about CSRF that year, and my now-canonical article was published in 2004. I didn’t fully appreciate my luck at the time, but my curiosity had led me to security during the most influential moment possible. The security standards we still use today were mostly established in those years, and I happened to be the one making a lot of them.

There was a moment when someone named Marc and someone else named Mark wanted to hire me. One was famous (Netscape), and the other was working on something called TheFacebook, which seemed like a silly name.

In 2009, I went to Iceland with my friends Andrei and Helgi. During the trip, we built a map journal called Landice. The sunset in Stykkishólmur was a turning point. I came back home with a desire to create scalability problems instead of solve them.

This began a new period. I moved into a shared studio in Dumbo that would become Studiomates. I met Tina, Jessica, and Cameron. I immersed myself in design and product.

I started Brooklyn Beta, perhaps the thing I’m most proud of to this day. Ira Glass interviewed Tavi Gevinson (when she was still in high school) and made a balloon animal for my daughter Tegan; Tony Fadell spoke about the iPod a week before he announced Nest; and Cory Booker dropped by on his way to campaign with Obama. John Maeda and Aimee Mann were in the audience, as were the founders of Kickstarter, Pinterest, Shopify, and Airbnb. Letterboxd was introduced there. It started small — about 100 people the first year — and grew to about 1,500 people for the final two years.

I don’t know exactly when it happened, but at some point I lost my spark. Technology was no longer inspiring. Developer experience became a thing — it’s sort of like trickle-down economics for technology. The web was rebuilt with JavaScript, and nothing worked anymore. Experimentation was replaced with extraction. Tech giants built walls. Google’s browser became dominant, and they started flexing that power.

Then came the blockchain, cryptocurrency, and Web3. The people building it were young and didn’t know the web we lost. All they knew was what remained, which made anything new seem like an improvement. I tried to get into it, honestly. I invented a card-trading game for the 2018 World Cup that was one of the first NFT projects on OpenSea. I backed Peacefall and won some tournaments. I bought Bitcoin and Ethereum. I gave it a chance. But nothing felt new and exciting.

Technology had a dark side, too. Cambridge Analytica. Myanmar. Brexit and Trump. Surveillance as a business model. Ethan put it succinctly: “the web I grew up in looks very, very different from the web today.” I wasn’t the only one feeling uninspired. Some of the people I trusted and admired the most got quieter. Maybe you did, too.

And on top of it all, we had a pandemic to contend with.

I pursued meaning in my work. After meeting a neuroscientist who had developed an algorithm to measure happiness, I founded a neuroscience company with him that aimed to help people live longer, healthier, happier lives. His idea was to have people rate events in their calendar to gauge how they were doing. My idea was to use photos instead. We built a good product and made meaningful progress in the science of mental health. But it didn’t give me my spark back.

Faculty remained through it all, doing good work, but in my absence its reputation had waned. In some ways, it felt like a reflection of how I saw myself at the time.

Some people had been talking about AI for a long time, but now it was everyone. The people hyping it were mostly the same people who were hyping blockchain and Web3. The people with a lot of experience and perspective weren’t. It was easy to dismiss.

But I’ve never been good at dismissing things. I’d given Web3 a chance, and I wasn’t going to pretend I was above giving AI one, too. When everyone started fawning over ChatGPT, my curiosity got the best of me.

AI had plenty of problems. It was wrong a lot. It certainly wasn’t being fueled by generosity. Instead of Sir Tim Berners-Lee, we had uninspiring billionaires. The money being burned was hard to fathom — companies like OpenAI were losing more, faster, than any company in history. The knowledge it possessed was taken without consideration for who owned it. It felt like a continuation of technology’s downward trend. To some of you reading this, that’s still all it is.

I started using it the way I used to use YouTube — to learn things. I even used it to diagnose a commercial furnace at Roost that wasn’t heating anymore. Everyday things.

Somewhere along the way, something changed. I stopped using AI to learn things I didn’t know and started using it to rediscover things I did. I rebuilt infrastructure I had neglected for years. I revived old projects. I made Landice work again. I started making things again.

Something else happened, too. I stopped thinking of myself as washed up. For years, I had described myself as a former whatever. I only ever allowed myself to be one version of myself at a time.

But depth doesn’t expire.

Building with AI has also helped me realize that my security expertise might matter again. I asked AI about CSRF, and it answered with my own explanations from decades ago. I thought that might bother me, but it didn’t. I never wrote those articles to accumulate status. I wrote them because I wanted to share what I had learned. I gave that work to the open web. I never imagined my words would be recited back to me by a robot. But maybe that's the tradition working as intended: people share what they know, so someone else can build on it.

For the first time in years, I see possibility. Not utopia. AI’s problems aren’t being exaggerated. Like every technology before it, it will reflect the people building it. But possibility is the right word for what I’m feeling, and I haven’t felt it in a while. Not just for young people who haven’t lost their enthusiasm. For people who have been here long enough to remember when the web was open, generous, optimistic, and built by people who simply wanted to make things and share them with the world. That sharing was an expression of our gratitude, and that gratitude is still there.

I think experience matters now more than ever. I think curiosity matters. And I think a lot of people who may have quietly counted themselves out have something important to contribute.

So here’s my birthday wish, for me and for you: let’s be curious and generous. I plan to spend a lot of my time making things again. I’d love some company.

I’m 50 today, and I’m just getting started.

Just you wait.

Chris Shiflett Boulder-based founder, designer, and developer. Co-founder of Studioworks and Schoolcase, and founder of Faculty, a product studio. Writing about building things on the web since 2000. More about Chris →