Recently, this blog turned twenty. In that time, I’ve written over 1700 essays, seven books, two traditionally published and five self-published, and created hundreds of podcast episodes, videos, courses and more.
This blog followed the formative years of my life. I wrote my first post when I was 17, still a senior in high school. When I started, I was closer in age to my children than to my current age.
The internet today is unrecognizable compared to the place I started writing two decades ago. In 2006, YouTube was less than a year old, Facebook was still limited to college students, Netflix sent DVDs in the mail, and Instagram, Twitter and TikTok didn’t exist yet.
The internet was a smaller, weirder place back then. Sharing writing online was a hobby for nerds like me who could set up their own website—normal people read magazines and newspapers. Today, nearly everything people watch and read is online.
The personalities that were attracted to blogging were also different. The mostly text-based media meant early blogging afforded quasi-anonymity. Despite using my real name, I didn’t tell many people I knew in real life I was blogging. Writing online allowed me to connect with people over shared interests, even when those interests didn’t always overlap with my real-life peers’.
Today, the idea of going into writing online as way of expressing yourself quasi-anonymously feels quaint. With the dominance of video and viral media, achieving celebrity is seen as the end goal rather than an unwanted side-effect of trying to share your perspective.
This blog feels like a bit of an anachronism. Here I am, still writing blog posts on a personal website like it’s 2006. I’m lucky that I got to build an audience during those early days, and that I can continue to write here despite my idiosyncrasies. It’s hard to say if I had been born twenty years later if I would have had such an opportunity.
On Changing My Mind
Precocity cuts both ways. My early arrival to the internet likely made my current career possible. But it also meant that I made a lot of early mistakes I probably wouldn’t have made had I began today.
Re-reading old essays sometimes makes me cringe. Watching old videos even more so. At some point, my essays stopped sucking by my own standards (admittedly, a low bar), and I no longer feel embarrassed by my writing. But, given that I started writing as a teenager, all my old writing (and dorm-room videos) are still there for all to see.
Intellectual consistency is another victim of starting so early. I’ve flip-flopped on many ideas. Sometimes more than once. So much so that it’s become a bit of a joke among my team members that my most popular essays begin with “I was wrong about __.”
These varying perspectives, taken over twenty years, mean I sometimes end up getting in disagreements with myself or with readers preferring a stance I took years ago. While I’d like to think my writing and ideas have gotten better, I’ve also changed as a person. The perspective at 17 and at 37 necessarily differs in ways that can’t simply be accounted for as accumulating wisdom.
I expect twenty years from now my perspective will be quite different again. Assuming, of course, I’m still lucky enough to spend so much of my time writing.
On Giving Advice
Writing online, of course, is a pretty good gig if you can get it. I have, for two decades, had my dream job. Being able to make stuff, share it online, and earn enough to survive was my dream at 17. It still is, although by now I’ve gotten so used to it that it’s easy to take for granted.
I have a lot of sympathy for people who email me asking how they might be able to do what I do. But I’m not certain I’m well situated to give good advice.
The metamorphosis of the internet means the path I took to get here literally doesn’t exist anymore. Back then, a nobody with a personal website could rank for top search engine terms, webcam footage could go viral on YouTube, and the hot thing for gaining subscribers was something called a “blog carnival.” (Seriously.)
If anyone reading this eventually does find success creating things online, it will certainly be through a very different route than the one I took.
While I can’t really give any help to someone who wants to replicate my job, I can hopefully offer some suggestions for keeping it. After twenty years, I think my only advice is to write the kind of stuff you like to read. That way, you’ll know you’ll reach an audience of at least one person.
I'm a Wall Street Journal bestselling author, podcast host, computer programmer and an avid reader. Since 2006, I've published weekly essays on this website to help people like you learn and think better. My work has been featured in The New York Times, BBC, TEDx, Pocket, Business Insider and more. I don't promise I have all the answers, just a place to start.