Newsletter 100: The Old Life as a Loser Columns

I’ve decided to start putting some of the best newsletter essays here on Medium, so more people can read them. You’re still better off just subscribing. This one is from March 2018, about the long-dead “Life As A Loser” series I wrote more than a decade ago. That series ran 200 editions — here’s the last one — and since we just hit the 200th edition of this newsletter, it seemed like a good time to revisit it.

The final installment of my old “Life As A Loser” column, which ran (roughly) on a weekly basis for about five years back before most reasonable people were even wasting their their time with the Internet, pubbed on March 29, 2004. That’s right: I quit the Life As A Loser series exactly 14 years ago last Thursday. If you knew me at the time that I wrote that column, you, like me, have never felt so old.

The Life As A Loser column came out of the earliest days of online publishing, back when people were just figuring out how to use it, on platforms like Diaryland and Blogspot and even Friendster. (I used to write a different paragraph bio every week on Friendster just to make dumb jokes.) The whole idea of the Web, this amazing new place, is that you could write as long as you wanted to, about whatever you wanted. And that was it! You weren’t trying to get a million people to read what you wrote; in fact, you had no idea how many people were reading it…