Ten Years of Overthinking It

Overthinking It began publishing on January 22, 2008. How in the world have we managed to keep it going for ten years?

Ten years ago today, Overthinking It published its first articles. Every year since then, I’ve written an anniversary post in which I express gratitude and try to say something OTI-worthy about the milestone (six, seven, and nine hold up OK, I think).

The gratitude is the easy part. I’ve never felt prouder of a body of work, and I am amazed every day by the incredible team that collaborates on the articles, podcasts, and videos. We’ve shared them with tens of millions of people around the world—some of whom we’ve gotten to know pretty well—and they have been consistently awesome. The Internet gets a bad rap these days, but we’ve somehow managed to build a supportive, challenging, compassionate, and brilliant community of smart, funny friends.

The current stock phrase for this sort of thing is “I’m humbled,” but I feel anything but humble; I feel overwhelmed, exalted, and so incredibly grateful. No way could any of us have done this alone. Thank you for joining us on the journey.

I believe in milestones. I believe in streaks and in striving to maintain them. When you work on something for years—a decade now, holy shit—you need to shape the time, to divide it and mark its passage somehow, to prevent it from becoming an undifferentiated flow. I get teased for it (“Matt, do we really need three distinct systems for measuring the podcast anniversary?!”) but I persist: You have to pop a cork and lift a glass every so often, or else even your best days will become just another day at the office. Cheerleading for OTI is not an obligation, it’s one of the perks of this job.

But reading back through all the anniversary posts, perhaps you notice that in recent years I’ve struck a note of warning amid the celebration. (Last year was a special case.) I had some misgivings. Originally I thought it was just us: every year it does get harder to keep this going. We all had a lot more free time when we started Overthinking It. As life wears on, it gets more complex, and you end up with more urgent responsibilities than “get that Game of Thrones recap posted before 3am!” And so we organize, we focus, we launch a membership program. (Join!)

But maybe it’s not just the inexorable march of the years that has me worried. I think larger trends and timing may have something to do with it as well. When we arrived on the scene, though we’d missed the golden age of first-person blogging, we were riding the tail end of the second wave of collectively written blogs. Digital publishing had such a bright future! There was gold in them there posts! More after the jump!

These days, digital publishing is a disaster area. User generated content was gonna save us, then display advertising was gonna save us, then affiliate marketing was gonna save us, then sponsored content was gonna save us, then direct support was gonna save us, and these days machine learning is gonna save us. The only constant in the industry has been that we need saving.

We’re not immune to the general downturn in the field, and we also feel the effects of a much more crowded marketplace for articles, podcasts, and videos. Frankly, the voice that made Overthinking It unique in early years—wry, knowledgable, highbrow/lowbrow—is the default mode of cultural criticism these days. You’re welcome.

I confess that it does keep me up some nights. But when you actually take stock of OTI and put the history of this effort in perspective, the thing that stands out is not how frequently it feels like the sky is falling, but rather how we’ve managed to thrive even with the constraints and threats we face. In 2016 we lost Gawker. Last year The Toast wound down. This week The Awl and The Hairpin announced they were calling it off. Pour one out—we mourn you till we join you. Why have we managed to keep our thing going?

I think it’s because Overthinking It is foremost a community of friends.

The founding group of OTI were college buddies. We met in school about ten years before starting the site. We were musicians and we wrote comedy and we tried to impress each other with smart jokes and dumb jokes and we kept each other entertained on an email list late at night while writing papers and we ate so much food from this particular pizza place that one night when we didn’t order delivery they called to ask if we were OK. We were more than OK—we didn’t know it yet, but we were lifelong friends. We’d just had Chinese that night.

That circle of friends has expanded to include more core writers, more commenters, more audience. It had to, and it has to continue: A community that’s not growing is dying. And believe me, I think every day about how to make that growth even more robust.

But here’s what stays the same: We delight each other. Would you believe, the most common message on our writers’ Slack is, “Hey, have you guys seen this?” And the most common response is, “Wow.” (Followed by fifteen hundred words of exegesis.) In the world, in our lives, whatever else is going on, this thing we do—writing, podcasting, arguing in the comments, making YouTube videos, doing Google Hangouts with the Full Harvey members—this thing is a blast. That’s why we all keep doing it. Because it’s fun. And it’s smart. And we’re lucky to be friends.

Happy tenth anniversary. Let’s keep subjecting the popular culture to a level of scrutiny…

4 Comments on “Ten Years of Overthinking It”

  1. Margo #

    Happy Anniversary! Your podcast has gotten me through many a workday. Hope you are around for another 10 years.

    Reply

  2. Coughin Ed #

    Woooooo! Hell yeah!

    Love you guys!

    Reply

  3. clayschuldt #

    Happy Anniversary! It seems like only yesterday I reading about prisoner theory as it relates to the Dark Knight

    Reply

  4. Joseph Well Actually #

    …it probably doesn’t deserve! (I always wanted to say that.)

    I stumbled across OTI at the tail end of my college career and its been one of my few constants over the past decade. Pop culture websites come and go, but you folks are a true inspiration. Cheers to ten amazing years!

    Reply

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