I used this dumb image because I could.

In Praise of Obscurity

Turns out, those years of struggle and failure were the happiest of my life.

Dennis DiClaudio
8 min readJul 15, 2022

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When I was in my late-20s and early-30s, I used to despair over how few ‘real’ people were reading the stuff that I was writing. And I was writing a lot back then. Not all great stuff, but some stuff that was worth reading. And nobody was. Or very few people were.

This was in the early-aughts’ lit zine scene that had sprung up online in the wake of Dave Eggers’ success with McSweeney’s Internet Tendency. A lot of us would-be writers immediately saw his success as an opportunity for ourselves. So, we threw a ton garbage at the site. Most of it was never accepted. I’d hate to look through the sludge of that slush pile. I imagine it represented a lot more eagerness that effort. Of course, there was some amazing, funny, insightful pieces published through the website, but they probably represented about one-third of one-percent of what was offered.

We didn’t get accepted. So, we took long hard looks at our work and tried to improve it. And then we still didn’t get accepted. Some of us gave up, no doubt. Some of us worked really hard until we were decent enough for the editors to read past our third paragraphs. And some of us took a different lesson. We decided to become the editors.

We built our own literary websites. Lots of them with a strong bend towards humor. Or at least the ones I focused on. That’s what mine was, anyway. We figured out how to put them up online and make them almost look real, and then we waited for the submissions to start rolling in. When they didn’t, we asked friends to submit. Then we went to McSweeney’s and asked their published writers to write for us. When most of them politely turned us down, or told us they would eventually get to it when they had something that was right for us, we turned to the online lit zines that others of us had built, and we asked those people to write for us.

Most of us weren’t used to anybody asking us permission to publish our work, so we were flattered, and we sent them something that McSweeney’s had rejected. And then they sent their stuff that McSweeney’s had rejected to our websites. And then we just started writing specifically for each others’ websites. We wrote weirder and weirder, more and more specialized, things specifically in order to get published on these small DIY websites that other hopeful writers were managing from their work desks when their bosses weren’t looking. Or we just jumped right to this part and didn’t bother with our own websites. We just tried to get published on theirs.

Oddly enough, nobody was reading these websites. Or nobody ‘real,’ anyway. It was almost entirely a culture of writers writing for one another, and reading each others’ works in the hopes that we might stumble upon the connection that would help us break through this purgatory and reach ‘real’ eyeballs. We didn’t have a term for going viral back then. We just wanted acknowledgement of our existence.

For most of us, this never happened. Or we had some minor success. Maybe some of it led to some job opportunities here and there. Maybe we kept our heads down and kept trying to ‘improve’ our writing. You know, make it more like the stuff that was getting published on actual paper. File away all the grain and strange textures. Make it nice and smooth, like the stories that we weren’t reading in the New Yorker. Maybe some of us eventually found some success with this effort.

But a lot of us, we just didn’t. We either lacked the ability or didn’t have an inclination toward ‘fixing’ our stuff. Some of us just wanted to write like us. And we wanted people to read it. And like it, hopefully. But we’d settle for read it.

Eventually, this culture of DIY lit zines dissipated. Probably in part due to the rise of blogs and social media. But, honestly, a lot of it was just that we got tired of trying. We started focusing on building families and paying mortgages and discovering the fancy hidden flavors in all these new IPAs. We moved on.

I moved on.

And, for many of the subsequent years, I thought upon that period of my life as a time of a failure. A time when I had tried my best and still come up short. A regret for me to carry with me into the old age home.

It wasn’t until quite recently that I realized that those were some of the most successful years of my life. Creatively, anyway.

I would eventually go on to publish four books. Non-fiction humor books. Some of them sold okay. Others, I think, sold about three copies. I also got a job writing full-time on the internet. I got a few short stories published in slightly upper-scale venues.

That was a period of professional success. Creative success, not so much. I was writing for money. But I wasn’t writing for me. I was writing into boxes, so that I would be able to continue writing into boxes. And, in time — not a whole bunch of time either — all that professional success melted away. And what was left was grunt work. It was internet content. I was spending all of my creative energy on things that I’d never be writing if I didn’t have to. Either contractually or in the hopes of making money off of it somewhere down the line. That somewhere hardly ever arrived.

Eventually, I gave up. I was receiving neither enough money nor fulfillment to justify continuing.

This, I assumed, was another in a long line of failures. The kind that pockmark so many creative lives.

Here’s the thing, though: All that professional success I’d achieved in those few small years when I was making a living off of my talents, that all had emerged organically from the period of professional failure I’d had just before it. The books that I’d managed to get published, the paid gigs I was lucky enough to stumble into, they were all the result of that work I was doing back when nobody wanted to read anything I wrote. Because it actually wasn’t nobody.

Thinking back, I see that I had a solid readership of somewhere between twenty and fifty people through the best of it. And not just twenty to fifty random people. They were twenty to fifty people who cared about the same shit as me. Who were able to see what I was trying to do and appreciate the effort. And applaud when I succeeded.

That I was providing the same aid and comfort to them didn’t make them any less real. It didn’t make their opinions matter less or their praise feel hollow. To the contrary, these were people who opinions and praise meant the world to me. You ever have a really funny person laugh at your joke? Or a genuine beauty admire the contours of your face? It feels fucking great.

That was this.

These were people who became my friends. Some of them lifelong. And they were the people who connected me to the people who would eventually grant me short-term professional success. These people liked my writing voice for itself, not for how many clicks it might pull in. And their opinions mattered to me, because I liked their writing voices. We all like each others’ work because it actually spoke to us. And inspired us. And maybe pissed us off a little in the best kind of jealous way.

While writing to please the people who already liked my writing, I was pushing the boundaries of what I thought I was capable. While writing for paychecks, I was hemming myself in further and further in order to fit myself into the smaller and smaller boxes I was being asked to fill. Eventually, there was nobody looking at my writing with any sort of jealousy or praise. Maybe the kinds of smirks you reserve for the cleverer entertainments that traipse across your work monitor. But they weren’t the types of reactions that inspire people to contact you and ask you to write for them. Or even just to dig through your online archives.

It should not have come as any sort of disappointment to find that this had happened to me. I was getting back what I had put in. And that was just enough.

Those years writing for brilliant online lit zines you’ve probably never heard of — Haypenny, Kittenpants, Yankee Pot Roast, Pindeldyboz, Eyeshot— and rejoicing when a piece got accepted, they made me as a writer. I’d call it a crucible, but I don’t think crucibles are supposed to be so lovely. So warm and inviting. Those were wonderful years. And I’m retroactively furious with myself for not appreciating it more at the time.

Today, I do UX for a living. If you don’t know what that is, it’s writing, in some vague sense. I’m making adult-person money for the first time ever. It’s a job I lucked into based on some very kind recommendations from a few of the people I was talking about a few paragraphs up. It’s a nice job. I don’t think about it a whole bunch after I turn off my monitor at the end of the day. There are no pieces of me in the Word documents I churn out.

This may sound like another failure. But I don’t see it that way. I was afraid I would, but I don’t. I see it as a gift to my creative life. It allows me to stop thinking about the money, acceptance, approval I was struggling to get from all that ‘creative’ stuff I’d been focusing on since I stopped writing for fun. Which has allowed for the opportunity to begin writing again for fun.
This thing here that I’m writing right now — what is it? an essay? a confession? — nobody has asked me to write it. Nobody knows it’s being written. I might not even show it anyone. I definitely won’t be submitting anywhere for publication. Most likely, I’ll just throw it up online without fanfare or expectations. This thing here is almost certainly not going to change my life in any appreciable way. And I kind of don’t even want it to. I’m happy with where I am in my life these days. I’m happy with the the low-key life I’m sharing with my four favorite mammals. I’m happy with the weird things I’m thumbing into my phone whenever the mood strikes me. I’m happy with whatever this weird thing here is.

I’m enjoying the process of writing — as opposed to the feeling of having written — for the first time in, like, twenty years? I like writing in the exact patter I want to with zero concern for reader comprehension. I like the colloquial quality of my writing. Its sentence fragments. The use of awkward words like “cleverer.” Not having to even think about editing it down into something I suspect might be more palatable to people who aren’t me. Maybe some people who aren’t me will read it. Maybe some of them will like it. Maybe you’re one of them. Truth of the matter, though, is I don’t give a fuck. (No offense.)

To the best of my personal self-awareness, I do not think that this is any sort of hope-filled end-around toward renewed professional success. As far as I can tell, I’m writing this for a readership of one. If anyone else wants to read it, that’s on them. But they’re getting it cooked to my taste. If they don’t like it, they can spit it out.

These days, I’m writing specifically for me. Which is convenient, because I have my tastes exactly.

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