My Story

If you’re reading this, you probably have been following my writing and/or life journey for some time, or have simply stumbled across this website like a drunk making their way to the filthy restroom inside a dive bar. If you are said drunk (or a teetotaler who happened to take a wrong turn off the digital highway) and have no idea who I am, allow me to introduce myself.

I started my writing journey when I was a small child. I’ve always had an overactive imagination and even now, I constantly daydream or fantasize about scenarios that will never happen. When I was a little boy my mother introduced me to reading (I knew who Stephen King and Edgar Allan Poe were before Dr. Seuss) and since we couldn’t afford a computer back in the 90s, she gave me her old typewriter. I took to it like a drunk to cheap bourbon.

Throughout my boyhood and teenage years, I wrote on and off—probably never finishing a single story—and my reading habits weren’t much better. I’ve always loved books and enjoyed reading, but it was rare I found the RIGHT books that held my attention long enough for me to complete them. Fortunately, my cousin owned a used bookstore directly next to my house so I got to try out a lot of books. Usually, these were picked by how interesting the covers were (many of which turned out to be inappropriate for a boy my age). As it turns out, I liked the cool fantasy covers from books by authors such as Michael Moorcock much more than I actually liked the books, which I most likely didn’t understand at such a young age.

Fast forward to my 20s and a life rife with personal struggles and those struggles’ faithful companion, poverty, and you had a young man desperate for an escape. That’s when my love for reading reemerged and with it, my desire to tell my own stories. Stories I felt were important and could help those who felt just as lost as I had been in those lonely days. The only problem, I was a terrible writer.

Enter Caleb’s renaissance.

For a few years, I wrote stories and submitted them to various publications but they were all promptly rejected. As they should’ve been! When I say I was a terrible writer I mean I had almost no understanding of good writing mechanics nor did I have many tools in my writing toolbox. Sure, I could tell stories, but every story was written like a poor impersonation of the author I was reading at the time. This led to a lot of stories that read like Stephen King if he’d grown up in the Appalachian mountains and dropped out of school to make moonshine for a living.

Delusional about my writing abilities and depressed by all the rejections, I did what any meathead amateur writer would do, I became a freelance writer! I found an online fitness magazine that specialized in gym satire pieces and reached out to them to see if they would be interested in PAYING for the work of an unpublished, unproven, unknown writer. If I was at all cognizant of how much I sucked I would’ve never reached out. But being young, dumb, and full of… ego, I did reach out and what should’ve been a surprise if I wasn’t so arrogant, they accepted my offer. I got my first-ever paid writing gig simply by asking.

I wrote satire pieces for that zine for at least two years and believe it or not, I had a lot of articles go viral. This didn’t just net me a lot of bonuses, it inflated my ego even more. I was an AMAZING writer, or at least that’s what I thought. Further inflating my head was that there were other fitness publications reaching out for my services. I had suddenly become a hot-ticket item.

Eventually, I left that publication and moved onto to one of their competitors who whooed me to their side. They paid more and seemed like a much more professional company. Unfortunately, that also meant I was now a little fish in a much larger pond. I went from being the head satire writer at the old place to one of 50 or so content writers at the new one. Not only was I competing with other writers for publishing spots (something I’d never done before), I suddenly had my abilities questioned by editors and had to prove myself as a competent writer over and over.

It sucked.

As much as it sucked though, the whole experience was invaluable. Not only was I building respectable writing credits, I was also learning how to write properly. All those grammar rules and writing mechanic things I’d overlooked for so long were finally hammered into me by my editors. To succeed, I had to learn how to write and not just tell good stories or make people laugh. The Chicago Manual of Style quickly became a good friend.

A few hundred articles (many viral ones) and some years later, I was feeling pretty good about myself as a writer. So much so that I started thinking of quitting the freelance game and moving on to my first love, writing fiction. But as someone who grew up in a household full of uncertainty (I never knew month-to-month if we would get evicted or not), I resisted change. So I stuck with freelance writing until the unthinkable happened: the owner of the publications (by then I was writing for the sister site as well) had sold the company without warning. The new owner IMMEDIATELY dumped all the staff writers, freelance contributors, and 99% of the editing team. And not just got rid of them but attributed himself as the author of EVERYONE’S work. All of those hundreds of articles I’d written, all the viral ones with thousands of comments, all the writing credits I’d accumulated over the years, GONE!

I won’t name those sites I worked for but if you were to find them, you can still read all of my articles. Only, they now have another person’s name on them. Talk about a real kick in the jewels. (Or like getting hit by a beer truck).

After that experience—which left a rather sour taste in my mouth—and the growing stack of rejections I’d received, I wanted to strike out and do my own thing. I’d toyed with the idea of starting my own literary magazine for a few years but didn’t really know how to go about it. So instead of diving headfirst into that endeavor, I figured I’d start small with an online literary journal.

Roping my good friend Spencer (who was only doing art at the time and had next to no interest in writing) into my wicked plan, I created the literary journal, Drunken Pen Writing (DPW for short) with the intention of working on the craft of writing.

Having so recently come from the freelance world, I still had the mindset of crafting clickbait viral articles, which we did a lot in those early years. Those articles brought us a lot more attention than I’d anticipated and I decided it was as good a time as any to start publishing my own fiction.

After getting Spencer fully onboard the writing train (editing the work of a then non-writer helped my writing skills tremendously, by the way), we both started experimenting with all types of writing forms: flash fiction, short stories, poetry, serialized fiction, micro-fiction, novellas, you name it and we probably tried our hands at it. Looking back, it was a lot of fun!

Early on I knew I wanted to help other writers reach their potential and gain an audience. Mainly because I was so jaded from all the rejections I’d gotten from the countless literary journals and magazines out there. I knew that even my early work was good enough to get published somewhere; a fact proved to me when I published them myself on DPW with good fanfare from our then-growing readership. All the strangers enjoying my work showed me that there was an audience out there for me. The problem was that many publishers don’t often give chances to unpublished authors.

I vowed to do my part in helping shine a spotlight on up-and-coming writers by publishing their work on DPW. In the six-plus years DPW was running, we’d published the work of some truly great authors. Many of them went on to win awards, get book deals, and really grow their audience. It wasn’t until some of the authors reached out to me after DPW shutdown that I learned we were their first publishing credit and that we opened the door for them to get published elsewhere. How awesome is that!

We eventually started the DPW Podcast, at Spencer’s urging, and that was a whole new set of tools I had to learn how to use. We also started getting press gigs and covered a whole bunch of events. That took us to a lot of cities around the east coast and allowed us to have so many wonderful and new experiences. I wish I could discuss everything in detail but this is already growing a bit too long, so I’ll skip to 2022 where the real heavy lifting starts.

For reasons I won’t get into here, we decided to shut down Drunken Pen Writing (though we did keep the podcast, which as of the writing of this releases new episodes every Tuesday). This left a bit of a void in my heart. And just like my freelance work, I suddenly found myself with hundreds, if not thousands of stories and articles but no writing credits. All that work and no way to link to it or share any of it with the world.

I’m not one to give up, though. So instead of getting down on myself, I decided to keep on writing. I’ve been working on my first novel for almost a year now and am over halfway done (as of December 2022). I also decided it was time to finally start submitting work again, more seriously this time, and get some damn proper publishing credits. After ten or so submissions I already got a piece accepted (I will post a link on my publication page once it comes out). That lets me know I’m on the right track on my writing journey.

There’s a lot, and I mean A LOT of stuff I’ve left out. But if you’ve read this far, just know that I greatly appreciate you and I hope you will continue following me on my journey. I don’t know if I’ll get back to updating my Twitter (my engagement has tanked dramatically since the pandemic) but I will definitely keep updating this site with fresh work.

Anyway, happy reading.

Cheers,
Caleb James K.