Most of my twenties were spent daydreaming. I worked boring day jobs—first in retail and then at kinko’s (for eight years)—and most of the time not spent actually working was spent thinking about all the other things I’d rather be doing, or would be doing once my shift ended. Whether it was publishing ‘zines, recording music, building websites, writing articles or designing graphics, I was always working toward something “else” when I was supposed to just be “working.”

Although I never found a way to turn playing music into a viable pursuit—whether due to lack of talent or lack of effort—by the turn of the century, I had already dabbled in doing professional graphic design and copywriting on the side, and had begun freelancing on the regular for the (now-defunct) Las Vegas CityLife. It was at that point that I became pretty much singularly focused on becoming a full-time writer. It was the first of my “side” interests that seemed to actually be leading to a career, something I never really considered and definitely had no interest in pursuing at a corporate copy shop. I threw myself into learning everything I could about media and publishing, spending many hours at libraries and bookstores, perusing and making notes from The Writer’s Market and various writing magazines, learning how to craft pitches and proposals, and getting a feel for the profession of freelance writing. I had started writing a nonfiction book based on my experiences growing up in the nascent Las Vegas “alternative” scene, and probably most importantly, started attending the University of Nevada, Las Vegas to work on a bachelor’s degree in journalism.

Only two years into my undergraduate program (but four years into a freelance sideline that expanded to several publications), I applied for a few media jobs that, in retrospect, I was probably under-qualified for, but I felt confident enough in my skills to at least put my resumé out there. And, improbably, I was hired by VEGAS.com, two years’ short of their bachelor’s degree requirement, to work on the travel website’s content team, writing copy for the site as well as various other tasks related to putting the company’s sister publications’ content on the web. It was, at the time, about as ideal a job I could imagine, and was my first “office” gig—something I’d always wanted. No longer was I spending my days daydreaming about becoming a writer. I was getting paid to be one (even if it was limited to brief show reviews and blurbs). I effortlessly switched to freelancing for the Las Vegas Weekly, one of those aforementioned sister publications, and continued working on several book proposals.

It was all very exciting. Not only was I finally doing more of what I loved to do—writing—but I was also becoming a formal member of the “media.” Even though I had been a freelance journalist for almost half a decade, being on-staff somewhere, having an email address with the company name in the domain, somewhat legitimized that status. It gave me access to more special events, more parties, and more people with the “right” connections. Pull quotes from my reviews appeared in ads for shows, I was making appearances on radio shows and in magazine articles, and I began writing for a litany of publications—art magazines, travel guides, blogs. Within a few years, I was handling not only all of that, but also editing UNLV’s student newspaper, The Rebel Yell, all the while maintaining straight-As despite also going through a divorce. I had a literary agent, a credit in Rolling Stone, and my eyes on going freelance full-time after I finished my degree. The fulfillment of the dream of becoming a full-fledged “writer” lay just beyond the horizon.

Then, just before my last semester at UNLV, I took a job as the editor (and only full-time staff member) of a new monthly magazine, Racket. I couldn’t turn down such an opportunity. Running my own publication? Writing whatever I wanted? Handpicking my contributors? Freelancing full-time would have to wait. Actually, almost all freelancing would have to wait. Because Racket was owned by a startup media company that was in direct competition with the owners of both the Weekly and the CityLife, I couldn’t write for anyone else in Vegas, assuming I even had the time. I still did the occasional travel guide or nonprofit contribution, but otherwise, all of my focus was on Racket. It was more than just a job; it was a lifestyle.

I was no longer interested in writing books, really, and because I had “arrived,” I didn’t have to work toward being anything anymore. I finished my bachelor’s degree, somewhat unceremoniously. In my free time, I taught myself how to shoot and edit video. I started recording music again. I formed a rock band for the first time in more than a decade. And even as the “lifestyle” of being a magazine editor in Las Vegas became my norm, it also began to wear on me. I started looking at other opportunities. The allure of doing this full-time was fading. The magazine ended up folding after 11 issues, but the company gave me an opportunity to launch another endeavor. This time it was an entertainment gossip blog, a somewhat tongue-in-cheek take on celebrity sightings and nightclub events and other frivolous bullshit happening in Vegas. Not surprisingly, I was already mentally one foot out the door by the time the blog launched.

So I found myself trading in my cozy office and editor’s hat to return to a cubicle, writing and managing content for a website again. This time, it was for a quasi-governmental institution. It wasn’t glamorous, but it paid very well, it never affected my life outside of office hours, and it afforded me the opportunity to pick-and-choose my freelance writing pursuits (including for various publications from the same publisher as Racket), while I moved on to my newest interest: making comics. The allure of being a freelance journalist full-time was diminished, especially in the face of a looming economic recession. And I was tired of telling other people’s stories. I wanted to tell my own, even if they were sprung wholly from my imagination.

Somehow, I found myself in the same place in my mid-30s that I was in my mid-20s: Working at a job in which I had little interest (despite it putting my skills to work and affording me and my now-wife a very comfortable, worry-free lifestyle), spending my days at the office daydreaming (or hammering at in between work) of publishing comics, playing music, making videos, writing articles or making art. I was so prodigious, few people—outside of family and very close friends—even knew or considered the fact that I would have a “day job.”

As time wore on, though—five years’ time—the notion of going freelance full-time was bubbling up again. But this time, it wasn’t to do the the kind of writing I thought I’d be doing a decade earlier. Not books and articles and essays, not the 20th century notion of putting text to paper. I had taken on more, well, mercenary forms of paid writing gigs—press releases, biographies, short reviews—and came to a realization: All of those other things I had been doing over the course of 15 years in various functions and positions while I was trying to make it as a “writer”—web design, illustration, video editing, graphic design, public relations—had all become tools in my kit, marketable skills on which I could capitalize. And although I was getting paid to do most of those things at my job, my tolerance for institutional nonsense was wearing thin, and with 40 only a few years away, I felt like the horns of the bull weren’t going to come my way again so easily.

And, so, after a year of planning and saving and building the right relationships, I left my cushy quasi-government job to focus on finally becoming a full-time freelancer … though not one strictly defined as a “writer.” Sure, I would be doing PR consulting and somewhat rote contract work to fill in the gaps, but otherwise I would be afforded the freedom to pick my clients, work on comics, screenplays and blogs when and how I wanted to, and spend time outside the nearly windowless walls of a cubicle-filled office that had been my day-to-day reality for too many years. It may not have been the idyllic vision of spending my time at a sidewalk cafe writing the Great American Novel that I dreamed of in my twenties, but it would have been good enough.

Would have been, that is, if I didn’t muck with the plan and come up with the crazy notion to invest my money and time into a new pursuit, a startup business that would end up redefining my reality in ways I never expected, nor planned for. A reality in which I’m moving further from being a “writer,” and yet closer to being what I may have actually been working toward since even before puberty.

To be continued…