Two Years Ago I Was Selling Insurance. Now I’m a Writer.

Journalism ain't what it used to be, but it's also not what you think it is.

Apr 21, 2023

Two years ago, I was selling insurance. I had never worked for any media organization. I had never been published. I was not elite-educated, nor did I have any postgraduate degrees. I had no familial connections. There are no writers, artists, professors, academics, scientists, politicians, or financial tycoons in my family tree; no one with bylines, letters after their name, powerful friends, or their own wiki page. Two years later, I’m a full-time professional writer and editor. Based on everything I thought I knew about the field just a few years ago, I’d have said this was impossible. There’s a secret hiding in plain sight that’s so easy to overlook. My journey is far from the usual one, but it’s not a story of perseverance, hard work, or talent (something my critics can agree on). It’s a story about myths, lies, and simple truths.

I fell in love with writing 20 years before anyone ever paid me to do it. I penned millions of words across articles, essays, short stories, screenplays, and novels. Most were seen by only a select few. Others were pseudonymously posted on obscure corners of the web. Toward the end of my tenure as a complete rando, my posts began building a modest audience. In January 2021, one of my readers, Ryan Favro, who had also become a dear friend, recommended that I seek a wider audience and pursue writing more seriously.

What stunned me about the suggestion was that it had never occurred to me. I had grown so accustomed to coasting through life; so familiar with letdown, underachievement, and complacency, that I effectively conditioned myself to stop dreaming big. I created American Dreaming a month later with a mailing list of 25 people (which included my mom). Ryan gave me the gentle prod I didn’t realize I needed. Without him, I’d still be selling insurance. Never underestimate your power to change people’s lives. He’s since become a Contributor here, writing some of the most widely-read pieces I’ve published.

If I was going to get serious, I had to change my writing habits, which were wholly unregimented and driven purely by inspiration. I could pour 10,000 words out if the mood struck, but then go months without jotting a letter. That wouldn’t do. I began this Substack with the promise to myself that I’d publish every week, and I have. Those early months were some of the most intellectually exhilarating of my life, but also some of the most challenging. For the first time, I was writing almost every day. I was meeting deadlines, albeit self-imposed ones. I was doing research, proofing, and fact-checking. Forcing myself to churn out articles on a regular basis was like trying to get in shape after decades of sedentary stagnation. I was straining muscles I never knew I had. But they got stronger.

I relentlessly shilled my work all over social media. At nearly every turn, I encountered this bizarrely hostile attitude toward self-promotion and hustle, as though trying to get ahead is somehow uncouth or in poor taste. I don’t know what twisted amalgamation of dashed hopes, jaded assholism, and misery-loves-company this online mindset sprung from, but it’s poison. I was trying to establish myself in a field where I had no credentials, no connections, and no résumé to speak of. If I didn’t advocate for myself, who the hell would? Often I got back only torrents of abuse. Other times the response was just silence, which was worse. But I was a salesman. I used those skills and calluses (I had long-since become desensitized to being told off by irate customers or hung up on by disinterested prospects). I knew the law of large numbers. I knew you had to kiss a lot of frogs to find a prince. Eventually, people took notice. Offers to write articles started landing in my email and DMs. In time, this expanded to editing and ghostwriting. One thing led to another, and here I am.

My journey is a far cry from the usual trajectory of professional writers. Journalism, as I have lamented, is not the trade it used to be, but too often a hobby for rich kids. As its prestige rose and pay-scale fell, the industry has come to be dominated by the affluent — those who seek status but whose independent wealth obviates any concern over money. My new peers are overwhelmingly the sons and daughters of the upper crust. The kinds of people who took gap years after high school to travel the world (who paid for this, I wonder?). The kinds of people who spent their 20s in perpetual formal education, or abroad, or doing unpaid internships, or engaged in the unbridled leisure-class hedonism euphemistically called “finding yourself.” The kinds of people who, if we’re being honest, never worked a day in their lives before their 30s.

As bitter as I sometimes feel when contemplating how much further along my writing career might be if I too had been a trust fund baby, my circuitous route made me the person I am. I spent my 20s in the real world, making ends meet, worrying about the pocketbook issues ordinary people worry about, and working with the public. Over the 13 years I spent as an insurance agent, I had over 30,000 conversations, either in-person or over the phone (a conservative estimate). I got to know humans. I served as an unpaid therapist, an unqualified financial advisor, and sometimes simply a shoulder to cry on. I loathed what I did for a living, but it was a PhD-level education in people. Having that to lean on as a writer is worth more to me now than a decade spent partying, LARPing, or getting a masters in feminist dance therapy.

The writerly disconnect with the common man fuels both mainstream media elitism and the populism of “heterodox” independent journalists. The individuals who comprise each side are mostly cut from the same socioeconomic cloth. It’s easy to denigrate everyday people when you have lived your entire life looking down on them from above. It’s also easy to venerate those you know nothing about. In a state of ignorance and incuriosity, “the people” become a Rorschachian void to be filled with your own projections and political biases. The reality is that the common man is petty, dishonest, unempathetic, egocentric, and almost neurologically incapable of taking responsibility for his actions. Just like the well-to-do. In many ways, my background has engendered in me not a love of the plebs, but a more informed critique of them.

My account may sound exceptional, but it needn’t be. The field of professional writing is cloaked in layers of carefully-spun misconceptions. Because nine in 10 elite writers have family money, ivy-league degrees, and punchable faces, the popular perception is that being a writer is reserved for a certain social caste. Those without credentials need not apply. Those on the inside, by and large, are only too happy to go along with this convenient fiction. Ask nearly any writer for advice about becoming a writer, and the most common response is direct discouragement. Aspiring writers are told how difficult writing is, how little it pays, and how hard it is to gain a foothold and steady income. As is the case with so much “advice”, it’s often dispensed more for the benefit of the giver than the receiver. People want to self-aggrandize; to play up their achievements and impress upon the listener just how herculean they were to accomplish. And they really don’t want competition. The air of false exclusivity surrounding writing kills both of these birds with a single self-serving stone. But it’s a lie.

I can’t speak to poetry, or short stories, or novels. If you want to make a living writing haiku, there are some basic market dynamics that will be tough to overcome. But short-form nonfiction — articles and essays — ain’t exactly quantum mechanics. Sure, you need to be well-read, able to write, and willing to put the time in, but that’s hardly a revelation. The more you do it, the better you get. Don’t quit your day job — start out doing it on the side and see how it goes. You might be surprised. We often hear how the media is shrinking. These pronouncements are based on narrowly-defined parameters (e.g. jobs working for newspapers). The advent of self-publishing, a growing global population, and smartphones in everyone’s pockets have opened up an entire world of possibilities. The time has never been more ripe to hang a figurative shingle over your own digital doorway.

Needless to say, the legacy media hates this development with an incandescent rage. No one at CNN, NPR, or the Washington Post is losing sleep over Jamie Paul (yet), but the knowledge that this industry can no longer be effectively gatekept by a privileged few absolutely keeps their ilk up at night. Individually, I am no threat to anyone, but thousands of others like me are eating into their audiences, taking bigger bites by the year.

To be clear, writing is not, outside of the uppermost sliver of earners, what anyone would call a lucrative career in monetary terms. This isn’t a great strategy to get rich. But making a living as a writer is not an impregnable fortress whose drawbridge is lowered only occasionally, and only for those with elite education, connections, and résumés. I said at the outset that my story wasn’t one of hard work, and that’s true. The affluent have an advantage, there’s no doubt about that. Wealth opens many doors. The types of people who pervade journalism may be well-off, but they are not, for the most part, intimidatingly talented writers. They are pampered mediocrities whose output is chiefly the kind of uninspired, hive-minded drivel that ChatGPT can easily automate. If you have half a brain, a whole lot of passion, an independent streak, and an internet connection, you can mop the fucking floor with these clowns.

Of course, success at anything takes work as well, but the cliché is correct: if you love what you do, it isn’t really work. I was never a workaholic as an insurance agent. When the clock struck five I practically slid down a brontosaurus’s tail and launched into my car with a wail of yabba-dabba-doo! I worked nights only rarely and when paid overtime. I never worked weekends. I cherished my time away from work, because I hated the job. Never in my life have I put in the kind of work I have since pursuing writing seriously, but I find that it only stimulates and energizes me, because I love it.

In the months to follow, I have some neat things planned for American Dreaming, but for the moment, I’m content to catch my breath and sigh in relief. As my Deadhead parents would say, what a long strange trip it’s been. But I made it, and you can too.

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