How I Built a Career that I Loved

The Path to Mastery

When I was six, I wrote a retrospective poem on my life titled “When I was Five.” (I can still recall writing the line: “When I was five, I didn’t have a Nintendo.”) My dad read it and told me it was good—so good he would send it to a friend he had in publishing. He never did get around to helping me launch a career as a poet, but it was nevertheless a powerful experience. This was the first time I can remember feeling good at something. My two best friends growing up were natural athletes and so I was always slower, weaker, less coordinated than the people around me. The feeling of efficacy I got from writing was undoubtedly one of the early seeds that would lead me to one day pursue an intellectual career. I had found the way I enjoyed using my mind: putting words on a page.

Exploration

That’s not to say I remained laser-focused on becoming a writer. I went through periods where my obsession was martial arts, or baseball, or music. But writing always lingered in the background. When I discovered philosophy at the age of thirteen, my interests shifted from writing poetry and fiction to nonfiction. I started writing essays on religion, philosophy, and politics just for fun. I wasn’t yet on the road to mastery—not self-consciously, anyway. I was just enjoying myself. 

The first true step on the road to writerdom came in my senior year of high school, when my journalism teacher, Brooke Nelson—a feisty ex-journalist who loved to cover my drafts in red ink—introduced me to the book On Writing Well by William Zinsser. Zinsser’s main piece of advice was that good writing isn’t fancy and ornate but clear, simple, lean. He advised writers to kill verbal clutter and reach for vivid verbs. This was the first time I can remember self-consciously working to develop a writing skill. 

By the time I graduated high school, I knew I wanted to become a writer. But I had no idea how to become one. I had no clue what kinds of jobs existed for young writers and no clue how I could get those jobs. Looking back, I shudder at how passive I was. I didn’t ask my writing teachers at college for advice. I didn’t hunt down writers online and ask them what I should do. I didn’t search for articles or books on how to become a writer. In truth, my desire to write for a living wasn’t a goal, but a fantasy. It was something I hoped would happen, but I was doing nothing to make it happen. 

That’s not quite true. The one thing I was doing was writing. I ran a blog, penned a (bad) novel, and later started my own publication for fans of Ayn Rand. I also started taking classes on communication and philosophy from the Ayn Rand Institute. That’s what finally led to my break. ARI was looking for a new writer to join their staff and when they asked the writing teacher, Keith Lockitch, who his best student was, my name was at the top of the list. I got an email inviting me to apply for a job and three weeks later, I was driving across the country from Virginia to California to start my career as a pro writer. I was ready to begin my apprenticeship. 

Apprenticeship

When I started at ARI, the first thing I discovered was this: I didn’t know as much as I thought I knew. I had been studying Ayn Rand’s philosophy for a decade, and yet being around experts like Onkar Ghate, Yaron Brook, and Alex Epstein quickly revealed to me that my understanding of Rand’s ideas and how to write about them persuasively was hopelessly primitive. I had arrived in California feeling like a wunderkind and now felt like a novice. At one level, the experience was disheartening. But at another level, I felt inspired by the discovery of a mountain I wanted to climb, and I made the commitment to do whatever it took to climb that mountain. 

What it took almost broke me. 

For the first two years, virtually nothing I wrote was publishable. I would sit at my computer for hours, carefully crafting two paragraph press releases, only to find them sent back by my editors time and time again. When something eventually would make it through the editing wringer, the final product would reflect only a few of my words—the rest had been rewritten by my colleagues. And that was the easy part. The hard part is that sometimes I would get something through the editorial process and then, at our weekly editorial meeting, our lead intellectual Onkar would explain to me in front of the group why it was wrong and ARI shouldn’t have published it. 

These were painful, frustrating experiences. But I remember telling myself: pay the price. Eventually, you’ll get good. I would spend hours after work reflecting on that day’s feedback, struggling to understand why my editors had made the changes they’d made, to understand how Onkar had seen what I hadn’t seen. I would read books, listen to lectures, stay up late into the evening trying to sharpen my thinking and improve my prose. I was engaging in what psychologists call “deliberate practice”—the painstaking work of skills development that pushes you outside your comfort zone and subjects you to rigorous feedback. It is how you become good at your work. 

One of my biggest assets during this time was my colleague Alex Epstein. Alex would eventually go on to become the world’s leading champion of fossil fuels. In those days, he was just getting started, and yet he already seemed to be decades ahead of me. He was able to take complex issues and make them simple. To present ideas with a level of clarity and persuasiveness that no one else could match. He was doing the kind of work I wanted to do the way I wanted to do it, so I started going to him with questions, asking him to critique my work, studying his writing until I felt I understood every word choice and every comma. I even let him use me as a practice dummy for his hobby of Brazilian Jiu-Jitsu, just so I could soak up more knowledge about philosophy and writing. In effect, I was trying to reverse engineer his success, the way that tech companies will try to reverse engineer a competitor’s breakthrough product. 

Alex was not one of those mentors who couched every criticism between two items of praise. He never attacked me, but if my work was bad, he was blunt and to the point. One evening I had him listen to a radio interview I had done during the financial crisis of 2008. His feedback: “It sounds like this guy”—part of how he made his feedback impersonal was to direct it to “this guy” instead of “you”—“It sounds like this guy is talking out of his ass.” And it was true. I was trying to explain why the financial crisis wasn’t the result of the free market, and while that much was accurate—the market was highly regulated—I really had no clue how the Federal Reserve worked, how Wall Street worked, how derivatives were regulated, and a lot else besides. Alex stressed that I had to make it a policy never to say anything I didn’t fully understand.

This may cause your interviews to be rough at the beginning, but they will be more interesting because the audience will be hearing you—not some guy parroting talking points. There’s no need to present yourself as an expert on Ayn Rand’s philosophy, let alone everything in the world. Just be honest: “I’m a guy who has thought about a lot of things and knows a lot of things, and although there’s a lot I don’t know, I’d like to share with you what I do know.”

Pills like these were tough to swallow, but I swallowed them on the premise that “The more you sweat in peace, the less you bleed in war.”

But I would be lying if I said that I displayed unwavering grit. There were moments during my first few years at ARI where I felt as though I wasn’t making progress. That I simply was not cut out to be a professional writer. I never quite got to the point of giving up, but I did sometimes wonder whether I should give up. And yet at the same time, I knew I was getting better. For long stretches I would stay at a plateau, but every six months or so, a bunch of things would click into place and in a matter of weeks I would rise to a higher level of ability. I could think better and write better. The improvements were palpable. The growth was intoxicating and made it easier to endure the long slogs where it felt like I was treading water. 

A turning point came when ARI’s then-president, Yaron Brook, tasked me to work with him on a book on the morality of capitalism—what would eventually become our national bestseller Free Market Revolution. I found the experience of working on a book liberating. Because there wasn’t a deadline attached to the project, I felt free to experiment, free to rewrite drafts nine or ten or twenty times in order to get them right. I would spend weeks researching a point and thinking about it to make sure I truly understood it. 

My biggest breakthrough came late in the project. Alex had written an essay on the morality of capitalism that I found explosively powerful and persuasive. Meanwhile, another writer I knew wrote a similar essay, only I sensed this one was completely ineffective. I spent hours comparing the two essays side-by-side, and comparing them to the work I was doing on my book. Suddenly, it hit me like a revelation: I could now articulate exactly what distinguished clear and persuasive writing from writing that would leave an audience cold. In particular, I saw that you couldn’t write from your agenda. You had to start from where the audience was and build a bridge, step-by-step, to where you wanted them to be. I saw how great writing had to anticipate the questions your readers would have and the objections that would occur to them. I saw how to use my philosophy to clarify an issue, rather than use an issue to try to sell people on my philosophy. For the first time, I felt in control of my writing and thinking in a way that had eluded me before. 

Experimentation

That was the moment my apprenticeship ended and I started the second phase of my journey: experimentation and refinement. I was now a pro-writer. I knew what I was doing and could reliably turn out publishable work. But I still had holes and blind spots. I hadn’t fully formed my own style and approach. I still relied on editors to save me from embarrassing mistakes. I had control over my writing but not full control. The best way I can describe it is that I was good but inconsistent, and I didn’t have the toolkit to identify and overcome my own flaws. 

Over the next six years, that’s the space I lived in. I wrote more books, each time pushing myself to be more ambitious and experimental. I continued studying communication and philosophy, but now I was putting more of myself into it. What’s my way of tackling this issue? What’s my way of communicating this idea? 

I was becoming more creative, but in 2017, I hit a roadblock. My third book, Equal Is Unfair, had come out the year before. It was the best thing I had ever written and I had expected it to catapult me into the national spotlight, the way Alex recently had with his book The Moral Case for Fossil Fuels. That didn’t happen. In part, I blamed my publisher, who had done nothing to market the book; they hadn’t even gotten the book into bookstores, which is really the only thing publishers contribute nowadays. But I also knew that ultimately the failure was mine. The book was good—very good—but it wasn’t great. And yet I had no clue how to make something great. I went through a period of months where I felt deflated and hopeless. 

The best way I can explain it is this. In high school, my main passion was guitar. I loved writing music, but I hit a point where my conception of what good music was went beyond my ability to play. My creativity was limited by my toolkit. That essentially led me to give up music. But I wasn’t going to give up writing. What could I do to reach the next level? Thankfully for me, that’s when Alex reached out with a job offer.

Alex had left ARI a few years earlier and had turned his advocacy of fossil fuels into a thriving business. He wanted me to help him. It would mean leaving ARI, a place that I loved dearly. It also meant stepping back from the spotlight. Instead of writing my books, giving speeches about my ideas, going on radio and TV to discuss my work, I would be behind the scenes helping Alex increase his impact. It would also mean taking a big risk. Alex’s venture involved far more uncertainty than working for a nonprofit that had been around for decades. I took the leap because I was confident that working closely with Alex would give me the skills I needed to reach the next level of my career. 

It was the right decision. And it was brutal. 

For the first year, I felt like a beginner again. Alex was demanding and the work was fast paced. At ARI I could lock myself in my office for weeks working on an article. With Alex, I’d have to turn around a major project in a day. And still: every word would have to be perfect. To make matters worse, meeting Alex’s standards meant hitting a moving target. Alex’s standards for “good” keep rising as he improved, and so every step forward I made left me further behind. And you have to remember: we weren’t simply writing op-eds for a newspaper. We were creating messaging for energy industry clients paying us five and six figures. If what I did wasn’t good, it mattered. 

What’s more, I was no longer just a writer. Alex tasked me with research, marketing, sales—areas where I had minimal experience and minimal aptitude. The challenge, responsibility, and pace of the work was crushing. For the first year or so, I felt terrified I was going to get fired, which is particularly frightening when your only skill is writing about ideas no one agrees with. 

And yet, just as had happened at ARI, I started to improve. I learned how to present ideas in a way that was truly persuasive. I learned how judge my own work with a far greater degree of objectivity. I learned how to continually raise my own standards rather than rely on someone else to catch my mistakes. And I also learned the art of intellectual entrepreneurship. I saw how to make my ideas valuable on the market, how to find high-paying opportunities, how to conduct myself when dealing with powerful people. After three years working with Alex, I’d built precisely the skills I had hoped to acquire. I had achieved mastery. 

And thank God. Because that’s exactly the moment when it all fell apart. In spring of 2020, oil prices crashed and we lost most of our clients overnight. Then came the pandemic and Alex’s high-priced speaking gigs dried up. He made the hard decision: I would have to find another job. 

Only I didn’t. I decided that to have the career I wanted, I would need to roll the dice and go out on my own as a freelance writer and communications coach. But by now I had the knowledge and skills to do it. I was able to make a living—a better living than I had ever made—writing and helping others overcome their communication challenges. 

I tell this story at such length because, while the details are unique, the essential contours of the journey aren’t. Everyone who achieves a career that they love has gone through some version of the same process: discover what they want to do—and develop the skills to do it well. 

That’s it. That really is all there is to it. 

This is a selection from my latest book, Effective Egoism.

Effective Egoism 101

The conception of earthly idealism I champion was defined by Ayn Rand. Here are three key works that summarize her perspective:

• Faith and Force: Destroyers of the Modern World by Ayn Rand

• Causality vs. Duty by Ayn Rand

• The Objectivist Ethics by Ayn Rand

And if want the full case for egoism, you can buy my book Effective Egoism: An Individualist’s Guide to Pride, Purpose, and the Pursuit of Happiness.