Build a Career that You Love
Lesson 5: Create Values (2 of 3)
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.
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.
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.
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.
What makes a career fulfilling
This lesson is about building a career that you love. But what does it mean to love your work? Just as pursuing happiness requires understanding what happiness is, achieving career success requires understanding what success consists of. Essentially, there are four ingredients that determine how fulfilling your work will be: money, mastery, autonomy, and mission.
Money
One of the ugliest features of our culture is that it teaches us to disdain money. Or, rather, it teaches us that we ought to disdain money. Since you cannot live without money, the actual result is to prevent you from discovering what a healthy attitude toward money would look like.
Let’s start with the obvious: it is deeply unhealthy to treat money as your supreme value. Money is a tool, and the question is always: how can I use this tool to serve my values? It should go without saying that you shouldn’t work a job you hate just so you can brag about your paycheck and drive a fancy car.
But if morality is about the pursuit of happiness, then it’s good to desire wealth, it’s good to earn wealth, and it’s good to enjoy the wealth you’ve earned. Is the problem, then, the desire for “too much” wealth? No such thing. There is no upper limit on how much money a person should pursue. The fact that you have earned a million dollars or a billion dollars does not by itself demonstrate that you have your priorities wrong. J. K. Rowling became a billionaire because millions of people loved her books. If you are doing work that you’re passionate about, then all else equal, the more money the better.
And the reverse is true. The fact that your income is modest doesn’t prove you have your priorities in order. There are people making $40,000 a year who overvalue money, refusing to take a pay cut to move to a role that is more fulfilling. The question isn’t: “How much?” The question is: “What role does money play in your life?” Philosopher Tara Smith puts it this way:
While there’s plenty to lament in contemporary society’s prevalent priorities, money is not the fundamental problem. In our eagerness to teach that money is not the most important thing in life, we have swung too far in the opposite direction, denigrating money as if it were worthless. While money and material goods are not inherently good, it is equally mistaken to dismiss them as inherently bad.
That’s because, she adds, “Making money (in the literal sense of creating wealth) is the very process of achieving values.” Money ought to be the insignia of creating value doing work you love—and it ought to be used in ways that genuinely promote your well-being. You shouldn’t sacrifice higher priorities to money, like career satisfaction and your most vital relationships—but nor should you treat your desire for wealth as a shameful secret.
I love money. I love the security it buys me: I don’t have to worry about how I’m going to pay my mortgage or feed my children. I love the freedom it buys me: I can fly off to California to celebrate my friend’s birthday and turn down work I find tedious and unsatisfying. I love the health that it buys me: I can visit the doctor regularly and hire a personal trainer to help me get in shape. I love the knowledge that it buys me: I can fill my shelves with books and hire brilliant teachers to coach me. I love the pleasure that it buys me: I can fill my home with beautiful art and treat myself to delicious food and relaxing massages. I love the time that it buys me: I can pay someone else to do my taxes and hire an Uber so I can work or sleep while I travel.
But I never forget my hierarchy of values. No amount of money can make up for an unrewarding career and an unfulfilling life. I long ago vowed that, unless I was in a situation where I literally couldn’t afford to put a roof over my head or food in my mouth, I would never place financial considerations above career fulfillment. I made the hard-nosed decision to establish a lifestyle that fit my income, instead of striving for an income that would support my lifestyle. For example, in 2017, I moved away from Southern California to a more affordable part of the country in part so that I could take more career risks.
But I don’t want to overstate the point. We face tradeoffs between career satisfaction and financial success much less often than people think. If you become good at your work, more often than not, you’ll be able to command a healthy income because you’ll be creating an enormous amount of value.
That’s been my experience. Early in my writing a career I was introduced to someone who worked in my previous field of business proposal writing. He wanted to lure me away and was willing to pay me a six-figure starting salary—far more money than I had ever made. I declined without a second thought. The reason I made that decision is because career enjoyment was more important to me than money. But I also believed that, once I honed my craft, I would eventually make far more money doing what I loved. And that turned out to be true. It took more than a decade, but I eventually reached the point where the major limit on my income was not what people were willing to pay me, but how much time I wanted to spend working with clients versus working on my own material. That’s not unusual. That’s the logical result of having lots of value to offer.
Mastery
The best jobs offer two intimately related kinds of spiritual rewards: practice pleasure and performance pleasure.
Think of a musician. Most of a musician’s time is spent practicing. Not practicing the way I used to practice guitar, where I’d sit around for hours strumming my favorite songs. No, professionals engage in serious, demanding practice where they push themselves out of their comfort zone in order to acquire new skills. In his deeply insightful book So Good They Can’t Ignore You, Cal Newport describes the practice regimen of a professional guitarist he met:
At my request, Jordan laid out his practice regimen for this song. He starts by playing slow enough that he can get the effects he desires: He wants the key notes of the melody to ring while he fills the space in between with runs up and down the fretboard. Then he adds speed—just enough that he can’t quite make things work. He repeats this again and again. “It’s a physical and mental exercise,” he explained. “You’re trying to keep track of different melodies and things. In a piano, everything is laid out clearly in front of you; ten fingers never getting in the way of one another. On the guitar, you have to budget your fingers.”
He called his work on this song his “technical focus” of the moment. In a typical day, if he’s not preparing for a show, he’ll practice with this same intensity, always playing just a little faster than he’s comfortable, for two or three hours straight. I asked him how long it will take to finally master the new skill. “Probably like a month,” he guessed. Then he played through the lick one more time.
This process is pleasurable, but not in the same way as performing on a stage. Performance pleasure is the pleasure of flow—of getting lost in a task that’s pushing you to the maximum of your potential without overtaxing your mental resources. It’s the pleasure musicians feel when they flawlessly play a song they recently mastered—or when they stand on a stage in front of a capacity crowd. Practice pleasure is more akin to the way you feel after a great workout. The workout itself was uncomfortable and grueling, but it leaves you feeling strong, confident, efficacious. It’s the pleasure of making progress and improving.
Bestselling author Daniel Pink calls this element of a fulfilling career mastery: the best jobs fulfill our “desire to get better and better at something that matters.” It combines our cultivation of rare and valuable skills, achieved through a challenging practice regimen, with the exercise of those skills, which results in flow experiences.
Not every job offers the opportunity to pursue mastery. If you’re stuck in a job you don’t know how to do, it can be deflating and anxiety inducing. I once was put in charge of implementing some new software for tracking business proposals. As someone who barely knew how to use Microsoft Word, it was one of the most unpleasant work experiences of my life. But by the same token, if a job is too easy, it becomes monotonous and mind-numbing. The best jobs hit the sweet spot: they force us to stretch and grow—but they don’t stretch us so much that we break. They give us the opportunity to perform at the peak of our current skillset—not struggle to do things we’re utterly incapable of or mindlessly repeat a simple routine.
Note that this is seldom inherent in the job. Whether or not a productive role offers the opportunity for mastery depends as much on us as on the job. This is why you’ll often need to change jobs whenever the opportunity for increased mastery vanishes. I spent eleven years at the Ayn Rand Institute. But I reached a point where I noticed my skills plateauing. Even though I loved the work, the organization, and my teammates, I made the hard decision to leave in favor of a role where I’d be in unfamiliar territory and need to develop new skills. In the short-term, the decision was costly. I went from feeling capable to feeling like an incompetent beginner. But in less than three years I had developed a new set of skills that made it possible for me to take the next step in my career: to work for myself. And that turned out to be the most important career move I ever made because it gave me the one thing that had been missing from my career: autonomy.
Autonomy
That challenging new job I took after I left the Ayn Rand Institute? As I mentioned, I lost it during the 2020 pandemic, just as I was about to close on my first home. I spent several terrified days thinking I might have to find a job doing something other than writing just to make sure my family could make ends meet. Then I got a call from a previous employer. They were eager to rehire me. I turned them down.
Or to be more exact, I made a counteroffer: I would work half the week for them freelance. Looking back, I’m surprised I had the courage to turn down the full-time role. The income from one client would not be enough meet all of my financial commitments and I had no idea whether I’d be able to find more clients, particularly in the midst of the pandemic. But the reason I insisted on a freelance arrangement was simple: I wanted control over my career. I wanted autonomy.
Autonomy is not a matter of whether you’re working alone or collaborating with others—it’s about the degree to which you are in charge of what you do, when you do it, how you do it, and who you do it with. In my case, what I was most interested in was being able to work whenever I wanted to work, and to say whatever I wanted to say. That’s why, despite the risk, I was willing to reject a generous job offer from an organization I admired.
(Full disclosure: during the writing of this book, I returned to ARI to help build a coaching program for their educational institution, Ayn Rand University. I have less freedom than when I worked for myself, but ARI still offers a lot of flexibility and, more importantly, I have a lot of autonomy with respect to how I build the coaching program. I point this out to highlight that autonomy doesn’t mandate working for yourself.)
The desire for autonomy is rooted in the fact that you have free will. As psychologists Edward Deci and Richard Ryan put it, “Autonomous motivation involves behaving with a full sense of volition and choice, whereas controlled motivation involves behaving with the experience of pressure and demand toward specific outcomes that comes from forces perceived to be external to the self.” The more say you have over your career, the more satisfying your career generally is because it is your own judgment and values that are shaping your life, not externally imposed duties. Even when things are hard, even when you’re busy, frustrated, flailing, and failing, you have the sense: I am the master of my own destiny. This is the course I chose because I believe it is the best one.
It’s easy to undervalue autonomy because control is often taken for granted. “Of course I need to have someone tell me when to show up to work and what tasks I need to work on. Isn’t that what a job is?” Worse, autonomy is seldom granted—it has to be seized by going into business for yourself, or negotiated for, often at the expense of the more conspicuous benefits of a higher salary. Daniel Pink notes that some of the most apparently successful workers—high-powered attorneys—often suffer emotionally because their jobs are generally extremely low autonomy. “Lawyers often face intense demands but have relatively little ‘decision latitude.’”
By contrast, many tech companies recognize the value of employee autonomy to both happiness and productive success. They tend to be more flexible in terms of when employees come to work. Netflix, for example, has no policy telling employees when to show up or how much vacation to take. They’re treated as professionals: so long as the work gets done, it doesn’t matter when or how they do it. Similarly, Google encourages its engineers to spend 20 percent of their time on a side project of their choice. The result is many of Google’s most notable products, including Gmail and Google Translate.
We’ll see shortly how to gain autonomy in your career. The point here is simply to underscore the fact that if you want a career you enjoy, it is often not the particular industry you’re in that matters most, but the amount of freedom you have to direct your work.
Mission
Mission is the belief that your career adds up to something—that you’re pursuing some larger, positive purpose than meeting this quarter’s goals. Many people, including Pink, equate mission with finding “a cause greater and more enduring than themselves.” Such sentiments reflect the influence of anti-self moralities—not any reality about what satisfies people at work. Cal Newport’s characterization of mission is far superior:
To have a mission is to have a unifying focus for your career. It’s more general than a specific job and can span multiple positions. It provides an answer to the question, What should I do with my life? Missions are powerful because they focus your energy toward a useful goal, and this in turn maximizes your impact on your world—a crucial factor in loving what you do. People who feel like their careers truly matter are more satisfied with their working lives, and they’re also more resistant to the strain of hard work. Staying up late to save your corporate litigation client a few extra million dollars can be draining, but staying up late to help cure an ancient disease can leave you more energized than when you started.
Yes, although there are lawyers whose mission is to fight for the often-maligned corporations who spearhead human flourishing and human progress. But the larger point is that mission has nothing whatever to do with looking for something outside of yourself that justifies your life. It is instead about shaping the earth in the image of your values. My own mission is to help people learn, live, and advocate ideas I believe are true. That mission drives me, inspires me, energizes me—and yet it is deeply selfish. I’m working to make the world a better place—a better place according to my standards for the sake of me and the kind of people I care about.
Almost any career can offer a sense of mission. When I worked with Alex Epstein at the Center for Industrial Progress, one of our goals was to teach members of the fossil fuel industry that their work wasn’t a necessary evil, but that in providing the world’s best source of low-cost, reliable energy they were promoting human flourishing for billions of people. By helping industry members see the larger purpose their work was aimed at, we empowered them to formulate inspiring personal missions that deepened their enjoyment of their work. We received thousands of messages thanking us and crediting our work for changing their lives. Mission, in other words, isn’t something reserved for so-called mission-driven companies.
But by the same token, it does take time, thought, effort, and choice to create a career directed toward a mission that resonates with you and inspires you. As much as I value the fossil fuel industry’s work intellectually, it doesn’t resonate with me spiritually the way it does for Alex. Working at CIP was valuable because it helped me build the skillset I needed to achieve my personal mission, but it didn’t allow me much scope to pursue my personal mission. That’s fine. Early on in your career, don’t expect to be in a position to formulate your mission. Focus on developing the skills that will lead you to mastery. But once you formulate your mission, fulfillment depends on making that the purpose that will direct your career choices.
How do you formulate a mission? By reflecting on what goals and activities actually energize and motivate you, and working to integrate them into a single, unified whole. I said that my mission is to help people learn, live, and advocate ideas I believe are true. I reached that formulation by noticing that there were a few activities that I found completely enjoyable to do and fully rewarding having done: writing (fiction and nonfiction), public speaking, editing, and mentoring people who shared my interests, convictions, and values. At first, these activities felt scattered. Sometimes I was creating my own content, other times I was helping people create theirs. But once I grasped that the kind of content I most enjoyed creating aimed to help “young versions of me,” I realized they were all part of the same mission: to empower those who share my ideas.
That’s what it means to build a career you love. It means to achieve a career filled with mastery, autonomy, mission, and enough money that you aren’t worried about money. In Pink’s words, “The most successful people, the evidence shows, often aren’t directly pursuing conventional notions of success. They’re working hard and persisting through difficulties because of their internal desire to control their lives, learn about their world, and accomplish something that endures.” But how do we do that?
Follow your passion—or create one
The main career advice we’re offered today is to “follow your passion.” Even family members who quietly nudge us in more “respectable” and remunerative directions will usually pay lip service to this advice. And it is not always bad advice. I more or less knew I wanted to be a writer from the time I was six, and I knew I wanted to write about philosophy from the time I was fourteen. Many professional athletes and musicians and soldiers have similar stories. If you know what you want to do, do it.
But what if you don’t know? Too many people go to college as a default then stumble on a job, asking themselves, “Does this feel like bliss?” And inevitably they’re disappointed, because almost no job feels like bliss at the start. Though there’s a deep satisfaction that comes from being on the path toward doing what you love, the early years are inevitably filled with tedious work assignments, difficulty, and struggle. I spent the first few years as a professional writer feeling like I had no idea what I was doing, receiving blistering feedback on my work, staring at a computer screen having no idea how to fill it with words worth reading. At several points I found myself questioning my path: maybe I would be happier as a teacher, or a psychologist, or an entrepreneur. It was only after I had mastered my craft, more than a decade later, that I could honestly say without reservation I had chosen the right path.
My experience isn’t unique. Cal Newport warns of the dangers of what he calls the “passion hypothesis,” the view that we achieve a career we love by first figuring out what we’re passionate about and then seeking out a job that matches our passion.
The more I studied the issue, the more I noticed that the passion hypothesis convinces people that somewhere there’s a magic “right” job waiting for them, and that if they find it, they’ll immediately recognize that this is the work they were meant to do. The problem, of course, is when they fail to find this certainty, bad things follow, such as chronic job-hopping and crippling self-doubt.
Trying to decide “am I passionate about this?” is a dangerous question early in a career because entry-level positions, “by definition, are not going to be filled with challenging projects and autonomy—these come later.”
The passion hypothesis says that your ideal career has been decided for you and your job is merely to find it. Worse, it implies that you don’t have to do anything to become worthy of that career: once you discover it, you are entitled to it. Both points are wrong. A career you love isn’t something you find—it’s something you create. It is less like stumbling on an abandoned treasure and more like fashioning a stone into a sculpture. You decide the final shape, but not through a mere wish. You have to work to make your vision a reality. The difference is that with a career you can start creating it before you know the final form it will take.
How is that possible? Because successful careers all have a similar shape. Their final form will be distinctive, but they universally share one fundamental characteristic: they all consist of value-creating activities. If you live on a self-sustaining farm, you’re trading your time and effort for the crops you need to sustain your own life. In a division of labor economy, you’re trading what you produce for what others produce, mediated through money. This is the trader principle: to get what you want from other people you must give them something they want.
Newport points out that often people who “follow their passion” fail because they are totally focused on what they want without genuinely thinking about whether they have something valuable to offer in return. They want a high-paying job—but don’t think about how to increase their company’s profits. They want a successful blog—but don’t think about how to give readers valuable content they can’t find anywhere else. They want a successful business—but don’t think about how they’ll be providing superior value to their customers, compared to existing alternatives.
The point is not that you should ignore what you want and fixate on helping other people on the premise that their happiness is more important than yours. No. A trader is not a servant. The point is that you live in a division of labor economy, and if you aren’t creating value for other people, then expecting them to provide you with rewards means treating them as your servant. It’s not billionaire CEOs like Jeff Bezos and Mark Zuckerberg who are exploiters—it is anyone who believes they are entitled to have their needs and desires fulfilled without offering anything of value in return. In Rand’s words:
A trader is a man who earns what he gets and does not give or take the undeserved. He does not treat men as masters or slaves, but as independent equals. He deals with men by means of a free, voluntary, unforced, uncoerced exchange—an exchange which benefits both parties by their own independent judgment.
The trader principle is the key to creating a career you love. As Newport observes,
The things that make a great job great, I discovered, are rare and valuable. . . . Basic economic theory tells us that if you want something that’s both rare and valuable, you need something rare and valuable to offer in return—this is Supply and Demand 101. It follows that if you want a great job, you need something of great value to offer in return.
This means that whatever it is you ultimately want to do, the foundation will be cultivating rare and valuable skills that allow you to offer something compelling in trade. Pick any field you find interesting and ask yourself: if I were world class in this field, would I have any difficulty creating a career that I loved? If I were an elite salesperson, or an elite singer, or an elite chef, or an elite software engineer, or an elite lawyer, wouldn’t that virtually guarantee I could design a job that would fill me with joy?
That’s the starting point of creating a career you love: developing rare and valuable skills. But which skills should you seek to develop? Even if you don’t have an intense career passion, you almost always have abundant career interests. There are fields that intrigue you and questions that excite you. Such nascent interests are signals to explore further. And the main thing you should be exploring is: how do I enjoy using my mind?
Every productive activity involves a distinctive way of using your mind: writing computer code is different from writing marketing copy. Agriculture is different from sales. Accounting is different from playing in an orchestra. It’s not simply that the industries are different, or the outputs are different, but the mental processes involved are different. What you’re striving to find are the kinds of processes where you most feel at home.
Harvard University neuropsychologist Howard Gardner has identified eight forms of intelligence. I don’t endorse his entire theory, but I find his categories useful for identifying the kind of productive roles that can fill your life with joy.
Logical-mathematical (think: software programmer or financier)
Linguistic (think: writer or public speaker)
Spatial (think: architect or taxi driver)
Musical (think: composer or music producer)
Bodily-kinesthetic (think: baseball player or construction worker)
Intrapersonal (think: poet or psychologist)
Interpersonal (think: salesperson or teacher)
Naturalistic (think: veterinarian or biologist)
When you’re deciding what kind of rare and valuable skills to build, you can be industry agnostic—but you can’t be mental process agnostic. Someone who feels most at home introspecting and reflecting on their emotional life (intrapersonal) will likely be unsuccessful and unfulfilled in a career relying primarily on logical-mathematical skills. Someone who feels most at home working out and dancing (bodily-kinesthetic) will likely be unsuccessful and unfilled in a career relying primarily on linguistic skills.
What you have to identify is the way of using your mind that feels most natural—the kinds of mental activities where time vanishes, where you’re fully engaged and fully alive. Psychologist Mihály Csíkszentmihályi calls this state “flow” or, a term I much prefer, “optimal experience.”
The best moments in our lives, are not the passive, receptive, relaxing times—although such experiences can also be enjoyable, if we have worked hard to attain them. The best moments usually occur when a person’s body or mind is stretched to its limits in a voluntary effort to accomplish something difficult and worthwhile. Optimal experience is thus something that we make happen. For a child, it could be placing with trembling fingers the last block on a tower she has built, higher than any she has built so far; for a swimmer, it could be trying to beat his own record; for a violinist, mastering an intricate musical passage. For each person there are thousands of opportunities, challenges to expand ourselves.
If you’re not sure where to find this kind of satisfaction ask yourself this: What do you do when you don’t have to do anything? What do you do when you’re supposed to be doing something else? It’s possible that your answer will be some form of passive mind-numbing, like frittering away your life on TikTok. But more likely there are activities that absorb you and compel you. Sometimes this will point you directly toward a specific career. For me, I spent every moment I could reading and writing about ideas—and I created a career reading and writing about ideas. More often what you’ll find is not a ready-made career path, but insight into the kind of mental work you enjoy.
Once you know how enjoy using your mind, then you can focus on building rare and valuable skills that are centered on using your mind in this way.
Develop your skills
Ira Glass is the creator of NPR’s revolutionary radio show This American Life. When he talks about his path to success he notes that he, like every creator, started out with a problem: there was a dramatic gap between his taste (his ability to know what good work looked like) and his skills (his ability to create good work). He succeeded because he kept working on his skills until he closed that gap. Most people fail because that gap is so painful and involves so much self-doubt that they give up.
Everybody I know who does interesting, creative work went through years where they had really good taste and they could tell that what they were making wasn’t as good as they wanted it to be. They knew it fell short. Everybody goes through that.
And if you are just starting out or if you are still in this phase, you gotta know it’s normal and the most important thing you can do is do a lot of work. Do a huge volume of work. Put yourself on a deadline so that every week or every month you know you’re going to finish one story. It is only by going through a volume of work that you’re going to catch up and close that gap. And the work you’re making will be as good as your ambitions.
For every field, there are foundational skillsets that are the price of entry. To be a musician, you have to be able to play your instrument. To be an accountant you have to understand bookkeeping. To be a real estate agent, you have to understand real estate contracts and the basics of sales.
The first steps on the road to mastery consist of identifying the skills your field requires and acquiring them. You identify them through reverse engineering. You acquire them through deliberate practice.
Reverse engineering means studying how others in your field became great and searching for patterns that you can emulate. It can be tempting to resist this kind of modeling in the name of originality, but originality doesn’t come from doing something that’s wholly new, but from building on what came before, adding your own spin, adapting what has worked in the past to your own unique context.
My screenwriting teacher, when he was getting started and wanted to improve his style, would copy, word-for-word, screenplays he admired. The idea was that this would help him internalize what it felt like to write lean, gripping dialogue. Cal Newport talks about spending weeks analyzing an important academic paper in his field until he understood it better than anyone else. The best way to do original work is by learning to do good work, and that means focusing not on originality, but on acquiring the skillset possessed by past masters. That’s where deliberate practice comes in.
The key word there is “deliberate.” I spent years “practicing” guitar, but I stopped improving because I was staying in my comfort zone, playing the same songs over and over again. Repeatedly doing something doesn’t lead to improvement, which is why most of us have driven cars for years or decades but aren’t elite drivers.
Deliberate practice, by contrast, means identifying a new skill you want to acquire or a weakness you want to overcome and then stretching yourself beyond your current comfort zone to build that skill. If I wanted to improve at guitar, I should have committed to learning songs slightly above my level of ability. I should have worked at playing them slowly until I could play every note perfectly. Then, I should have started speeding up, a bit at a time, only increasing the tempo when I could play without mistakes.
The reason I didn’t do that is because pushing yourself outside of your comfort zone is uncomfortable. You can strum your favorite songs for hours. Deliberate practice involves such intense mental focus, tension, and stress that you can only do it for two or three hours a day before you’re depleted.
For deliberate practice to lead to improvement, it must involve feedback: you have to know when you’re succeeding and when you’ve made a mistake—and ideally that feedback should come as rapidly as possible. With a musical instrument, you usually know immediately when you’ve made a mistake. In other cases, you have to rely on mentors to guide you. A surgeon in training, for example, will have a senior surgeon watching their every move and giving real-time advice. As a writer in training, my task was harder. I usually depended on feedback from editors, which would come hours or even days later.
As you reflect on the skills you need to develop to achieve mastery in your field, think about how you might go about practicing those skills. How can you push yourself outside your comfort zone in a way that involves the feedback necessary to gauge your progress? Then commit to a practice regiment that will supercharge your growth.
This is the foundation of success. The only way to do good work . . . is to work.
Crash your career
A major myth claims that there are “tracks to success,” and that you’re in constant danger of falling off this track: by not getting that high prestige job straight out of college, by not getting into an Ivy League school, by not graduating at the top of your elite high school, by not getting into the elite pre-school. This is madness.
Success has nothing to do with social status. It has to do with creating a career that you love, and unless your mind, heart, and soul compel you to make partner at a top law firm or work at Goldman Sachs, then anyone who tells you that your future happiness depends on following some pre-determined track is lying to you.
I became obsessed with philosophy when I was fourteen and spent all of high school doing the minimum necessary to get by while I devoured the works of my favorite thinkers. I graduated with mediocre grades, selected a mediocre university, and ended up finishing college at a less-than-mediocre night school. My first adult job wasn’t at McKinsey. It was packing boxes in a shipping warehouse. And yet, despite no impressive credentials, by the time I was thirty I was a bestselling author writing about philosophy.
Or take my friend Chad. Chad moved from Iowa to southern California after high school and was working in the mail room of a nonprofit when he met champion bodybuilder Mike Mentzer. Chad studied Mike’s unique approach to bodybuilding and used that knowledge to start his own gym in Hollywood.
Or take my friend David. He was a self-described computer geek who was obsessed with swing dancing. By the time he was in his mid-twenties, he had become so prominent in the swing dance community that he was able to make a living teaching people the Lindy Hop and Balboa.
Or take my friend Keith. He dropped out of college to become a serial entrepreneur. His latest venture was as co-founder of a company that creates online science lessons that more than 50 percent of elementary schools in the US use. In 2020, Keith sold the company for $140 million.
Success is not a track someone else paved that you have to walk down. It is an open-ended path you have to carve. You need to view your pursuit of productive passion as an adventure. You don’t have to know where to start. You can plunge in anywhere.
But how do you get started? How do you launch your career when you can’t create much value?
The traditional answer is: earn credentials, submit job applications, go on job interviews. Often this approach is paired with a sense of entitlement: I have a degree; I deserve to make $50,000 a year.
No. You deserve only what other people find it in their self-interest to pay you. To build your career, you have to stop thinking like a bureaucrat checking boxes and start thinking like an entrepreneur. To be an entrepreneur, you know that you’re entitled to nothing and that what matters is not your credentials but your ability. Your orientation must be to demonstrate that you can create value.
In almost every case, you won’t be able to create much value at first. That’s fine. That’s a problem your journey toward mastery will solve. Your competitive advantage at the beginning is your ability to work cheap. If you don’t cost much to employ, you don’t have to create much value to be profitable to employ. For those who can afford it, a tried-and-true method to get started in any field is the ability and willingness to work for free.
But just as important as your willingness to work cheap is your eagerness to grow. An employer can typically select among cheap entry-level workers. What will make you stand out, whatever skills you have or lack, is hunger. Ambition is the trait great employers look for in young people—above all, the ambition to learn.
When I watched young writers at the Ayn Rand Institute, I had one rule of thumb for judging them. Did they proactively seek out opportunities to learn? Did they devour the works in our library? Did they come to me or other senior writers with questions and for feedback? Did they implement our advice or look for reasons to dismiss it?
Of course, demonstrating that you’re hungry requires getting your foot in the door. Writing “ambitious” on your job application accomplishes nothing. You have to learn to signal ambition and ability. In my case, the whole reason I got hired by the Ayn Rand Institute is because I had been blogging about Ayn Rand’s philosophy for years. I created a public record, not only of my writing ability, but of my commitment. You can imagine ARI’s leadership saying, “If this is what he does in his free time without pay, imagine what he’ll do full time for a salary.”
You can do the same thing in any field you want to enter. Stop thinking in terms of credentials and start thinking about how you can demonstrate your ability to create value—how to demonstrate that you have the skills, hunger, and salary requirements to be profitable to a company from day one.
Find your path. Take your first step. Then move forward by leveraging your increasing set of rare and valuable skills into increasingly satisfying work.
Leverage your career capital
You have only one fundamental career bargaining chip: your rare and valuable skills. This is your career capital. As you amass that capital—as you become so good they can’t ignore you—people will want to hire you and work with you because you can help them get what they want. But it’s this career capital that will allow you to get what you want, and a common mistake is to trade away that capital solely for financial rewards.
Often a better approach is to leverage most of your career capital in exchange for more fulfilling work: work that will take you further on the road to mastery, work that will give you more autonomy, work that will bring you closer to the achievement of your mission.
The most straightforward path here is to start your own business. Once you have sufficient career capital to do valuable work, starting your own business puts you in the driver seat of your career. By business, in this context, I’m including everything from working as a freelancer to launching a Silicon Valley startup.
I’m convinced that many more people should go into business for themselves. Too often they overestimate the risks and underestimate the benefits. The risks seem magnified because many who do start businesses don’t begin by building the career capital that makes success far more likely: they don’t know the industry, they don’t know their market, they don’t have rare and valuable skills, they don’t have a competitive edge—they’re going on nothing but hope and a prayer. This rarely works. Even entrepreneurs who are successful at a young age, like Mark Zuckerberg and Bill Gates, have almost always spent years building relevant skills, and typically have seen success before they formally launched their enterprises. Zuckerberg, for instance, started Facebook as a hobby and left Harvard only when the company was growing so fast that making it his full-time career was the only way to keep the company going.
But what if you don’t want to work for yourself—at least not yet? You can still pursue mastery, autonomy, and mission. Newport tells the story of Lulu Young, a highly talented software developer. Her first work project after college was in quality assurance. She used what on paper was a boring job with minimal upside to automate the testing process and save her company a bunch of time and money. She continued to innovate and add value to the company, but after a few years she stopped using her career capital to bargain for a promotion or a raise and did something else.
To regain some autonomy from a succession of micromanaging bosses who had been tormenting her, she demanded a thirty-hour-a-week schedule so she could pursue a part-time degree in philosophy from Tufts. “I would have asked for less time, but thirty was the minimum for which you could still receive full benefits,” she explained. If Lulu had tried this during her first year of employment, her bosses would have laughed and probably offered her instead a “zero-hour-a-week schedule,” but by the time she had become a senior engineer and was leading their testing automation efforts, they really couldn’t say no.
That’s the method: build career capital, then bargain for a more fulfilling role at your current company or a new company—a role where you have more opportunities to learn and grow, more control over your work, and more chances to tackle projects aligned with your personal mission.
We’ve now seen the process that will lead to a career you love. If you discover the way you enjoy using your mind, pursue mastery, and leverage your career capital into roles that enhance your autonomy, creativity, and mission, you won’t have “found” your passion—you’ll have created it.
Don’t lose focus
I’ve been stressing the central importance of work in life, and the virtue displayed by dedicating yourself to productive achievement. But I know a lot of high achievers who are unhappy and unfulfilled, or at least filled with a vague guilt that they should be achieving even more.
So let me start by distinguishing devotion to career from workaholism. Workaholism isn’t primarily a matter of how much time you spend at work, but why. Is work, for you, a source of creative joy or is it an escape from personal problems? Do you love the work itself or do you love the image of yourself as a high-powered attorney, a business mover and shaker, an altruistic crusader? Is your standard of success your own enjoyment—or is it comparative: being richer, more powerful, more admired than others? Workaholism is an addiction, and what a person is addicted to is escape from negative feelings—above all, feelings of self-doubt.
In From Strength to Strength, Arthur Brooks tells the story of a woman who had achieved enormous success on Wall Street, but who was not particularly happy.
Her marriage was unsatisfactory, she drank a little too much, and her relationship with her college-age kids was all right . . . but distant. She had few real friends. She worked incredibly long hours and felt physically exhausted a lot of the time. Her work was everything to her—she “lived to work”—and now she was terrified that even that was starting to slip.
Brooks asked her why she didn’t do the obvious thing and cut back on her work. It was, after all, making her miserable. She replied: “Maybe I would prefer to be special rather than happy. . . . Anyone can do the things it takes to be happy—go on vacation, spend time with friends and family . . . but not everyone can accomplish great things.”
The first time I read that line—“I would prefer to be special rather than happy”—my blood curdled. Because what it means in practice is: “I want to throw my life away so that someone will pat me on the head and tell me I’m important.”
Work plays a crucial role in building healthy self-esteem. It’s through your work that you take responsibility for your own life, grow your capabilities and confidence, and gain a sense of efficacy. But it’s a tragic mistake to tie your self-worth to some conventional image of “success.” My admiration for achievement is limitless, but success without happiness doesn’t make your life special. It makes it tragic.
Even those who avoid the trap of workaholism can often find themselves experiencing work as a burden or a source of guilt. Shonda Rhimes gave a commencement speech where she noted that people often express awe at how she manages her life as an in-demand screenwriter and mother of three. “[P]eople are constantly asking me, how do you do it?” Her answer: “I don’t.”
Whenever you see me somewhere succeeding in one area of my life, that almost certainly means I am failing in another area of my life. If I am killing it on a Scandal script for work, I am probably missing bath and story time at home. If I am at home sewing my kids’ Halloween costumes, I’m probably blowing off a rewrite I was supposed to turn in. If I am accepting a prestigious award, I am missing my baby’s first swim lesson. If I am at my daughter’s debut in her school musical, I am missing Sandra Oh’s last scene ever being filmed at Grey’s Anatomy. If I am succeeding at one, I am inevitably failing at the other. That is the tradeoff. That is the Faustian bargain one makes with the devil that comes with being a powerful working woman who is also a powerful mother. You never feel a hundred percent OK; you never get your sea legs; you are always a little nauseous. Something is always lost. Something is always missing.
I don’t think it has to be this way. It all comes down to how you judge yourself. Too often people hold themselves to impossible standards. They judge their performance in one area of life as if it were the only area of life: What kind of mother would I be if I were nothing but a mother? What kind of husband would I be if I were nothing but a husband? What kind of creator would I be if I did nothing but work?
But a standard that’s impossible to meet is a bad standard. A mother’s responsibility is not to be there for every moment of her child’s life. A CEO’s responsibility is not to reply to emails twenty-four hours a day. Your responsibility is to envision a whole life; a life that involves work, and connection, and rest, and recreation; to structure your life so that you attend to your most important values; and then, when you are at work or you are with your children, to be fully present. You will miss things, and that will suck. But it should not be a source of guilt.
That, really, is the lesson I want to leave with you. Work should never be a source of guilt. I love stories of intrepid creators who chain themselves to their desks in pursuit of ambitious goals. I’ve admiringly told many of those stories in my books. But that is not what the virtue of productiveness demands, and you should not feel bad if you work your ass off from 9 to 5 then clock out and attend to your other interests. What productiveness does demand is that you center your life around productive achievement, in whatever way and to whatever extent fits your vision of what you want from life. There is no moral obligation to limit your work to forty hours a week if what you want demands far more of your time and attention. But there is also no moral obligation to become a slave to your work.
In fact, the more I’ve gotten to know high achievers, the more I’ve been impressed with how many of them jealously protect their non-work time. They work more than the average person, sure. But when they sign off, they sign off. No Slack. No email. No one foot in, one foot out. Their self-image isn’t wrapped up in pretending to be some machine that does nothing but work. They’re out to live—not to impress anyone or prove something about themselves.
And when they are at work? What they strive for is not ceaseless, frantic activity but what Alex Epstein calls relaxed productivity. Yes, anyone whose work matters to them will face times of stress and tackle projects that demand long hours and limited rest. But the producers I most admire don’t wear such moments as a badge of honor. More often, they view them as a failure: had they planned better and executed better, they wouldn’t have had to resort to Herculean measures.
So whether you end up working forty hours a week or eighty hours, keep in mind: the measure of your success is not how much you work—but how much you enjoy your work . . . and your life.