I could not change my life because I was still myself

This is part 1 of a 2-part series on “how to master a craft”. This shorter part deals with the why; the second part (out later this week and over 8,000 words) deals with the how.

If a hardened criminal convicted of murder can change their life, so can you.

In the 1960s, Jimmy Boyle was one of the most feared gangsters in Scotland.

When Jimmy was sentenced to life in prison for a killing in a gangfight (an act he maintains he did not commit), he was certain his life was over.

In 1973, however, a way out presented itself. Jimmy was transferred to an experimental art therapy program that provided inmates with creative outlets to help them forge new identities.

Jimmy found his outlet—the key to changing his life—in a block of clay.

During a rather tender moment in a BBC documentary, a now much older Jimmy gives us a glimpse into the moment that changed his life.

“She brought in a seven pound of clay, and I did a portrait, and it was like a dam burstin’ from me,” he says. “It was the first positive thing I’d ever done in my life. It was like a gush coming out—a feeling I’d never known in my life.”

Jimmy devoted himself to the craft, and it provided him with self-esteem (I believe this is that gush he speaks of), which is far more addicting—and conducive to happiness—than a life of crime.

When he was released from prison in 1980, Jimmy went on to become a successful sculptor. But that’s not all he did.

His work had changed him. He was now capable of impactful and beautiful action. He started an organization that provided art therapy to recovering addicts. He went on to publish several novels.

While I’ve never run an underground money-lending ring or thrown fists in a gangfight, I resonate a lot with Jimmy’s story.

Like him, at one point in my life, I felt stuck, spiritually sick, and unsure of how to escape my current life.

I was working a job I hated, cold calling property managers, and I wanted a way out. But I was caught up in old habits, old identities, and I lacked the soft and hard skills to do so.

I could not change my life because I was still me.

Also like Jimmy, it was a certain type of quest—to get freaking good at something—that forced me to change myself, and as a result, my life.

Jimmy and I are far from the only people who have used such a quest to alter their realities:

• Rich Roll, now a successful podcaster and athlete, was an out-of-shape, burnt-out lawyer when he devoted himself to long-distance running.

• The singer-songwriter Jewel escaped homelessness by focusing on honing her musical talents.

• Jack London fled his life of backbreaking labor through a commitment to the craft of writing.

Today, I want to help you understand why a mastery quest is the best way to reinvent yourself—and thus your life—by sharing the story of how it changed mine (as well as two books that cooperated to show me the way).

Here’s what I learned about personal growth and lifestyle-reinvention during my quarter-life crisis, when I went from software sales rep to full-time writer.

“No amount of security is worth the suffering of a mediocre life chained to a routine that has killed your dreams.” - Maya Mendoza

I was 24 years old and desperate to get off my life path.

I worked at a tech startup in NYC, cold calling property managers in a futile effort to sell them software designed to improve their tenants’ quality of life (a value proposition I soon learned to replace with “double your staff’s efficiency”).

Why did 22-year-old Sam choose this line of work?

Simply put: I wanted to make money, get out of my parents’ house, and continue living the college lifestyle I had been living. Plus, my friends and girlfriend were there, and I had recently watched The Wolf of Wall Street before sending in the resume.

It wasn’t even a bad job. At first, I enjoyed its newness. My boss took me to get dumplings and gave me an “impact award”. There was a Nitro Brew keg in the kitchen. I played foosball with the Salesforce engineer.

But the work was so misaligned with who I was and what I cared for that it slowly exhausted and depressed me.

I am an introvert with creative tendencies—though I had lost this self-knowledge somewhere in the social pressure crosswinds of young adulthood. So that job, which was essentially small-talking people all day, was draining the life out of me.

To make matters worse, I am self-directed in nature. I was never someone who enjoyed the authoritarian aspects of school, being told where to be and what to study. The 9-5 corporate lifestyle, though it has its perks, just wasn’t for me.

To get some air, I spent my weeknights playing FIFA with my roommate or watching Netflix, and my weekends partying, all the while feeling guilty about neglecting the blossoming interests that were calling out to me: namely, reading and writing. I kept making daily routines and plans to change my life—to get out of this job—and failing to stick to them.

I had left college with a half-baked dream of becoming a creative of some sort—potentially a filmmaker—but I had made zero progress on such a goal over the past two years, and I felt miserable about it. There was a pile of books on my bedside table that was nothing but a symbol of my failures.

On those wild Saturday nights in NYC, I would often stay out at the bar until the horrible sun rose. It always appeared to me as some angry God, side-eying me for ruining the next day he had given me, punishing me with a hangover.

This was a trend: I was always willing to stay out later, to have one more drink, to dance to one more song.

I like to go out with friends, but that’s not what was driving it. I did not want to leave the bar because I did not want the night to end. I did not want Sunday, and the week ahead, and the rest of this comfortable yet malaise-inducing life I had created for myself, to come.

A year later, I was out of that world, no longer a bored and aimless sales rep.

Instead, I was a full-time writer, running a small yet successful freelance writing business and spending the rest of my time working on creative writing projects, reading books, mountain biking (terribly), and hanging with friends and family.

My life was still far from perfect, and always will be. I still had days when I was unhappy or anxious. I was not rich—to this day, I make less money from writing than I did in tech sales (though I’m hoping that might change soon).

But, in 2021, my life felt much more exciting and meaningful than it had from 2018-2020. It was more aligned with my authentic interests. I felt like I was becoming who I was meant to become, rather than someone our society has pressured me to be.

So, this begs the question: how did I go from burnt-out, aimless sales rep to full-time writer in one year?

What enabled me to change my life after the other attempts failed?

I’m 30 now, and I’ve thought a lot about this; I’ve come to one conclusion:

I was finally able to get out of my rut because I finally did what all those characters were doing in the movies I was watching to escape from my reality.

Like Bilbo Baggins, I packed my bags and set off on an adventure—an adventure that meant something to me, and that I’m still very much on.

When I was 23, a book helped me see what I was missing from my life.

In The Happiness of Pursuit, Chris Guillebeau argues that the key to a meaningful life is not pleasure-seeking. I’m sure this idea came as somewhat of a shock to a young man who, though a reader of the American Transcendentalists, had spent the last four years living the fraternity lifestyle.

Instead, the answer to the good life is throwing the full weight of your soul into challenging quests, whether that’s biking across the United States, building a dog-grooming business, or becoming a world-class chef.

This idea reoriented my worldview. It woke me up to the reality that meaning and joy come from devotion to a hard, meaningful quest that aligns with your values, not throwing a killer party or raking in $12,000 in commission.

But I still had questions, mainly: What type of quest should I go on?

The author was travelling to every country in the world for his quest, so I had the idea that I would quit my job and travel Southeast Asia for a while.

But I ended up throwing out that idea. I knew from experience that not all have equal power to change oneself and one’s life. When I graduated from college, my friend Ted and I went backpacking through Europe for 2 months.

On that trip, I built confidence, had new experiences, and changed hopefully for the better (certainly developed a taste for late-night kebab). But when I came home, I was still stuck with the same problems:

What do I do with my life? How do I earn a living? Who am I now that I’m not a college student? And the most important of all: Who am I striving to become?

Another book helped me find the right type of quest.

In Mastery, Robert Greene marshals the beautiful idea that we all have a life’s task: a discipline, field, or skill we are naturally attracted to. He says that the long-term cultivation of this craft is a great source of fulfillment and power.

That was it. That is what I needed: a good devotion to some craft (what I now call a mastery quest). It took me a while to land on writing—which is odd since it was what I did naturally as a kid—but once I did, I was off.

In 2020, with $10,000 saved up, I quit my sales job and moved back in with my parents in Massachusetts.

I had set my sights on one thing and one thing only: to become a great writer, and I would do everything required to make it happen. It was the first time I had truly committed to something long-term in my life. And the positive effects were immediate.

All of a sudden, life began to feel exciting again, like it did on that first day of college when a new adventure was ahead of me.

This time, though, the adventure wasn’t social in nature. It was mental (hilarious, since college is supposed to be for learning).

My life also felt much more focused. A born novelty-seeker with many interests, it became easier to decide what to focus on and spend my time doing.

If something helped me progress on my quest, I chose that option. If it undermined the quest, I eschewed it. I organized my life and my days in ways that would help me become better at writing. Simple as that.

It’s ironic; while quests are full of chaos and uncertainty, they provide you with the principles necessary to navigate your way through it. The man lost in the bewitched forest searching for the golden lizard probably feels less lost (at least spiritually) than the person with no quest sitting at home watching Deal or No Deal reruns for the third hour straight.

For example, it was immediately obvious what the first step in my quest must be—a mini-quest in its own right. I needed to make a living from the written word. I knew I needed a lifestyle business that would allow me the free time to hone my craft and not drain me. So, I began building a freelance writing business.

That year, I buzzed with energy.

With a worthwhile quest in mind, my curiosity had taken off, attracted to everything that would help me progress, and I followed it where it led.

When I wasn’t cold pitching or working on articles, I was reading books and practicing my craft. I was studying exceptional blog posts, essays, and novels, trying to figure out how they worked. And I was attempting (the keyword there) to write my own pieces as well. I had my failures. My first client called my writing “rough around the edges,” and I received many rejections and no-replies.

But after about a year of this period of intensive self-education, practice, and business building, I was able to earn enough from my writing to move back to New York City.

But it wasn’t just a new business and craft skills I had to show for it.

When you attempt to master a craft, you have to build a lot of transferable skills in the process.

For example, I learned marketing to market my writing, planning to help me reach hard goals, and persistence to finish articles that seemed above my abilities. These skills have helped me achieve more exciting mini-quests, like starting this newsletter and growing it to 14,000 subscribers.

At 25, when I finally unpacked the last box in my NYC apartment, much of my life was the same.

I had the same girlfriend (now wife), same friends, same predilection for a good party and inability to wake up early; but the texture of my life was completely different. I now felt that I was going somewhere—somewhere that mattered.

These days, if I do ever stay out until 5 AM, it’s because I’m having fun, not because I’m dreading tomorrow. And I owe it all to that decision to commit to a mastery quest.

“Adventure shatters the oppressive, insistent reality as if it were a piece of glass. Each adventure is a new birth of the world, a unique process. How can it fail to be interesting?” Jose Ortega y Gassett

You cannot change your life because you are still yourself.

You have to change yourself first—your worldview, your habits, your skills.

The problem is, the self is not something that changes easily—certainly not in one day. Like the body, the mind prioritizes homeostasis.

It chooses the stability of old habits and worldviews over the new. It’ll choose to stay in a comfortable, familiar situation if you let it, even if that way of living is insidiously draining your soul, one day at a time.

So how do you get it to change, in a way that feels natural and perhaps even exhilarating?

You do it through the oldest trick in the book—the one novelists and screenwriters use all the time.

There’s a reason stories are called change-making machines.

You put a protagonist into a story, they encounter obstacles, and to overcome those obstacles, they must learn new wisdom, habits, beliefs, and skills.

By the end of the story, they’re a new person, with a new worldview, a new identity, and in most cases, a new life.

So you be a protagonist.

You throw yourself out of your comfort zone. You go on an adventure—preferably a long one, ideally a difficult one—for nothing changes the self more effectively, and more thrillingly, than a meaningful quest.

As a 30-year-old who went from a directionless, scattered, shallow life to an intentional, focused, deeper one, my answer, which is certainly not the only answer, is this:

Go on a mastery quest. Devote yourself to a craft.

The pursuit of mastery is the best type of quest for reinventing you and your life.

It pushes you into obstacles you don’t know how to handle. And this forces you to develop the skills, knowledge, and character traits required to overcome them.

If you are a curious person, such an adventure in self-education is the most natural, effective, and thrilling means of life transformation I’ve found.

It doesn’t matter what that craft is as long as it aligns with your interests and values:

• A great businessperson

• A great long-distance runner

• A great mathematician

• A great fiction author

• A great accountant

• A great interior designer

• A great Judo fighter

• A great literary critic

• A great painter

• A great parent

• A great farmer

• A great philosopher

• A great religious or community leader

• A great thrower of parties (although we saw how that turned out for Gatsby)

So pick a craft that you are obsessed with, and go try to become great at it—without, of course, ruining your relationships or becoming an arrogant jackass (but you won’t do that).

If you pursue mastery, the rest should take care of itself.

Later this week, I’m releasing an ultimate guide (10,000+ words) on how to teach yourself a craft, skill, or artform and progress towards mastery.

I’ll provide guidance for each of the three phases of a good mastery quest:

1. Picking your mastery craft (criteria, selection methods, the value of specificity)

2. Preparing for the journey (mindset, turning pro, monk mode)

3. Mastering the craft (learning tactics, designing a self-directed apprenticeship)

For each phase, I’ll share methods I learned from studying dozens of masters across various fields.

These helped me teach myself writing as someone with no experience or training, and they apply to basically any craft you want to teach yourself, whether it’s woodworking, marketing, piano, songwriting, martial arts, or parenthood.

Happy studying!

- Sam