When I was going through my quarter-life crisis, the simple act of devoting myself to mastering a hard craft brought much-needed depth, direction, and fulfillment to my life.
For that reason, I’ve been wanting to write this piece for years.
An in-depth ultimate guide on self-directed skill acquisition.
Everything I wish somebody told me when I was pulling my hair out trying to teach myself the craft of writing.
It’s a biggie, over 20,000 words.
Below, I’ll teach you the learning methods used by masters across a variety of disciplines—art, business, writing, sports. (It’s way more than just deliberate practice!)
I’ll also share the ideas that were most helpful in my own self-directed apprenticeship, when I went from untrained, mediocre writer to full-time writer (in a year).
My aim is to help you go on your own transformational mastery quest.
To:
Pick one skill, artform, or discipline you’ll obsess over
Develop the mindset and meta-skills that lead to improvement
Make steady progress towards mastery (and not waste as much time as I did)
As you’ll see, mastery isn’t a product of credentials or genetics.
Instead, it’s a matter of dedication, volume, imitation, practice, and, most of all, love.
Table of contents
Introduction
Key idea: mastery as a quest
What is mastery anyway?
What does mastery feel like?
Why go on a mastery quest?
Phase 1: Pick One Craft
The 3 criteria of a good mastery quest
Challenging
Aligned with authentic interests
Not (too) deranging
A note on specificity
3 methods for finding your craft
Method 1: Childhood
Method 2: Life Missions
Method 3: Personality Test
How many mastery quests can I have at once?
What if I have multiple interests and can’t prioritize?
Phase 2: Prepare for Your Quest (Mindset, Meta-Skills, and Setting)
Accept this painful truth
Decide to turn pro
Look at your life through hell’s eyes
Embrace mediocrity (and how to get past it)
Disappear for a while (you’ll come out of it)
How to build discipline
Train your deep work capacity
Engage in meta-learning
Phase 3: The Self-Directed Apprenticeship (Hone Your Craft)
Think in terms of projects (the real secret)
Engage in deliberate practice
A caveat on deliberate practice
How to choose which sub-skills to drill
Imitate your idols
Soak in excellence
Dig for the portable principles
The swipe file
Using AI as your skills analyst
Volume is a cheat code
Join a scene
Find a mentor (even an online one)
Be the person who knows everything
Develop social intelligence
Neglect
Focus on this above all else
Getting Started
How to get started on your self-directed apprenticeship (Protocol and Checklist)
Checklists for phases 1 and 2
How to start your first project (and schedule your day)
5 examples of first projects & daily learning schedules
Aspiring Novelist
Home Cook
Guitarist
App Builder
Public Speaker
Closing
The quest is the point
Introduction
Five years ago, when I quit my sales job to become a writer, I had no formal training in the craft of writing.
I had never taken a creative writing class, and I didn’t know any practicing writers. All I knew was that, one day, I wanted to be great—to be like the writers I admired.
I don’t feel embarrassed saying this. No one makes fun of you for wanting to be a great parent. So why should it be odd to express one’s desire to be a great writer, actor, woodworker, producer, or financial analyst?
Anyways, at the start of my quest to master writing—and make a living from it—my amateurishness revealed itself in many frustrating and embarrassing ways.
My first freelance client told me my writing was “rough around the edges.” My pitches were almost always ignored, and my portfolio of samples rejected.
In the act of writing, I often struggled to call the right word to mind. I couldn’t seem to maintain deep focus for more than an hour. And I wrote awkward sentences that confused readers, as well as myself…
I was, in short, mediocre.
At the time, I suspected that my peers thought me bonkers for quitting a stable job to start a freelance business based on a craft I hadn’t honed.
But more than likely, that was just me, projecting my self-doubt onto them.
After all, back then, I did not know how to learn a new skill—not in a systematic way at least. Like most people, I thought it was a matter of talent and credentials: born a master or trained to be one.
I didn’t know that learning—and eventually mastering—a complicated craft is more about curiosity, volume, observing others, and practice than it is about having access to the right genetic code or elite training programs.
That was five years ago.
Since then, after writing over 1,000 blog posts/newsletters/essays, spending thousands of hours immersed in great writing, studying the inner mechanics of exemplary works, exposing myself to different genres, reading craft books, and getting occasional feedback from readers and editors, I am much better than I was.
I’m no Charles Dickens or Joan Didion, but I’m comfortable saying I have entered the early stage of mastery in at least one sub-genre of the larger craft of writing: that is, blogging/newsletter writing.
I make a living from it, command top rates from tech publications, have a newsletter of nearly 15,000 subscribers, and recently released an ebook I am proud of.
And although I still trudge my way through many parts of the essays I write, now and then I experience the sublimity of decisions flying at me with ease.
During that period, especially in the first year of self-directed apprenticeship, I also learned a tremendous amount about what it takes to teach yourself new skills.
And I have come to believe this:
With the right mindset and learning techniques, a total beginner can teach themselves the fundamentals of a new craft in a year. And over the longer-term (3-5 years), they can enter into the earlier stages of mastery, provided they devote themselves to the craft, put in the hours, practice intelligently, and don’t give up.
While the general timeframe of mastery depends on the complexity of the craft and how you define mastery, we are all capable of developing the foundations of mastery—intuitive pattern-recognition, creative originality, a knowledge of the key principles, and executional abilities—in 3-5 years.
After all, most people overestimate what they can achieve in one year, but underestimate what they can achieve in three.
Whether it’s cooking, writing, app building, teaching, carpentry, or hog wrestling, to teach yourself a craft, you just need to know the learning methods that reliably lead to mastery, and to apply them regularly.
And that’s what I’m teaching today in this ultimate guide (the longest one I’ve ever written on Substack).
Had I known about these techniques earlier, it would’ve saved me hundreds of hours wasted on the wrong learning activities. It would’ve shortened my learning curve and helped me get the benefits of competence—from increased pay to more confidence and opportunities—in far less time.
This 3-part guide is for paid subscribers.
To learn how to set up an effective self-directed apprenticeship, you can either take out a paid subscription ($8/mo) or buy the PDF guide ($20). Thank you for your support. It helps tremendously.