The Art Of The Quit: The 7 Foundational Beliefs You Must Hold Before You Quit Your Job And Get Paid To Be You
The riskiest move isn’t quitting—it’s staying too long.
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Dear Friend, Subscriber, and Category Pirate,
“Should I stay or should I go now?” - The Clash
If you’re asking the question, (you know) you already know the answer.
Not logically—yet. But emotionally. Intuitively. Deep in your bones.
There’s something inside you that knows:
This isn’t it.
You know you're more creative, more entrepreneurial, and more valuable. Still, you hesitate. Because somewhere in the back of your mind, that old tape plays:
“Winners never quit, and quitters never win.”
That’s a lie.
When done right, quitting is a catapult to a future of your design—where you own your time, your creativity, and your earning power.
Winners quit all the time.
Brian Chesky quit odd design jobs to co-create Airbnb.
Sara Blakely quit selling fax machines door to door to create Spanx.
Shonda Rhimes quit odd jobs to write hit shows like Grey’s Anatomy.
John Grisham quit his job as a small-town lawyer to write legal thrillers.
JK Rowling quit as a secretary and went on welfare to write Harry Potter.
Oprah Winfrey quit as a news anchor to launch her own show and empire.
Jeff Klimkowski quit his investment banking career to co-found DUDE Wipes.
They all traded the (seemingly) safer path in roles they knew, in systems built (largely) to reward sameness, to bet on themselves. They choose to be different. Got creative. Found exponential success. And became more entrepreneurial.
The value of their value was undervalued, so they got busy.
Want to listen to this mini-book instead? Head to the audiobook version:
Knowing when and what to quit is a core skill for a legendary career.
If you work at a company of any size, you must come to terms with reality: there are about six to twelve people who run the show. If you’re not one of them, no matter what you do, you’ll never be in control of your future.
Now, don’t get us mis-con-screwed.
There are perfectly good reasons (and seasons) where working for someone else, or staying inside a big system, is a legendary thing to do. Some people have legendary careers inside big companies. That’s cool.
But most of us will have to quit, whether you want to be an entrepreneur or be more entrepreneurial. Or you want to be a creator, or be more creative. Either way, quitting isn’t a failure. It’s a skill.
(A high-stakes, high-agency, career-altering skill.)
But not all quitting is created equal.
Don’t quit just to:
Avoid the past.
Spite someone else.
Get relief from pain.
Run from something you hate.
Dodge work slowly sucking your will.
Instead, quit to:
Create the future.
Pursue joy and pleasure.
Make a massive difference for others.
Do work you adore and absolutely love.
Design a career that gives you life and restores your soul.
Quitting is a skill that requires courage, timing, and emotional readiness—and most people never develop it. We practice interviewing. We practice presenting. But we never practice walking away.
We tolerate sucking at quitting.
Even though it can be one of the most important decisions of your life.
So, if your current path isn’t the one that lets you share your greatest gifts, you owe it to yourself (and the world) to quit. And start designing something different. If that’s the kind of leap you’re considering, then what you’re asking isn’t (really):
“Should I quit my job?”
It’s something deeper: “Is it finally time to bet on myself?”
A quitting story:
By 2013, our friend Andrew Muse had reached what felt like the pinnacle of the ski bum dream.
He was living in Park City, Utah, snowboarding every day, managing a house full of friends, waiting tables at night, and picking up scraps of sponsorship as a low-level athlete. He made just enough to cover food. Sometimes, he’d get a pair of sunglasses or gear in exchange for tagging a brand on Instagram. It was a good life, but not a sustainable one.
And he knew it.
Instead of clinging to a lifestyle and career that had no exponential future, Andrew made a decision.
He moved into the garage, bought a $500 truck camper, and committed to a six-month road trip. He pitched hundreds of outdoor brands, cobbled together a few deals totaling $1,200 a month, and set out to create a 12-episode YouTube series called Tiny Home Adventure.
But before he left, he made sure he couldn’t go back.
After the final shift at his super ding-dong restaurant job, he superglued his dress shoes to the manager’s office floor.
Not out of spite, but out of certainty. He wanted to leave no doubt—not to his boss, not to his friends, and not to himself—that he was done settling. He was going to design his own career. Tiny Home Adventure was not just a road trip. It was the first day of a life he was building from scratch.
That night, he didn’t just quit a job.
He committed to getting paid to be him.
So instead of slipping out quietly, he declared: I’m burning the boats. His goal wasn’t to go viral or get rich. He thought, “If I can do this for six months, that would be a win.” He didn’t have a safety net or a backup plan. Just a camera, a dog named Booter, and a dream to get paid to do what he loved.
It worked—until it didn’t.
On the way home from filming the final episode, Andrew fell asleep at the wheel and crashed.
He lost (almost) everything: his truck, his home, and most devastatingly, his beloved dog. The project was supposed to launch him into Season 2. But he found himself sitting on the side of the road, shattered.
Then, something unexpected happened.
People showed up.
His Superconsumers donated, reached out, and rallied around him. A firefighter who responded to the crash eventually helped him adopt a new puppy. And outdoor companies started calling—not just to console him, but to ask how they could help him rebuild.
So, he did.
Season 2 of Tiny Home Adventure launched with GoPro as a sponsor.
More projects followed. He built a real business as a creator, adventurer, and storyteller. Ten years later, he’s still going—traveling the world, working with companies like Ford, GoPro, and Outside TV, and filming new content with his dog, Kicker.
But that’s not the point.
The point is: He gave up a comfortable life to create a meaningful one.
He designed a career he loves around joy, adventure, and creative autonomy. As he says, “The dream is to keep doing what I love, and create enough value for others that I can keep doing it.”
Feeling that pull?
Maybe you’ve built something solid: A stable job, a good salary, a LinkedIn that looks impressive.
And yet, “This can’t be it” keeps playing in your head.
That voice (generally) does not go away. It won’t stop, no matter your job, salary, or title. What we’ve learned from studying thousands of creators, entrepreneurs, and executives who made the leap is this:
The people who create legendary lives aren’t the ones who cling to the wrong career.
They’re the ones who know when to jump ship.
They do it to get paid to be themselves, in a category of one, that they designed. If you’re even a little bit curious about doing this for yourself, know this kind of life doesn’t start with a perfect business plan. It starts with a decision:
I’m not here to be a copy. I’m here to create.
This mini-book breaks down what that requires.
You’ll see the 7 beliefs you need to internalize at the DNA level to quit with confidence.
You’ll get the 5 practical questions you must answer before you pull the ripcord.
We’ll introduce you to real people, like Andrew, who quit and never looked back.
By the end, you’ll know exactly where you stand. We can’t make the leap for you. But we can give you the map, the compass, and the courage to trust in yourself.
Grab your parachutes, pirates—we’re jumping in.
The Art Of The Quit
Let’s start by rejecting the premise.
For decades, the Knowledge Worker career playbook sounded like this: “Work hard. Be loyal. Climb the ladder. Don’t be a quitter.” Quitting was treated like moral failure, a sign of weakness, proof you didn’t have what it takes.
But that playbook was written for a world that no longer exists.
The old rules made sense in the Native Analog industrial age, when loyalty was rewarded, pensions were guaranteed, and career paths looked like straight lines. But we’re not in that world anymore. We’re in a world where:
Job security is a mirage.
Middle management is melting.
AI is rewriting what it means to “create value.”
People are waking up to the idea that they’re responsible for designing their career. At Category Pirates, we’ve spent years tracking this shift. And here’s what we know after running a survey with a nationally representative sample of 1,000 US adults. (Sadly, no service exists to survey 1,000 pirates…yet.)
77% say they wish they could be paid to create (aka, their different makes dollars)
75% believe they have unique skills that set them apart (aka, they are different)
67% believe their work has a big positive impact (aka, they make a difference)
56% dream of starting their own business (aka, they can capitalize on this)
Together, this means 1 in 3 US adults want to be a Creator Capitalist.
In the next decade, we predict the number of people who break free to work independently will grow 10x.
Personal and financial freedom are simply too enticing, especially as traditional job security disappears and AI becomes core to (almost) every role. On top of that, the share of single-person households in the U.S. tripled from about 8% in 1940 to 28% in 2020. When you only have to worry about feeding yourself, taking the leap is significantly easier.
If you’re reading this, there’s a good chance you’ve felt the tug:
Maybe you want to be more creative in your work.
Maybe you’re stuck in a good job with good pay, but your side project lights you up.
Maybe you were just laid off or fired. (No shame, Pirate Christopher’s been fired plenty.)
Whatever the reason, you’ve landed at the same question millions of people are quietly asking:
Should I quit?
It’s one of the most difficult, emotional, and high-stakes decisions you’ll ever make. And almost no one teaches you how to make it. Sure, there are tactics (spreadsheets, savings plans, side business income goals, etc).
But the bigger issue isn’t how to quit—it’s when to quit. And more importantly…
How do you know when you’re ready to quit well?
Quit too early, and you might fall flat on your face.
Quit too late, and you could waste years of your potential.
We don’t pretend there’s a one-size-fits-all answer. But after running our own businesses and working with hundreds of entrepreneurs and creator-led companies, we’ve identified a clear pattern:
There are internal signals (what you believe).
And there are external signals (what you’ve built).
Quitting your job to chase your own path is not just logistical. It’s emotional, psychological, and existential. Quitting isn’t just changing your work—it’s confronting fears. It’s about becoming the person you were always meant to be. Doing the work you feel called to do. Getting paid to be you.
That’s where the panic (often) sets in.
What if I’m not ready?
What if I lose everything?
What if I disappoint people?
You’re not crazy for asking those questions.
In fact, if you’re NOT asking them, you probably haven’t thought deeply enough.
We’ve talked to hundreds of entrepreneurs, executives, creators, and consultants who hit the same moment of truth: Stay safe… or start something.
The ones who made it had three things in common:
They believed something in their bones that made quitting feel not just logical, but inevitable.
They did the practical work to ensure that when they jumped, they didn’t crash.
They did the math and their homework to confirm if they should quit.
We’ve already written about the third point. So, this mini-book is here to help you think about the first two. Not just decide if you should quit, but know when, why, and how to do it right.
If you’ve made it this far, we’re guessing you’re not “some people.”
You’re different, and you know it.
You don’t want to die with your best work still inside you. You don’t want to keep being the MVP of someone else’s business. You don’t want to keep pretending the Monday meeting matters. You want to wake up and feel proud of the life you’re designing. You want to produce results that matter for people who (actually) give a damn and value your value.
You want to build something that makes a difference.
You want to build something that’s yours.
So, if you’re standing on the edge of your own next chapter, this is your framework.
Let’s dive into the internal compass: the seven beliefs you must feel in your bones before you leap. These aren’t platitudes. They’re a litmus test.
If even one of them is waking you up at night…
You might already know your answer.
The 7 Foundational Beliefs You Must Hold Before You Quit Your Job And Get Paid To Be You
These seven truths will help gauge your readiness to become a Creator Capitalist.
These are about mindset, identity, and emotional readiness. You can believe all of these and still not be ready to quit today, but they’re necessary for quitting well eventually. Each one helps you answer:
“Do I believe I’m the kind of person who can thrive after I quit?”
But a word of caution, it's not enough to simply nod your head.
These beliefs must hit deeper. They must keep you awake at night, whispering relentlessly that it's time for change. Because when you're truly ready, they won't just live in your head—you’ll feel it in your heart. It might sound woo-woo, but we’ve found it to be true.
Some of this will feel spiritual.
This is because our deepest emotions and aspirations resonate profoundly with the eternal and universal.
We’d love to give Chris Stanley a special shoutout, as he very graciously helped us build out these beliefs. He’s an awesome pirate, and you should check out his newsletter on creating mini-books. And another special shout-out to Mike Maples, Jr.—much of this was inspired by his awesome podcast with us about becoming a Creator Capitalist.
Now, here’s what you need to believe before you quit:
Belief #1: You Are One Of One
If you want to quit your job and build something of your own, you have to start by rejecting one of the most dangerous lies in business: