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.
Arrrrr! 🏴☠️ Welcome to a free edition of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. For more: Dive into an audiobook | Listen to a category design jam session | Design a career you love in Creator Capitalist
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. However, most of us will have to quit, whether to be an entrepreneur or become more entrepreneurial. 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.
You don’t want to 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 Booter. 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. Ten years in, he’s built a real business as a creator, adventurer, and storyteller. And 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 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:
You are a rare resource—not just in the world, but in the history of time.
Replaceable.
That’s how traditional companies see you.
Not as a person. As a cost. A cog. A line item. A warm body who can be slotted into a box on an org chart and replaced when necessary.
This belief is embedded deep in the corporate system.
It’s why performance reviews feel sterile. Why job descriptions are copy-pasted from the internet. Why your ideas get flattened into PowerPoints that someone else presents. It’s a system built to strip away what makes you different and reward what makes you the same. And the moment you start seeing yourself as a resource, you stop thinking like a category of one—and start living like a commodity.
Here’s a truth:
There has never been another person exactly like you in the history of the universe.
And that’s not a motivational poster. It’s a strategic insight. There are things you’re naturally gifted at, that set you apart from anyone else—your unique combination of life experiences, interests, obsessions, insights, quirks, skills, stories, instincts, and contradictions. These are your asymmetric advantage. The thing that gives you the right to charge more, attract Superconsumers, and design work no one else can replicate.
Thousands of years ago, the poet-warrior David wrote a song that captured this idea:
“You created my inmost being; you knit me together in my mother’s womb. I praise you because I am fearfully and wonderfully made.” – (Psalm 139:13-14)
And if quoting the Bible is awkward, don’t worry—we can make it more awkward by going full math nerd. Dr. Ali Binazir, a Harvard- and Cambridge-trained physician, once tried to calculate the odds of you being born. Here’s what he found:
Assume your dad met ~10,000 women in his lifetime.
Odds of meeting your mom? 1 in 10,000.
Odds of liking each other enough to have a kid? 1 in 10.
Odds of that specific sperm and egg combining to make you? 1 in 40 billion.
Now repeat that for every generation back through 30 generations.
The math comes out to this:
The odds of you existing are 1 in 102,685,0001.
Said differently:
Winning the Powerball jackpot (108 odds)
Picking a specific atom from the universe (1080 adds)
Flipping 200,000 coins and all land heads (1060,206 odds)
Dr. Binazir’s conclusion: “The probability of you being born is basically zero. And yet, here you are.”
So yes. You are one of one. You’ve always been one of one. And if you can’t see it yet, that doesn’t mean it’s untrue. It just means the system you’re in has done a really good job of convincing you otherwise.
Believe it like Beyonce. Irreplaceable.
If you don’t see it, others won’t either.
When you embrace the fact that you are different, everything changes.
Take Holley Miller.
She started her career as a life sciences marketer who realized she had a unique strength: reimagining product categories. At a time when most companies focused on feature sets and clinical language, Holley led a strategic repositioning of a product line that grew from $25 million to $100 million in revenue.
She wasn’t just a director of marketing—she was a category designer in disguise.
Once she recognized her “one of one” value, she didn’t stick around hoping for a promotion. She founded Grey Matter Marketing and built a team to help her scale. Now, she teaches life science CEOs about the problem of unreliable revenue and how category design solves this problem.
When you internalize that you’re one of one, you start operating differently.
You realize that being replaceable in a job is not a reflection of your potential—it’s a reflection of a system that’s allergic to originality.
Being irreplaceable starts with being undeniable in your difference.
Creator Capitalists don’t wait for permission.
They make their uniqueness so obvious it becomes impossible to ignore—and invaluable to the people who need it most. So, say it with us: You are not a better version of a job title. You are not a polished resumé. You are not “hardworking” or “detail-oriented” or “a team player.”
You are one of one, and that’s where all of this starts.
Think back to Andrew. He didn’t build a content empire by being “better” than pro athletes or elite filmmakers. He wasn’t the best snowboarder, the best videographer, or the best photographer. But he was the only one doing all three, on the road, with a dog, in a $500 camper. So, he embraced that his mix of grit, GoPro storytelling, and love for dogs made him irreplaceable.
Never downplay what makes you different.
Belief #2: Your Fully-Realized Self Is More Valuable Than A Copycat Version Of Someone Else
There’s a trap that ambitious people fall into, especially when they’re just starting out:
“If I just do what [successful person] did, maybe I’ll get what they got.”
We mimic their routines. We reverse-engineer their frameworks. We study their business models, read their books, take their courses, subscribe to their newsletter, copy their brand voice, match their prices, and recreate their funnel.
It feels smart and strategic.
But here’s the problem:
The second you copy someone else’s category, you put a ceiling on your own.
If you’re walking a worn trail, the best you can hope for is an easy path.
But following someone else means you become a shadow. A watered-down version. A slightly worse copy of something that already exists—and no one pays top dollar for that.
Copying might get you noticed, but it will never make you legendary.
You know who taught us that? Dickie Bush.
Dickie was making multiple six-figures a year working in finance at BlackRock. A job many people work for their whole careers to achieve. It was smart, stable, and prestigious. But on the side, Dickie was writing online, in public. And instead of copying the style of New York Times journalists or trying to get featured in Forbes, he leaned into a completely different kind of writing: Practical, short-form Twitter threads that made complex ideas simple.
And it worked.
Because he wasn’t trying to be a slightly better writer than anyone else, he was trying to be the only one doing what he was doing.
His writing side business exploded. He teamed up with Pirate Cole, and they built Ship 30 for 30 and the Premium Ghostwriting Academy—digital education businesses for online writers that made 4x more than his BlackRock job. Then 10x more. And it’s still growing.
Now, Dickie and Cole are running a multi-million-dollar company built entirely on being different and delivering value in a way that only they can.
That’s the power of original thinking in a category of one.
Here’s what this says about the creator economy:
The more you try to blend in, the more invisible you become.
Nobody needs another generic coach, consultant, ghostwriter, agency, SaaS founder, or Substack newsletter that sounds like ChatGPT wrote on autopilot.
That’s why category designers like Mike Maples Jr. tell people to stop chasing competitive advantage and start building comparative advantage.
Competitive advantage is what corporations fight for: We’re faster. Cheaper. Better.
Comparative advantage is what Creator Capitalists bet on: What can I do that no one else can touch?
Mike puts it this way, “There’s no better version of you than the best version of you.”
Said differently: Stop trying to copy or compete on the things that aren’t in your wheelhouse.
It’s a matter of identity.
(Read that one again. ☝️)
Trying to copy someone else’s voice, offer, niche, business model, or success path almost always leads to burnout. It’s exhausting trying to be someone you’re not.
That’s what Pirate Eddie realized.
He was taught that being a partner at a super ding-dong consulting firm meant being extroverted, having gravitas, and loving French wine and food. Then, he was enlightened when a mentor told him, “Don’t pretend to like things you don’t like. People can tell. You’ll be miserable. And you won’t want to succeed. Instead, hang out with people you like, who like similar things you like. You’ll want to do it and be successful.” So, he hung out with other introverts. He was folksy and friendly, telling funny stories about Hawaii that somehow always tied back to the strategy topic at hand. He stopped trying to be a vaunted partner and started to get paid to be Eddie.
You are not here to blend—you’re here to break (and make your own) mold.
So stop mimicking the crowd, and start designing your own category.
Now, how does this translate into quitting your job?
It comes down to motivation and mindset.
Ask yourself: Why am I really considering this leap? Is it because I’m passionately driven to pursue my own vision, or just because I hate my boss/co-worker/job and envy the Instagram lifestyle of a digital nomad entrepreneur?
You need to be brutally honest.
Chasing a fantasy or someone else’s idea of success will not sustain you through the difficult moments of building your own business. The only thing that will is a genuine love for the category and the cause you’re going after.
Does your commitment to your craft and mission exceed your need for status, recognition, or quick money?
Our friend Gina Bianchini, founder & CEO of Mighty Networks, eats, sleeps, and breathes digital communities—and she has for over a decade.
There were many times when her vision that communities were the future of human connection, education, marketing, and social media groups seemed questionable. Gina’s been on this for over a decade, and she’s walked through fire for her dream.
Now, Gina’s the Category Queen of a market category she designed.
You want to be in it for the right reasons, instead of superficial ones. If you’re quitting your job to work for yourself, you might not have a fancy title anymore. You might not get external praise or validation for a while. You almost certainly won’t have a steady income at the start.
Do you love the actual work enough to endure that?
Are you so bought into the mission that you’ll walk away from opportunities that don’t align?
Even if they’d pay you more?
This is a gut-check.
If your current side business or new career is something you would gladly do for free (at least for some time) because it fulfills you, that’s a good sign.
It means you have the internal fuel to last a while. Conversely, if you’re mainly excited about running your own show because you think you’ll get admiration or you’re solely fixated on the potential payday, you might struggle when reality sets in. Because building something new (often) comes with initially being overlooked, doubted, and underpaid.
Remember: There are zero cover bands in the Rock and Roll Hall of Fame.
You want to earn your place on the stage?
Belief #3: You Were Born To Solve A Specific Problem
Too many people never ask themselves: “What problem was I born to solve?”
Not: What’s my passion?
Not: What do I like doing?
Not: What am I qualified for?
But what unique pain, puzzle, or possibility do I see that most people miss—and can’t stop thinking about?
If you don’t ask that question, you end up doing work that keeps you busy but leaves you empty.
You might be respected (even successful).
But you’ll feel the quiet ache of potential left untouched. Your value is not being valued. This belief, that you were born to solve a specific problem, is one of the deepest mindset shifts a Creator Capitalist must make.
Because it moves you FROM generalist TO specialist.
FROM chasing gigs TO becoming the go-to.
(A category of one.)
For instance, our friend Andrew didn’t set out to solve a business problem when he quit to design a career around adventure. But through his work, he solved a human one: he made freedom feel possible. His content helps people believe they, too, could live differently—more freely, more creatively, more aligned. He didn’t realize the problem he was solving until the feedback poured in:
“You made me take my kid camping for the first time.”
You reminded us what life could feel like.
You don’t just have skills. You have a calling—and that’s always tied to solving something that matters.
That’s what Nick Bennett realized.
Nick spent years as a successful marketer with a great salary and strong reputation. He was doing all the right things and climbing the ladder. But behind the scenes, he was helping solopreneurs leverage sales and marketing to leave their corporate life and become independent.
He started to notice:
The real challenge wasn’t tactics. It wasn’t branding or “product-market fit” or niching down. It was emotions.
Fear.
Self-doubt.
The loneliness of the leap.
That’s the problem Nick was born to solve: Helping solopreneurs master the mental and emotional game of entrepreneurship, not just the mechanics.
So, he went forward on his skis.
At first, it was just a private text thread with a few fellow creators. Then, coaching offers. Then, a paid membership. The emotional support he was offering for free started getting results. And those results created momentum. The more people Nick helped break through their fears, the more referrals came in. He didn’t try to become a Creator Capitalist.
He just solved a problem he couldn’t ignore, and the market came to him.
That’s how this usually works. You don’t have to shout to be in demand. You have to solve something specific that people care deeply about. And prove it with results.
Here’s what that might look like for you:
What kinds of challenges do people come to me for again and again?
What problems have I solved (formally or informally) that led to breakthrough outcomes?
What do I love solving so much that I’d do it for free—because it fires me up?
If you’re thinking, “I could do this all day, and they would pay me again tomorrow for it.”
Good.
Now, test it.
Does the problem you solve have pricing power?
This is your external validation. Not just that you can solve a problem, but that people are willing to pay a premium for that solution and tell others. Go back to someone who paid you for your side work and ask them the following:
Were you happy with what you paid me?
How do you measure how happy you were with what you paid me?
How much more would you have paid? (Where it’s expensive but still worth it.)
Pricing power is the surest sign of demand. So is timing power. That is when people bend to your schedule. We know one of the most sought-after board members in Silicon Valley. When he calls, people stop what they are doing and take the call.
You might be unique and awesome and have a heart full of purpose.
But if you haven’t yet figured out how that translates into a product or service people will pay for (and keep coming back for), then you’re not ready to quit the day job. The best time to leap is when your independent (or new) thing isn’t just a hopeful concept, but something with real momentum that pays.
“Momentum” doesn’t necessarily mean you’re making six figures (though that would be a clear sign!).
It means you have clear signs of sustainable demand:
You’ve consistently earned more from your side business in recent months than from your paycheck, and it wasn’t a fluke one-time event. You’ve been able to raise your prices or rates, and customers still eagerly buy, indicating pricing power (people value what you do enough to pay more).
You’re not maxed out by your own labor. You’ve found ways to scale your income beyond just trading your hours (maybe through digital products, hiring subcontractors, automation, building custom AIs, etc.), meaning the model is leverageable.
New business comes in organically. Your customers refer others. There’s buzz building without you having to hustle for every single sale. In short, you have word-of-mouth working in your favor.
If these signs are in place, staying in your day job may actually become the riskier move, because you’re holding back something that’s ready to fly.
Belief #4: You Were Made For This
This belief hits different.
It’s not about goals, or skills, or strategy. It’s about identity. Because at some point in every Creator Capitalist’s journey, there comes a moment when they stop asking, “Am I good enough?” and start wondering:
“Was I made for this?”
This belief isn’t just philosophical. It’s deeply practical.
Because when you start to feel that your entire life (your story, your scars, your zigzags, your weird interests and side obsessions) has been pointing you toward this next move, quitting doesn’t feel reckless.
It feels inevitable.
That’s what happened to Pirate Christopher.
As a teenager, he was part of a rock band in Montreal. They wrote songs. Booked gigs. And performed in front of thousands of people. He thought he’d spend his life making music. But instead, he ended up building companies, designing categories leading billion-dollar brands, authoring bestselling books, teaching, advising, and creating content that millions of people now learn from. It seemed like a “pivot” (to say the least). But it wasn’t. The throughline was always there.
Creativity. Communication. Performance.
It clicked for Christopher in his early twenties, when he saw keynote speaker and big-time tech advisor Larry DeBoever light up a stage at a tech conference.
Larry was bold, funny, smart, courageous, and sharp. He wasn’t just delivering insights. He was making you think. Performing, challenging, giving. And in that moment, Christopher had a thought that changed everything: I didn’t know you could do that. If Larry could be Larry, (maybe) Lochhead could be Lochhead. There’s truth to the saying “You gotta see it to be it.” Seeing Larry being so legendary and letting it rip was a revelation that he could design his future.
This is what it means to believe you were made for this.
You stop trying to become someone new and start reconnecting with yourself.
So ask yourself:
Do you have a handle on the emotions that inevitably come with quitting—the fear, self-doubt, and potential loneliness—so they won’t sabotage you?
Designing your own career requires radical resilience.
It means talking back to impostor syndrome. It means showing up on the days you’d rather hide. It means designing a support system that helps you stay grounded when the stakes are high. And reminding yourself, on the hard days, that nothing about this journey is random.
Because when you feel supported, you stay in the game long enough to start winning.
And yet, even when you know you’re on the right path, fear doesn’t disappear. In fact, it often gets louder. The closer you get to doing the work you were born to do, the more your inner critic screams.
WHAT IF I’M WRONG?
WHAT IF I’M NOT READY?
WHAT IF I MESS THIS UP?
You will be scared. You will feel alone at times. You’ll lie awake at night thinking about health insurance, unpaid invoices, and whether your parents were right about getting a “real job.” But none of that means you’re on the wrong track.
It just means you’re building something real.
Belief #5: Short-Term Pain Is The Price Of Long-Term Freedom
Let’s get honest about what this actually costs.
Because quitting your job to do your own thing isn’t all upside. At least not right away. And anyone who tells you otherwise is either selling something or skipping chapters.
There is pain involved.
There’s friction, uncertainty, and the kind of tension that makes your stomach turn at 2 a.m. There are moments when you’ll question everything: your timing, your judgment, your bank account, your sanity. This is the tax you pay for freedom.
(And that tax is due up front.)
The trap is underestimating the cost of staying too long and overestimating the cost of leaving.
Too many people imagine the worst-case scenario if they quit: falling behind in their career, looking foolish, running out of money, and having to get a job again.
What they rarely calculate is the opportunity cost of staying put. The missed revenue, missed relationships, the missed creative growth. The time with family they’ll never get back. The difference not made. The slow erosion of their own ambition.
Pirate Eddie learned that lesson the hard way.
He didn’t leap at 25, or even 35. He waited until 43. By then, he had the capital, the network, and the skills. But he also had doubts.
Am I being ungrateful?
Is this just a midlife itch?
What if it all falls apart?
Looking back, Pirate Eddie waited for the wrong reasons: to secure legacy pedigree and titles.
At 39, he had a seminal conversation with his boss, Steve Carlotti, the CEO of his old firm. Steve told Eddie he saw two career paths for him: guru or CEO. Eddie needed to choose one.
The answer was obvious to Steve, but not to Eddie at the time.
Eddie loved creating new Intellectual Capital. His work generated billions in client impact and millions in revenue for the firm. But he also knew that being CEO meant managing people, politics, and problems—80% of the job wouldn’t be creation. It would be noise.
He almost said yes anyway.
Because the title was tempting. It felt like proof. Prestige. Power.
But Steve said something that clarified everything:
“Being CEO means 80% of your job is other people’s problems.”
Introvert Eddie said, “No, thank you,” and happily pursued the guru path.
A few years later, Harvard Business Press offered Eddie a book deal. And Eddie wanted the title “author” badly. So, he stayed at his firm longer than he should have—partly to help the book launch, partly to solidify his platform, partly for his ego.
Would Harvard Business Review have published the book if he had left? Maybe.
Did staying help with the press and speaking tour? Probably.
Was staying worth it financially? It cost him millions in revenue.
More importantly, it cost him years with his kids—and four years of agency. Not because he wasn’t ready. But because he was afraid to walk away from what was working.
That’s the pattern we see over and over again.
People who are willing to endure a little short-term pain (financial instability, awkward pivots, a bruised ego) are the ones who build long-term freedom. Because they’re not optimizing for safety. They’re optimizing for legendary.
So ask yourself:
Are you willing to shrink your lifestyle in the short term to invest in your long-term freedom?
If your answer is yes, you’re in rare company.
Because the truth is, not everyone is built for this.
(Know anyone who can’t think or plan much past a few days? Or someone who burns money as soon as they make it? Humans like instant stimulus response.)
There are people who will choose the illusion of stability over the real work of designing their lives. They’ll stay at the job that drains them. They’ll keep performing for a system that doesn’t care. They’ll talk themselves out of the leap for one more year.
Then another.
Then five.
But as a Creator Capitalist, you play a different game.
You understand that discomfort isn’t permanent. (Legends are forged in fire.) You know that temporary pain is a down payment on permanent leverage. And you’re willing to walk away from “pretty good” to chase “exactly right.”
Just look at a fellow subscriber and pirate, Chris Stanley.
He and his family sold their house, ditched the traditional career path, and moved onto a sailboat so he could go all-in on building The Independent Adjuster’s Path—his podcast and training business for independent insurance adjusters. No fancy launch. No viral moment. Just years of steady effort, consistent value, and belief in the mission.
Now, he’s built a $700K/year business, lives on his terms, and gets to wake up every day doing work that’s fully aligned with who he is. But it started with letting go.
And that’s what this belief demands.
Let go of the idea that everything should feel good immediately.
Let go of the myth that the right decision is the easiest one.
Let go of the comfort that’s keeping you stuck.
Freedom is worth more than convenience.
And you can’t buy it on sale.
Belief #6: Your Greatest Self May Not Look Like You Expect
One of the hardest parts of quitting isn’t financial—it’s psychological.
Because quitting your job isn’t just leaving a paycheck. It’s letting go of an identity. The version of you that’s done everything right. The job title you worked hard to earn. The professional persona that makes sense to your LinkedIn connections, your family, your colleagues.
And here’s the mind-bender most people never see coming:
The version of you that ends up the happiest, wealthiest, most creatively fulfilled might look nothing like the one you’re trying to protect right now.
We see it all the time.
People quit thinking they’re going to become one thing, only to evolve into something completely different. Not because they failed. But because they stopped clinging to who they thought they were supposed to be. And started becoming who they actually are.
You might think you're a writer. But you’re really a strategist.
You might think you're a coach. But you’re really a community builder.
You might think you’re here to sell your skills. But you’re here to sell your story.
Transformation is rarely tidy.
(Sometimes, it’s just the right age or stage for you to do something different.)
Even our friend Andrew started out thinking he wanted to be a pro snowboarder. Turns out, his real superpower was something different: building a niche career as a photographer and videographer that combines creativity, outdoor adventure, and emotional storytelling. The life he has now didn’t exist when he started. It only emerged because he stayed flexible enough to evolve.
You must be brave enough to follow the path that feels right, even when it looks weird on paper.
And if you’re not open to surprise, you might walk right past the life that’s trying to find you.
Humility matters. You have to be willing to release the version of success you’ve been sold. You have to be willing to see that the next phase of your life might not come with a fancier title or a bigger team or a shinier office. But it might come with more legendary, more joy, more peace.
And often, more profit, too.
Pirate Christopher talks about this all the time.
As a younger man, he resisted the label “creative.” He wanted to be taken seriously and didn’t want to be the “weird one in marketing.” Until he realized creativity wasn’t a weakness. It was his superpower. What made him a great songwriter as a teenager also made him a great storyteller, strategist, and speaker. What made him captivating on stage at 16 still made him captivating on stage at 46.
He thought he was supposed to be a rock star. Turns out, he was—just not in the way he imagined.
This is one of the most liberating parts of the Creator Capitalist journey.
You don’t have to become someone else. You have to become more of yourself than you’ve ever allowed before. But to do that, you need one thing above all else.
Openness.
Can you stay open to the possibility that the most valuable, impactful, and fulfilling version of you might not look like you expect?
If the answer is yes, then you’re closer than you think.
Because the people who win in this new world are the ones who stop trying to climb ladders and start building rooms where they belong. A place where their quirks are advantages. Where their weirdest, wildest traits become their most valuable assets.
Which brings us to Jill, the florist.
Recently, Pirate Christopher helped work a weekend pop-up at his wife’s family farm. One of the new vendors, Jill, who sells wild, big, and strange flowers, was setting up a stall. He struck up a conversation. And she casually mentioned that she used to be a global fashion executive. She opened international markets, built supply chains, and launched luxury brands across Asia-Pacific.
Big job. Big salary. Big career.
She walked away from all of it because:
“I realized I just really love flowers.”
So she built a new life one arrangement at a time. Because her (flower) superpower is creating beauty in small batches. It would’ve been easy to dismiss that dream as too small. Too soft. Too niche. But she’s not “just a florist.”
She’s a Creator Capitalist.
Here’s the point: Your greatest self is not hiding behind another promotion.
It’s in the parts, places, and paths you may not expect.
Belief #7: Getting Paid To Be You Is The Ultimate Wealth
Let’s say the quiet part out loud: You want to make good money doing work that feels like you.
Not work that drains you. Not work that checks boxes. Not work that makes your LinkedIn feed impressive.
You work.
The “I can’t believe people pay me to do this” stuff.
We call this earnership—the feeling of building something from scratch, putting it out into the world, and realizing people love it.
Once you experience that, it’s nearly impossible to go back.
You stop thinking like a Knowledge Worker and start thinking like a Creator Capitalist. And once you get paid to be you, you never look at traditional employment the same way again.
Take Jeff Klimkowski.
As a kid, it was his dream to become an investment banker.
When he was in high school, he would make his sister drive him to school so he could read the Wall Street Journal in the mornings. He chose to go to Indiana University’s Kelley School of Business because of its reputation for funneling students into investment banking. Jeff spent 13 years in investment banking. He worked his way up from an analyst to the Managing Director track.
But on the side, Jeff had helped co-found DUDE Wipes—the now Category King of flushable wipes.
It started as a joke between friends. Something fun. Something different. But over time, it started to grow. The Dudes appeared on Shark Tank, landed national retail deals, and started making real revenue.
And that’s when Jeff faced the question:
Stay with the job I trained for, or go all-in on the work that’s truly mine?
He had seven figures in deferred compensation at his investment banking job, and people in his life thought he was crazy for even considering walking away.
But he walked.
Now, DUDE Wipes is doing over $200 million in retail revenue.
And Jeff runs a company with friends he trusts, in a market he helped create, with a business he co-owns. He doesn’t wonder what would’ve happened if he bet on himself. He lives it.
This is what happens when you stop selling your labor and start selling your lens.
You get leverage from your ideas. You attract the right people. You own the upside. And you promote yourself by becoming irreplaceable to your Superconsumers. That’s what makes getting paid to be you the ultimate wealth.
It doesn’t just give you income—it gives you agency.
The freedom to work on what excites you.
The ability to say yes, and the power to say no.
The space to create what the market hasn’t seen yet.
And the joy of watching people not just buy your work, but thank you for creating it.
But don’t mistake this for a lucky break. This kind of life doesn’t happen by accident. It happens when you build Creator Capital on purpose.
Financial Capital: savings, income streams, or a cushion to support your leap.
Reputation Capital: credibility in your niche, social proof, what you’re known for.
Relationship Capital: a circle of collaborators, customers, and peers who know your value.
Intellectual Capital: your frameworks, your systems, your unique POV—documented, refined, packaged, sold.
You don’t need to have all four fully built before you quit.
But you do need to know where you’re strong and where you need to shore things up.
Have you built enough Creator Capital to believe that getting paid to be you is not just possible, but practical?
If you’ve been quietly building on the side—posting content, teaching, working with a few clients, running a paid newsletter, creating digital products, growing an audience—then the answer might already be yes.
And if the answer is no?
That’s not a reason to stay stuck. It’s a reason to start building right now. You don’t need permission to design your own category. You just need momentum—and belief that your ideas are worth betting on.
Because when you get paid to be you, everything changes.
You don’t chase recognition. It finds you.
You don’t hustle harder. You move smarter.
You don’t dread Monday. You looking forward to it.
And at the end of the day, you don’t have to pretend to be someone else to make a living. You get to look in the mirror and say: This is mine. I built this. I love this. And I get paid for it.
That’s what wealth really looks like.
The Quitter’s Checklist
If the 7 beliefs above are the internal compass—what you believe in your bones—then this checklist is your external dashboard.
These are the practical, tactical, and rational questions you need to answer before you walk into your boss’s office and say, “I’m out.” This list doesn’t guarantee success. But it gives you the clearest signal we’ve seen that you’re ready to succeed.
Each one helps you answer:
“Do I have the infrastructure and momentum to quit right now?”
Ask yourself:
Does your side business have pricing power? If customers are finding you, paying you a premium, referring others, and returning for more, you’re onto something real.
Does your Superpower consistently generate incremental or exponential outcomes for others? If you’ve created massive value in your job, freelance work, or side business—value far beyond what you were paid—that’s a strong signal your skillset can stand on its own.
Have you built enough Creator Capital to hold fast during the leap? You don’t need it all, but you do need enough. Enough money to breathe. Enough proof to pitch. Enough people in your corner.
If you can confidently say yes to most (or all) of these questions, here’s your permission slip:
You’re ready to begin.
Remember: Beliefs ≠ Readiness.
You can feel called to quit—and still crash if you don’t have cash flow, confidence, or a community.
You can also have a working side hustle—but still sabotage yourself if you haven’t emotionally detached from your current career identity.
One without the other is a setup for regret.
If you only have the beliefs, you risk jumping without a parachute. If you only have the checklist, you risk staying stuck in a job that doesn’t fit, forever waiting for the “perfect moment” that never comes. You need both.
Because quitting your job to design your own career isn’t just a decision, it’s a transformation.
And transformation requires both conviction and proof.
Quitting Isn’t The End. It’s The Opening Scene.
You don’t get one life.
You get a series of lives—if you’re brave enough to let the old ones die.
There’s no perfect moment to quit work you don’t love and commit to a career you design for yourself. No official permission slip. But there is a moment where you stop waiting and start becoming.
The world doesn’t need more people who stay.
It needs more people who leave on purpose.
If you’re ready, take the leap.
Because the risk of staying the same is greater than the risk of change.
Arrrrrrr,
Category Pirates 🏴☠️
P.S. - Have you quit a “good enough” job to design your own career?
In a comment below, tell us how it went, what you learned, and the one thing you’d want someone to know before they make the leap.