by Peter Young
I come from a world where everyone is programmed to fail.
A Counterculture world of politically fashionable beliefs that all converge in a dark middle-age ghetto of Doordash jobs, hostile roommates, and wistful stories about their glory days.
When the inevitable crash-out happens, they’re told their failure is “valorous.” Or the fault of “systemic forces.” Or a righteous beacon of defiance against capitalism. Or whatever.
I was one of the few who got out. Rejected employment, built and sold a weird internet business, and retired young. Broke my outlaw ancestral bondage. Defeated the punk-to-Trader-Joes-manager pipeline.
These are the 20 lessons, belief revisions, narrative violations, and acts of countercultural heresy required for your escape.
If you’re reading this, you’re in a similar world. And you know it’s not working. Maybe it’s “punk.” Maybe “anarchist.” Maybe juggalo. Maybe you’re a collectivist communist anti-facist furry. The umbrella term I’ll use here is “Counterculture.”
For the purpose of this manifesto, “Counterculture” is any collectively held paradigm that ostensibly positions you against the mainstream, while constraining your fate to the most mainstream thing ever: W2 employee status until death.
Don’t shoot the messenger, but your scene doesn’t encourage you to greatness because it hates you. Because it thinks you can do no better than selling soap at the farmer’s market.
These constraining beliefs will vary, but a few from my world:
A tapestry of beliefs reframing failure as not just excusable, but righteous. These examples have some truth, but if a belief doesn’t serve you, there is no point in believing it.
This is a 20 part belief-detox.
Eventually I looked around and my Counterculture and realized it wasn’t working for anyone. Even the “success stories” were miserable (I’ll support your anthropology PhD pursuit, or low-six-figure design job, but I will not envy you).
I had no money, so I started by changing the only thing I had control over: My assumptions around what was possible. Assumptions like (for example) “people like me can never own homes.” Since the old ones weren’t working, I replaced them with their opposite. Even an insane belief is better than one that actively holds you back.
The new beliefs (my top 20 below!) served my desired outcome (never having a job), and didn’t just serve the collective delusions of the septum-ring class (because why would I model my life after someone I would never trade lives with?)
My freedom exploded (in a good way). My resources piled up. And in less than 10 years I went from destitute to permanently retired. My originally flimsy thesis was vindicated: it’s your beliefs that determine the outcome of your life, not material resources.
This is the list I give to friends who haven’t made it out, but want to – the 20 beliefs hardest for anyone in Counterculture to adopt. But it’s either the temporary pain of revising your beliefs, or the permanent pain of driving for Uber.
Let’s say you’re super “punk rock.”
It starts out awesome. Tour with your band. Hitchhike the country. Live rent free in abandoned mansions. Write zines and do weird art and live on $3 a day. And it is awesome, because I’ve done all of it.
Better than awesome, it’s the peak way to spend your 20s and 30s. But slowly, “living for the day” reveals its hidden costs – the mounting debts that accrue as you borrow against the future.
You awaken to it slowly. You start to look around, and your slightly older contemporaries who “kept it real” aren’t aging so well. And things start to look very dark.
Check in with them again at 40 and the stories are bleak. Managing a Trader Joes in Canoga Park. 50 hours a week (25 of it on Zoom) on the “user experience” team for a boring tech company. Touring the 200-cap venue circuit six months a year in a metalcore band and subsisting off shirt sales. And those are the success stories.
The typical stories are worse. GoFundMe’s for personal expenses. Stocking produce at the natural foods store. Going home to two roommates half your age. Hustling your art on Etsy because it’s the only skill you took from your punk days.
No one told them the “selling out” vs “righteous misery” binary was a false one. You can maintain the adventure of youth and avoid the bleak horror of adulthood without abandoning principle. But to do so you must commit tribal apostasy and counterculture suicide.
What got you here, won’t get you to where you need to go.
Everything that follows is heretical to “cool” people — you know, the people who think they’re cool. The ones with carefully crafted social media opinions optimized for “likes.” The hordes whose social currency comes from their “really strong opinions” — hoping you don’t notice their actual lives betray the credibility deficit beneath their words.
Upgrading your life has one less obstacle when you stop considering people who don’t have control over theirs as “cool.”
You can externalize all blame for your condition and win favor from Scowly Mc Hand Tattoo, or you can have freedom in the second half of your life. But you can’t have both.
As one of the few who got out, here are the 20 “revisions of belief” to detox from Counterculture, defeat the “work work work die” mandate, and get the last laugh.
What got you here, won’t get you there.
The logic goes: “My 20s were awesome. I’m going to do more of what made my 20s awesome, and more 30s and 40s will be super super awesome.”
But the things that once served you, will come to enslave you.
I briefly lived in Olympia, Washington in my mid-20s. I remember stepping out my door onto 4th Ave and finding an abundance of 40+ year old guys, sitting on curbs, often carrying guitars, who wanted your attention. They wanted to play you a song for a dollar, or sell you a poem. And if you stopped to talk, they’d go on about their glory days: how their band opened for Soundgarden once, their ex girlfriend was Courtney Love, or they were picked up hitchhiking by Jerry Garcia.
Alternately, you’d hear about their unfortunate present: A “greedy” landlord who made them relocate the van they are living in, the fantasy lawsuit they plan to file against the police for harassment, or how they’re just $10 short on a bus ticket to the Rainbow Gathering.
At one time, these guys were living the dream while most were sitting in a classroom or cubicle. But now, not one person would trade lives with them. They failed to adapt, and what liberated them now enslaved them.
What got you here, won’t get you there.
Keep the principles, change the model. You don’t have to sell out, but you have to adapt.
I’ve known many who tried to escape employment and failed. None strayed far from their comfort zone.
Vegan recipe blog. Reselling vintage clothes. Selling their art on Etsy. If you keep doing what you know, you’re limited to some variation of what you’ve always gotten.
Massive progress comes from massive discomfort.
When I started a tech business, I wasn’t just technically unskilled, I was technically inept. I didn’t just not have a tech background, I didn’t know what “tech business” meant. I didn’t just lack proficiency in coding, I couldn’t write a single line (still can’t). But I followed the friction, threw myself into a cauldron of doing Really Hard Things for years, and retired early as a result.
The magic only happens far, far outside your comfort zone.
You’re on a train right now. And the train is very clear about where it’s going.
Want to know where your life will be in 10 years? Look at your peers who are 10 years older.
Do you aspire to their life? Great news: that will be you. Their life will be yours.
Do you shudder? Bad news: That will be you. Their life will be yours.
Everyone thinks they’ll be the exception. You won’t be the exception.
If you don’t like what you see, burn everything down and run.
I was below the poverty line for the first 15-ish years of adulthood. Middle class for about 3 years. And in the top 4% of income and/or net worth for the years since. And “middle class” was the worst, by every measure.
When you’re poor, you can wake up and decide to hitchhike to Oregon. Or hop a freight train just to see where it goes. Or live in an empty broom closet and live off dorm dining hall scraps (I’ve done all three). You have total time freedom, nothing to lose, and are constrained only by your imagination and resourcefulness.
When you’re resource-rich, you can do all of the above. And the bonus of having the means to acquire anything that can’t be stolen or scavenged.
(When done well, poverty is often better than resource-rich in a “less is more” way, but that’s outside the scope of this article).
When you’re “working class,” you get none of the upside of either, and all the downside of both. Zero time freedom (they let you out to the prison yard on weekends, and a bonus two weeks a year if you behave). Expensive infrastructure to maintain (apartment near your job, car to get to work, and “work clothes”). Can’t go where you want. No off ramp (impossible to save enough to retire early). No option but to work until you’re too old to enjoy the freedom.
Of all the ways to sustain living, middle-class is the closest to death.
Employee Brain lives in “value extraction” mode: “What can I get out of this job? How can I extract the biggest wage for the least effort?
Counteculture Brain is often worse. “Who has a couch I can sleep on? What chain store is easiest to steal food from?” (No disrespect – I owe many years of glory to the generosity of strangers and shoplifting from Whole Foods. Huge fan.)
The mindset required to Exit (i.e. escape permanent employment) is the opposite: A “value creation” paradigm. I.e. Asking how much value you can create for others (and get paid in return). As an entrepreneur, you are paid in proportion to the value you generate for customers – the pain you alleviate, the status you provide, the money you generate for them.
I was almost a lost cause. My “value extraction” patterns ran deep. For years, I travelled the country, scanning the landscape for “value” I could “extract.” The stores I could shoplift from. The empty dorm room I could move into (illegally). The thrift store dumpster where I could scavenge for resellable goods. Nearly a pure “extraction” lifestyle.
Transitioning to entrepreneur (value creation) wasn’t just a mental pivot – it was a direct 180. In business, you’ll provide tons of value – often going years with no value returned to you.
Any Counterculture-saddled escapee works against the drag inflicted by a lifetime of extraction bias.
You’ll never escape 9 to 5 until you prioritize creating value over extracting value. (Unless your methods are criminal).
Or $10k. Or $50k. Whatever buffer is required to start and fail a few endeavors before one of them hits. Everything after that is just compounding.
Counterculture / employee / civilian brain believes money works linearly: $100,000 requires twice the effort as $50,000. But it’s not linear. It took me years to hit a net worth of $1 million. From there, I hit $2 million in 90 days.
Securing that first 10k, 20k, or 50k is the hardest. The rest is just discipline and compounding.
Many businesses require only $100 startup capital. The temptation when you’re destitute is to only launch what you can afford. But the lower the barrier to entry to an enterprise, generally, the more competitive. If you commit to a startup idea, get thrilled if it costs $50k to start. It means you’ve filtered out 99% of your competition.
So suffer, steal, fight, scrape save to get that first $10k, $20k, or $50k. After that, the rest is just 1. compounding, and 2. not being stupid.
Counterculture is saturated with unhappy, Netflix-addled zombies who have done most things wrong. That’s a good thing (for you). They serve as “contrarian indicators.” They are showing you the Way – the exact path to where you don’t want to go.
Miserable people provide a clear inverse blueprint on what not to do. Failure leaves clues.
Watch what they do, and do the opposite.
Look around at the people you don’t want to be. Look at what they read. Look at what they do in their spare time. Look at who they spend time with. Identify their influences. Listen to how they speak.
Then eliminate all of these from your life.
Look at the people you don’t want to be, and do the opposite.
If they watch short form videos all day. And Netflix at night. And go to bars. And listen to the Bernie Sanders podcast. And take numbing psych drugs. Then never do these things. They’re telling you what doesn’t work. Believe them.
Your inputs are your outputs. When people who aren’t where you want to be tell you what their inputs are – pay attention.
Of all the ways to accrue resources, employment is the least efficient.
Employment is indefensible, except by two attributes:
Comfort: Employment will give you the “steady paycheck.” Just don’t be late three times in 90 days, get replaced by AI, say anything weird on social media, etc etc.
Conformity: Employment will get you a nice pat on the head from your parents and other automatons for your obedience. Good boy.
If “comfort” and “conformity” are your two highest virtues, then a W2 is for you.
Employment is indefensible by all other measures.
In the world I come from, the worst crime is “selling.” The second, third, and fourth worst crimes are high profit margins (greedy), monetization of anything intangible (super greedy), and doing anything associated with “rich white males” (just because).
Punk bands who remind you to check out their merch table after the show are mocked. Investing yields are “blood money.” And any business you start that doesn’t involve tshirts, soap, or baked goods is called an “MLM scam.”
The life you want is on the other side of cringe. No exceptions.
Cringe means mastering email copy. Studying persuasion & sales. Speaking clearly and with confidence. Asking for large sums of money in exchange for a product or service. Entering strange arenas like affiliate marketing or SaaS. Breaking down ROI to clients. Building rapport by using specialized jargon. Building ugly websites that convert well. It’s all cringe.
Embrace the cringe or end up working for those who do.
Whatever you plan to do “only for a year or two,” you’ll be doing in 20 years. Very few exceptions.
When you’re desperate, you’ll do anything. You want the quickest path to subsistence level income. Even if your ambitions are large, the temptation is to start small. “Work your way up.” Always sounds good in theory, but in practice: the placeholder becomes the permanent.
It’s easier to get on a train at the station than it is to get off while it’s moving. There is the almost unavoidable peril that whatever you start, you’ll still be doing next year, and in five years, and 20 years after that.
Most start their employment-exit journey by defaulting to safety. They focus on “getting by” income, and worry about the Big Exit later. They focus on safety before pursuing the Prize.
They start a new endeavor and apply the following logic: “I’ll do this thing for a little bit to get on my feet / get some momentum / gain experience, then work up to a more ambitious goal next.”
So they start selling cupcakes at the farmer’s market. Or take a comfortable job as event coordinator for a non-profit. Or an undergad program for computer science. “It’s just temporary…”
Fast forward five or ten years. They’re still barely paying rent with cupcakes. They’re trying to convince you their non profit job “isn’t that bad.” Or they’re so deep in student debt, they’re still trying to climb their way out with a job they hate every moment of.
In economics, the concept is called “path dependence.” Whatever gets swung into motion early, has long lasting consequences that can’t be undone down the road. A thing in motion stays in motion and all that.
Starting with “stable income” is usually a stalling tactic. I sold used books on Amazon for too long, surrendering to the Two Deadly Sins of freedom: “Easy” and “Comfortable.”
Like okay, you do whatever you need to to survive. Maybe you’re disabled or have children. Maybe circumstances force your risk tolerance to be low. For most, this is the story they tell to delay doing the hard part first.
To the extent it’s at all possible, don’t start a thing you won’t want to be doing in ten years. Start the big thing now.
You can’t hit a target if you don’t have one.
Pick your Exit Number. This is the net worth number where you confidently can say you never have to work again.
This number is your unhealthy, all-consuming obsession. You will pursue it with the zeal of a thousand Gods. Thunder will rain down as you march through a battlefield of horned demons and unsupportive ex-girlfriends towards the Number. If your Number could get a restraining order, go far past that line. Every obstacle is obliterated as your gaze remains fixed on the Number, and all that awaits you on the other side.
The Number is not a goalpost to be moved. It is not subject to the whims of your shifting fancy. It is a fixed number past which you have exited the system.
This is not an income number. This is not even a “net worth” number (your house isn’t liquid, and if you sold it, you would just replace it anyway). This is an “investible assets” number.
Achieving your Number does not mean you stop. It means you can stop. Its achievement is not marked by the last thing you ever do. It is marked by the last thing you ever have to do.
The Number is most commonly chosen as the number you can invest and live comfortably off your interest and dividends. While controversial, the “4% Rule” is a starting point – the number you can invest and live off 4% of that figure each year (usually, but not always, a safe number past which you’ll never run out of money).
A Number gives you a Holy mission of existential proportions. Something to fight for, bigger than any obstacle, rendering everything in your path a mere annoyance to be vanquished on your march to Freedom.
Don’t start something without an off ramp. If you can’t retire from it, don’t start it.
The goal is a “liquidity event,” not income. Building something, often for years with little or no pay, for a large, event-driven sum.
This means beginning with the end in mind. And the end is selling the equity in what you build (preferably you own 100%), hitting your Exit Number (the number you need to never work again), and removing yourself from the system forever.
You can almost never “income” your way to the finish line. You can sometimes “revenue” your way to the finish line. You can very, very often “liquidity event” your way to the finish line. Always know the exit plan, and back it up with math.
Your freelance writing business can’t scale. Your nursing career “pays the bills” but ends in social security checks. Your 9 to 5 is not an asset. You can’t sell your 9 to 5.
Start a thing. Build it into a sellable asset. Sell it. Retire.
That’s the formula.
This is the clear visual and emotional vision that lets you know when you’ve won.
You already have your Exit Number. The Visual North Star is the precise consequence of your Exit. Not only what your life looks like when you hit your Number, but what it should look like long before – when you have engineered your fantasy life outside of “9 to 5.”
“I’ll know I’ve won when my life looks like this: ____.” Answer that question and hold that thought.
My Visual North Star was childishly simple, but it was a metric I fixated on until it was achieved. And when I actualized the fantasy, I knew I’d “made it.”
Living in hotels.
When I could live in hotels full time (if I wanted to), I knew I’d made it. Basic, 3-star, mid-range hotels in the $130 a night range. Add $20/day for gas, and another $50 for fixed and discretionary expenses. Before I’d made a penny online, I knew $6,000 a month was the baseline target.
But saying “$6,000 a month” doesn’t have a lot of emotion or energy behind it. It’s cold and quantitative. Switch it up to “living in hotels,” and it evokes an image of extreme freedom. One lifeless, the other energizing. My North Star would offer me the ability to pull off the freeway anywhere, on a whim, and check into anything that wasn’t Motel 6. This fueled me through the obstacles that were to come.
Write down every detail of what things will look like after you’ve “won.” You may notice this exercise is also the lowest common denominator of “personal development” literature. They always tell you to write everything down in detail. It’s basic because it works.
The power of this is in the concept of “structural tension.” Any gap between the clear goal for what you want, and where you are right now, is psychically uncomfortable. And the mind creates valuable tension in an effort to bridge that gap.
Your Exit Number resides in the practical and rational side of your brain. Your Visual North Star is pure emotion. This is the visual fantasy you drift away to in the darkest moments of your desk job.
The vision can be as granular, or as broad and postcard-image as you choose (“living in hotels” is pretty basic, but it worked for me). What matters is that it meets two criteria: It must be specific, and it must elicit emotion. This creates the “structural tension” that pulls you towards its achievement.
More than anything, your success is defined by your Exit “vehicle.” Your Exit Vehicle is the model (usually a business model) you plug your efforts into to achieve your Exit.
10,000 hours applied to one vehicle can yield 1000x the results as the wrong vehicle. Your vehicle will either constrain or amplify your efforts.
Vehicle example #1: Doctor. Many think being a doctor is a “good job,” or that doctors are “rich.” To be a doctor, you’ll study or be in training for an average of 26,000 hours. You’ll work an average of 50 hours a week. Your average salary across all specializations will be $300,000 a year. And your income will have a ceiling. You will never make more than the top salary your field allows.
You invested 26,000 hours and $350,000 to guarantee you never make more than $300,000 a year.
Vehicle example #2: Hedge fund management software. You’ll make nothing during the development stage (which could be a year or more). After which, you’ll charge $1,000 a month to as many hedge funds as you can sign up. There are 50,000 hedge funds. Your revenue will have a ceiling of $600,000,000 (With upsells and new products, your revenue is theoretically unlimited.)
The hedge fund product creator will spend vastly less time to launch than one studies and trains to be a doctor. One path has an income ceiling in the low three futures, while the other is in the high nine figures.
In the same way that walking vs. flying defines your travel time, your Exit Vehicle defines the time required to Exit.
Each vehicle has either a very clear and defined ceiling (e.g. the income of certain professions), or a more general theoretical ceiling (total addressable market of certain businesses). If you’re going to put the same effort into any vehicle you choose – choose the one with the biggest upside.
You can still plug your passions into a model, but the model is your highest impact decision.. You’re not going to open a coffee shop. You’re not going to sell DVDs on eBay. You’re going to pick an Exit Vehicle that will most effectively convert your time into capital and accomplish your Exit.
When mapping your Exit, default to the hardest thing. Pursue friction. Chase a long learning curve. Follow the fear.
Retiring young is an exceptional outcome. To pursue exceptional outcomes, you must act exceptionally. That means doing things the rest won’t do, can’t do, or fear to do.
You’re plotting to escape the herd. Don’t do herd things.
When you do crazy difficult things, you enjoy a crowd-free zone. You effectively have no competition. 99% of people encounter friction and abort.
Here’s a sample of things the people you don’t want to be (the herd) will never do:
This list eliminates nearly every Exit Vehicle worth pursuing.
Friction and difficulty is a positive indicator. An encouraging signal that the path is correct. Because everything that’s easy is saturated and has low upside.
W2 Employee Brain cannot handle this concept. Moving in the direction of challenge is the violent opposite of the Everyman’s default setting. Wage Mind buys lottery tickets. Wage Mind obsesses over crypto gambling. Wage Mind asks how to “get” the money, playing out a cartoon scenario in their mind of retirement being a big bag of money they have to locate and pick up. Wage Mind believes in “get rich quick.”
Your Exit Vehicle will never be spoonfed to you by 1,000 Facebook ads and YouTube “influencers.”
Everything you want is on the other side of obscurity, confusion, challenge, friction, and fear.
Focus is a laser that cuts through all obstacles. Attention dedicated to one thing is 10x more powerful than attention directed to two.
When you assume the responsibility for writing your own paychecks, you’ll face an unlimited number of options. Be slow to choose. But when you choose, commit with high conviction – at the expense of everything else.Never dilute attention across two or more of your options. Pick a path and pursue it with extreme commitment.
“Everything is the same as nothing at all.”
Too many options can be worse than too few. It’s a thousand times easier to be 100% committed than 99% committed. Very little will restrain progress more than moving towards a goal with one foot on the gas, and one on the brake.
I only succeeded because I refused to “dabble.” I concentrated my efforts (and risk) on one vehicle, and went all-in.
Counterculture advice is contempt, masked as concern.
Your tribe wants to keep you down because you make them look bad. Reject their advice wholesale.
When you have a job, no one gives you their opinion on it. When you make your own job, everyone has an opinion. And it’s the people who are the least qualified to weigh in (employees) who have the most to say.
Interpret what follows literally: Your tribe hates freedom. They hate dissenters. They hate successful escapees. And most crucially: They hate themselves for never escaping. And they will not hesitate to mask their contempt with “concern” and “opinions.”
People would rather be consistent with their tribal identity and miserable than break from the tribe and be satisfied. They know – often consciously – they’ve lived their life to appease both their family and social circle. Seeing someone take the risks they are afraid to lack triggers a visceral response that takes the form of “concern.” Like:
Their advice has an agenda, and the agenda is to enforce conformity. Counterculture tribes that ostensibly formed to challenge conformity, are the most vicious in enforcing it.
Reject tribal hall monitors and their conformity mandates disguised as “advice.”
Just like criminals have to follow smaller laws to break bigger ones (personally confirmed), you have to do boring things to avoid a boring life.
The exemplar of geriatric life is the 40 year old who so committed to keeping his “youthful spirit” that he exists in a groundhog day loop of band practice, bars, and “working on my art” for 20 years – to then find himself imprisoned when he inevitably caves to the pressures of age and finds himself unprepared and lacking options.
A barely less tragic variant is the punk rocker who followed a tracked life, settling down in a “career” early, who then applies a cosmetic overlay of “rebelllion” to sell the “I’m never growing up” facade to himself and the world – a life of side projects and taking his “PTO” to fly out to the “music fest.”
All of this could have been avoided by doing boring things directed towards a goal of never being boring again. Embracing a “humility era,” in which you do things you don’t want to do, to lay the foundation for never having to do these boring things again.
This is the paradox of the optimized life: the people who fear the fate of the “working stiff” are most often the ones who most insure that is the fate they will suffer. Likewise, this is the paradox of Counterculture: the life they aspire to is exemplified by the “capitalists” they hate most.
The thing you want – a life with no alarm clocks, going anywhere you want whenever you want, doing nothing or doing everything and answering to no one – only comes after doing a lot of strategically boring things.
Do the things you don’t like temporarily, in order to do the things you do like forever.
Don’t take advice from anyone who isn’t where you want to be.
Countercultures bring tribal pressures as deep as any religion. Add to this that most Countercultures have pretense of no hierarchy. Combine those, and behold the result: Everyone has an opinion, and expects their opinion to be given weight and consideration.
Never accept opinions from anyone you wouldn’t trade lives with.
The opinions of people on the sidelines do not hold equal value. Their lives are the products of those opinions, and their opinions aren’t just time-wasting – they’re dangerous.
The example of their lives is conclusive evidence their opinions are not valid.
If you don’t envy their life, then don’t take their opinion.
A final lesson.
Once you “make it,” weird things start to happen. And not obvious ones, like airport lounges. Your friends start to get weird. You become a traitor who abandoned that implied oath that you’d all go down with the ship together.
As your freedom and resources expand, your friendships with W2 filers contract.
Too simple to call it jealousy. By escaping, your existence becomes hostile – a reminder of what is possible.
At this stage, you’ll realize many friendships were theatrical productions in which you are cast as the Reinforcer Of Delusions, a supporting role given the unspoken direction to provide no evidence a W2 fate is anything other than inevitable. To remind them their fate is optional is to go off script, and be demoted from the role.
The spell violation of your Exit casts you as a hostile reminder that their lives could have turned out different. That maybe decisions played a larger role in their fate than “capitalism.”
If they don’t cheer when you score – may they be forever dead to you.
-Peter Young

