11 Short Lessons I Learned In Year 6 of the Real World

Every year around this time, I make it a point to share ideas and advice I wish I’d known about earlier. Most of them come from conversations with people who are a lot smarter than me, some come from books, and I’ve learned a few the hard way.

Nauseatingly cliche as it sounds, living in L.A. has taught me a lot, mainly because it’s a city filled with so many wild success stories—and even more cautionary tales of failure, burnout, and stupidity.

I wrote down a lot of stuff in my Notes app over the past year, but these 11 lessons stuck with me:

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1. Opinions are the most interesting when they involve someone changing their mind to form them.

2. Never take the last bite of something you didn’t pay for.

3. Stop kicking cans down the road. If you need to fix your car or renew your insurance, do it right away. Letting all of those little bullshit to-dos pile up in your head slowly grinds away at your sanity.

4. Most people would rather plan a yearly vacation than build a life they don’t need to escape from.

5. I heard someone talking about the “fuck yes or no” motto for making decisions. (If your reaction to choosing something isn’t “fuck yes!” then you shouldn’t do it.) Then someone smarter pointed out this was incredibly stupid considering important decisions are never simple. If I had only ever done things I was 100% certain about, I wouldn’t have much to show for myself. Conversely, I’ve wasted time and energy on “fuck yes’s” because I didn’t think things all the way through.

6. Figuring out how to use fancy new tools is less important than figuring out the things that never change.

7. Your best friends should be people who don’t really understand how you earn your money. Beware of people who are over-eager to know “what you do for a living.”

8. Whoever needs it less, wins.

9. Forget taking care of the low-hanging fruit. Always do the hardest thing first, whether that’s doing the workout you hate, waking up early to work on a side project, or sending an email to that person you’re terrified of.

10. Step letting people guilt you into consuming “classic” books/movies/music. A lot of stuff is popular simply because a small group of nerds decided it was. Life’s short, do what you want. Murakami nailed it: “If you only read what other people are reading, you can only think what other people are thinking.”

11. People never fully forgive or forget—they just get busy.

The 5 Best Books I Read In 2023: Art Heists, Y2K Death Spirals, and Bullshit Jobs

Unsolicited book recommendations are, generally speaking, worthless. Most of the stuff you’re “supposed” to read comes from articles that are stuffed with affiliate links, videos from people who are paid off, and book clubs you got pressured into joining.

That’s not to say you should take my list for gospel. But I guarantee if you pick any of these up, you’ll be shocked, moved, or at the very least, entertained.

A shameless plug before we dive in—Belt Magazine named my book, A Bar in Toledo: The Untold Story of a Mafia Front Man and a Grammy-Winning Song, one of their best reads of 2023. If you’re into the mob or music history, you’ll dig it.

Anyway, if you only read a few books this year, you can’t go wrong with these five.

1. Bright Shiny Morning by James Frey

I wanted to read a book about Los Angeles after I moved here to make sense of the city, or at least attempt to. A lot of stories about LA are fairy tales—this one is the opposite.

Bright Shiny Morning is a brutally honest portrait of chasing (and sometimes realizing) dreams in a merciless, moral wasteland. In four parallel stories, the book follows a homeless alcoholic, a closeted actor, a disgruntled maid, and a young runaway couple from Ohio—all of whom are clawing their way through a different stratum of LA.

Critics slammed this book when it came out in 2008 because it broke a lot of rules—intentional grammar/punctuation errors, jarring interstitials—but that’s what makes it memorable…and why it’s still in print after 15 years.

Hillary Frey (no relation to James) at the Observer put it better than I could: “[Frey] leads you into the hills high above Hollywood, shows you the most spectacular view of the hideousness that is Los Angeles, and then abandons you to make the only choice you can: to jump.”

2. The Art Thief: A True Story of Love, Crime, and a Dangerous Obsession by Michael Finkel

A 23-year-old dude living in his mom’s attic decides to steal $2+ billion worth of fine art from museums across Europe with nothing but a Swiss Army Knife—what could possibly go wrong?

Stéphane Brietwieser pulled off more than 300 heists before shit finally hit the fan. But unlike most art thieves, he had no intention of flipping his loot and getting rich. He was just addicted to the rush of stealing and the pursuit of beauty.

Michael Finkel got a lot of praise for his addictive storytelling in this book—rightly so. But I think he deserves just as much credit for examining the psychology and inevitable consequences of letting your obsessions go unchecked.

3. New Millenium Boyz by Alex Kazemi

Take a Y2K coming-of-age story, add blackmail, Satan worshipers, and a bunch of drugs, and you get New Millenium Boyz. The main character, Brad, is trudging through his senior year of high school when he meets two transfer students who drag him down a sick, twisted path that pushes him to his darkest impulses—and it’s all being videotaped.

This book is deranged, raunchy, and full of dialogue you’d be mortified to read aloud. But more importantly, it’s a reflection on growing up alienated and confused in a post-Columbine world, which few people are gutsy enough to recount as honestly as Kazemi did here.

4. Bullshit Jobs: A Theory by David Graeber

A decade before AI scared companies into cutting the fat, David Graeber’s essay about bullshit jobs went viral, forcing millions of people to wonder if their work was pointless. By popular demand, he expanded his essay into this book.

Graeber argues that more than half of modern jobs are bullshit, meaning they don’t add any direct value and could be eliminated without causing a blip on the radar.

I went into this book expecting Graeber to make fun of box tickers and paper pushers, which anybody can do. But I quickly realized he’s more concerned about the consequences of bullshit jobs. Getting paid to do (almost) nothing might sound sweet; Graeber thinks it’s dehumanizing.

It sucks that Graeber died in 2020. He’s one of the only people whose opinion about “the future of work” I’d actually listen to.

5. Eileen by Ottessa Moshfegh

Perverted, creepy, darkly funny—all the qualities that got me hooked on Moshfegh are on full display in Eileen, which I think is her best book, even though it was her first. Sure, it’s a crime/mystery novel. But not the kind you pick up at the airport on the way to Florida. Her writing is somehow disturbing, charming, and addictive all at the same time. Protect this woman at all costs.

Honorable Mention

The Men Can’t Be Saved by Ben Purkert

It’s a cliche compliment, but this is a book I wish I could’ve written. Purkert figured out how to explore early-20s angst, corporate bullshit, and dysfunctional romance—all without making you cringe. Much of the plot revolves around the advertising industry (it’s clear Purkert spent more than enough time there), but it’s less about work and more about how work shapes your soul.

The Final Testament of the Holy Bible by James Frey

This is probably the most unique book I’ve read, in terms of structure and style: a fictional depiction of what might happen if the Messiah returned in the 21st century, written in the form of Biblical scriptures. The plot is aggressively sacrilegious and won’t win any fans at church book clubs. But once you get past the initial shock, it’s impossible to ignore the fact that Frey wrote this to explore the religious impulse, not bash it.

Close to Home by Michael Magee

Sean, the book’s main character, did everything right for the first 22 years of his life. But after punching a stranger in the face, he’s forced to grapple with the trauma and secrets he buried as a kid. Set in working-class Northern Ireland, Magee dissects what it’s like to navigate the limbo period between your past and future.

That’s it for now. To stay up to date on my latest articles and projects, sign up for my newsletter. There are readers from seven countries and everyone is welcome to join.

17 Lessons I’ve Learned After 5 Years in the Real World

It’s weird to think I’ve been out of college longer than I was in it. Over the past four years I’ve recapped some harsh but valuable lessons I’ve learned in the real world  (2019, 2020, 2021, 2022). But 2023 has been the most instructive year by far, mainly because I went through the process of publishing my first book and moving to Los Angeles while running my marketing business.

Will I look back five years from now and realize some of these lessons were misguided? Probably, but who cares? Better to change your mind than cling to ideas because you’re afraid to contradict yourself.

Speaking of which…

1. The worst person you can lie to is yourself.

2. Most people prefer socializing with people who find them interesting—not people they find interesting.

3. If you start a creative project by calculating how fast you can earn $__________, you should stick to your day job.

4. The only time to take someone’s advice seriously is if they have something to lose by being wrong.

5. Some “silly” purchases actually net you money because they scare you into working harder to maintain them.

6. The idea that having a day job is incompatible with creating art or starting a business is just a lame excuse to not try. You can accomplish more with a few hours of deep focus each week than you can with months of unstructured time.

7. Good habits almost never survive bad environments.

8. Stop trying to fill the 5-10 minute gaps between meetings, chores, tasks, etc. You’ll feel better if you just wander around aimlessly, stare outside, or (if you dare) think.

9. If you want to “find more time to read” look at the screen time breakdown on your phone.

10. The new cult of AI dorks fail to realize that the most compelling thing about art is that someone suffered to make it.

11. You’re never “ready” to make life-changing decisions. Prepare yourself to jump before you spot the landing.

12. The harder you try to define yourself, the less you know who you are.

13. Don’t bet against the person who just keeps showing up every day.

14. “Someone who says ‘I am busy’ is either declaring incompetence (and lack of control of their life) or trying to get rid of you.” – Nassim Taleb.

15. The fastest way to eliminate distractions is to stop doing work you hate.

16. Become a regular somewhere (a restaurant, coffee shop, etc.) and tip generously. It feels good and normalizes not freaking out about small amounts of money.

17. Many self-proclaimed cultured people won’t drink cocktails out of plastic cups but will gladly read novels on a Kindle—or worse, listen to them.

Cities That Push vs. Cities That Pull

There’s something strange about the greatest Italian painters: all of them lived in Florence, a city 1/10th the size of Indianapolis. Leonardo da Vinci, Michelangelo, Donatello, the list goes on—all Florentines.

Meanwhile, Milan had just as many people with virtually identical DNA but failed to produce legendary painters. Two Italian cities 180 miles apart, but a world of difference between their creative outputs.

When you consider the context, this actually wasn’t strange at all. Florence was bankrolled by the Medici family, which was obsessed with art. Meanwhile, Milan was fixated on agriculture and politics.

There had to be painters with the same raw talent as Michelangelo in Milan. But they lacked the most important ingredient for success: living in Florence in the 1400s.

Fast forward 500+ years and the same phenomenon applies to us. Some cities push you toward your potential; other cities pull you down to your comfort zone—socially, professionally, physically.

You can transfer information across fiber optic lines at breakneck speed, but you can’t transfer energy, ambition, or momentum. This is why, despite trillions of dollars being invested in “collaborative technology,” people still migrate to cities that are calibrated to their skills and tastes.

Paul Graham wrote that cities send you messages, whether you realize it or not.

“A city speaks to you mostly by accident—in things you see through windows, in conversations you overhear. It’s not something you have to seek out, but something you can’t turn off.”

New York tells you to go to work. Miami tells you to go crazy. Denver tells you to go outside. I’ve lived in LA for about eight weeks, which mostly tells you to reinvent yourself (a dangerous message for the insecure and impulsive).

Regardless, you want to find a city that speaks louder than the voice in your head that gives you permission to waste your life.

It doesn’t matter how disciplined you are or how many gurus you follow. It’s impossible not to be influenced by the people and places that surround you day after day. That’s why people can’t lose weight when they live with gluttons and can’t moderate their drinking when they live in fraternity houses.

When nobody around you cares about the same stuff you do, there are no consequences for throwing in the towel.

“At any given time there are a few hot topics and a few groups doing great work on them, and it’s nearly impossible to do good work yourself if you’re too far removed from one of these centers,” Graham writes. “You can push or pull these trends to some extent, but you can’t break away from them.”

Take San Francisco, for example. Despite the valiant efforts of keyboard warriors posting videos of homeless encampments and open-air drug markets, the smartest minds in tech flock there without hesitation. Why don’t they all just move to tax havens and connect with their devices?

Because it doesn’t work, that’s why.

We love to romanticize going off the grid and living as “digital nomads.” But when push comes to shove, we crave being in the orbit of like-minded people. That’s what produced the device you’re reading this on. And that’s why the best music, the best food, and the best art come disproportionately from a few hotspots.

Make no mistake: LA isn’t paradise. There’s hellish traffic and there are wild gangs of TikTokers dancing in the aisles of grocery stores. Come here in search of an endless vacation and you’ll be sorely disappointed.

But you’d be lying to yourself if you didn’t feel pushed to work a little harder, train a little longer, or at least fire off that email you’ve been scared to send.

The irony is cities that push are often painfully inconvenient. But anything worthwhile in life comes with a tax. Stress is the tax you pay to leave a cushy job. Criticism is the tax you pay to make art. Money is the literal tax you pay to surround yourself with resources.

You can whine about it, or you can pay up. But you can’t say you never had a choice.

In the history of planet earth, it’s never been easier, faster, or safer to uproot your life than it is right now.

And if that scares you, all the more reason to do it.

17 (Semi-Controversial) Lessons I’ve Learned from 4 Years in the Real World

(Image credit: Ricky Ortiz)

If I had my own version of the expression “the cobbler’s children have no shoes,” it would go something like: “the writer’s website has no articles.”

My go-to excuse for my idle blog is that I’ve been busy over the past year—which is true, but a lame excuse nevertheless. I wrote a book which was supposed to come out in November but is now slated for September (update: it’s out). Most recently, I left a cushy job to run my marketing business full-time.

Like many idealistic twenty-somethings, I’ve been fighting (often unsuccessfully) the pull towards the digital world that we’ve all become so complacent with over the past two years. That means more traveling, less social media, and working from places that are more than 20 feet from my bed.

Along the way, I’ve picked up some challenging but ultimately helpful lessons from people way smarter than me. As usual, I compiled them into a list—a tradition I started the year after I graduated from college (here are the editions from 2019, 2020, and 2021).

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1. They say your real friends show up when you’re struggling. That’s incorrect. Real friends show up when you’re doing great (or better than they are). If you’re skeptical, post on social media how you’ve been feeling “down in the dumps” then post about achieving a goal that none of your friends have—see which one results in more conversations.

2. Notice that the people who discourage creative projects, taking risks, and buying fun stuff have never done anything creative, taken any risks, or bought anything fun.

3. You can’t call yourself successful until you can tweet without wondering whether you’ll get a strongly worded email afterward.

4. Most manager-types are incompetent and 100% replaceable; they keep their jobs through inertia and politics.

5. Be careful how “productive” you become—it’s easy to turn yourself into a bottomless pit for other people’s tasks.

6. One well-written email to the right person can do more for your career than a four-year degree, MBA, or (God forbid) an online course.

7. “An unbelieved truth is often more dangerous than a lie.” – Luke Burgis

8. Fear, jealousy, and anger are toxic in large doses, but necessary in small doses as fuel to build the life you want.

9. Your parents want what’s safe for you, not what’s best. Those are often extremely different.

10. Don’t ask smart people “What should I do?” Ask “What would you do in XYZ situation?”

11. “Better to stand tall in a mud puddle than lick boots in a parlor.” – W. E. B. Du Bois (paraphrased)

12. A subconscious reason you ask for advice is so you have someone to blame if things go to shit.

13. Obsessing over socio-political drama (transgender swimmers, Joe Rogan’s podcast, etc.) is just an excuse to not focus on yourself.

14. Before you get baited into a political argument, ask your opponent if they can name the three branches of government.

15. Job-hopping is the fastest way to earn more money in your twenties until you can start a viable business.

16. You want to be the loser at a table of winners, not the inverse.

17. Don’t expect anyone to understand, care, or help.

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As I mentioned, my book comes out later this year. In the meantime, you can drop your email below to get a teaser and first dibs on pre-order bonuses as soon as they’re available.




Of the books I read in 2021, these 5 are worth reading again

I thought 2021 would be less of a time warp than 2020. I was wrong. We got stuck in a 365-day limbo period between the old normal and the new normal, and by the time we caught our breath the year was over—again.

One antidote for chaos is a daily routine, which for me includes reading first thing in the morning. It’s way easier to make a dent in a book before email, work, and social media inevitably drain your mental energy. Anyway, out of all the books I read in 2020, I wanted to highlight five that are worth re-reading.

But first, a shameless plug. If you subscribe to my newsletter, you know I have a book of my own coming out soon. I hoped it would be finished in time for the holidays, but after some unexpected delays we’re looking at an early 2022 release date.

In the meantime, you can drop your email below to get a teaser for the book and first dibs on pre-order bonuses as soon as they’re available.




Now, onto some recommendations.

Four Thousand Weeks: Time Management for Mortals by Oliver Burkeman

Most productivity writers tell you how to use your time. Burkeman questions whether time is something you can even “use” in the first place. If that sounds meta or Zen-like, that’s because it is. Once you accept that life is a never-ending conveyor belt of to-dos, you can start living like a human being instead of a machine.

I can’t do this book enough justice in two paragraphs. If you’re a recovering productivity nerd who’s burnt out with tools, gimmicks, and empty platitudes, buy this book immediately.

Favorite quote: “Nobody in the history of humanity has ever achieved ‘work-life balance,’ whatever that might be,” he writes, “and you certainly won’t get there by copying the ‘six things successful people do before 7 a.m.’”

A.A. Gill Is Away by A.A. Gill

The late A.A. Gill makes today’s travel writers/bloggers sound like dilettantes. From famine-stricken Sudan to porn studios in California, Gill has a super-human knack for making you feel like you’re right beside him: seeing the sights and conversing with locals. This collection of essays was published in 2005, but they’re perennially fascinating, hilarious, and (depending on your taste) offensive.

Favorite quote: “Most journeys in all of the world start not with bright expectations, a sense of adventure or a bucket and spade, but an empty stomach.”

Wanting: The Power of Mimetic Desire in Everyday Life by Luke Burgis

Why do you want the stuff you want? The answer is disappointing—or liberating, depending how you view it.

Wanting is based on the French philosopher Rene Girard’s theory of “mimetic desire,” which states that we want things simply because other people want them too. This force affects everything from high school dating scenes to Wall Street board rooms. The only way out is, paradoxically, to accept that you don’t desire anything independently—even if you’re a self-proclaimed iconoclast.

I guarantee this book will make you rethink your job, your friends, your wardrobe, and more.

Favorite quote: “An unbelieved truth is often more dangerous than a lie.”

True Story: Murder, Memoir, Mea Culpa by Michael Finkel

After being ousted from the New York Times for fabricating a story, Michael Finkel became pen pals with one of America’s most wanted murderers, Christian Longo. Why? Because Longo randomly decided to assume Finkel’s disgraced identity after fleeing to Mexico.

Finkel’s first-person narrative of his bizarre experience reads like a thriller novel. But as the title implies, this is a true story—one that’s too wild to fabricate. If I didn’t have to work, I would’ve read this book in one sitting.

Favorite quote: “I hated him in the intense way that you can only hate someone you’d once truly cared about.”

A Confederacy of Dunces by John Kennedy Toole

You might not think a novel written in the 70s by a literature professor could make you laugh out loud, but you’d be wrong. Dunces chronicles the misadventures of Ignatius J. Reilly, a slovenly, grouchy, obese, self-described intellectual who lives with his mom. Between his bouts of writing, Reilly works (and fails miserably) as a hot dog vendor and a file clerk at a pants company. The dialogue, storylines, and attention to detail are all genius-level.

John Kennedy Toole tried for more than a decade to publish his book, but his failure tragically drove him to suicide. It wasn’t until Toole’s mother showed the manuscript to the novelist Walker Percy that it was published. Eleven years after his death, Toole was posthumously awarded the Pulitzer Prize for Fiction.

Favorite quote: “I am at the moment writing a lengthy indictment against our century. When my brain begins to reel from my literary labors, I make an occasional cheese dip.”

 

I hope you enjoy these books as much as I did. Speaking of books, don’t forget to join my newsletter to get a sneak peak of my upcoming book and first access to pre-order bonuses. 

16 Life Lessons I’ve Learned After 3 Years in the Real World

I have a habit of writing down ideas and advice I wish I’d known a long time ago (you can check out my lists from 2019 and 2020). Some of them come from conversations with smart people, many come from books, and I’ve learned a few the hard way. I’ll spare the verbose introduction about the “silver lining of the pandemic” and get straight to the good stuff:

 

1. Goals are overrated. Instead, focus on a system of small, daily improvements. Then, as Bill Walsh said, “The score takes care of itself.”

2. Idolizing a politician is like believing a stripper who says they love you.

3. “It’s difficult to get someone to understand the truth when their salary depends upon them not understanding it.”

4. Most people don’t do well in positions of power. We’re very certain how we would handle a situation better than whoever is in charge, when in fact we would react the same way, or worse. Accepting this bias makes you much less likely to judge others’ actions.

5. Introductions (Hey John, meet Sam) are infinitely more valuable than referrals (Tell John I sent you.) Deals are built on the former, not the latter.

6. Wisdom rarely wears a suit.

7. Proactively plan how you’ll handle conflict—in relationships, at work, at home. This will save you from making embarrassing knee-jerk reactions when people inevitably piss you off.

8. Most success stories are just post hoc constructions of luck and random events organized into a catchy 200-word bio. Or, explained visually:

9. Taking investing advice from someone who lives in their parents’ house (“Buy Tesla/Dogecoin/GameStop!”) is like taking fitness advice from a guy gorging on donuts.

10. Shame is the least efficient way to change someone’s behavior; having skin in the game is the most efficient. (For more on this, read about why you should blackmail yourself.)

11. There are no geographical solutions to psychological problems.

12. Happiness often hinges on your ability to enjoy luxuries without letting them become necessities.

13. If your organization values people who signal that work is being done instead of actually doing the work, quit immediately.

14. Your teachers told you to learn, then start. High achievers start, then learn.

15. Most successful people aren’t public figures (that is, they aren’t posting pictures on private jets in Tulum.) There’s a reason for that.

16. Good ideas come from conversations. Great ideas come from shutting up and listening.

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Have you read these 5 life-changing books? Get the list here, plus monthly history lessons to help you navigate modern problems.

To get ahead, you should always be losing (just by a little)

Image credit: Sports Illustrated

How would you push an elite athlete into peak performance mode?

Maybe you’d scour scientific journals to find the optimal diet or training regimen. Maybe you’d fork up a few grand for a motivational speaker. Or maybe you’d have them put their paycheck on the line.

Jonah Berger, a professor at the University of Pennsylvania’s Wharton School, has a different theory— one that’s grounded in our evolutionary biology.

In 2011, Berger and his team analyzed 60,000 high-level basketball games, including 18,000 NBA games, to observe how a game’s score influences effort and ultimately performance. For the most part, their findings were what you’d expect: teams that establish big leads in the first half almost always win.

“For every two points a team was ahead, its chances of winning increased by about 7%,” said Berger. “Except for this major discontinuity right in the middle.”

Teams that were down by only one point at halftime were more likely to win than teams that were ahead by one point.

This might seem like a fluke. A one-point deficit is a hyper-specific instance to study. Besides, one point isn’t much in basketball — the game might as well be tied, right?

“The fact that the game is close is precisely the point,” says Berger. “The effect is present only when the team is just slightly behind. A team in that situation knows it can compete and recognizes it must work harder in the second half to achieve its goal.”

The “Slightly Behind Effect” isn’t just limited to the hardwood.

During the 2011 FIFA Women’s World Cup final between Japan and the U.S., a commentator noted how odd it was that Japan always seemed to step up their game when they were behind.

Most recently, Tom Brady and the Tampa Bay Buccaneers sat in second place in their division behind the New Orleans for nearly the entire 2020 season. On January 17, the Bucs beat the Saints and advanced to the conference championship. On Sunday, they won the Super Bowl.

“I find it com­pelling that the losing team always had something more to give,” says Berger. “Why aren’t they working their hardest always? Shouldn’t it be impossible to increase the effort and motivation of an elite sample like that? I think it says something about human nature that we exert a bit more effort when we’re slightly behind.”

Professional athletes might seem like an exception — they’re genetic freaks hardwired to win at all costs. So what about everyday people looking for a competitive edge in the classroom or their careers?

Image for postIn 2011, Berger conducted an experiment in which he told subjects they were competing with a person in another room to see who could type the fastest — the winner would receive a cash prize. After one round, Berger gave the subjects feedback, saying that they were far behind, slightly behind, tied, or slightly ahead of their competitor. Only the people told that they were slightly behind picked up the pace significantly in the second round. Overall, the subjects in the “slightly behind” group performed faster than the “slightly ahead” group.

Human beings evolved to strive, not to settle. Getting too comfortable makes us vulnerable to someone who’s hungrier — literally and figuratively. That’s the basis of Austin Kleon’s quote: “If you ever find that you’re the most talented person in the room, you need to find another room.”

There are, of course, limits to the Slightly Behind Effect. In order for it to work, you have to be within a realistic striking distance. Facing a blowout at halftime might even make you give up, just like a startup comparing itself to Amazon would be deflating. However, a healthy dose of competition lets you to dip into mental and physical resources you didn’t even know you had.

In other words, it pays to be losing —but only by a little.

Have you read these 5 life-changing books? Get the list here, plus monthly history lessons to help you navigate modern problems.

The Only Cure for Distractions Is Finding Work You’re Obsessed With

Credit: Carl Richards

 

Why am I distracted?

That’s usually the last question you ask yourself when a deadline is looming. With each passing minute it becomes harder to focus. So you check your email (again), you drink another coffee, you put it off until tomorrow when you’ll “have more time.”

You’ll do anything except ask yourself: Why am I distracted in the first place? In other words, you treat the symptoms, not the illness. And the illness is doing work you hate.

As children, we all had primal inclinations. We were drawn to activities that seized our attention and sparked our curiosity. We enjoyed them, not because of their perceived value, but because we developed an emotional connection to them.

We all remember spending hours on end fully immersed in our favorite activities: drawing, writing, acting, building, designing, cooking, and so on. It wasn’t hard to focus. In fact, you probably had to be dragged away to return to what you were “supposed to be doing.”

Fast forward to life as an adult. Our attention spans are shriveled. We eagerly anticipate the next smartphone notification, like rats pressing a lever for food. The TV glares in the background. Anything that offers an escape from work, even momentarily, is joyfully welcomed. We’re working for the weekend.

So, what’s the disconnect? And why does it occur?

Contrary to what some productivity gurus might pontificate about on social media, the problem isn’t a lack of work ethic or even the tiny distraction machines we carry around in our pockets. Those are cop-out answers. The problem is settling for work that isn’t engaging enough to make distractions irrelevant.

“Once you choose a career that doesn’t suit you, your desire and interest slowly wane and your work suffers for it,” says Robert Greene, author of Mastery. “You come to see pleasure and fulfillment as something that comes from outside your work.” (Emphasis mine).

Greene goes on to say that it’s our subconscious desire to conform to our parents’ expectations and social norms that pulls us away from our primal inclinations and inevitably separates us from our truest selves.

Jason Fried, the founder of Basecamp, says that distractions can serve a purpose: “They tell us that our work is not well-defined, our work is menial, or the project as a whole is useless.”

While this observation seems bleak, it offers insight into how we can conquer distractions: We have to seek out work that aligns with those primal inclinations and ignites the same curiosity we had as kids.

In order to do that, the first step must be inward. Set aside the noise and look for patterns throughout your life: What do you think about in the shower? What do you do for free? What could you talk about for hours on end? Or as Jerry Seinfeld puts it: “Find the torture you’re comfortable with.”

Whatever that is, it’s your ticket to freedom.

All masters, from Maya Angelou to Michael Jordan, followed their inner voice. They didn’t need to microdose psychedelic drugs or buy caffeine supplements. They were simply obsessed with their work.

You and I are no different in that we learn faster and work harder when we’re emotionally invested in a project. Time management expert Laura Vanderkam mentions this in her TED Talk: “Time is highly elastic. We cannot make more time, but time will stretch to accommodate what we need or want to put into it.”

There is a sense of urgency that emerges when you strive towards something you care deeply about. You forget you even have an iPhone. Psychologists refer to this as being “in the flow” – a state in which, to some degree, you become immune to distractions.

Make no mistake: every project can’t flow effortlessly from your fingertips. There will be meetings you dread. There will be grunt work. That’s part of the process.

But when you’re chronically distracted, the solution isn’t hacking your brain to get more work done. It’s taking a look in the mirror and asking whether you’re doing the right work in the first place.


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Ryan Holiday Is Reviving a 2,000-Year-Old Philosophy, One Email at a Time

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Around 9 a.m. when millions of people are checking sports scores and scouring Twitter, about 300,000 people are starting their day with something different.

Stoicism.

This ancient philosophy that emphasizes the values of temperance, detachment, and discipline originated in Ancient Greece, but today it lives in the email inboxes of professional athletes, entrepreneurs, politicians, and working class folks alike.

The catalyst? Daily Stoic: a worldwide community that applies the principles of ancient Stoic wisdom to modern life — founded by a college dropout.

But before we learn about Stoicism’s digital renaissance, we have to go back to the beginning, to the Stoa Poikile.

What Is Stoicism?

Image for postAbout 2,300 years ago, a haggard man named Zeno sat down at the Stoa Poikile (Painted Porch) in Athens to teach people that discipline — not pleasure — was the key to the Good Life. Zeno was a wealthy merchant destined to follow in his father’s footsteps. But just as he was entering the prime of his career, his life took a surprising twist. On a voyage from Phoenicia to Athens, his ship sank along with his possessions.

While stranded, he picked up a copy of Socrates’ dialogues. Zeno was so enthralled that he asked the bookkeeper where he could meet philosophers like this. From there, he studied under the most influential thinkers of his era: Crates of Thebes, Stilpo, and Philo — all of whom laid the foundations for his own teachings.

Despite his wealth, Zeno lived an ascetic life. He understood that people suffered because they pursued possessions instead of virtue. According to the ancient biographer Diogenes Laertius, Zeno joked, “Now that I’ve suffered shipwreck, I’m on a good journey.”

Zeno’s students were initially called Zenonians, but later came to be known as Stoics — a tribute to the Stoa Poikile where they gathered.

From the beginning, it was clear that Stoicism would be different from other philosophies.

For starters, it was taught in a public space while others were reserved for private classrooms. It was also action-oriented. The Stoics weren’t interested in arcane theories — their goal was self-mastery, which could be accomplished by practicing four virtues:

Courage: stay true to yourself

Temperance: control your impulses

Justice: do the right thing

Wisdom: pursue truth

Stoicism quickly became the most popular philosophy in the Roman Empire, and for good reason. It was relevant for the rich and the poor, the powerful and the meek alike.

In fact, the three most popular Stoics were a political advisor (Seneca), a former slave (Epictetus), and a Roman emperor (Marcus Aurelius). Their insights — along with many others — have helped countless people overcome adversity and find meaning.

To sum up Stoicism in one sentence: we don’t always control what happens to us, but we always control how we respond — a timely adage if there ever was one.

Despite its practicality, Stoicism was largely the focus of scholars and historians in the post-Enlightenment era. Of course, the term “Stoic philosophy” doesn’t exactly do itself much justice today.

The adjective “stoic” has become misconstrued with emotionlessness; and the word “philosophy” conjures up images of stuffy professors and thick textbooks. But Stoic philosophy differs from lecture-room philosophy in one distinct sense: It’s not something you believe or study, it’s something you do. It’s a way of life.

Taking Stoicism from ivory towers into the real world would require the work of someone intellectual yet tech savvy — perhaps someone a bit controversial.

Stoicism Gets an Unlikely Advocate

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Ryan Holiday isn’t exactly the poster boy for philosophy.

As American Apparel’s twenty-year-old marketing director, he deliberately ran ads that violated the policies of publishers’ websites, just for the publicity. As Tucker Max’s publicist, he started fake boycott groups and defaced his own billboards, knowing reporters wouldn’t be able to resist the outrage. Faking lawsuits, leaking documents, emailing from fake addresses — if it could help his clients sell something, Ryan Holiday wasn’t above it.

Then he exposed his secrets in the polarizing tell-all book Trust Me I’m Lying — all before he turned 30.

“I was disgusted with how it all worked,” Ryan told The New York Times. “The idea of the book was, I’m going to put all these things in a giant pile and light them on fire.”

At the same time he was pulling off shameless publicity stunts, this self-proclaimed media manipulator was quietly piquing his audience’s interest in something much different than marketing:

Stoicism.

In 2009, Ryan wrote Stoicism 101: A Practical Guide for Entrepreneurs as a guest post on Tim Ferriss’ blog, which generated nearly 400 comments. From there, he published more blog posts on his own site and recommended dozens of Stoic-inspired books in his monthly reading recommendation emails.

By 2014, just two years after everyone pegged Ryan Holiday as the Don Draper of digital, he took a pay cut from his publisher to write The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph.

On Amazon, it’s categorized under “Philosophy Movements,” but the book is the antithesis of what you’d find on a college syllabus. The pages are packed with enthralling stories of people like John D. Rockefeller, Steve Jobs, and Amelia Earhart applying the timeless principles of Stoicism to overcome adversity in pursuit of greatness.

“No one wakes up and says, ‘I need philosophy today,’” says Holiday. “Instead, they wake up with problems they need solutions to.”

It’s a peculiar — but ultimately empowering — hybrid of history, psychology, philosophy, and self-help. Nobody knew if Stoicism would gain as much traction today as it did on the Stoa Poikile — even with a master publicist behind it.

And then the numbers came out: 30,000 copies sold in just six weeks.

But that was just the beginning.

Stoicism Garners a Cult Following

Arnold Schwarzenegger. Nick Saban. LL Cool J.

Image for postThese are just a few public figures who have a copy of The Obstacle Is the Way on their bookshelf, along with half a million others. But the case of how Stoicism became the self improvement strategy du jour is a curious one.

There are no viral “life hacks,” miraculous claims, or A-list celebrity endorsements. No split screen appearance on The Today Show. And yet, the book made its way into the New England Patriots’ locker room on the way to their 2014 Super Bowl Victory.

There’s something about the book’s message that transcends socioeconomics, race, gender, age, and location. Something, as the subtitle emphasizes, timeless.

Ryan Holiday is a marketer by trade, which raises the question: Was popularizing Stoicism his plan all along?

“It did strike me when I first read the Stoics that this was way more practical and relevant than the esoteric academic and Wikipedia definitions of philosophy,” says Ryan. “But I definitely didn’t see it exploding quite the way it has.”

Ryan points out that Stoicism tends to have resurgences when times get tough. “Often people look to Stoicism to get them through periods where there are large societal shifts that they can’t control.”

It makes perfect sense that today, in the midst of civil unrest and a global pandemic, people find solace in repeating that powerful dictum: I don’t always control the world around me, but I can control how I respond.

Building on the runaway success of The Obstacle Is the Way, Ryan launched a new venture to introduce Stoicism to a wider audience, Daily Stoic: an online resource dedicated to solving everyday problems with ancient wisdom.

The bread and butter of Daily Stoic is their newsletter. Each morning, Ryan sends a short (~500 word) note inspired by prominent Stoics. October 7th’s email included an anecdote about Marcus Aurelius’ response to the Antonine plague, which killed over 60 million people, and how we can heed his wisdom to endure the nightmare we’re currently experiencing.

One would think simplifying and sharing this once-obscure wisdom with the masses is a noble pursuit. But not everyone was happy with Stoicism’s renaissance.

Can Philosophy Be Too “Trendy?”

Whether it’s a stuffy university professor or an irate Instagram follower, there have always been critics of Ryan’s modern interpretation of Stoicism. These philosophy “purists” argue that Stoicism should never be monetized via sponsors or “diluted” into bite-sized snippets in an email.

A constant barrage of cheap shots might discourage some people. But Ryan holds his reputation as Stoicism’s publicist with great pride.

“Of all the horrible things to be accused of, making philosophy popular and accessible doesn’t feel like a particularly bad one,” he says. “Some people want to keep these ideas hopelessly obscure and opaque so they and their university buddies can debate them for a living… and pretend that isn’t ‘monetizing’ philosophy either. They’re just doing it on the taxpayer and student dime.”

The name Stoicism derives from the Stoa Poikile, or “painted porch,” which was one of the primary places to share ideas 2,000+ years ago. But today, we don’t share ideas on a porch. We read emails, listen to podcasts, and watch videos. This is how Stoicism will spread, and Ryan is willing to do whatever it takes to generate the funds to make it happen.

“That we fund Daily Stoic by selling products to people who want to buy them seems more than fair,” he says. “That we sometimes accept ads for the podcast or email, like most other content providers, including the New York Times…only a crazy, entitled person would be upset by this.”

Purists might be complaining that modern audiences aren’t absorbing “authentic” Stoicism. But ironically, Daily Stoic is driving unprecedented sales of the original texts. As of today, Marcus Aurelius’ Meditations has nearly 8,000 reviews on Amazon.

“At the end of my books I always have a ton of suggestions for primary sources to go to next,” says Ryan. “I love seeing the spike in sales of the classic texts from Marcus Aurelius and Seneca and Epictetus. I feel like I’m paying forward what was done for me.”

Daily Stoic Makes Philosophy More Accessible Than Ever

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Since launching Daily Stoic in 2016, Ryan and his team have sent over 130 million emails — the equivalent of four full-length books. They’ve amassed an audience of more than 300,000 and maintained the same open rate for six years — a testament to their audience’s devotion.

While the morning newsletter is the hallmark of Daily Stoic, it has gradually expanded into a niche empire. As far as content, the Daily Stoic website publishes editorial-length profiles, and interviews. Their YouTube channel boasts nearly a quarter million subscribers. Daily Stoic’s fastest growing medium is the podcast, which gets more than three million downloads per month (mainly through the email list).

Ryan even launched a Daily Stoic store with a product catalog that includes pocket-sized medallions, prints, courses, and even a hand-sculpted bust of Marcus Aurelius. Zeno himself would’ve never seen this coming.

Is Stoicism Here to Stay?

The Lindy effect, coined in 1964, is a theory that the longer an idea survives, the longer it will last into the future. In other words, the idea ages in reverse.

Considering Stoicism survived the Victorian Era, the Enlightenment, the Renaissance, the Civil War, the Industrial Revolution, and the dot-com bubble, it’s safe to say this philosophy won’t fade into oblivion anytime soon — especially if Ryan Holiday is running Daily Stoic.

Most recently, Ryan released his tenth book: Lives of the Stoics: The Art of Living from Zeno to Marcus Aurelius, which debuted at #1 on the Wall Street Journal bestseller list. This collection of mini biographies dusts off powerful lessons about happiness, success, resilience, and virtue that are as applicable in modern America as they were in Ancient Greece or Rome.

Pop psychology life hacks capture millions of clicks these days, but the Daily Stoic community isn’t fazed. All the wisdom they need was written 2,000 years ago — and it’s waiting for them in their inbox every morning.


Have you read these 5 life-changing books? Get the list here, plus monthly history lessons that help you navigate modern problems.