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14 Brutally Honest Lessons I Learned After 2 Years in the Real World

Last summer I published a list of lessons I learned after a full year of working in the real world. Since then I started a new job, moved, made some money, lost some money, and spent time around a lot of interesting people (some admirable, others complete trainwrecks). Like last year, I wrote down the lessons I learned along the way—mostly from people smarter than me. The ones on this list had the most impact: 

1. Study the people you don’t want to be like just as much as you study people you admire. A reverse role model tells you precisely what not to do.

2. If you find yourself chronically procrastinating, you don’t need productivity hacks or another cup of coffee. You need a new job. Doing what you love gives you a virtually unlimited supply of energy.

3. Deliberately making yourself uncomfortable once a week (if not daily) helps you feel alive. Our lives are entirely too convenient and cushy. Try waking up at 4 am, walking home (the long way), or cooking something that isn’t categorized as “easy.” Anything to break up the malaise.

4. Giving yourself a raise is more gratifying than receiving a raise from an employer.

5. Instead of saying “See you later” or “Take care,” say “It was good to be with you.” It’s more intentional, and you can tell it resonates with people you care about. I picked this up from a mentor of mine, Matt Hall.

6. Resist the impulse to take a stance on every hot button issue. 99% of the time, saying “I don’t know” sounds a lot smarter than whatever flimsy opinions you hack together after reading a few headlines.

7. If you knew the extent to which brands objectify you in marketing meetings (“our target consumer craves a sense of belonging”) you wouldn’t buy from most of the brands you love.

8. When you can’t define what you want out of life, you copy what other people “want.” That explains the millions of miserable souls with generic business degrees, fitness Instagram accounts, and Patagonia quarter-zips.

9. Making your accomplishments appear effortless is more impressive than bloviating about your early mornings and late nights.

10. The employees who survive—and thrive—are those who can sustain the same levels of energy, resourcefulness, and hunger as they had when they first got hired.

11. If you feel insecure when someone tells you how much money they make, consider that they had to tell you how much money they make.

12. You will never regret supporting a family-owned restaurant instead of eating Chipotle, Dominos, or Jimmy John’s for the umpteenth time.

13. If you work 9-5, you have about three hours of pliable time daily. Your life is the compound effect of how you put those three hours to use every day.

14. Nobody has it all figured out, especially the people who look like they have it all figured out.

Have you read these five books to base your life on? Get the list, plus seven strategies I stole from marketing geniuses to promote your work.


Honor Roll Students Rarely Change the World. Here’s Why.

If you scroll through the barrage of college graduation pictures this month, it will be difficult to point out which students will go on to change the world. It will, however, be easy to point out the students that (probably) won’t.

You can identify them because their gowns are adorned with a myriad of colorful tassels, stoles, pins, ribbons, etc. They spent the past two decades chasing approval from their parents and teachers: memorizing data, regurgitating trivia, and correctly filling bubbles next to arbitrarily selected multiple-choice questions—in other words, playing by the rules.

This is why their careers will end, in the words of T.S. Eliot, not with a bang, but a whimper.

Pursuing quantifiable success, especially in school, tends to go hand-in-hand with a reluctance to pursue originality. You become so preoccupied with checking boxes that you can’t lift your gaze to see, much less think, outside the narrow confines of a syllabus or job description.

Accordingly, we see swarms of straight-A students flock into systems-oriented careers: engineering, accounting, medicine, finance—domains in which you can win by simply following rules. Not that there’s anything wrong with that. You get a healthy, predictable salary, benefits, and 401K package.

But you probably won’t change the world.

The chief characteristic of an innovator is a deep aversion towards the defaults that others accept in order to “succeed.” But that aversion comes with a cost, especially in childhood.

Research demonstrates that elementary school teachers routinely discriminate against iconoclasts. Their least favorite students are the “troublemakers” who don’t conform to lesson plans and who don’t shy away from butting heads if someone else in the class says something wrong or stupid. Meanwhile, their peers who follow every rule to a T become, predictably, teachers’ pets.

Make no mistake: Successful students usually become successful adults, albeit in tightly restricted niches that promise six figure salaries and “stability.” But as psychologist Ellen Winner points out, only a fraction of gifted children evolve into revolutionary adult creators.

When psychologists study history’s most renowned entrepreneurs, artists, and leaders, they discover that the vast majority were underwhelmingly average students: John McCain, Thomas Edison, and Elvis (who actually failed a music class) just to name a few.

Conversely, if you follow child prodigies (or that kid who aced every spelling test) into adulthood, you’ll find that few grow up to make waves in the world. As the psychologist Adam Grant says, “Practice makes perfect, but it doesn’t make new.”

My previous and current bosses were notorious underachievers in the classroom. One proudly asserts he earned “straight Cs.” The other was expelled from numerous high schools and barely graduated from college. Both have made more significant contributions to the world than their “VP of strategic business sales development analyst” counterparts who got a pat on the back from the dean of students after walking across the stage.

Neither inquired about my grades or even where I went to college.

Sure, two people is a small sample size. But it’s enough to make the case that arguing with high school teachers over fractions of percentage points to boost my GPA was a catastrophic waste of time and energy.

The point here isn’t to denigrate honor roll students, but rather to note that being on the honor roll has no correlation with making any meaningful difference in the world once you exit the nerf-like environment of school.

If you want to applaud the tassel-bearing students on Facebook, knock yourself out. Just consider that making the honor roll isn’t as much of an honor as it is a token of obedience.

(If you’re giving a valedictorian speech, feel free to plagiarize as much of this blog post as you want).

Have you read these five books to base your life on? Get the list, plus seven strategies I stole from marketing geniuses to promote your work.


Alive Time vs. Dead Time: Two Ways to See Your Time in Quarantine

In the spring of 1802, a Scottish lawyer and aspiring writer named Walter Scott sustained an injury that would ultimately catapult his career. The 31-year-old was kicked by a horse, a tragedy that confined him to his bed for nearly a month. But rather than writing in self-pity, Walter Scott picked up a pen.

The words he wrote in recovery became the first canto of The Lay of the Last Minstrel, his breakthrough narrative poem that thrust him into literary stardom.

“Success or failure,” he said, “is caused more by the mental attitude even than by mental capacities.”

Amusing trivia aside, this anecdote about Walter Scott is a lens through which to see our current situation, which for most people is isolation. Depending on how quickly we can flatten the COVID-19 curve, most of us will spend the vast majority of this spring confined to our residence—much like Walter Scott was two centuries earlier.

There are two ways to categorize the time we have on our hands: Alive Time and Dead Time (terms coined by the author Robert Greene.)

Dead Time is passivity personified. It’s sitting idly as the clock ticks away. It’s compulsively refreshing your news feed in search of the latest coronavirus update. It’s the pathetic cycle of complaints coupled with inaction.

In contrast, Alive Time is taking control of your situation—not the other way around. It’s learning new skills while shedding bad habits. It’s reading, exercising, reflecting, planning, and communicating.

A recent Gallup poll found that nearly half of Americans say they “don’t have time to do what they want.” Well, here’s time served up on a silver platter: massive blocks of solitude with all the information in recorded human history at your fingertips (the internet) coupled with technology that can connect you with people on any corner of the planet in seconds.

One would hope that we leverage these unprecedented opportunities during this downtime. Indeed, some of the greatest ideas were conceived in times of despair. But a brief scroll through Facebook or Twitter will quickly dash your hopes. Your timeline is almost certainly littered with links to fearmongering content, memes, and requests for TV/movie recommendations—all avenues leading to Dead Time.

The premise of Stoic philosophy is that we can’t always control what happens to us, but we can control how we respond. There’s arguably no theme as timely as this, given the current situation.

You’re confined to your house or apartment. Will you start the project you’ve been putting off or numb your mind with another episode of God-knows-what?

You’re forced to work from home. Will you adapt and find a new way to get an edge or slack off because nobody’s watching?

You’re told to practice social distancing. Will you go for a run or polish off a pint of ice cream?

The right activities are just as accessible as the bad activities. But choose wisely, because when the dust settles and life ramps back up, you’ll have to answer what will surely be the most popular question this year: What did you do during your coronavirus quarantine?

Have you read these five books to base your life on? Get the list, plus seven strategies I stole from legendary marketers to promote your work.


Amateurs Invent Things. Geniuses Steal and Improve Them.

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In 2002, a young computer programmer decided to flip the script—or code, rather—on how people interacted online. He was fed up with trolls, spammers, and anonymity in general. Instead of fanning the flames of cyber-anarchy, he set out to create a social network that could mirror the real world.

“I wanted to bring that real-life context that you had offline online,” he explained. Instead of hiding behind pseudonyms like Cyberdude307, he envisioned a future where users displayed their real names, occupations, schools, and locations.

He wasn’t the only person who shared that sentiment. By 2004, the social network blossomed to more than 75 million users. TimeVanity Fair, and Fortune sang its praises. Google tried to buy it for $30 million. Within two years, a previously-nameless programmer cracked the literal code that sparked the social media boom.

If you’re like most people (including myself), you almost certainly thought this was the story of Mark Zuckerberg and Facebook. But Facebook didn’t launch until 2004. The company we’re talking about is Friendster and the programmer’s name is Jonathan Abrams—two names you’ve probably never heard of.

There were dozens of Friendster rip-offs in the early 2000s, one of which was Facebook. There was Google’s version, Okurt, along with MySpace which made an early splash. But none of these networks could run stride-for-stride with Facebook. What was a college drop-out (Zuckerberg) doing that even Google couldn’t figure out?

As Tim Wu points out in his book The Attention Merchants, Facebook’s ascent had nothing to do with better technology. They just identified their competitors’ weak points and reverse-engineered a better product.

“Facebook was actually providing not something new but an enhanced representation of an existing social reality,” says Wu. “The networks, so-called, were there already: Facebook simply made them visible, graphically manifest, and easier to keep track of.”

Facebook’s steal-and-improve strategy is far from an anomaly. From tech to art to music and everything in between, survival (and success) is typically more dependent on marginal improvements than massive innovations.

We think of Uber as the first ridesharing app, but it was actually a polished version of a failed startup called Taxi Magic. We think of the iPhone as the first smartphone, even though IBM made its own phone with a touchscreen and email functionality a decade prior. Rather than trying to predict what people wanted, Uber, Apple, Facebook waited for the dust to settle before throwing their hats in the ring.

The steal-and-improve strategy extends into entertainment as well. “Hotline Bling,” “Old Town Road,” “Sicko Mode,” and countless other hits incorporate samples from decades past. The best movies and shows replicate the same narrative DNA of plays written 2,000 years ago. Even this article you’re reading is stitched together by ideas from other writers.

For all the glamor associated with being first to market, history is quick to remind us that it’s almost always better to be second—or fifth, or fiftieth. Whatever. Just make it better.

Ironically, when you ask yourself, “What can I steal and improve?” instead of “What can I create?” you end up creating better stuff. Let someone else do the legwork, spend the money, and make the mistakes. Then swoop in and fill in the gaps.

But don’t take my word for it. David Bowie: “The only art I’ll ever study is stuff that I can steal from.”

Have you read these five books to base your life on? Get the list, plus seven strategies I stole from legendary marketers to promote your work.


How to Deal With an Insane Boss, as Told by a Stalin Survivor

During World War II, Soviet dictator Joseph Stalin called a meeting with several music composers who were tasked with writing a new national anthem. Stalin, crippled by insecurity, relied on intimidation to get his way. He green-lit millions of executions during his reign, which was no secret to the composers gathered in this meeting. One slip-up would land these guys in a labor camp, where they would be literally worked to death.

Upon hearing the new anthem, Stalin unleashed a fit of rage. He hated it. Like clockwork, he cornered the weakest person in the room—a novice composer—and hurled a slew of threats and insults. The young man stumbled over his words as his life flashed before his eyes. Stalin could smell the fear on the guy’s breath.

Just as the situation began to spiral out of control, another composer, Dmitry Shostakovich, diffused the situation. He casually mentioned that blaming the young, inexperienced composer for a lackluster job wouldn’t solve any problems. Shostakovich proceeded to ask Stalin what he thought the best process to compose the new anthem might be. Always eager to prove his expertise (despite his ignorance), Stalin took the bait, ultimately sparing the composers’ lives.

How, in the face of one of the deadliest dictators in the history of human civilization, did Shostakovich keep his cool? Most importantly, he understood that Stalin thrived off of fear. Trying to plead and rationalize with him would be as effective as smoothing water with a flatiron.

Instead, he used a mother-like approach, seeing Stalin for the chubby, insecure child that he was. He brought him down to the level of a flawed human being rather than accepting the macho persona that intimidated millions of others. In this moment, Stalin wasn’t a deadly dictator, but a toddler throwing a temper tantrum.

This ability to set emotions aside and see through outward appearances is as valuable in our own social encounters today as it was during Stalin’s reign. Take a powerful, overbearing boss for example—someone who seems impossible to please. Your gut reaction might be to place him on a pedestal to win his approval. That’s the trap he wants you to fall into. In order to get the upper hand, you’ll want to take a page out of Shostakovich’s book and shatter that pedestal. Demythologize him; he’s a child who never grew up; he’s desperate for attention and probably has more insecurities than you do. By empathizing and seeing him through a new lens, you’re less likely to play into the drama like the first musician did with Stalin.

“The key to staying unintimidated is to convince yourself that the person you’re facing is a mere mortal, no different from you—which is in fact the truth,” says Robert Greene, author of The Laws of Human Nature. “See the person, not the myth. Imagine him or her as a child, as someone riddled with insecurities. Cutting the other person down to size will help you to keep your mental balance.”

Your boss—or anyone who seems intimidating—probably has more money, more control, more freedom than you. But don’t let that distract you from the fact that they don’t have it all figured out. Nobody does. Once you see people as they truly are instead of some arbitrary character you’ve made up, things get a lot easier.

As the cultural critic Neil Postman wrote, “It is certainly true that he who has the power to define is our master, but it is also true that he who holds in mind an alternative definition can never quite be his slave.”

Have you read these five books to base your life on? Get the list, plus seven strategies I stole from legendary marketers to promote your work.


The 5 Most Fascinating Books I Read in 2019

dominic vaiana

No need for a verbose introduction here. There’s enough of that from recipe bloggers and English majors. Here are the five best books I read in 2019.

5. Hate, Inc.: Why Today’s Media Makes Us Despise One Another by Matt Taibbi

Most people assume that the news exists to educate or at least inform them. But as Taibbi points out, the news is a consumer product designed to keep you angry, confused, and tuned in for as many hours as possible so networks can rack up advertising revenue. 

Taibbi, a Rolling Stone journalist, is as informative as Noam Chomsky and as entertaining as the New Yorker. And before you pull the liberal bias card, notice that Rachel Maddow occupies just as much of the cover as Sean Hannity. Translation: nobody is safe from Taibbi’s critique. 

Favorite quote:

Mass media makes the act of watching more important than words. It can take rage and defiance, and in a snap turn it into obedience and submission. Listening in anger to your favorite political program, you will act like a person who is shaking a fist at power, when in fact you’ve been neutralized as an independent threat, reduced to a prop in a show.

4. Stillness Is the Key by Ryan Holiday

I make it a rule for myself to read anything this guy writes. That rule has yet to disappoint.

While most authors, influencers, and public figures are peddling “life hacks” to help you do more, Holiday offers a different, time-tested strategy: slow down. Drawing from the lives of monks, politicians, and athletes, this book is a plea to hit pause and a guide to achieving the headspace that’s so rare in our get-it-yesterday culture.

(If you read Hate Inc. and Stillness, you’ll never want to watch the news again. Seriously.)

Favorite quote:

If you believe there is ever some point where you will feel like you’ve ‘made it,’ when you’ll finally be good, you are in for an unpleasant surprise. Or worse, a sort of Sisyphean torture where just as that feeling appears to be within reach, the goal is moved just a little bit farther up the mountain.

3. Skin in the Game: Hidden Asymmetries in Daily Life by Nassim Nicholas Taleb

Should you trust a surgeon who doesn’t look like a surgeon? How do corporations led by Ivy League grads go bankrupt? Why do we prefer complex solutions over simple ones? 

These are the type of questions Taleb wrestles with. Bouncing between politics, finance, personal responsibility, and academia, Taleb argues that our society is plagued by people who talk without ever putting their neck on the line. In other words, they don’t have skin in the game. If you want to minimize your risk of failure and embarrassment, Taleb says, follow the Silver Rule: Do not do unto others as you would not have them do unto you

Favorite quote: 

If your private life conflicts with your intellectual opinion, it cancels your intellectual ideas, not your private life.

2. The Perennial Philosophy by Aldous Huxley

After 16 years of Catholic school, you start to feel like that way is the only way. Obviously this isn’t the case, which is the central theme of this book. Huxley draws on dozens of religions to highlight how they all converge at a central point. Belief, faith, whatever you want to call it is more akin to art than science–there are plural truths. Regardless of where you’re at on the spectrum, this book is a monumentally important step to escaping your bubble and becoming culturally literate.

Favorite quote:

To suppose that people can be saved by studying and giving assent to formulas is like supposing that one can get to Timbuctoo by poring over a map of Africa.

1. The Laws of Human Nature by Robert Greene

From the man who wrote the second-most requested book in prison libraries comes a treatise on the unconscious and conscious biases that define the human condition. Greene’s thesis isn’t exactly uplifting: We are deeply flawed creatures that frequently act against our own self interest. However, his vivid storytelling and brutally honest analyses give you a sense of control over your thoughts and behaviors as opposed to the millions of people who are slaves to themselves. 

This book clocks in at 600+ pages, but it’s worth its weight in gold.

Favorite quote:

We see people not as they are, but as they appear to us.


If you want more book recommendations like these, I send one out each month via my newsletter. If you’re new to the list, you’ll get some bonus material as well.

Forget Role Models. You Need an Anti-Model. Just ask LeBron James.

“When I was a kid, I asked my mom one time, ‘Where’s dad?’ She shut that shit down early. [She said], ‘I got this. It’s just me and you.’”

This is LeBron James on his HBO talk show, The Shop, candidly recounting his experience growing up without a father. Born to a sophomore in high school, the odds were stacked against him. But as we see today, LeBron James didn’t just survive despite the absence of his father—he thrived because of the purpose it instilled in him.

“My whole life I grew up resenting my father. Everything was like, ‘Fuck pops, he left me. Why would he do that to my mom?’ My mom was sixteen years old when she had me. And I was like, if I ever met him, we’re going to blows,” James explained. “As I got older and as I became more of an adult, I started to realize and think to myself, ‘Damn, what was he going through?’ Was it things that he couldn’t control? He’s the reason I am the father I am today. Because I always wanted to set an example and have the father figure in [my kids’] lives so they never had that resentment.”

Instead of succumbing to the anger he harbored against his father, LeBron bent it into a tool that he could wield to become the father, husband, and person his dad never was. It was by reflecting upon the man he didn’t want to become that unlocked his potential.

He’s onto something.

From preschool to the professional world, we are urged to find role models. We write essays, read books, and learn about the men and women who “made it” in hopes that we can replicate their success—even a fraction of it. We are prodded with questions like: Who do you admire? Who is your mentor? Who do you want to become?

These are valid, but they fail to address the question that’s equally important, yet often ignored: Who do you not want to be? In other words, who is your anti-model?

Most of us mock or shame the losers, idiots, and crooks we see in the media or in our own lives. We are disgusted by the millionaire who neglects his kids, the politician whose life is plagued by scandals, the neighbor having an affair. We are told to turn a blind eye towards these people, but it’s actually studying them closely that gives us the advantage.

“Fools learn from experience,” said Otto von Bismarck. “I prefer to learn from the experience of others.”

If you can’t define who you don’t want to be, your odds of becoming that person soar upward. Having an anti-model solves this problem. Find someone whose life is a train wreck. In LeBron’s case, it was his (absent) father. Maybe it’s your tyrannical boss, an insane relative, or a crooked public figure. Examine the decisions they’ve made, the people they associate with, how they live, how they’ve fucked up. No need to waste your energy casting judgement—just counter-imitate them. Notice how they give you an instruction manual for living a miserable life.

Do the inverse.

In philosophy this is called Via Negativa—the Negative Way—which aims to describe a concept by defining what it is not, rather than what it is. It’s a recipe for what to avoid, which tends to work better in domains that are opaque and open-ended, i.e. what you should do with your life.

Growing up (and still today), I never had someone who fit neatly into the definition of “role model.” There are plenty of people whom I respect and ask for advice. But replicate their lives? Absolutely not.

When you idolize people, you set yourself up for disappointment. You become so entrenched in who they are that you lose track of who you are. Role models, left unchecked, blunt idiosyncrasies.

Not to mention, what if this person you adore turns out to be a complete monster? Prior to 2009, Tiger Woods was the ultimate role model for young golfers across the world. Then they found out he was having sex with strangers in pancake houses and church parking lots.

To set the record straight, this isn’t an argument against role models—it’s an argument that anti-models can add as much (if not more) value to your life. We squander so much precious time defining what success looks like. The problem is, that definition of “success” fluctuates daily—sometimes hourly.

Better to define failure and let success define itself.

Have you read these five books to base your life on? Get the list, plus seven strategies I stole from legendary marketers to promote your work.


Post-Game Interviews Aren’t Boring—They’re Brilliant

Post-game interviews are arguably the most insufferable aspect of professional sports, if not the entire entertainment industry.

I remember sitting in front of the TV as a kid, eagerly waiting to obtain some slice of genius from my beloved NBA and NFL superstars, only to have my hopes dashed by their strings of empty clichés that my own volunteer coaches could have mustered.

Even as an adult, I feel thwarted every time an athlete or coach stares blankly into Erin Andrews’ microphone and regurgitates the same platitudes about focusing on the fundamentals, sharing credit with teammates, taking it one game at a time, whatever.

If you’re unfamiliar with the robotic banality of post-game interviews, here’s a snippet of Tom Brady’s press conference after winning his sixth Super Bowl (the most of any player in NFL history)

Reporter: Tom, that was a remarkable win. Can you walk us through what happened?

Brady: Yeah, we grinded it out. It was tough. [The Rams] made every play tough tonight. I give them credit. It was an incredible win.

Reporter: When you came out to the field for your last drive, what was going through your mind?

Brady: You gotta make yards…We moved the ball decent…and just a great win for our team.

And here’s All-NBA forward Kawhi Leonard after winning the 2019 Finals MVP:

Reporter: How special was it to receive the MVP award from Bill Russell?

Leonard: Obviously I didn’t come out in the series trying to win it. It was a whole group that played collectively. I just kept striving and pushing…but everybody deserves it.

Reporter: What went through your mind when Steph Curry had that look? Did you think the game could be in [the Warrior’s] hands?

Leonard: I wasn’t too worried about it…I just was focused on the rebound.

This stuff is comically boring—always has been and always will be.

Each week, TV networks pay overdressed sportscasters to shove microphones in athletes’ faces and implore them to give the audience a glimpse into their world. And each week, we sit in front of the TV and think that maybe Russell Wilson, Jimmy Butler, or Mike Trout will actually open up this time and tell us what it’s really like to be physically superior to 99.99% of people on Earth.

But without fail, they let us let down. Wilson, Butler, and Trout jog back to the locker room while we roll our eyes at their lifeless sound bites. What gives? Are elite athletes really as inarticulate and stale as they sound? Are they holding something back? A combination of the two?

Anybody who has examined an NFL playbook or considered the precision required to exchange a baton while running 24 miles per hour understands that athletes aren’t brain dead—they can’t afford to be. Otherwise they would implode.

Most of us assume that highlight-reel athletic feats require superhuman concentration and physical mastery. How else could Howie Kendrick make contact with a 90-mph fastball—much less hit a grand slam—to win the NLDS with 56,000 people jeering at him?

But what elite athletes possess (and convey in post-game interviews) isn’t “focus.” In fact, they’re not even thinking at all. The real answer to that timeworn question—“What was going through your head?”—is depressingly simple:

Nothing at all.

It’s this mind-numbing simplicity that enables athletes to be wholly present without being conscious of the stakes. For true professionals, performance is reduced to muscle memory and pure instinct. They don’t just sound like robots, they are robots (at least during the game).

When Tom Brady says, “We moved the ball” or when Kawhi Leonard says, “I was just focused on the rebound,” they’re not saying it ironically—they actually mean it.

“For top athletes, clichés present themselves not as trite but simply true,” said essayist David Foster Wallace. “Or perhaps not even as declarative expressions…but as simple imperatives that are either useful or not.”

When you take up a new sport or hobby, you always get the basic instructions: “Keep your eye on the ball!” Then you grow older and feel pressure to get an edge, so you pick up obscure drills or rituals, which inevitably trip you up and overcomplicate the craft. But after you get over this semi-pro barrier, it all becomes simple again: It really is about keeping your eye on the ball.

To be a professional is to be ruthlessly simple—and this isn’t limited to the purview of professional sports.

Jerry Seinfeld doesn’t come up with new material every day because of some cool bio-hack—he sits at a desk and writes on a yellow notepad until he thinks of something funny. Yo-Yo Ma didn’t become a master cellist by following a secret formula—he has logged more than 60,000 hours sitting at the cello throughout his life.

This is what separates professionals from amateurs: to understand that the Super Bowl is just another game; that starting a business is just identifying a gap in the market and closing it; that writing a book is just sitting at the keyboard every day until you finish the last chapter.

Once you grasp this, you’ll never see a post-game interview the same way ever again.

Have you read these five books to base your life on? Get the list, plus seven strategies I stole from legendary marketers to promote your work.


My First Two Jobs “Weren’t Hiring”—Here’s How I Got In Anyway

dominic vaiana anteambulo

In ancient Rome, members of the social elite would often appoint an anteambulo—which translates to “one who clears the path.” An anteambulo was typically a writer or performer who was talented but lacked resources to move upward—they were First Century starving artists.

This anteambulo would literally walk in front of his patron, clearing both the metaphorical and physical paths: communicating messages, finding opportunities, eliminating inefficiencies, and making the patron’s life easier. In exchange, the anteambulo would receive food, housing, protection, and—if he played his cards right—a career.

Aside from being born into the upper crust of society, becoming an anteambulo was arguably the most efficient way to ascend the social hierarchy. You traded favors for favors. The person who cleared the path could ultimately determine his own destination.

Fast forward 2,000 years and the concept of an anteambulo is, tragically, little more than a relic of ancient history. But the underlying principle may be the most valuable piece of career advice out there. It allows you to eschew traditional hiring processes and essentially hack the system.

Let me explain.

After finishing an internship with a marketing agency during my senior year in college, I told my boss I wanted to parlay my gig into a full-time career. There was only one problem: They weren’t hiring. I was tempted to start cold calling random agencies who were actively seeking entry-level employees, but I had recently read about the anteambulo concept in Ryan Holiday’s Ego Is the Enemy and decided to give it a shot.

What could I do to make these guys’ lives easier?

How could I turn this into a favor for them instead of a favor for me?

What could I bring to the table to make their agency better?

With those questions in mind, I typed a (lengthy) “reverse offer letter” to the senior partners outlining what I wanted to do for them:

I will write a book with you.

I will manage the agency’s blog and newsletter.

I have fresh creative ideas that I want to share with your clients.

And much more.

I didn’t request a salary nor a title—I just wanted to work. After a few email exchanges, I had a job offer and started the following month. Holiday was right: If you make yourself useful enough, it doesn’t matter who’s hiring.

15 months later, I needed a change of pace. Through a chance encounter, I met a VP from NoCoast Originals and mentioned I was open to new opportunities. She thought I’d mesh well the team, but of course, they didn’t have any open positions.

I tried the same strategy, but this time the wheels got stuck in the mud. After two reverse offer letters and four meetings, nothing had transpired. So instead of bringing ideas to the table, I brought something better: a client.

Through that VP, I met a public figure who wanted to write a book, but didn’t have the time nor the writing chops to go at it alone. I told him I’d love to collaborate with him to write it and brought the idea to the partners at NoCoast. I explained that the project could open new doors for their agency, and most importantly, pay for my salary.

Done.

I’m not saying this process is an exact science. It might not work in every industry. But what do you have to lose by hustling? The worst case scenario is being ghosted via email; the best case is a new job. Everyone is waiting to be swept off their feet—they just don’t know it.

A few additional notes on this anteambulo stuff:

1. The best jobs aren’t on Indeed or LinkedIn. You’ll be happier if you carve out your own niche, especially if you like to create stuff.

2. If you have to wait for an assignment to be given to you, you’re doing something wrong.

3. Your job is to make your boss’s life easier, not make your own life harder.

4. It’s not about optics (working long hours, playing martyr)—it’s about efficiency and execution.

5. Don’t expect to take credit for your work. In fact, letting important people take credit for your ideas is half the battle.

Oh, and most importantly, don’t expect any of this to happen overnight. So, stay on the radar, but don’t be a creep. Send an interesting email every couple of weeks. Ask smart questions. Work for free.

Remember, “Create a job that doesn’t exist for someone we don’t know” is about as close to the bottom of a busy person’s to-do list as you can get. Act accordingly.

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