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.

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.

If you’re reading this, you’re probably familiar with the concept of “inbox zero:” the process of maintaining zero (or as few as possible) emails in your inbox. For most people, inbox zero is an exercise in futility. It inevitably devolves into a game of digital whack-a-mole instead of a strategy for mental clarity.

There is, however, another zero-based productivity strategy that’s easier to apply—and far more important.

I call it: Calendar Zero.

Last month, I pointed out that most social “obligations” aren’t actually obligations. I’m talking about happy hours, networking events, parties, meetings without agendas, etc. None of these are inherently bad. But you can only jam your calendar with so much nonsense before your day is dictated entirely by other people.

Let’s be clear: The point of Calendar Zero isn’t to live some utopian 4-Hour Workweek life where you sleep until noon. The point is to create breathing room for the few vital activities that actually move the needle in your life: deep work, exercise, reading, family time. If you’re accepting every calendar invite and attending social functions during the week, that’s not going to happen. Something’s gotta give.

This dilemma isn’t limited to the purview of iPhone-carrying business people in the 21^st century. The Stoic philosopher Seneca talks about it in a passage which is equally relevant today as it was 2,000 years ago.

“No person hands out their money, but to how many do each of us hand out our lives? We’re tight-fisted with property and money, yet think too little of wasting time, the one thing about which we should all be the toughest misers.”

On second thought, that passage is more relevant than it was 2,000 years ago. We balk at splitting an Uber or lending money to a friend. But when it comes to our time, we’re lax as can be, squandering it on pointless events, phone calls, and meetings. Ironically, time is the only asset we can’t recoup.

Ryan Holiday, an outspoken calendar purger and author of the forthcoming book Stillness Is the Key echoes this sentiment:

“I want two or three things on [my calendar] at most. The rest is for me. The rest is not allowed to be scheduled. And if it is scheduled, it better be because I’m getting paid or I really, really wanted to do it. Everything else is for suckers.”

This would seem to be common sense: I won’t let somebody else set my agenda. But that enthusiasm gets zapped as soon as you see those invitations. FOMO sets in. You have to preserve your social ties. So you meet for drinks, take the meeting, wander aimlessly. After all, declining these invitations could burn bridges.

Or so we think.

In my experience, rejecting invitations actually engenders more respect than pimping out your schedule just so you can stay relevant. That’s not your ticket to act like a self-important asshole. But it should empower you to carve out large blocks of uninterrupted, unscheduled time to use as you please.

I wouldn’t be able to write, read, exercise, and sleep for eight hours if I wasn’t ruthless about what makes its way onto my calendar. That doesn’t make me a martyr, that’s just the tradeoff I’m willing to make. People wonder why their life isn’t in order while they sit with a drink in their hand at 7 p.m. on a Tuesday.

So, get acquainted with the “reject” button on your calendar. Get comfortable with telling people, “No thanks, I can’t today.”

After all, an inability to say no doesn’t make you busy. It makes you a 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.

Over the past year of living in the real world (I refuse to say “adulting” in an un-ironic sense), I’ve tried to do more observing and thinking instead of speaking. Along the way, I jotted down ideas and advice that I either learned the hard way or was taught by someone a lot smarter than me. Here are 16 that really hit home.

– Your boss doesn’t care about effort. Your boss cares about execution. If you think working 60+ hours a week will earn you a raise, you will be sorely disappointed. Your job is to make their life easier, not make your own life harder.

– There is an inverse relationship between how much of your life you document on social media and how much you can truly enjoy life.

– Most social “obligations” aren’t actually obligations. You don’t need to attend happy hour, date people, or go to “networking” events. Time is your most valuable asset—spend it diligently.

– If you’re tempted to make an impulsive purchase, ask yourself three questions: How will you feel about this in 10 minutes? How will you feel about this in 10 weeks? How will you feel about this in 10 years? That last one will save you thousands of dollars.

– Meetings over lunch or coffee are generally less productive than speaking with someone face-to-face. At restaurants, you’re hungry, distracted, required to spend money, and the waiter will inevitably disrupt your conversation. Sit down at a table with two chairs first thing in the morning and say what needs to be said.

– Being able to draw from a wide swath of insights and experiences is more advantageous than specializing in a narrow field. For more on that, read this book.

– You can pretty easily judge the character of someone by watching how they treat people who can’t do any favors for them.

– Alcohol tastes better when you drink it as a reward rather than a coping mechanism.

– Talking about your salary is almost universally a poor decision—that goes for bragging about making a lot or complaining about being broke. Both are nauseating. It’s better to keep people guessing, anyway.

– Learn to be okay with spending time alone (without an internet connection). If that makes you squirm, you have work to do.

– Figure out who the important people are in your scene (hint it’s not as many as you think). Don’t offend them. Make them look good. Don’t demand credit for the work you do. Repeat.

– Always have a side project. It keeps your mind active, your skills sharp, and your opportunities open.

– People are loyal to political parties only to the extent that it’s convenient for them or confirms their beliefs. A hardline conservative says state-funded programs are a communist disease until he needs social services for his daughter’s disability. A “progressive” preaches the value of tolerance until he’s triggered by the slightest off-hand remark or tweet. Important issues are complicated. Treat them accordingly.

– People make time for what (and who) they value. If your health and education are important to you, you’ll find time to exercise and read books. If you care about someone, you’ll find time to see them.

– Before you speak, ask yourself: Do I have something valuable to say, or am I just talking to be heard? When you’re just starting off, it’s usually the latter.

– If you play by the rules long enough, it becomes your game.

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.

I wasn’t sure if he wanted a pat on the back or a pity party.

A friend of mine recently landed a big-time tech job in Silicon Valley, a gig that most ambitious 20-somethings would drool over. But no less than a week after starting, he took to Instagram to announce that he’d been working past midnight every day.

Ah yes, the classic dark/empty office picture with “1:28 AM” stamped over it to subtly remind the peasants that they don’t #grind as hard as you. As if it’s a badge of honor to squander your waking hours so the boss can kick back in his Ferrari.

But wait, you say, the grind never stops – Gary Vee told me so.

Actually, the grind should stop. Every day.

The idea that chipping away at your free time can boost productivity is just that: an idea. There’s a brick wall waiting for your brain after you cross the 9-hour threshold of deep work. Your eyes drift. Your writing becomes sloppy and passive. You make mistakes that most 4^th graders wouldn’t.

But the try-hards on #TeamNoSleep don’t care. For them, quantity is more impressive than quality. Work turns into a competition: Oh you worked until 9 last night? Well I’ve been up since 4 a.m. and haven’t even eaten today. 

I don’t know how or why it happened, but we created work porn—and we’re obsessed with it. We broadcast and gawk over the superficialities of work instead of appreciating its value. We think a 60-hour work week at 70% effort is sexier than 35 hours at 100%. We glorify the all-nighter, the hustler who cranks out the project after slamming six Red Bulls at 4 a.m. We don’t hear about the guy who completed the same project over the span of a month, even though he didn’t look like a zombie the morning of the presentation.

Trading free time for more work has nothing to do with passion or work ethic. If anything, it’s a mask for insecurity. If you’re skeptical, take it from Ryan Holiday, one of the world’s most successful young writers:

“If you’re working all the time—that is, if you don’t get to leave the office until midnight and got there at 5 a.m.—you’re doing something wrong. You’re either working for an idiot who is going to burn you out, or you’re the idiot and you haven’t figured out the short cuts.”

That, or you just like to play martyr.

And if you cheer the workaholics on, you’re part of the problem.

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 rabbit runs faster than the fox, because the rabbit is running for his life while the fox is only running for his dinner.”

That’s the gist of the Red Queen hypothesis: adapt or die. Slow rabbits get eaten, increasing the number of fast rabbits in the gene pool. A fox must be quick to catch a rabbit, but only quick enough to stay well fed. You can think of it like an evolutionary arms race in which predators constantly apply pressure, forcing their prey into fitness.

Bottom line: the animal whose life is at stake has more incentive than the animal whose dinner is at stake.

It’s tough to come up with a better analogy to describe the professional world. On a micro level, it’s the new kid in the office proving he’s worth a paycheck pitted against the lifer who knows he’ll get a paycheck whether he shows up a nine or noon. On a macro level, it’s the disruptive startup pitted against the stodgy conglomerate (think Netflix vs. Blockbuster.)

At first, the pecking order always seems irreversible. But the proverbial rabbits realize something that many proverbial foxes don’t: once the rabbit trains itself to run just fast enough to escape the fox, the game is over. The foxes starve and become extinct while the rabbits repopulate.

Of course, nobody cares about the rabbits until the fox can no longer keep up. But that’s the point. If you’re the rabbit (i.e. under 30 and don’t have a corner office), bide your time. Assess the terrain. Figure out how shit works and who the important people are (hint: there aren’t many of them.)

While your “superiors” are resting on their laurels, you’re calculating, plotting, observing, reading—remember, if you play by the rules long enough, it becomes your game.

It’s the startup versus the household name; the trailblazer versus the incumbent; the wunderkind versus the starch-shirted conformist. Will all the rabbits escape the foxes? Doubtful. But it’s worth it to go down trying.

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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.

I do not know what Victor Ramirez did to warrant solitary confinement. Frankly, I do not care. When I decided to participate in Lifelines to Solitary, a nonprofit prison correspondence program, my intention wasn’t to preoccupy myself with legal deliberations nor take perverse pleasure in someone else’s pain. Rather, I had questions that only someone like Victor could answer:

How does someone living through hell on earth manage to put one foot in front of the other every day? How, when you are locked inside a windowless concrete box for 23 hours a day, is it possible to find solace? How is it possible to live a life of meaning when you’ve been severed from life as you know it? How is any of this possible when we, with our endless luxuries, oftentimes can’t seem to bear life’s blows? How is any of this possible?

The bleak reality is that for many in solitary confinement, it is not possible. The psychological damage of extended solitude and sensory deprivation combined with untreated mental illness and physical and mental abuse forms a toxic brew that compels thousands of people in solitary confinement to take their own lives. The U.S. Department of Justice reported that between 2001 and 2014, suicide was the leading cause of unnatural death in federal prisons. Suicide accounts for seven percent of all deaths in prison, roughly four times greater than the portion of suicides outside of prison.

Based on what Victor told me, people in solitary confinement may spend up to three days a week, sometimes longer, without leaving their cells. Neglect is common. Inmates may be denied basic supplies such as soap and food. They are allowed to shower once every two days, though temperatures soar to above 100 degrees in the summer. Inmates with mental health issues are frequently mocked, harassed, and abused by prison staff. Many injure themselves, ironically, for temporary relief in the form of a trip to a different cell. “They do whatever they want with us.”

The question remains: how does one endure such a nightmare?

Through Victor’s broken English, I began to see that his life in solitude reflected that of another Viktor: the author and Holocaust survivor Viktor Frankl who understood that everything can be taken from a man besides the last of human freedoms: the decision not to submit to what Frankl called “the powers which threaten to rob you of your very self.” Plainly, Victor Martinez and Viktor Frankl both refused to fold into what the system wanted them to.

All of us suffer to some degree. But it is how we accept this suffering, how we bear our proverbial crosses, that determines whether we walk the path of dignity or the path of death. There are times when Victor’s prison goes on full lockdown. Through no fault of his own, he loses his one hour of time outside his cell. “I’ve gotten used to [it],” he told me. “It doesn’t bother me. I shower out of my sink, do exercises, and draw.”

Rather than allowing these circumstances to cripple his mind, as many of us would, he doubles down on the seemingly insignificant possessions that nobody can take from him: fitness, art, books. For Victor, living a life in which he wants less makes him infinitely richer than we who have everything and desire more.

I asked Victor about faith. “I truly don’t follow no religion, but I respect them all.” He admires Buddhism for its emphasis on self-discipline and modesty—and it shows. While I am, relatively speaking, many times richer than Victor, I don’t experience a fraction of the joy that he told me he receives from an hour outside, a meal, or a letter in the mail. What are immense treasures for him are trivialities, or even inconveniences, for you and me. He recognizes, as the Stoic philosopher Seneca did 2,000 years ago, that “It is not the man who has too little that is poor, but the man who craves more.”

Ralph Waldo Emerson once wrote that “Every man I meet is my master in some point, and in that I learn of him.” This perennial truth was validated through my exchanges with Victor. I have worked alongside millionaires, studied prominent thinkers, and received an education reserved for a privileged few—and yet, a man without a high school diploma was, in some vague sense, my teacher.

Victor Ramirez taught me that hope does not die when we are stripped of physical and mental possessions, but when we forget that life is independent of those possessions. He taught me that professed faith and religious rituals are useless without a life of faith, one in which we transcend race and creed to pursue and experience truth, beauty, and goodness. And most importantly, he taught me, as Nietzsche put succinctly, that “He who has a why to live for can bear almost any how.”

My correspondence with Victor ended abruptly for reasons unknown. In the last letter he wrote, he did not conclude with any complaints or grievances. Instead, he maintained the same stoic indifference that enabled him to endure his fate.

 “Take care of yourself,” he said. “And please forgive my spelling, it’s not the best.”

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Have you read these 5 books to base your life on?

Mastery of any craft is elusive, but mastery of writing may be the most elusive of all. There really is no point at which someone can say they’ve “mastered” writing – you can only creep infinitely closer to it. We can’t objectively measure or score language like we can in golf or chess. We only recognize great writing when we read it. And no matter how much praise or respect a writer may receive, he or she will always admit that their ideas never quite align perfectly with what ends up on paper (or on the screen.)

Such uncertainty drives many away from the pursuit of writing, but nobody can fully escape it. We’re not all journalists or authors, but we have emails to send, memos to write, and presentations to give. Fortunately, plenty of remarkable writers have shared (either directly or indirectly) their priceless insights which can help make this tough job a bit easier to bear.

Since I started writing for myself and on behalf of clients, I’ve set aside time each day to study legendary writers in hopes of capturing the essence of what separates their language from the clutter. There’s no point in keeping what I’ve learned to myself, so I decided to go through all the notes I have and condense them into what I’ve found to be the 11 most valuable lessons.

Here they are:

Read voraciously – Samuel Johnson 

Johnson said that “The greatest part of a writer’s time is spent in reading; a man will turn over half a library to make one book.” This lesson is not just reserved for authors, though. It applies to business proposals, job application essays, and blog posts. Whether we need factual evidence or stylistic influence, books lay the foundation for the written word. There’s no telling how many ideas and lessons there are to be discovered in books, even ones unrelated to what we write, that simply can’t be found on TV or in everyday life.

Have something to say – Arthur Schopenhauer

Schopenhauer once observed that there are two types of writers: those who write because they have something to say and those who write for the sake of writing.

If you ask a teacher how to become a better writer, they might suggest going to writer’s groups, contributing to a publication, getting an MFA, or just spending hours writing. But they never tell you to go do interesting things. This is what Schopenhauer is talking about: no amount of literary skill can conceal a lack of knowledge or experience.

Example: a grammatically flawed but passionate firsthand account of
being detained overseas is likely more captivating than a “professional”
journalist’s coverage of the same story. Experience provides us with a perspective and a unique voice. It doesn’t just give us words; it gives us something to say.

Rewrite somebody else’s work…word for word – Denne Bart Petitclerc

Denne Bart Petitclerc was abandoned by his father at the age of five, after which his mother sent Denne and his older sister to an orphanage in San Jose, California. Semi-illiterate, Denne was known to have transcribed Ernest Hemingway’s short stories word for word in order to get a feel for his style. A stroke of luck even allowed Petitclerc to meet his childhood idol. Petitclerc would go on to work for several newspapers and eventually became a Korean War correspondent for the Santa Rosa Press Democrat as well as a screenwriter for several TV series and films.

Bottom line: If an illiterate orphan can learn to write well, so can you and I. Don’t worry initially about imitating anther writer. After enough practice your own voice will emerge.

Understand the whole before addressing the particular – Robert Greene

Greene has earned a reputation as perhaps the most prolific researcher of any author alive, a skill that’s exemplified in his books. For Greene, writing is the easy part of being an author. The challenge is wrapping his head around a raw, complex idea. So often we start writing without a game plan – before we know it we’re bogged down by insignificant details on the first page and end up calling it quits after 150 words. Readers can tell when a writer has constantly bounced back and forth between research and writing: sentences are jumbled, there’s no sense of coherence. But organizing all facts and research materials before setting out to write eliminates confusion as to how a piece should be structured. 

Eliminate distractions – Cal Newport

With a Ph.D. in computer science and five published books, Cal Newport understands that writing demands long periods of uninterrupted focus. In his book, Deep Work, he argues that the skill of intense concentration will increase in value as our culture becomes more and more distracted. This doesn’t mean we have to go off to some remote location in order to be productive – unplugging will usually suffice.

“Start with training your cognitive fitness before diving into your first big writing project just like you’d train your cardiovascular fitness before trying to run a marathon,” says Newport. “In other words, National Novel Writing Month would be a lot more successful if it was preceded by National Don’t Use Social Media Month.”

Cut off the fat – William Zinsser

“Don’t say you were a bit confused and sort of tired. Be confused and tired,” says Zinsser. “Good writing is lean and confident…every little qualifier whittles away some fraction of the reader’s trust.” This advice might seem petty or insignificant, but straightforwardness has a profound effect on a reader. These qualifiers that Zinsser mentions are like training wheels for writing: we use them because we’re unsure whether our language is valid enough to stand on its own. But once we ditch them they’re gone forever. 

The first draft of everything is shit – Ernest Hemingway

Trying to write a polished piece from the get-go is a recipe for frustration. Hemingway even rewrote the ending of A Farewell to Arms 39 times before he was satisfied. There’s no need to get flustered when a masterpiece doesn’t pour forth from your fingertips like Hollywood portrays. It’s reassuring to know that even the most elite writers looked at their work and knew it sucked; however, what separates them from the the amateurs is the willingness to sit back down and get it right.

Seek out negative feedback – Tim Ferriss

Ferriss says that the first question he asks when receiving feedback on his books is “What should I cut?” He’s known for ruthlessly cutting anything that’s not essential both from his own work and the work he edits, a lesson we can all learn from. It’s tough hearing someone tell you those sentences you painfully strung together just aren’t that good, but this ego check is exactly what we need to mature as writers. It’s been said that when someone tells you something is wrong with your writing, they’re usually right. But if they tell you how to fix it, they’re usually wrong. Think quantity before your give yourself the quality cop-out. You can always cut.    

If you’re stuck, write a letter – Anne Lamott

Even after extensive research and multiple drafts, there are times when putting one word after another can seem unmanageable. This, Lamott says, is when we should convey what we want to communicate in the form of a letter to someone important to us. By explaining what you want to tell them in an informal way, it can provide the raw material needed to create a more coherent, polished piece of writing. Another alternative is to call someone to talk on the phone about the topic. You’ve never heard of anyone getting “talker’s block.” Spill your guts out, then turn it into an outline. Let it evolve from there.

Exercise strenuously – Ryan Holiday

For centuries, writers have relied on physical activity to unglue their minds. It’s like the figurative reset button on the creative process – once you hit a wall, intense exercise brings in a new wave of ideas. Holiday goes for a 6-8-mile run every single day after he finishes his morning writing. But he runs for something other than just the  physical benefits – “It makes me better at my job,” he says. Holiday even recalls rushing home during a run 2013 because he came up with the introduction to his book, The Obstacle is the Way, in the middle of it. All the thoughts that once seemed clumped together seem to sort themselves out after exercise. That’s because there’s nothing else to dilute them. It’s you versus yourself, which can be frightening until we realize it’s exactly what we need to take our productivity to the next level.

“Faire et se taire” Translation: Shut up and get on with it – Gustave Flaubert

At the end of the day, all the advice, workshops, and books in the world can’t save us. You know what to do next. 

A Few Bonus Tips

Use a thesaurus

It’s easy to fall into a routine of repeating the same words over and over. Aside from reading lots of books, a thesaurus is the best tool to revitalize your vocabulary. Apple even has a great thesaurus app that comes built in to every Mac computer. Just don’t go overboard. Rule of thumb: if you have to look up the definition of the word you think sounds cool, you probably shouldn’t use it.

Keep a commonplace book

When you find a good quote, idea, or piece of advice, write it down. You never know when you might need to reference it later. This simplifies the research process, especially if you’re a pen- and-paper type of person. I write my notes on 3×5 index cards and organize them by category. 

Read your work aloud

Mistakes are often easier to hear than see. This exercise can also save you from sounding pretentious or artificial. Learn to trust your ear.

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Here are 5 books to base your life on, plus 7 strategies I stole from marketing geniuses to promote your work.

If you follow stand-up comedy, you’ve probably heard horror stories about famous comics bombing sets early in their careers. It’s as if catastrophic embarrassment is a rite of passage in order to earn the “funny” badge. Patton Oswalt was heckled and called a faggot. Omid Djalili fell off the stage. Jerry Seinfeld blanked and stood in silence for 30 seconds.

Given the endless list of first-time flops, coupled with the fact that cajoling strangers into laughter is painfully difficult, nobody in the right mind would voluntarily do stand-up comedy unless somebody lined their pockets. And yet, being the compulsive doer and hyper-ambitious person that I am, I took the plunge.

There was a big problem, though: I hadn’t given a solo speech since Communications 101 during my freshman year of college. Even then, I was shaky.

I’m a prototypical introvert: I prefer solitude over company; I enjoy talking, but not around crowds; I have ideas; but I express them better in writing than aloud. Frankly, I’m the opposite of the “entertainer” archetype: a gregarious, chatty, think-on-your-feet kind of person. But there was no turning back.

After embarking on a long string of nights that involved dozens of rewrites and copious amounts of caffeine, I had my set memorized. It was eight minutes worth of opportunities to forget lines and make a jackass of myself, but I figured that shame would be nothing compared to the regret of not trying.

During the hours leading up to the set, I knew there wasn’t anything I could do that would make a difference. I already put in the work, so I didn’t bother cramming. When I walked on stage, I zoned out (in a good way), like what happens to an athlete in the middle of a competition. I generated some laughter (presumably with me, not at me) which put me at ease—other than that, everything was a blur. More than anything, I was preoccupied with whatever my next line was.

Eight minutes later, I handed over the mic without getting heckled or falling off the stage. I was baffled as to how I managed to survive that set without a panic attack or even a slight slip-up that would’ve thrown my entire set off kilter. So, the next day I did some research as to why people willingly abandon their comfort zones, and more importantly, how they hold themselves together. That’s when I came across Free Trait Theory, originally proposed by Harvard psychologist Brian Little.

Free Trait Theory states that our personalities are sort of like rubber bands: they can stretch, permitting us to act “out of character,” but only to a certain extent before they break. We are born and culturally endowed with personality traits like introversion, but we’re capable of putting on different masks when we’re involved with projects that “we consider meaningful.”

Like telling jokes about the social tension of an Uber ride and the monotonous living hell of grocery store checkout lines.

“Introverts are capable of acting like extroverts for the sake of work they consider important…or anything they value highly,” says Little.

Now it made sense: I didn’t survive the stand-up set because I can memorize material or because I forced myself to become an extravert for eight minutes—I survived because I valued the creative challenge. Daring to write, memorize, and perform a comedy set was important enough that I was able to override my pre-set temperament and “stretch” my personality to its limits.

An important side note: while the performing aspect of comedy is geared towards extraverts, the art of the material itself is a task for those who keep to themselves. Comedy demands intense attention to social nuances that most people don’t pick up on, brutal self-criticism to admit your first drafts are shitty, and perfectionism to select the right word at the right time using the right tone.

Let’s set the record straight: I’m not ditching my career to go on tour as a comic. But if I do opt to stretch my personality again, I know it better be for something important—because I don’t want that metaphorical rubber band to snap.

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Keith Ferrazzi mustered up the chutzpah to approach the former chairman of Goldman Sachs and ask him for a favor. This was no mid-level executive; this was a head honcho at one of the most powerful institutions in the history of civilization.

But Ferrazzi’s favor would be far different than the ones we’re accustomed to asking.

“How long is your to-do list right now?” Ferrazzi asked.

“Well,” the chairman replied, “There are about 20 important things I need to be working on right now.”

Ferrazzi didn’t miss a beat: “Would you do me the biggest favor in the world and pick one thing on that list that you think I could add any value to, and please give me an assignment?”

“I’ll tell you what,” said the chairman, “Stick around for my next meeting and I’ll have plenty of work you can do for me.”

Now, with a foot in the door, Ferrazzi had the ear of one of the most powerful guys in the world, all because of a benign question.

Whether you think Goldman Sachs is a bastion of evil or doing “God’s work” is irrelevant. Take a step back and consider the situation: this chairman had pockets deeper than the Grand Canyon and a rolodex of the world’s power elite in his pocket. Why would he waste his time with some eager beaver with a mysterious agenda?

To answer this question, we need to put ourselves in the shoes of the chairman. He’s busy. He’s stressed. He’s accountable to thousands of employees and shareholders. Does he want to take some up-and-comer under his wing? No. He needs to get shit done. And that’s why Ferrazzi got his foot in the door instead of the thousands of schmucks who had approached the chairman over the years. He understood that clearing the path ultimately determines its direction.

Most of us live in a silo of our own imaginations, thoughts, and desires—we assume that people are selfless when in reality they’re in the same boat as us: they need help, just different kinds of help. We need an opportunity, they need a memo written, an interview transcribed, a story to reference, and so on. It’s our job to create symmetry between their needs and ours.

Of course, most people don’t realize this (or refuse to acknowledge it), which leads to absurd questions like:

Would you like to meet for coffee?

Do you have any internship/job opportunities?

Can I pick your brain?

Will you be my mentor?

Contrast those questions with the technique Ferrazzi used:

Is there any work I can take off your hands?

Could I handle an assignment you don’t have time for?

The common denominator with the latter is that it appeals to self-interest rather than mercy. There are no strings attached to these offers, no quid pro quo implications.

But wait, you say, I need an internship, a job, or [insert formalized relationship]—why would I offer to do some one-off project with no contract or payment structure?

This is a toxic thought process, and it’s exactly why the internet is rife with cynics and sympathizers claiming there are no opportunities. Someone is supposed to come knocking on our door and serve our dream job on a silver platter.

Yeah, right.

Almost every work opportunity I’ve developed started with bringing something to the table: a connection, a relief valve for grunt work, a useful quote. Did they all pan out the way I wanted? Not by a long shot. But I learned something valuable: you have to plant as many seeds as you can, because you never know which one is going to shoot up out of the dirt and blossom.

No matter how skilled or ambitious you are, you’ll always find yourself in the position of approaching people who are higher up on the totem pole. Whether you need them to fund your startup, advise your nonprofit, or just offer advice, it’s your ability to tactfully ask for help that will determine how far you get—so you might as well do it right.

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