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Lately, I’ve been thinking about the importance of actually choosing a book. When you or I choose a book to read, we choose to preserve it and allow it into our minds and worldviews. We also choose to be open to change, in some way. When Sherry Turkle asks Jacques Lacan why he didn’t explain himself more simply, she recalls him saying, “You don’t try to speed-read. The idea is to have an experience that changes you.” So it is with books.


When I choose books and the authors that write them, in a sense, I’m voting with my time and money. And so are you! So thank you for reading this, and for trusting and allowing me to suggest books to you. It’s a responsibility I take seriously. Here are this month’s Best of Books recommendations:


Dear Girls by Ali Wong


In her stand-up comedy, Ali Wong’s excellent performance, timing, and delivery gets the spotlight over her storytelling. Fortunately, her memoir provides a chance for her writing to shine. I caught myself laughing out loud at some moments, none of which I’ve excerpted—for the passages to make an impact, you need to read them along with the rest of the stories. Wong happens to make the stories funny, which is the craft she’s honed through years; but they all demand to be taken more seriously than simply as a joke. When I was deciding whether to buy this book or not, I noticed that reviewers tended to focus on the more sensational parts—sleeping with homeless people, holding in a fart during yoga class, bombing in front of Eddie Murphy, etc.—but that doesn’t do this book justice. I found Wong’s memoir to have plenty of very practical advice, particularly in the stand-up section, that applies well to all sorts of endeavours. 




On miscarriages: It helps so much to know you're not the only one who has had one, because then you realize it's not your fault.


On control: It was the first lesson in having kids: You cannot control anything. Whatever dreams you had of how things were going to go down, they ain't gonna come true. Kiss goodbye your fantasy of delivering your baby in a rain forest, or in a Buddhist temple surrounded by frangipani flowers, and get ready to shit your pants emotionally and physically.


On suffering: At first I felt guilty about taking [Vicodin] while breastfeeding but then I talked to my pharmacist friend Aileen, who had just had a C-section with twins a month earlier. Her response to my questions about the safety of it was: "You have suffered enough." That became my mantra for motherhood from there on out. 


You have suffered enough.


If you can make it easier, make it easier, and don't feel guilty about it.


On stand-up comedy: The act of doing stand-up itself isn't that hard. Getting onstage in front of strangers, writing and performing jokes, and even bombing, is the easy part. It's everything else surrounding it that's so difficult. The road. Traveling. Spending hours on the Internet to book the cheapest flights possible. Eating a boatload of fried food with ranch dressing because there are no other options. Fending off creepy-ass men. Steering clear of your idols and funny colleagues who you've learned tend to sexually harass women.


On practice: When you're starting out, stage time is so valuable. Even now, I don't get paid for a lot of sets I do locally at these bar shows, where the audience hasn't bought tickets and I'm there to test out my latest joke about my butthole. They're just there to have drinks and I'm there to workshop new material.


On failure: Nobody is great at stand-up comedy right away and it’s important to have room to experiment, find your voice and, most important, to fail.


On stand-up comedy classes: A comic once told me to never take a stand-up comedy class because it's hacky. And it is hacky. If you disregard my advice and pursue stand-up, please at least do not ever take one of those courses. Doing the open-mic circuit is real stand-up comedy class. 


On stand-up comedy 2: But I think all you need to be a good stand-up is to have a unique point of view, be funny, and enjoy bombing in front of strangers. You really do have to learn to like bombing a lot. Even now, when the audience is too good, sometimes I think, I didn’t deserve that. You'll know you're a stand-up when, after a spectacular bomb, you don't feel like you want to quit, but instead the opposite: You want to go up again. 


The Empathy Diaries by Sherry Turkle


Sherry Turkle is one of the most prominent researchers on how technology is shaping the people that use it—namely, every single one of us. You may know her from her very popular TED talk. For most people, that would be the pinnacle, but it’s actually probably one of the less interesting accomplishments. In The Empathy Diaries, Turkle makes the case for humans being more empathetic with each other. This was a really great read, and Turkle’s book itself is a representation of the vulnerability she tries to make the case for. I really appreciated her self-awareness, and willingness to share the more difficult parts of the journey. It’s simultaneously a landscape of post-WW2 New York City, a portrait of growing up with a modest upbringing, and working hard to make the most of one’s gift. I really liked this book and plan to get started again on Life on the Screen (which I’d picked up and put down a year ago) and Turkle’s other books, very soon.




On understanding: So technologists become invested in the promise of electronic medical records and forget how important it is for physicians to make eye contact with patients during their meetings. … These days, our technology treats us as though we were objects and we get in the habit of objectifying one another as bits of data, profiles viewed. But only shared vulnerability and human empathy allow us to truly understand one another.


On immigrant sacrifices: I learned about how hurt my grandfather was that one of his brothers had changed his name from Bonowitz to Banner. My grandfather loved his brother. He didn’t want to judge, but he didn't approve. Mostly, he was pained at what it took to get ahead in America.


On political reality: This was Bonowitz political reality: The people who had saved the Jews did not like the Jews. So to survive, Jews had to get people to do the right thing regardless of their private feelings. We had to change laws before we changed hearts and minds.


On learning to correspond: In Rockaway, when I was eight and recuperating from appendicitis, my grandmother took my desire to understand how the world beyond Brooklyn worked and turned it into a game. I was given the task of planning a family trip. She found a book of states' chambers of commerce and departments of tourism. She taught me how to compose a formal letter of inquiry and provided stationery, envelopes, and stamps. I began to write away for itineraries, maps, and hotel information all around the country. The status of this trip always lived between reality and dream. None of the trips I planned actually took place. But all of that writing away for information and receiving piles of mail in return expanded my world. The post office was mine. People all across the United States were willing to tell me things I wanted to know.


On objects: I was armed with a powerful idea: To be good at a job, you had to love the objects associated with that job. I found this idea in a book that Milton had brought home from work, How to Choose the Right Job for You. The book explained that if you love hammers, wood, and tools, think about being a carpenter. If you enjoy tidying things up in files, think about office work. In other words, imagine yourself with the objects of your craft. My mother relaxed by walking through the fur and evening gown departments at downtown department stores. It was natural that she should think about being a nightclub singer. I loved fountain pens and beautifully bound notebooks. I could see myself as a writer, like Jo March in Little Women.


On shared sadness: I think of this moment often because it had to be the first time I was given a clue that my mother was ill, and I chose to not pay attention. Or rather, I paid close attention and did what the grown-ups signaled they wanted from me: to pretend not to notice what was happening. I knew I could receive no comfort, because no one would admit that anything sad had happened. It was a very particular loneliness: knowing that people around you were also sad but that you couldn’t be sad together.


On not understanding: When I consider elementary school, I think that permission to not understand was its greatest gift. Later in life, I would come to a rough patch, say, in French social theory, and if I was understanding something but not much, I would say to myself: This is only the beginning. This isn’t your last chance to read Derrida. Keep at it.


On insecurity: The most insecure people often seem like the most obnoxious ones.


On etiquette and shame: For years afterward, I tried to learn a way of being that would make me at ease in the world without blaming myself for what I didn’t know along the way. How to hold a fork. How to write an academic paper. How to order in a restaurant. My second goal was to find a way for my family to participate without feeling diminished.


Hustle Harder, Hustle Smarter by Curtis “50 Cent” Jackson


Curtis Jackson (and an anonymous ghostwriter) wrote one of my favorite books of last year. I was re-reading it this month, and realized I needed to post the long overdue recommendation for Hustle Harder, Hustle Smarter. It’s an iteration of The 50th Law, which I recommended in April 2020, co-written by Jackson and Robert Greene, updated with new stories and firsthand business experiences. I really loved the spirit of this book; ruthless, independent, optimistic—the virtues of capitalism at its finest. It is still getting me through challenging times and experiences. While Jackson occasionally dunks on his rivals, he also reveals some of his own personal challenges—namely growing up without a father and how that led to his own difficulty with family and being vulnerable. I included more excerpts than usual for this one, because I got a lot of it.


On rehab after getting shot: I decided that if I stayed in that house and didn't follow my rehab plan, then I had already lost. When fear interrupts your routine, or makes you rethink it in any way, it's gotten its hooks deep in you and will hold you back forever. "Cowards die many times before their deaths," wrote Shakespeare. "The valiant never taste of death but once." I wasn't trying to go out like a coward.


On true passion: Someone with a strong passion stance, on the other hand, will really dig in. Get their feet planted and shoulders squared up. So no matter how hard the world pushes back, or how much negativity gets thrown their way, they ain't budging an inch. That's the sort of energy I want to work with. The type of people I'm willing to put my money behind. A strong passion stance is what separates the hustlers who win from the people who always seem stuck in place…. I'm looking for the same kind of passion in the people I work with. Maybe not putting your life on the line, but at least being willing to consider it. Might sound dramatic, but that level of commitment is often what it takes.


On a flexible vision: It's also important to accept that your vision can—no, make that should—change. 


On optimism: That has to be your constant attitude on the street. "I'll get it back on the next one."


On losing everything: I'm sitting at my desk in my office as I write this. Looking out my window I can see a guy on the sidewalk selling peanuts. If I lost everything tomorrow, I'm not jumping out this window. Nope, the next day I'd be out there on the opposite corner setting up my own peanut stand. Let's call it 50's Nuts. Maybe to make my cart stand out, I'd introduce chocolate-covered nuts and some cherry-coated ones, too. Because I'm offering more selection than my competition, I'd create a little buzz on my block. Then I'd figure out a way to use that buzz to get 50’s Nuts over to Yankee Stadium and sell them in the stands. And after that, open up a restaurant in the concourse. And then another one back in Manhattan. And before you know it, I've got a chain. And with that, I'm back in the game, baby!


On confusion: Whenever you feel confused about a situation, it's imperative that you find a way to turn the volume down and reconnect with what you're truly feeling. For me, working out definitely helps quiet that noise. At some point in the workout, the physical exertion I'm putting myself through seems to wash all the BS out of my system. I can literally feel myself breathing the distractions out of my mind. 


On starting the $150m Vitamin Water deal: Once I'd sold Chris on my vision, we hatched a plan. During a commercial for my Adidas sneakers that showed me working out in a boxing gym, we snuck in a shot of me taking a sip of Vitamin Water.


It was barely half a second, but it was enough. A friend of Chris's who worked at Glaceau saw the spot and reached out to see if I'd be interested in an endorsement deal. They had just developed a new product called Formula 50 (because it contained 50 percent of the RDA of seven vitamins and minerals). Who better to sell Formula 50 than me?


On negotiating: Whatever his reasons, Sha clearly let things get personal. This is the other huge mistake people make when they start negotiating. They take offense at what's being offered because they feel it's an unfair representation of what they've put in.


Please understand this: negotiations are not personal. 


On negotiating 2: You should always fight for your worth, but never take offense that you have to fight in the first place. When you do that, you're moving off of emotion. It might not be fair, but to get what you want, you can only move off of strategy. Anything less will leave you hustling backward.


On income not reflecting value: Even as I was hustlin' on the set, in the writers' room, and on the promo runs, I never for a second thought my true value was only $17,000 an episode. That was just the number I had to agree on to jump-start the process. My true value was going to lie in executive-producing and starring in a hit TV show that would birth multiple spin-offs — and multiple revenue streams. Everything I was doing in Season 1 was meant to put me in a better position to make that happen.


On execution: It seems like an obvious enough approach, but we spend a lot of time waiting for permission to do shit instead of just making it happen. We fall into the trap of thinking the so-called gatekeepers—a boss, an executive, an agent, a critic—have to unlock that door ahead for us when, more often than not, it's already wide open, just waiting for us to walk through.



I read most of the late James P. Carse’s Finite and Infinite Games. The main idea was about how two types of people play two different types of games in this world—a finite game in which the goal is to win, and an infinite game in which the goal is to keep playing. I came across it from Alex Danco’s blog post. Danco works at Shopify, which I have a hunch is also where Tobi Lutke found it (and loved it!). It was very philosophical, the reading equivalent of an abstract painting, to say the least. I can’t say I found it as practical as the three main suggestions, but it’s worth mentioning.  


My podcast with Chris Do at The Futur came out this month. So did this piece in Fast Company, in which I covered visual artist Big Mike’s ways of being creative during his lunch hour


I write a new note card almost every day, and covered how I organized my notes at my blog. If you’re interested in daily creative process, I wrote more about them here. I also wrote about the creative process, and my very early experiments in collaborative writing with OpenAI’s language model GPT-3.



I hope that some of these passages unlock the hidden doors of your mind. Maybe some will serve as catalysts for change. And remember, they’re signposts. It’s up to you whether you want to apply them or not. Reply to this and let me know which quotes or books resonate with you, what you think of the newsletter, and if there’s anything I can support you with.




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