How to Network at an Unstructured Happy Hour

Many years ago, as a 15 year old, I snuck into a tech and business event in San Francisco. My basketball-ready height masked my age at events like these. (Or if it didn’t, no one ever bothered to vocalize their suspicions.) I had my schtick down: When I arrived at 5pm at the downtown venue, I registered at the front desk, grabbed a name badge, and carefully dodged the various registrants who were standing around tall tables and munching on carrots and bell peppers, pretending to be enthralled in conversation.

Once I found my way to the bathroom, I entered a stall, closed the door, and sat on the toilet. And then I waited, staring straight ahead at the beige bathroom stall door. Nature did not call but that wasn’t the point. The clock was ticking — that was the point. After about 15 minutes the networking happy hour ended, the main stage speaker took the microphone, and it was time for me to symbolically flush the non-soiled toilet and re-join the gathering to watch the speaker. At the conclusion of the formal programming, I bee-lined my way out of the hotel before the networking started up again.

I was a young entrepreneur; I had read the various business books that extolled the virtues of networking. But converting knowledge into action in this area required having answers to questions that made my palms sweaty:

Doesn’t everyone already know each other? What if the other person finds me boring? Would I ask for their contact information afterwards and if so, would that be awkward? What are you supposed to talk about?

Fast forward 21 years later and I now work in an industry (venture capital) that has me hosting and attending these sorts of previously-terrifying gatherings all the time. And I don’t mind it. (You can learn almost anything!)

Now, despite my current comfort with unstructured networking hours, I far prefer more structured gatherings. Assigned seating. Assigned speaking roles. Small groups. I tend to avoid unstructured events.

But…if you find yourself attending an unstructured networking cocktail hour, here are some tips:

Barge into existing conversations. It may seem easier to approach someone who isn’t speaking to anyone. But actually, a person who’s staring down at their phone may actually be on their phone for good reason. Instead: join a group of two already in conversation. Odds are you are not interrupting two best friends talking about confidential topics.

When you approach and turn a twosome into a threesome, just use a simple opening line: “Hey how’s it going? I’m Ben” and extend your hand for a handshake. (Until such time as we ban the stupid norm of handshakes and replace with the Japanese bow…) Another terrific thing to say, per Nick Gray, right as you join a larger conversation: “Please continue.” This avoids the awkward round of introductions among people who’ve already introduced themselves to each other. As a late joiner, you can just vibe in when the time is right.

As you’re talking to someone, don’t scan the horizon looking for someone else more interesting. Give the person you’re talking to your full attention. It’s dreadful to be on the receiving end of someone whose eyes are darting around. Let’s all treat others the way we want to be treated: give the person you’re talking to at a cocktail party your full attention. Take comfort in the knowledge that you know how to extract yourself from a conversation if necessary.

Don’t get trapped in one conversation the whole time. A common fail mode in a cocktail party setting is being unable to extract yourself in order to go talk to someone else. It can be intimidating to break off from your conversation partner and wade into the unknown until you’re find a new mate.

If you’re in a two-person conversation (you and the other person), there are two basic/obvious options: “I’m going to get a drink, it was really nice talking to you” and “I’m going to head to the restroom, it was really nice talking to you.” The advanced option? Don’t make up an excuse. Just say, “It was great talking to you. I’m sure I’ll see you around.” Put out your hand, and then wander off. And pray you don’t bump into the person a minute later before having paired off again.

If you’re in a three (or more) person conversation, it’s easier. Say: “Excuse me for one sec” and then step out and walk decisively away without waiting for a formal reply, and let the two others carry on.

If you see someone standing on their own, awkwardly, while you are in conversation with someone, invite them into your conversation. Literally gesture to the person, waving them into the circle, with the phrase, “Come join us.” If you want to be especially generous, quickly bring the new person up to speed on the conversation: “We were just talking about this book Jane read on the history of Morocco…” And if you’re feeling particularly assertive, try to keep the conversation going versus reverting into self-introductions from everyone standing in the circle – which will inevitably be repetitive for most of the people standing there.

Now… when you’re in the conversation itself:

Don’t saturate a conversation with overexplaining and drawn-out stories. Smart people are sometimes tempted to unload all their special knowledge and insight and clever explanations into a conversation. They flood the zone.

Speaking too much is the obvious sin. Don’t do that. Don’t speak for more than 60-90 seconds straight. This is true in almost any meeting context but especially true at cocktail parties or happy hours.

One version of this sin is more subtle because it’s an activity that’s otherwise lauded by experts: storytelling! Stories are indeed a great way of making a point. At their best, nothing beats them. The issue is, as Sasha Chapin has pointed out, storytelling in casual work conversation can also go horribly wrong. A story that isn’t tight quickly becomes a worse situation than boring non-story delivery of facts.

Drawn-out, painful stories are torturous in any social interaction. But it’s especially problematic in cocktail parties where there’s faster cadence expected.

Bottom Line: Try to avoid unstructured cocktail parties when you can, but if you must, consider these techniques to make your time more worthwhile. 1) Barge into existing conversations and say “Please continue” 2) Don’t scan the horizon while talking to the person, 3) Don’t get trapped in one convo, excuse yourself to “get a drink” and go find others to mingle with 4) Invite lonely stragglers into your conversation, 5) Don’t saturate cocktail conversation with overexplaining and drawn-out stories.

And if you’re hosting your own cocktail party, Nick’s book will show you how. If you want deeper frameworks on how to build your network, The Startup of You shows how.

Team Player vs. Me Player

On a collaborative team, a great employee should be a team player: helping their colleagues hit *their* individual priorities. Do favors for them, offer feedback when asked, build social capital. Whatever it takes to help the company succeed.

As Fred Kofman says, “Your job is not your job. Your job is to help the overall team/company win.” Fred’s diagnosis of much organizational dysfunction is that employees become too absorbed by their individual project list and lose sight of the common goal. His canonical example is that of a defender on a soccer team who thinks his job is to defend (not let the other team score goals) while his actual goal should be for his team to win the game.

Yet a star employee must *also* stay focused on nailing their own individual projects and KPIs. It’s possible to be too much of a team player — to the detriment of your own performance, which ultimately impacts the org and the workflows you’re responsible for. In this circumstance, you don’t set enough boundaries and you get “used” by your co-workers.

Senior, savvy operators tend to have good intuition on how to balance their time between “my KPIs” vs. “others’ KPIs”. When I’ve hired more senior people, their savviness at navigating the favor-trading dynamics that circulate inside every team — their understanding that they need to be a team player and also they need to nail their own task list and not get taken advantage of — sets them apart from less experienced folks.

It’s one of the things you pay for when hiring someone senior onto a team.

Impressions from a Longer Stay in Tokyo (2023)

I was fortunate to spend bunch of time working from Tokyo recently. After visiting three times prior for 1-2 week trips, spending extended time there deepened my understanding and appreciation for Japan. Here are a wide range of impressions and lessons from this fall:

Tokyo remains a world-class city — as clean, functional, and fun as ever. From my first visit in 2006 to today, Tokyo remains dynamic and vast and mysterious. The world’s largest city has always been a fun spot for adventurous tourists; these days, for those interested in longer stints of visiting or living, Google Maps + Google Translate + various on-the-ground evolutions makes Tokyo significantly more accessible to non-Japanese speaking expats than 20 years ago.

Now’s a good time go visit. It’s comparatively cheap. Go spend more time in Japan. Go spend time in Tokyo and just walk around the neighborhoods. Go spend some nights in ryokans and at onsens and in small towns and in the other larger cities. Go, go, go.

The Japanese smooth out the rough edges, in a quest for perfection. So much has been written about the Japanese aesthetic, quality of service, cleanliness. From the explicit exposition of someone like Noah Smith who called Tokyo the “world’s great city right now,” to the lyrical moods of Murakami (my various book reviews of his epic novels), or the poetic reflections of Pico Iyer, whose book A Beginner’s Guide to Japan I’ll quote at times in this post.

So let me share just one anecdote on the overall topic of Japanese perfection. On one of my first days in our private office in Tokyo, some light jazz music suddenly began playing out of a speaker built into the ceiling. I couldn’t figure out how or why the music started. 30 mins later, the music hadn’t stopped, and I grew concerned that what was supposed to be a quiet, private office in a coworking space actually was subject to some building-wide music system steered by a jazz aficionado building manager. (Hey, it could have been a worse genre of background music.)

I pulled out Google Translate and typed English sentences: “There is jazz music playing in my office. I did not turn it on. Why is it playing? Can you turn it off?” Google Translate spit out out the Japanese version and, clutching my iPhone, I swung open the door to my office to stomp to the front desk and inquire.

As it happens, two men were already standing outside my office in official, erect poses. What luck. I clicked “Play” in Google Translate to ask my pre-loaded question in Japanese. They micro head bowed as they listened — the micro bow where your head drops ever so slightly in rapid succession: the most common type of bow in Japan.

Then they spoke back into my phone: “Deep apologies,” Google’s translation’s said back to me. “The jazz music means the fire alarm system is working. We are conducting a test of the fire alarms in the building. The jazz music plays if the alarm is working. Thank you very much. Thank you very much.” They proceeded to deeply bow and walked off. Only then did I notice they were wearing fire department helmets.

It had never occurred to me that a fire alarm building test could be anything other than bone-tinglingly loud.

It turns out that the Japanese have figured out ways to smooth the jagged edges of modern living. Yes, there’s a dark side to smoothing out the edges in a question for perfection. Here’s Pico Iyer: “Perfection, in fact, is part of what makes Japan wonderfully welcoming to foreigners, and unyieldingly inhospitable, deep down.” But all visitors and most long-term visitors never get “deep down” — they just enjoy the wonderful surface. They exist in the mid-depth warm bath of perfection.

Singaporeans follow the rules because of laws. Japanese do so because of culture. In my observations of Singapore, I pointed out the cleanliness and orderliness of the society — and the frequent public signage reminding locals of the fines or caning that result from littering, excessive noise, taking photos up the skirts of women on the subway, or engaging in other uncouth conduct. In Japan, it’s as clean and orderly as Singapore, but there are no warning signs. I’m not even sure there are well understood laws around littering and noise. Yet the population upholds the norms perfectly and voluntarily. (There’s a neighborhood clean-up competition in Tokyo where people walk around and see who can pick up the most trash.)

How rules/norms are enforced illustrates a key difference between Japan and Singapore: Singapore is a 58 year old country with various immigrants from across Asia who cohere into a single society. Japan is a thousands-year-old culture that’s pure Japanese from top to bottom.

No jaywalking even if there are no cars — extrapolate this norm society-wide. There’s no jaywalking across the street on a red light. No matter if there are no cars to be seen and the sidewalk is a narrow distance. Wait until the hand turns green. Always follow the rules. This leads to some frustrating moments: Want to move a table around in a private room at a restaurant? Want to ask for someone at a hotel or serviced apartment to make an exception to some arcane building rule that doesn’t matter? Good luck.

When you follow the rules, you fit in. Here’s Iyer on fitting in: “Japanese couples on honeymoon traditionally plan matching outfits for every hour of their trip. Even girls on a Sunday shopping spree often sport the same hairstyles, false eyelashes and white boots. Fashion becomes less about standing out than fitting in, at least within the micro-group of which you are a part.”

Japan is at once futuristic and stuck in the past. There’s a lot that’s quite analog in Japan. Starting with the emphasis on paper. Sign a lease for an apartment and you’ll have a million pieces of paper to sign. In that shuffle, one important piece of paper in the stack explains how to open your physical mailbox — to receive yet more paper. When you rent an office, one of the key features that gets explained? How to open your mailbox to receive print mail — to supplement your home mailbox. When you hire a tour guide, the first thing she does upon greeting you? Hand you 7 different pieces of paper explaining the different aspects of the upcoming tour. (The one place you won’t find paper — in public bathrooms, for drying your hand, because of the prominence of air blowers, which are the worst. )

On the other hand, Japan has a reputation for being a blade runner, robot friendly, futuristic country, too. I didn’t see too many robots. The most telling futuristic attribute of Japan today may be the invisible macro stuff: low birthrate and low religiosity, for example. Among the visible are its efficient mega cities. Tokyo and Osaka, with their small densely packed apartments and constant redevelopment, portends our increasingly urban future as we seek more energy efficient ways of living.

The reels that go viral on Instagram promote the wacky side of Japanese culture and there’s certainly some of that. These aspects of Japan feel neither forward looking nor backwards looking but rather an artifact of its singular, isolated culture that stands apart from the harmonized globalized soup of developed countries.

In our residential building in Tokyo, for example, there was a daydreaming competition in which several dozen people sat out in our courtyard and competed for who could daydream the longest without falling asleep. Local reality TV shows are truly bizarre and involve many similar types of “competitions.” Harajuku also offers an otter cafe (sit with real live otters).

And the weirdness may be a result of an inclination of Japanese people to retreat within versus engage with a broader, normalizing sphere. The Japanese have separate words for the self inside the home and the one that’s out on the streets. Here’s Iyer: “Nowhere else I’ve been, in fact, are individuals so disengaged from the political domain… they turn their backs on the public sphere, and make fantastic worlds out of their passions, counter-societies out of their hobbies.”

Will globally relevant startups be born in Japan? Unclear, with many reasons to be optimistic or pessimistic. The knock on Japan has long been its risk adverse, salaryman culture which stymies the freewheeling individualistic rebel who might otherwise aspire to be the next Steve Jobs. It has, indeed, been awhile since Japan birthed new innovative companies. The Panasonics and Sonys of the world are old. Rakuten is a more recent hit but there’s aren’t many.

Is there reason to be optimistic that startups could blossom in Japan? Based on my conversations and casual poking around on the ground, I’d say it’s decidedly unclear. On the positives:

– Japan’s highly skilled workforce appeals to companies seeking non-China options in this moment — it might lead Japan to be a natural deep tech manufacturing partner to Western allies. I could see semiconductor, deep tech, nuclear energy, and related startups flourishing in the next couple decades in Japan.

– A novel reason for optimism I heard from my friend Alex Rampell at a flashy a16z event in Tokyo this fall: if you can change the culture to be more risk seeking and entrepreneurial, you can change the entire culture all at once. It’s the silver living of a more “collective”, homogenous mentality: change could happen quickly and comprehensively if and when it happens at all.

– The government wants a thousand startups to flourish — a Japan business federation, with the endorsement of the ministry of economy, wants to see “100 unicorns by 2027”. Lots of governments try to stimulate the startup economy so this is not unique but helpful as a baseline. I suspect the government will pump considerable capital into venture funds and startups in the coming years.

– Finally, Tokyo benefits from Hong Kong’s decline in terms of attracting expats in search of a good, first-world base for doing work across Asia. Tokyo benefits not as much as Singapore in this respect but it’s the second biggest beneficiary. To some, Taipei is seen as too risky given China’s ambitions, and Seoul the same given the possibility of war on the Korean peninsula. The quality of life in Tokyo is spectacular and the weather is better than Singapore and it’s easier than ever to not speak Japanese and still find your way around. It’s easy to see founders and VCs from around the world who seek an Asia outpost might set up shop in Tokyo.

A central reason for pessimism, at a human behavior level, seems to be the cultural impediments that are by now well written about. A preponderance of risk-adverse cultural pressures from age zero to 18 squelch a lot of entrepreneurial instincts and it doesn’t seem like that’s changing.

Framed differently, there remains a reverence for authority and age-based seniority hierarchy that suffocates the opportunity for some creative youth to flex their wings. Pico Iyer: “In terms of wealth distribution, Japan in 2017 was ‘the most equal’ society on the planet; many CEOs in Japan earn less than some of their employees do. But in terms of the gulf in public status, Japan is much more unequal than the United States. There’s no overturning the hierarchy.”

At a more macro level, Japan’s population decline is what it is — likely devastating to long term growth — and seemingly impossible to solve without a massive overhaul to how the country thinks about foreigners + immigration. (Interestingly, Korea’s demographics are worse than Japan’s.) Meanwhile, it’s still impossible for immigrants of any kind to achieve authentic “Japanese” status in the eyes of locals. One friend who’s third generation Japan native (i.e he was born and raised in Japan, as were his parents and grandparents) — but who’s ethnically Taiwanese — told me he’s not considered truly Japanese by any local companies or investors. (Here’s a counter argument about why to expect more immigration to Japan.)

All in all, I wouldn’t bet on a startup revolution the next 10 years in Japan. Beyond that, it’s possible but hard to say.

Quiet envelops public spaces. I was admonished a couple times, by a shop owner, for talking too loudly on my cell phone standing outside a restaurant on a public sidewalk. It turns out people don’t talk on their cell phone at all in public. Malls are generally quiet. Honking is rare. Talking loudly on the subway never happens. You find yourself constantly embarrassed at how loud American tourists are.

So safe, so clean: Little children wander around on their own in the big city. You’ll see kids who are barely five years old walking alone on big city streets of Tokyo — wearing cute little hats and rectangular box backpacks. As in Singapore, children can walk around and lick the streets if they want without a care in the world. Leave your wallet somewhere, and someone will try to return it. Etc. Walking big city streets packed with people and not caring at all about your safety — what a feeling.

Sumo is fun. Try the practice session more than the tournament. We went to both the official sumo tournament in Tokyo and to a practice stable off-season. While the live match was a fun atmosphere — thousands of people in a big stadium — it’s pretty slow going, with each match taking mere seconds and various ritualis between each match taking many minutes. So, advice for tourists: Don’t sweat trying to figure out how to go to an actual tournament, just check out a practice stable workout. You can find many such tours online and you’ll get up close and personal with the wrestlers and see much more real action, one after the other, with no ritualistic delays included.

One fascinating moment from visiting a sumo stable was when the sumo master said his own son, of sumo age, is staying in school and not wrestling. This guy goes around the country to recruit young talent to stop out of school and wrestle full time…but to his own son, he says, “Get an education.”

Restaurant and food observations. Japan is such an incredible food country. Some general observations on restaurants and eating generally, followed by food specific comments:

  • No matter how many people sit at a table, generally only one menu will be put down at the table, for the group to share. What could explain this cultural norm?
  • There’s a bag container next to each table to put your briefcase or bag or jacket. Without fail — a bag container. Is it to keep your individual bag clean? Or to keep the floor clean and tidy for the collective aesthetic?
  • Even in meals where they offer western cutlery, I encountered multiple instances of forks eschewed in favor of spoons. Spoons to eat a salad, for example. Always few knives — not as dramatic as in Singapore (which never offered knives) but still scarce.
  • Too many tourists stress about finding “the best” ramen place, the best sushi, the best whatever. Don’t do that. Just wander around and walking into random restaurants that seem popular with locals and using Google Translate to scan the menu. Rolling the dice works in Tokyo.
  • Many casual restaurants have table dividers to allow single patrons to eat alone without having to make eye contact with anyone else at a shared table. There’s something a bit eerie about a restaurant full of people — mostly businessmen — slurping their noodles in otherwise silence, head down, talking to nobody, even as they all share a table.

In terms of the food itself:

  • I found myself newly appreciative of soba noodles, and of the “soba soup” you eat at the end that’s the broth that cooked the soba.
  • I learned to love natto, the breakfast superfood that’s a sticky set of beans.
  • Eating miso soup nearly every day — at breakfast, as part of set menus for lunch and dinner — gets you in touch with all the different styles of miso: the carrots or mushrooms or what have you on the inside; the clear or darker broth.
  • Fruit is delicious and of a luxury variety, and what’s in season matters at lot. 7-11 carries the seasonal fruit.
  • Nigiri sushi was quite good but not dominant in the diet. What you notice relative to Western sushi is the quality of the rice — the texture of each individual bead of rice. Sashimi is far more popular than nigiri.
  • I hadn’t had high end tempura before until eating at this place. Quite a step up from the usual assorted tempura side dish served at U.S. sushi restaurants.
  • You notice the lack of bread in the diet.

It’s all Japanese people, no immigrants (other than in convenience stores). In Tokyo, it’s Japanese people wearing suits and ties walking into epic skyscrapers. And it’s Japanese people cleaning hotel rooms, bathrooms, and dishes in the back of the restaurant. Japanese people working on the construction sites. The only place I reliably saw immigrants? Convenience store workers. Speaking of which…

Convenience stories rock and the meals are very much ready to microwave. It’s well known that 7-Eleven, Lawson’s, Family Mart, and Mini Stop all rock. And not just because, say, the triangle rice squares with salmon inside — onigiri — are addictive. What’s less well known is that all the fresh food and ready-to-heat meals — which get freshly delivered 3x/day to convenience stores in Tokyo — contain clear microwavable re-heating instructions for how long to heat the food at different wattage levels. Everyone microwaves their food in plastic containers. You’d easily see 20 people in line for lunch at a 7-11. There are more than 50,000 convenience stores in Japan, including convenience stores just for the elderly. (Convenience Store Woman is a fun novel and a bestseller in Japan.)

They’re the best fans in baseball. All the fans singing the same song at the same time, for different players, is also quintessentially Japanese: united, orderly, respectful.

Rituals over philosophy. A gym has a million little rules about where you can wear your shoes, how you change, etc. And an onsen has even more. The Japanese love rules, processes, and — in a grander sense — rituals. Here’s Iyer: “When he gives lectures in the West, I heard the Dalai Lama say, the audience tunes out the minute he starts speaking about ritual and comes to life as soon as he speaks about philosophy; in Japan, the formula is reversed.”

And on religion: “Shinto has no texts or doctrines; Buddhism in Japan is so much a matter of rites and recitations that for centuries no one even bothered to translate many of its canonical texts into Japanese… “The most important things in our practice,” said the Zen teacher Shunryu Suzuki, “are our physical posture and our way of breathing. We are not concerned about a deep understanding of Buddhism.”

Other random observations and odds and ends:

  • Colors and culture: Taxis in Tokyo show a red light on the front of the car to indicate their availability, and a green light to show they’re full. Similarly, in Japan (and in China and Korea perhaps elsewhere), when a stock is going up, a news finance TV show will show it in red font, whereas when a stock is plunging in value, it’ll show in green. Red = good fortune and success.
  • As a train pulls into a metro stop in Tokyo, the station plays a distinct jingle so that passengers who aren’t paying visual attention can know it’s time to get off for their stop.
  • The Japanese seem obsessed with golf. Golf stores and ranges at every corner at in Tokyo, seemingly. At the gym, I saw a lot of people working with their trainers on golf-specific movements and strength exercises.
  • Shoehorns are everywhere next to sitting/shoes areas. Shoehorns are also included in business class amenity kits in Japanese airlines. Part and parcel with a shoes-off-inside culture, but it’s not something I’ve noticed elsewhere in the Asia (the shoehorns per capita, that is).
  • Summers in Tokyo are hot and sticky. The Japanese society isn’t built around A/C in the way that Singapore is. So the humidity can get to you in summer. One government initiative is called “Cool Biz” — encouraging folks to dress more casually in the summer to stay cool, and forego the suit and dress shirt look that 99% of businessmen wear to work year-round.
  • Single use plastics everywhere. Individual, single bananas wrapped in its own plastic. Individual rice crackers — perhaps 30-40 of them in a package, all individually plastic wrapped! Saltine crackers in packets of four, each wrapped in plastic. Apples wrapped in plastic. On and on.
  • Toranomon Hills is an up and coming and terrific neighborhood for expats. The Mori buildings are phenomenal. And the neighboring Shimbashi district is great.
  • Dogs treated are as children, adorned with luxury clothing and strollers.
  • Napping in public seems socially acceptable. I saw literally hundreds of different people nap in public during lunch hours or early afternoon siesta hours.
  • The dense web design in Japan is fascinating. Locals prefer what to to my eye are super overwhelming pages, stuffed with content from top to bottom.
  • Twitter is so popular here. Look over someone’s shoulder on the metro — and they’re on Twitter. Japan is the second most active market for Twitter after the U.S.
  • Japanese people seem very into stretching. There’s a great chain in Tokyo called Dr. Stretch in which Foot Locker-dressed trainer will stretch you out. Better than a massage! At the gym, many personal training sessions involved a trainer on the floor stretching out their client.
  • This nine minute history of Japan is amazing and remains one of the best history videos on YouTube.

Starting Over Again

From an email from the wonderful meditation teacher Phillip Moffitt, who has led two long silent retreats I’ve attended (and wrote about here), on his new year’s teaching:

The theme that I’m going to be exploring this year is the importance of starting where you are and then proceeding with a commitment to starting over again as many times as it takes. I view both of these character traits as both central to Theravada Buddhism and to practical empowerment on the street of life with all of its difficulties.

Non-Fiction Writers Who Throw Heat

Freddie deBoer, a brilliant prose stylist himself, in 2013 highlighted non-fiction essayists and bloggers who “throw heat.” His explanation for why he admires these writers, at the sentence level, contain some gems. Below I excerpt the best descriptions from deBoer on what he loves about other writers. The bolding is mine, not Freddie’s.

First, from Freddie, on the rarity of gorgeous prose styling in the realm of ideas-driven nonfiction writing:

Prose style is typically besides the point in professionally published nonfiction. When people say they want to be writers, in the sense that they want to write for websites and magazines rather than to write a novel, usually it means they want their ideas to be their currency, not their words. Attention to style and voice is more often found in creative writing than in the kind of writing that is referred to, unfortunately, as “content.”

But prose matters. Ideas matter too, but ideas are cheap and easy to find, and good prose certainly isn’t.

On Ta-Nehisi Coates:

I have complained, in the past, about the way that some of Coates’s fans have treated him as the Wise Black Sage. This is a political complaint, of course, one about white guilt and white condescension and the role they still play in defining the reputations of black writers. But it’s also a statement about the shame of reducing writing of this quality to empty piety. Nothing drains writing of its life more surely than treating it like church. Coates is a far more playful, more unpredictable writer than that, and a far more radical one

“And it’s that way that I want to understand his writing— appropriate to its mission, defined in its scope, and lit always by history and also by fire.”

On Choire Sicha:

The endless, stupid debate about irony has always been predicated on misunderstanding. Irony is a neutral quality; there is no such thing as too much or too little in the world. What people fear, and rightfully so, is the blank, unearned sarcasm that wallpapers the internet. The failure is not of attitude but of experience. 13 year old boys have no right to wax cynical, and so many of the people who operate in an idiom of showy disinterest have neither the experience nor the discrimination to have earned such a stance, which like all weapons must be distributed with discretion. Sicha, on the other hand, has earned his default posture, however you’d like to define that, through understanding: all cynicism comes first through kindness. Sicha wants enough for people to wish that they do their best but is wise enough to know that they won’t…

Weariness in writing is dangerous territory. Deployed clumsily, it risks degrading your work and insulting your audience. Take, for example, film critics who spend every review letting you know how terribly tiring they find it to write about movies. You can always just quit. But, in spite of that danger, when you find the genuine article— when you find someone whose exhaustion is not an affect, but a profound moral conviction— there’s something lovely about it. Sicha is a writer who knows not just how to write like a tired man, but why.

On Caity Weaver:

People say Caity Weaver is funny, and yeah— she’s hilarious. But what I more value in her writing is something that’s much rarer for someone who writes multiple pieces a day: the capacity to surprise. She is, as they say, effectively wild.

On Yasmin Nair:

Don’t get me wrong: Nair is not some “kids these days” scold. I like those best who articulate their beliefs with strength and resolve but without certitude. It’s a tricky line to walk, to remain alive to the limitations of your own understanding without descending into an affected, “look at how open minded I am” pose. To be corrigible, but not manipulable; to listen to advice but to follow your own. On a typical day I feel like doing both is impossible. When I read Nair I feel not only that it’s possible but that I should have already gotten it together to get there, a long while ago. There’s little more to ask of a political writer: when I read Yasmin Nair I whisper to myself, “Be smarter; be better.”

On Jacob Bacharach:

Plenty of people try to squeeze too much into their sentences, but Bacharach can stuff them in, then stretch his arms out so the sentences expand like an accordion, and like an accordion, they make sweet music. The man can pack a suitcase. Same with his references: many try what he tries, few succeed. If you’re going to weave obscure references through your writing, for god’s sakes, you better know what you’re doing. If you aren’t careful you can end up sounding like Dennis Miller trying out his new Toshiro Mifune joke on Dan Fouts when its 31-6 midway through the third quarter. I’ve never read a reference from Bacharach that didn’t precisely land, whether I got it or not; if not, the fault was me, not him. It’s like when someone mumbles and you apologize to them for not understanding.

On Edith Zimmerman:

Self-deprecation is a seductive quality, in writing and in life, and it’s essentially always a mistake. Tell the world that you’re a loser and the world will believe you. What was amazing about Zimmerman’s work at The Hairpin was how she could demonstrate her value in a way that conveyed how she was barely holding it together. It wasn’t “sometimes I feel confident, sometimes I feel insecure!,” which is an angle that should be packed into a rocket and sent into the sun. It was “there’s really no space between the feeling like I’m a pretty cool person and the fact that I just lost a shoe between the subway car and the platform.” For me, personally, it’s not at all that there are times when I feel cool and times when I feel shitty about myself. It’s that the personal momentum that creates the former ensures the latter. Self-confidence is like Mario Kart, where no matter how fucking far ahead you get, the game is rubber banded so that some a-hole who kept hitting the penguin always gets the blue shell at just the wrong time. But sometimes, you’re the one who’s behind, you get the blue shell, and it feels pretty good, because fuck Donkey Kong, anyway. Edith Z really knows how to write about those feels.

If the nadir of our condescending “single lady writer livin’ the dream in NYC” fantasy is Carrie from Sex and the City doing her “I’m a klutzy self-doubting person but I got the shooooooooooes and also I’m horrid and really I get feminism and all but sluts are a thing,” then the flipside is Zimmerman, who writes like someone who is brilliant and funny and really put together but also spends a lot of her time with lipstick on her cheek. I never got swagger, never thought it was real, and don’t know why people want it. To humanize success in the aspirational lifestyle that so many people crave— to make it seem ridiculous without ever ridiculing anybody— that’s a beautiful thing.

On Maureen Tkacik:

Derision is a mode that people think is easy, but it couldn’t be harder. You can’t sell it; by its nature, contempt must indicate effortlessness on the part of the person feeling it. I could write a 3,000 word essay and not approximate the deserved scorn or inherent feminism in the five words “Crap Emails from a Dude.” The woman can just sling it, funny as fuck and so wonderfully mean it can cause the screen on your laptop to bubble. I was Facebook friends with her but I ended up clicking unfriend because I was afraid I would post something stupid and she would write a comment so cutting I’d jump out a window. Is my name on this thing? I’m a little worried. That’s the kind of heat I’m talking about here. And I’m no hothouse flower.

On Wesley Morris:

I don’t share his taste for movies. But his writing reminds me that admiration is better than agreement. He’s got all the tools: precision, ambiguity, concision, expansiveness, minimalism, maximalism, reverence, mockery. Heat. Always, throwing heat.

Morris’s style is conversational except when it’s soaring, playful when not reflective, unfussy except when fussy is perfect. I know that can be true of any writer, but Morris can cycle through each and all within a single sentence. That might sound like stylistic schizophrenia, and it would be if Morris weren’t up for it. He makes it seem effortless, juggling registers and syntax, making the next mental turn seem inevitable even as your marvel at how unexpected it is. The digressive and allusive thing is a common style, and though I am inclined to love it, I’ve come to find it predictable and stale. But Morris makes it inimitable and fresh; his references don’t push, like so many of ours do, trying to uncomfortably occupy an argumentative space where they don’t quite belong. His digressions meander without distracting. In all of it, he trusts the interior logic of his style, a kind of DNA internal to his prose, a self-replicating design that spools out beautifully into complex patterns in all directions.

I am reminded, when I read good prose, that all complicated things can masquerade as simple, if only they achieve true beauty. American prose style has been strangled, for forever, by the serial killer called minimalism, a dimwitted ghost of somebody’s misunderstanding of Raymond Chandler’s parody of Ernest Hemingway’s homage to a Sherwood Anderson who never actually existed. I have read writer after writer ruining themselves, under the profoundly mistaken notion that a sentence of five words has twice the power of a sentence of ten. The advice to “write less,” always expressed as some sort of rare, sage wisdom, now has the character of your grandad looking around your new Kia for the choke. It’s bad advice that has been left on the stove for ages and has become tough and stringy. But so many people still want to chew.

Morris, right now, is my go-to for the refutation: with words, there is no such thing as too few or too many. There is only wrong and just enough. If you are in the habit of giving advice to young writers, and you pull out the same tired advice about adverbs or using no alternatives to “said”— as if that were the root of the problem— I’d ask you to consider that every bad writer has already heard that advice. No one who has contemplated writing for more than a half hour could have possibly missed the appeal to minimalism. If that advice solved the problem, we wouldn’t be surrounded by shitty prose.