Late last month, I returned from a two-week retreat at a Zen monastery in the south of France.

I want to say it was a pilgrimage, but the word seems too serious and devout. A better description would be a power-up. It felt like scooping up a bright yellow star that charged me up with bright, happy energy …

… wading out into a refreshing mountain stream of Zen practice and standing on a solid, submerged rock, feeling the current flow all around me …

… sitting in a circle of two dozen friends, singing songs, not just hearing but feeling the combined sound of our voices in my heart. (That one is not just a metaphor!)

The monastery, Plum Village, was founded by Vietnamese Zen master Thích Nhất Hạnh in the 1980s, and has grown into a cluster of “hamlets” separated by a few kilometers, two for nuns and one for monks. All of them host many retreats throughout the year.

Plum Village is the hub of a worldwide movement to find a more mindful way of living. Both the monastery and the mindfulness tradition that share its name provide a vibrant, peaceful, fully-present alternative to our distracted, violent, materialistic society.

You can see that resistance in the peaceful way people walk, stopping to take a few calming breaths whenever they hear the sound of a bell. (Which is pretty frequently there!) People are not using their phones. They’re not rushing. They’re enjoying the moment, the flowers, the sunshine, each other.

Today, back at home in Silicon Valley, sitting in the technological heart of the U.S. economy, I’m thinking about how I might carry that way of being forward into my daily life.

I have been practicing in this Buddhist tradition since 2018. I’ve been living in the heart of Silicon Valley since 1995. While I don’t tend to mix my Buddhist practices with my writing and editing business, I’m wondering today if maybe a little more mixing might be a good thing. We are facing an epidemic of loneliness and a hollowing-out of the structures that used to give our lives meaning. Atomized and alone, too many of us have become addicted to an always-online lifestyle, losing control of our technologies, and gradually losing touch with the ordinary wonders of life.

So let me share a few snapshots from the trip and why I feel called to share more from this community of resistance.

It’s easy to be mindful in Plum Village, so it’s a good place to practice ordinary mindfulness. Not just sitting down to formal meditation, but walking, eating, and talking mindfully. There’s a lot to enjoy about French countryside in which it’s located, with rolling hills, forests, vineyards, wheat fields, sunflowers, and ancient stone farmhouses and stone barns. The best thing about this landscape is that you can walk right through it, admiring the grapes, meeting the farm dogs, smelling the heat coming off the wheat fields and the big, cylindrical bales of hay.

My favorite time of day was just before dawn, listening to a tremendous chorus of songbirds in the forest next to me, watching the sky begin to lighten as I drank a cup of strong Vietnamese coffee that my roommate Clay had made.

After my predawn coffee I would walk up the hill, through a fragrant pine forest, past the big lotus pond, and into the meditation hall for the morning meditation, often with several hundred voices joining in on the chants -- a powerful burst of concentration in vocal form, resonating through my chest and belly, then echoing in my ears as we settled into a long, comfortable silence.

A few mornings, instead of going to the meditation hall, I went to sit on the broad deck of the little house where Thích Nhất Hạnh used to live. I sat there contemplatively, watching color fill the sky over the distant hills as the sun came up, hearing the sound of a distant church bell, dangling my legs over the edge and noticing vivid purple flowers below the fruit trees.

I grew to love spending time with the monastics, with their shaved heads, long brown robes, and slow way of walking. When I first started practicing meditation with this community, almost a decade ago, monasticism seemed like a quaint anachronism, cute but slightly embarrassing. Now I see these monks and nuns as pioneers in a movement, people who have dedicated their lives to cultivating mindfulness and joy 24-7. The depth of their practice is palpable. Just being around them gives me a feeling of calm and equanimity -- a kind of mindfulness contact high. Most of them are quite playful and easygoing, leading us in songs, games, and dance; offering tea; organizing meals for hundreds and leading almost every aspect of the retreat.

Among the monastics was Sister Chan Khong, the longtime collaborator of Thích Nhất Hạnh, herself now in her 90s, but sharp and joyful, with glittering eyes, a love of music, and a robust sense of humor. I was fortunate to visit her along with a small group of friends. We sang a few songs for and with her, and she commented, “I didn’t know we were going to have an opera!”

Sister Chan Khong is a true pioneer of peace work and social work. She started collecting rice to feed hungry families when she was a teen in Vietnam; later she was instrumental in building social programs to provide relief to war victims. For decades after her exile from Vietnam, she continued sending medicine and money to families shattered by Vietnam’s decades-long war and its totalitarian postwar government, and to refugees in countries around the world. She did all this with tremendous energy, cheerfulness, and optimism.

Meeting her was one of the high points of my life.

I asked her for advice on how others could cultivate a spirit of generosity similar to hers, and she answered honestly, “I don’t know.” Ha! Fair enough. So I acquired a copy of her book, Learning True Love, which addresses my question. It was clear from this book that she got her generous spirit from her parents and grandparents, who had been generous to the families around them. Generosity begets generosity. So that was my answer right there.

What if I tried to live like that even when I’m not in the French countryside? What if I put down the phone, engaged all my senses, walked a little more slowly, and savored a little more of each moment?

What if I practiced being a little more loving, a little more open, and a little more generous every day?

Field notes

Viral exceptions: “In software, an edge case might throw an exception. In urban robotics, it goes viral.” A recent post by Serve Robotics CEO and cofounder Ali Kashani (a client): Building robots in public

Hope. This 20’ high mural appeared on the back of a grocery store while I was out of town. I love it.

Writing prompt: Every Wednesday, I share a writing prompt / meditation with the my writing circle. I thought I’d try sharing these from time to time in Substack. (This one helped me write the post above.)

LMK what you think — should I keep sharing these?

That’s it for now. Write back if you have a minute.

Take care,

~Dylan~

The “five things” format dates back to the days of Livejournal, apparently. I was prompted to try it by this piece by Summer Brennan.

1.

“Things would go so much better for them if they just listened to me and took my advice,” Natasha said, and I was thinking how much I agreed with that. For example: The big man with the bike he had parked straddling two racks in the Caltrain, half an hour earlier, so his ride not only overlapped and blocked in two other bikes but also made it difficult for anyone else to strap another bike into either rack. I had put my bike in, after some fiddling, so it was more or less aligned with one of the racks, but it was still pinning down the front end of his. Of course he wanted to get off before I did -- his bike lacked a destination tag so no one could have known, but I might have guessed -- so as he was unstrapping his bike I got up to pull my bike away, making it easier for him to get out.

“Thanks,” he said.

“No problem,” I replied, and then, like an idiot, I added: “You know, it would be easier if you didn’t double-park across two racks.” He shrugged and turned away.

Then, after a pause, he turned back to me and said, “I didn’t really ask your opinion.”

“You don’t have to take up all that space, is all,” I said.

“Look at those racks down there,” he said. “There’s tons of room. You could have just gone down there.”

“But why would I? This one has plenty of room and it’s right by the door.”

“I’m not listening to you,” he said, putting his earbuds back in and turning away.

“That’s fine, I’m not listening to you either,” I shot back, cleverly I thought.

For the next few minutes, we stayed like that, not looking at each other or listening to each other, like two little boys after a playground tiff, until the train bumped to a stop, the lights flashed, the PA announced its warning, and the doors hissed open to let him out.

2.

K said I seemed rattled yesterday, after I told her about some criticism I’d received on my book proposal. “Not rattled, disgruntled,” I said. It was fairly useful feedback, and I agreed with a lot of it, but it still had left me feeling deflated. But okay: “Maybe a little rattled,” I acknowledged.

3.

I was desperately in need of a swim so I skipped both of the 7am meditation-on-Zoom communities available to me on Wednesday mornings and drove over to Coyote Point, the cove halfway down the San Francisco Bay that’s been my primary swimming hole for a decade. The water was calm and the air mild despite a rather moody layer of overcast -- but to my horror the tide was quite low, only about 3/4 of a foot above MLLW, a measure of the lowest tide. The receding water had exposed bright green seaweed-covered rocks up and down the beach. I knew from the tide chart that the water was so shallow as to be barely swimmable, and that it would soon be totally unswimmable, so I got ready quickly and waded out. I was probably 50 feet out into the squish and much before the water touched my knees, at which point I lay down into it and did my shallowest, most delicately flattened breaststroke until I was maybe 150 feet offshore and the water was finally deep enough to permit a crawl stroke without my hands digging into the muck. Then I swam with ease, away from and alongside the shore, down to the protruding rock that looks like a big, rectangular couch plonked down into the water, then swam back to the start, going as shallow as I could get before being forced to stand up and wade back out through the murky bottom again.

Fortunately there’s a shower next to the beach.

4.

I’ve read several essays recently that have me increasingly convinced that LLMs are a very poor writing tool in almost every way. (Example: What 370,000 college essays tell us about A.I.’s effects on creativity, by Rebecca Winthrop.) I want to make an exception for using AI as a brainstorming partner or as a way to get feedback and perspective on drafts I’ve written -- and for using AI tools to provide line edits and copy edits -- but it may be that even these uses narrow the field of possibility and guide the writer toward more conventional thinking and phrasing.

I know that, for me, the experience of asking AI to draft something is profoundly discouraging and debilitating to my sense of style. Once that draft exists, it is a struggle to edit it back toward a more human form. The field has already narrowed: More original possibilities go forever undiscovered, their absence unnoticed.

At the same time, I have been helped by AI tools when doing research, extracting insights from large bodies of data, summarizing transcripts, and distilling the main points from excessively long, wordy documents. I have used AI as a writing partner, to give me feedback on drafts of more formulaic pieces I’m working on, and I’ve created a Claude project for each of my clients, to provide a check on their preferred tone and corporate messaging. In some cases, I’ve used Claude or ChatGPT to summarize or rephrase things when I just can’t find it in me to write another paragraph about the same enterprise topic I’ve been writing and rewriting a dozen different ways for a client over the past 18 months.

So what’s my POV on AI and LLMs? Conflicted. Suspicious. Increasingly uncomfortable with it. More committed than ever to writing without it. But I’m not sure I am willing to stop using it entirely. In other words, I can’t condense my thoughts into a pithy statement just yet.

But let’s be honest: A lot of people are already using AI to create content.

I did a quick poll on this on LinkedIn, and 42% of the people in my network use AI to help with writing/content creation in some way. So I was inspired to do a slightly more nuanced poll.

Is using AI for generating content at work a net benefit or a net cost? Help me get some data on this and take a short, 3-minute survey.

5.

There’s something powerful about gathering in a room with other people to work on our writing together. There were four of us in the library yesterday, and another six online, and for an hour, all of us were working in silence, except for the scribbling of my pen and the tapping of their keyboards. It’s a pleasantly organic, embodied experience, writing like this; it reminds me of the old days in the newsroom when six or twelve of us were huddled around a large table in one room, working, together. Except in the writing circle, none of us are on deadline, and we’re all there just to support one another in our various writing projects. I noticed, at the end of that hour, that my heart rate had slowed and my anxiety levels were lower.

In other words, I was much less rattled. Maybe on the Caltrain ride home, I thought to myself, I’ll be able to avoid getting into another pointless argument with someone who isn’t even listening.

Field notes

Writing circles: If you’re interested in finding an online writing circle like the one I described above, check out Foster.

Not writing: “If the only way for me to not end up with a mistake ever again is to literally stop using AI, that’s just not realistic. If the answer is to stop writing, that’s not out of the realm of possibility.” In other words, he’d rather stop writing than stop using AI. WIRED: We Asked the Future of Truth Author to Explain How He Used AI. It Didn’t Go Well

Mary Ruefle, on listening:

via R. O. Kwon

Relaxation: My dog Lucy knows how to chill out better than anyone.

Speaking of relaxing, I am going to France for a 2-week mindfulness retreat at Plum Village. I will be almost entirely offline. See you later in June!

And thank you, as always, for listening.

~Dylan~

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At Tennessee Beach, on the Marin headlands just north of the Golden Gate, jagged fins of soft, striated rock curve down on either side of a verdant valley mouth flecked with yellow and purple wildflowers, opening onto a coarse, dark, sandy beach. The rock walls appear vividly reddish from a distance, but resolve into a whole range of reds, oranges, yellows, and even pale greens up close. The beach slopes steeply down to the slate-hued ocean. Waves appear and immediately crash against the shelving bottom, then draw the water back to sea with a powerful subsurface suction.

I jumped into the sea here, with a few friends, on Monday. We swam straight out into the ocean, then turned right, past more rocks -- black and streaming with foam from the ceaseless pounding of the waves -- until we could see another beach, and past that, a jagged and primeval natural bridge bending down into the water. Through the arch, we glimpsed another cove, seeming as inviting and unreachable as Paradise.

Swimming in these parts comes with a sense of connection, but also fear. You don’t know what could be in that water. Under the surface, you can’t see much beyond your own hands other than the green of the sea. The rocks command respect; the open ocean, awe. You can enjoy swimming here, if you know what you’re doing, but you don’t fuck around, or you might find yourself swept out to sea, or perhaps tossed against a barnacle-covered boulder. Or maybe pounded against the rock, and then swept out to sea -- and what’s left of you eaten by a shark.

Or not! We had a lovely swim, enjoyed the frisson of fear and the uplift of wild beauty, and then we swam back, elated and refreshed. Maybe even a little transformed. We spent an hour on the beach soaking up what little solar radiation came to us through the overcast, sharing our snacks, and talking.

Swimming, for me, is where I find myself, my friends, and my purpose. It renews me and reconnects me with the universe.

I got a chance to talk about that on the air this week, with my old friend Megan McFeely’s radio show, Inner Life.

In this half-hour conversation, recorded a couple of weeks ago, she asked me to share how swimming led me to discover a deeper, more inward part of myself, and what I understand “inner life” to be.

I was delighted by the invitation and enjoyed the conversation very much, but I find that I’m a little nervous about sharing it with you now.

In the family I grew up in, talking about your feelings was a bit like discussing your genitalia or your poop. Everybody has these things, that was understood, but after the age of 5 or 6, it wasn’t really appropriate to talk about them much.

My father was a psychologist, but he wasn’t the kind who talked a lot about feelings; he spent his career researching how scientists think and make decisions. Spirituality was actively discouraged, and we had no religious traditions. We were atheists, really, but with the intellectual humility to call ourselves agnostics.

When I started experiencing the universe in a more mystical way, as a teenager and young adult, I had no place to put these experiences, no vocabulary with which to understand them. I threw myself into art and poetry, seeking a channel for the kind of transcendence I longed for. Later, I threw myself into journalism and technology, seeking a way to put bread on the table, and the transcendent part of life receded.

Much later, I found swimming, which woke me up to the fact of my body and my breath, which re-opened the door to the mystical. Through that, I found my way to a meditation practice. Eventually, I found a meaningful path for understanding my inner life and a guide for living ethically, via the Buddhist teachings, or the version of them that has come to us through through China and Vietnam, then carried into the West by Thích Nhất Hạnh. It’s a humanistic kind of mysticism, one that prioritizes connection with others and a recognition of how our individual existence is deeply interconnected with everyone else’s, and indeed with everything in the universe. Thích Nhất Hạnh calls this interbeing.

That slowly developing insight, which started with swimming, has had an effect on my writing, which Megan kindly asked me about. It has made me more aware of writing’s role connecting us to one another, even in my professional work. Even if you’re writing about enterprise software, there is a human, somewhere, making a decision — and that’s who you want to inspire, persuade, or connect to.

So here I am, awkwardly sharing this conversation about my inner life in hopes that it might connect with you.

If you want to hear how swimming led me to meditation, which hopefully made me a somewhat better father and writer, check out Inner Life on KMUN in Astoria, Oregon. Mine is the May 25 episode.

You can also listen to it on Spotify or iTunes.

Field notes

Haiku workshop: Earlier this month I hosted a haiku party in San Francisco. We combined fragments and phrases scribbled on index cards to create mix-and-match haiku, and then added two more lines to create mix-and-match tanka (five-line poems). It was a fun, creative, and interactive evening!

One of my favorites:

 the swoosh
 as she walks up and down Market street
 new summer dress

 the old men on the corner
 stop talking for a moment

Writing prompt: In the Wednesday Writers circle I facilitate, I share a meditation or a writing prompt every week to kick off our hour of companionable silence. Recently, I’ve been sharing prompts from Suleika Jaouad’s Book of Alchemy, and they are bangers. All of the prompts are preceded by short essays by various authors. This one comes from Esther Perel:

What was the last time you felt someone was truly listening to you? What was it like to be heard?

Until next time,

~Dylan~

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Photo credit: Country Gentleman, 1920

I’ve been saying for awhile that AI is a useful tool but that it’s no replacement for thinking things through yourself, which is what the process of writing helps you do.

The notion that AI could just write things for you is based on a misunderstanding about how writing works. It seems to presume that you have thoughts in your brain, and the goal is to get them on the page as quickly as possible, and that how you describe these thoughts in language is just a negligible and tedious issue of word choice.

That’s wrong, because the very word choices and sentence structure are what create meaning. You can only understand and shape the meaning of what you’re writing by getting down in the thick of it, wrestling with words and phrases and all their connotations and associations.

If you delegate that to a machine, you might be generating content, but it’s not what I would call writing, because a) you haven’t thought through the implications of all the language, b) you’re missing out on the fundamental value and pleasure of writing, which is using your brain to filter ideas through language, and language through ideas, in dialog with an audience (real or imaginary).

I would add, also, that c) the content AI produces is probably extremely generic, and d) it’s likely to contain errors.

There are ways to address this, but in my experience, it’s far easier to just write a first draft yourself. You can’t just 10x yourself as a writer with AI.

Lowered expectations

Various writers have been making similar kinds of statements recently, indicating that people’s expectations of AI have exceeded what it’s actually capable of:

Naval Ravikant said recently that AI is not really having an effect on how he runs his new company, Impossible. Yes, his team uses AI tools, but it’s not changing the way the company fundamentally works.

John Herrman spent some time with OpenClaw and found it didn’t really help him automate his life -- in fact, it just buried him in more decisions, required him to think of his life as a kind of “company,” and required a lot of configuration and maintenance.

Minas Karamanis, a physics prof, talks about how AI might be able to produce decent scientific papers -- but that the real point of physics is not to produce papers, but to produce scientists. The “grunt work” is where the learning happens, he notes.

Claudio Nastruzzi in the Register shares the term “semantic ablation” to talk about the weird way AI writing is so generic and boring.

Michael Gerlich published a paper in early 2025 finding that the more students used AI, the more atrophied their critical thinking skills became.

Bhikkhu Sujato, a Buddhist monk, writes about how AI generates “counterfeit meaning” and asks: “Why should we listen to anyone who uses AI? We know they are willing to offload their own cognition to a machine.”

Christopher Mims, in the WSJ, talks about how our evolutionary past lets machines with linguistic fluency fool us into believing they are conscious. At the same time, though, Mims explains that these models are becoming more reliable tools.

(I am embarrassed to notice that I have bookmarked a lot of dudes who are critical of AI. I clearly need to expand my reading to include more women who write on this subject.)

Perhaps it’s time to get a little more precise. “Artificial intelligence” has always been a misleading term. What OpenAI, Anthropic, and others are building now are large language models (LLMs) -- massive systems that use neural networks to model how language works.

Bhikkhu Sujato and Christopher Mims, in the links above, both correctly identify that we mislabel the appearance of linguistic fluency as “consciousness.” We compound the problem when we call it “artificial intelligence,” which was always kind of a marketing term more than a technical description. Now that the category is blowing up, and the models are incredibly sophisticated, a lot of people are getting tricked by the misnomer.

A better term might be “computerized confabulators” or maybe just “language generators.” (I’m talking now about the ones that produce written language, leaving aside images and video and such for now.)

Watch your fingers

LLMs, or language generators if we want to call them that, are powerful tools for working with language. But you’re making a fundamental category error if you regard them as “writers” or “thinkers” or “intelligent” in any way.

This is a bit like being so impressed with the speed of a power saw that you call it an “artificial carpenter” and decide to fire all your skilled tradesmen and just buy a bunch of Skil Saws instead. Maybe there were people who did something akin that in the early days of power tools, but if so, it quickly became clear that what these tools actually did was change the way carpenters worked, rather than replacing them outright.

It also became clear that people using power tools without the appropriate skills could easily get themselves in a lot of trouble.

Similarly with LLMs and writers. They are powerful tools for assisting writers and speeding up parts of the writing process, like combing through interview transcripts for quotes or parsing lots of web research. They are great brainstorm partners. They are good at suggesting additional sources and related lines of thinking to consider. They can act as writing partners, giving you feedback on drafts and suggesting questions or problems you might want to follow up on. They can even help with proofreading.

But if you let an LLM write for you, you’re probably producing extremely average content. You’re taking a risk that it will include inaccurate facts.

And you’re missing out on the opportunity to think through a topic for yourself. You’re cheating yourself of the chance to be surprised when you discover, after the eighth paragraph, that a term you used in the first isn’t bearing the weight you wanted it to. You’re missing out on the pleasures of solving complicated puzzles of how to balance denotation, connotation, pacing, and rhythm.

And you’re cheating your readers of the chance to connect with your one unique, wild and precious self.

Life of Pi author Yann Martel recently answered the question of whether he’d use AI this way: “Why would I? It’d be like hiring someone to have sex for you.“

Or hiring someone to do the crossword for you, or to pet your dog for you.

I’m not as resistant to the technology as Martel, or as Bhikkhu Sujato above. But I am jealous about retaining the fun bits of writing for myself.

And as a reader, I look to authors and newsletter writers and bloggers for human connection, not mere words.

My advice: Use LLMs, but know their limits. Never let them write your first draft. Never let them have the last word.

And hold on to your hat, for tomorrow is another day.

Housekeeping note

I’m back on Substack, after a two-year sojourn hosting my newsletter on Ghost and then Buttondown. I wanted to be on a platform that I controlled, but found the experience rather lonely.

For a small newsletter like this, the community and network effects of Substack outweigh the control and revenue benefits of the other platforms. Plus, it turns out my people are here. That includes most of the writers I know from Foster as well as my listener poet friends.

I will say that Buttondown is a joy to use, and it’s got the best, most responsive customer service team I’ve ever encountered. If this newsletter ever blows up enough that it could stand on its own, I would go back.

The final step in my six-part POWERS process for team-oriented content production is to study the results.

If you don’t pay attention to the effectiveness of your content, it’s difficult or impossible to improve it. What may be worse is that it’s also impossible to prove that the content was worth the investment.

So studying the results — quantitatively and/or qualitatively — is an essential final step. It allows you to close the loop and start the next content project smarter and better prepared.

Most of the teams I’ve worked with have done this step only sporadically. As valuable as the exercise is, teams often have difficulty finding the time to do a proper retrospective (or, as we call them in the newspaper and magazine business, a post-mortem) on all but the biggest projects.

Still, I urge every team I work with to make time for this whenever possible. Even if it’s an informal review by a couple of team leaders, rather than a formal retrospective involving all team members, there is still value in assessing what worked and what didn’t.

The more you can make this kind of review habitual, the faster you will be able to identify and correct production problems, improving your processes and getting more efficient at producing good content quickly.

Here are a few different ways you can measure the effectiveness of your content.

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Today’s solar eclipse was far from total where I was. In Northern California, the Moon blocked at most about one-third of the Sun. Of course, I watched it, with Karen, sitting in our driveway with a colander (to make a constellation of pinhole-camera crescent Sun images on the ground). We chatted with our neighbors, one of whom lent us his eclipse glasses. We tried to convince the recycling truck driver to take a look, but he said he was too nervous.

I am a little sad that I couldn’t be back home in Ohio, where I grew up. My hometown, Bowling Green, was scheduled for about 4 minutes of totality today — although clouds might have obscured the sight. I have been thinking about returning for this event for several years now. But my life circumstances aren’t favorable for such a trip right now, so I settled for a partial eclipse from here.

I thought back to the 2017 total eclipse, which I watched from Oregon, along with my family, on a trip that my late father had planned years in advance.

So I wanted to share an essay (with some embedded haiku) I wrote about the experience.

What was your experience of the eclipse? Write back or drop a comment on this post — I’d love to hear from you.

Instead of sunrise and sunset, Buckminster Fuller suggested we use “sunsight” and “sunclipse,” words that make explicit what happens in a more accurate, heliocentric view of things. The Sun does not move; we, carried along on the surface of the Earth, turn away. The Sun didn’t go anywhere. It became hidden, for a while, behind the Earth. Then, some hours later, we turn back into the light, and the Sun appears to rise as it becomes visible, bit by bit, over the limb of the very planet we stand on.

By this way of thinking, a solar eclipse is a special instance of sunclipse. Instead of the Earth, it’s the Moon eclipsing the Sun. The fact that it appears to do so rarely, and that it does it so perfectly, with the disc of the Moon almost exactly matching the disc of the Sun, has to do with the relative sizes and distances of the three bodies. A perfect celestial coincidence.

It’s easy to imagine a different solar system in which eclipses of the Sun by our Moon never happen or happen constantly; where the apparent size of the Moon is much smaller or much larger than the Sun. Nevertheless, here we are, on this particular planet, where eclipses of the Sun by the Moon happen rarely enough and locally enough that they are worth seeking out.

As I stood there in a field adjacent to a motel parking lot in far eastern Oregon, watching the August 2017 eclipse happen with my wife, my children, my father and my stepmother, this experience of celestial motion touched me deeply. Just how deeply would not become apparent for several years. But that moment of witnessing the Moon covering up the Sun, plunging us into almost-night, caused something to start moving in me.

Like a struck bell, I experienced a vibration that continued long after the Sun returned to view and the black disc of the Moon slid away and disappeared into the blue light of day.

Annie Dillard has written about the experience of totality, when “the sky snapped over the sun like a lens cover.” She writes that at that moment, she left the world of the living and entered a dead universe, her mind light-years distant, looking at her husband through the eyes of ancient ones living in the Euphrates River valley harvesting einkorn with stone sickles. She wrote: “It was all over.”

Unlike Annie Dillard, I did not lose my mind right away. In my case, it took time.

…

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Dylan Tweney - Notes from a totality

If you’ve been following along the past few weeks, I’ve been going through the stages of the POWERS process for creating and publishing content as a team.

For the most recent stages of the process, check out my pieces on getting started writing, writing as a team, and the role of an editor.

Today, I’m going to share how my teams approach one of the final steps: Getting ready to release the content product. (That’s the R in POWERS.)

Whether you’re publishing to an internal blog, handing copy off to an internal design team, or submitting an article to a news publication that takes op-eds and bylines, you want to ensure that you’re doing everything you can to make the handoff smooth and seamless. The easier you can make it on the recipients, the more likely they’ll be able to publish your content quickly.

Like a crew of astronauts or the flight crew on a commercial airliner, a content team will greatly benefit from having a preflight checklist to ensure everything is in order before you press Send.

First, though — I would like to ask for your feedback. Is this team-writing process useful to you? Would you find it useful to have a book (printed or electronic) that served as a detailed guide and handbook for writing and producing content as a team?

Prepublication

Although the content may be publication-ready, there’s almost always a bit more work before you can drop it into your content management system or send it off to the op-ed editor who’s promised to look at it. There’s metadata, such as the author’s full, correct title and bio. There’s often a call to action that you need to add at the end, including a trackable URL with a UTM code. You’ll probably need some imagery, including possibly the author’s photo, any charts or diagrams to illustrate specific points within the piece, and a “hero” image for the top of the piece.

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Release management for content products

A few weeks ago, I used an image in this newsletter that I wish I hadn’t.

It was a picture of a little sign on someone’s desk that said, “Write without fear. Edit without mercy.”

I kind of regret using that image because editing without mercy is not my style. I can be blunt, yes — but I also try to be kind.

I’d rather say something like, “Write without fear. Edit with clear-eyed compassion.”

The goal of an edit is to improve the copy — and, ideally, to improve the writer in the process. You can’t do that if you’re merciless, because while you might be making the words better, it’s entirely possible that you’re hurting the person behind them.

The best editors know how to improve copy and writer at the same time. That takes a clear understanding of how language works, what the rules are, and which rules you can get away with bending or breaking. It also requires compassionate insight into the writer and an understanding of how they might benefit from your feedback.

By the way, that applies whether you’re editing someone else’s work or your own. Revise your own words with the clear eyes of an editor, but be compassionate to your writing self while you’re doing it.

Why we edit

Editing is an essential component of any writing process, whether it involves one person or a dozen.

Editing is crucial because it’s the quality-control phase: It eliminates errors, strengthens weak copy, reduces inconsistencies, and ensures that the copy aligns with the client’s goals, tone, and expectations for excellence. 

Editing is also important because it frees up the writer (or writers) to simply write. Write first, then edit. Separating creation from optimization is, it turns out, an extremely useful step in facilitating easier and less painful writing. When you can turn off your internal editor, it becomes easier to let the words flow, knowing that you or your editor can catch and correct any problems later.

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What does an editor actually do?

You know that feeling when you're staring at a brand-new Google Doc, and it's completely white except for the blinking cursor in the upper left?

Sometimes this blankness is an open field of possibility, but more often than not, it's stress-inducing.

For individual writers, it can lead to writer’s block. Or it can lead to a desperate banging away at the keyboard in hopes that something good will come out. 

I’ve been struggling with the latter response this week as I’ve been working on some personal writing projects. I don’t know exactly what I want to say, yet, but I’m putting a lot of different things onto the page. Maybe some of them will work out, but probably most will just go into the scrapyard.

This can feel good, in a perverse sort of way, if you’re a solo writer and it’s part of your creative process. But if you’re part of a team tasked with producing content, creative angst isn’t going to be a healthy addition to the team dynamic.

That's why a good collaborative writing process is all about avoiding the blank page. 

I don’t want anyone on my team to be facing an impassively blinking cursor, not knowing how to get started. At every step of the way, everyone should have something to start with: an outline, an assignment brief, or just an email from a client asking if we could write something for them.  …

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Avoiding that "Untitled document" feeling in Google Docs

If you’ve been following the team-writing process I outlined a couple of weeks ago, you’ll reach a point where you have an assignment brief (however brief it may be) and an outline. Now, you’re ready to write.

In some ways, this part should be the easiest. You’re well-prepared, and you’re not staring down a blank page. Quite the contrary: My team-writing process gives you a roadmap that spells out exactly where the writing needs to go and what needs to happen at each point. 

What you need to do now is fairly straightforward:

• Write through the outline until you have a complete first draft

• Take a break (get a cup of tea, or let the draft sit overnight)

• Go through your draft line by line to revise it and clean it up as necessary

• Share the draft with the rest of your team

No problem, right?

In fact, a lot of the writing advice you’ll find in books and online won’t apply at this point. With a well-structured team-writing process, the challenge at this point isn’t so much about discovering your voice or getting the creative juices flowing: It’s more about filling in the outline and creating the first draft of what the client wants.

In the simplest case, you start at the top of the outline and go through it section by section, writing paragraphs that correspond to each bulleted (or numbered) item. When you reach the end, you’re done with the first rough draft.

If the team has prepared a good outline, you should have everything you need to create this draft right there: Examples, sources, references, links, a writing style guide, and so forth. Ideally, the team has already spelled out the specifications for what you’re creating in the assignment brief, so you know what length you’re aiming for, along with any other essential characteristics, such as style, guidance on headlines and subheads, and so forth.

Still, problems do crop up. So here are some tips for writing through your outline with minimal hassle.

Write the way you speak. Business writing tends to get too stiff and formal, with many complex sentences, dependent clauses, and excessive passive voice. I think this is because people get it into their heads that they need to de-personalize the copy or write in a more “official” style because they're writing for an organization. This never works out well. 

Instead, start your writing by putting down on the page, as directly as you can, what you would tell a friend about the topic. If it helps, imagine telling your mother, your significant other, or a curious and intelligent niece or nephew about it. Leave out the casual chitchat phrases you’d put into a normal conversation, but otherwise, put what you’d say straight onto the page.

If it’s too weird to imagine talking to someone or too difficult to translate that into typing, imagine writing an email to a friend or coworker you like and trust. 

Some people I know find it helpful to speak aloud as they write — to test sentences out by walking around and saying them out loud. When they sound right, they sit back at the computer and start typing.

Other people (including myself) have found it’s sometimes easier to dictate a section of text. Turn on your computer’s speech-to-text dictation and just start talking to it.

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How to write - and how to avoid writer's block

The heart of a well-organized writing project is an outline.

This is a surprisingly controversial statement. I know many writers hate working with an outline, and for creative projects, their reluctance is understandable.

But for team writing, some kind of outline — even if it’s just a basic set of bullet points — is essential.  

Without an outline, you’re writing aimlessly, wandering across the page, not knowing where you’re going. (This can be fun for creative writing; in business writing, it’s torture.) Without an outline, the assignment is like a monkey on your back. Without an outline, the writer you’ve given the assignment to will have no idea how to organize what they write and may well produce something that completely misses the point. Without an outline, the client has no guidance on what to expect and may well be surprised (often unpleasantly) by the draft your team eventually produces.

You can start writing without an outline but you’ll likely run into all these problems and maybe others. Even if the outline is quickly done and you only share it with a small number of people — or even if it’s just for yourself — writing an outline is the simplest way I know of to make writing easier, faster, and to get a better-finished product at the end.

The outline turns an assignment from a bear into a beautiful racehorse, from a headwind into a tailwind. 

Three basic ways of outlining

There are several different kinds of outlines, so getting clear about what might work best for your team is helpful.

• Formal multi-level outline with Roman numerals, capital letters, etc.

• Informal multi-level outline with bullets and sub-bullets

• A simple single-level list of bullets

The formal outline is something that most of us learned in school. It goes something like this:

I. You start with Roman numerals for the top-level headings.
   A. Next-level headings use capital letters.
       1. Then you switch to Arabic numerals.
            a. And maybe even lowercase letters for fourth-level headings.
       2. It’s relatively easy to see how ideas and sub-ideas group together.
   B. But sometimes it can feel a little laborious filling all this out.
II. And by the time you get to the end …
   A. You might feel like you’re filling out a form.
   B. Especially if you want to make sure every section has at least two sub-points.

Needless to say, this is not the most useful approach for most practical content creation. If you’re producing an academic paper or a very structured piece of long-form content, such as a textbook or a user manual, this kind of formal outline can help make a complex structure clear. But for most projects under a few thousand words, this kind of approach is overkill. Besides, its formality induces a kind of stiffness, and it’s easy to lose any sense of narrative flow.

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Three ways to write an outline - plus one that is better than all the others

The idea is that you sit down with some blank pages in front of you and just start writing, either for a set amount of time (10 or 15 minutes) or until you’ve filled up a certain number of pages (2 or 3). 

Don’t worry about what’s coming out; just focus on writing words. Or, if you get stuck, you can do some doodling and just enjoy the way the lines spill out of your pen onto the page.

The important thing is to keep the pen moving.

Freewriting is a fabulous exercise for unlocking your inner creativity.

It’s also pretty much the opposite of how you want to start with a collaborative team writing project — unless your goal is to spark maximum creativity. In that case, give everyone on your team some blank paper and some pens, and free up an hour for them to start scribbling ideas.

This is not a bad idea, actually, and more corporations should consider creativity workshops like this instead of trying to figure out what formula will let them use AI to produce as much cookie-cutter SEO content as possible without human intervention.

(Prediction: Within the coming year, AI content will be so generic and ubiquitous that we’ll start prizing actual stories from actual human beings. We will crave human connection amid the coming flood of AI-powered bullshit, and the real human voices will — I hope — stand out like lighthouses on a foggy night.

If you want the help of an experienced journalist and storyteller so that you can be the lighthouse instead of the fog, let’s talk.)

That said, most content projects don’t aim at stimulating wild creativity but at producing a specific deliverable: A blog post, a byline, a white paper, or an e-book.

When kicking off a writing project like this, it's beneficial for everyone to agree on a few key things:

• what we’re doing

• when it’s due

• why we’re doing it

Such alignment is as necessary for a small project like a short blog post as it is for something big like an annual report. 

But that doesn’t mean content teams always do this. I've worked on plenty of projects that started without a clear idea of what we were doing. It inevitably leads to wasted work and confusion down the line.

Client: "We need a byline on topic X. We'll put our CTO's name on it."

Me: "Great. When is it due, and what's the goal?"

Client: "It's an open deadline, but we'd like it by the end of next week. The goal? We need some media hits, but we don’t have any news to announce, so the goal is to publish this byline.”

Me: “Okay …”

Two or three weeks later, we’ve created a draft, and we're deep in revisions when it suddenly emerges that the CTO has different priorities or that the client has decided to focus on a more urgent press release. The draft is put on the back burner. A month after that, the client returns their attention to the piece but decides to rework it so they can attribute it to the CMO instead. Someone else, from the CMO's team, starts editing the draft and wonders what the hell this is and who produced this, because it doesn't align with anything the CMO talks about.

Sigh.

These kinds of direction changes happen all the time — and part of writing as a content team means being flexible enough to roll with the changes that are an inevitable part of organizational life. 

However, having goals spelled out at the start provides a framework that will make everyone's life slightly saner. 

Two tools can help you get closer to sane in your content projects: A project kickoff meeting and a well-structured assignment brief.

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How to start a writing project with a team

Most people think of writing as a solitary activity undertaken by lone geniuses operating under various degrees of inspiration and sheer tenacity.

But business writing is not usually the expression of a single individual's talent — it is generally, and often by definition, the expression of an organization's collective intention. And with real-time, collaborative, online editing platforms like Google Docs, collaborative writing has taken on an even more interactive dimension. It's now possible for you to be working on a document at the same time as others, adding text, leaving comments, and changing words — while other people's variously colored cursors dance through the page doing their own things.

Collaborative writing unlocks powerful new possibilities and enables organizations to create copy that benefits from the talents and knowledge of a whole team of people.

It can also be infuriating, confusing, discouraging, and waste much of everyone's time. It can produce flat, bland, safe, bureaucratic copy, and reads like it was written by a committee — because it was.

How do we make this work better? How do we maximize the benefit of working together while minimizing the process's frustrating and counterproductive parts?

Over and over again, I’ve found that organizing content creation into stages is the key. It creates a process your team can follow. Perhaps even more importantly, it provides language for discussing what’s needed, requesting help, diagnosing what went wrong, and coming up with solutions.  

Introducing the POWERS process

After some recent brainstorming, I developed a hopefully not-too-dorky acronym to make these stages more memorable: POWERS.

• Prepare

• Organize

• Write

• Edit

• Release

• Study the results

I’ve used some variation of this approach, albeit without the acronym, in the last several roles I’ve been in. It helps clarify what the team needs to do at each stage and how each content team member (or its clients) can best contribute.

Only the middle step, the actual writing, is an individual exercise. Everything else in this process involves multiple people, in principle, if not in fact. However, if you divide up the writing of a large project into smaller pieces and assign a different part to each writer, then it's also possible for the writing stage to be team-oriented.

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The POWERS process for effective team writing

Dylan Tweney's six-step method for collaborative content creation

Hello everyone!

I’m starting a new chapter today. Actually, I’m starting a whole new book.

For the past six weeks, I’ve been working on the manuscript of a short book about a topic that has informed most of my career: How to write better. Unlike most writing books, this isn’t aimed at the individual writer or would-be author. I’m writing a book aimed at content teams — groups of writers and editors working together to create something collaboratively. 

In short, this book will be about how to write as a team.

Writing as a team? What does that mean?

I’ve done a lot of writing and editing as part of collaborative teams. I’ve been a magazine editor, an online news journalist, a freelance writer, an independent content consultant, an in-house communications chief, and the head of editorial at a PR and marketing agency. 

Throughout my career, I’ve been part of creating thousands of news stories and blog posts, hundreds of bylines, scores of speeches and presentation talk tracks, dozens of research reports, and many, many other types of content. I’ve contributed to half a dozen print books as an author or editor, helped launch about a dozen publications and blogs, and participated in half a dozen website redesigns. And I’ve taken part in a handful of content management system transitions (excruciatingly painful, every one of them).

In other words, almost all of the content I’ve helped create has been a collaborative effort. And when you’re creating content collaboratively, a host of issues crop up that most writing manuals don’t cover. Issues like these:

• The engineer who wants your team’s help to revise something they’ve written to make it more publishable, but who can’t let go of specific technical descriptions that they insist are necessary for accuracy — which make the copy almost unreadable.

• The top executive who needs your help writing a speech but is so concerned with specific wording that he’s still asking you for revisions backstage, shortly before he’s about to go on.  

• The research firm that keeps revising the results of a survey, forcing you to make endless revisions of the supposedly final report up until the day before it’s scheduled to be published.

• The key member of the writing team, brilliant but inconsistent, who decides that they’ve had enough of your feedback and quits, leaving you to scramble to find someone else to cover their responsibilities. 

All of these have happened to me and the teams I’ve been part of. In fact, every story above has happened to me multiple times! 

In the moment, each of these incidents felt like a crisis. Yet my teams and I delivered the content we needed to, on time and as promised. In some cases what we delivered exceeded expectations, sometimes by far, delivering results that were 10x or 100x the investment our clients had made. 

The teams that produced this work were prepared to handle these unexpected curveballs to varying degrees. Sometimes we had a solid game plan, well-organized project management, and all the resources we needed. Other times? Not so much.

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Writing as a team

My first swim in open water, about ten years ago, was in the shallow, protected waters of Coyote Point, a cove halfway up San Francisco Bay. I was nervous, hyperventilating, wearing too much neoprene, and probably didn’t swim longer than about ten minutes. So how did I get from that point to being able to swim six miles in the open ocean without stopping?

Practice, practice, practice, as the old joke about Carnegie Hall goes. But first I needed to find a swimming buddy or two.

After that first swim, I knew I wanted more, but I was nervous. I didn't feel comfortable swimming by myself, and I didn't know anyone else who swam in the Bay, apart from a coworker at a previous job. He was notorious for swimming in the San Francisco Bay every morning before work. This guy was a member of the Dolphin Club, one of two century-old athletic clubs on the shore of Aquatic Park, near Fisherman’s Wharf, and he was rumored to be a fast and accomplished distance swimmer. At the time I assumed (wrongly) that the Dolphin Club and the South End Rowing Club right next door to it were accessible only to the brave, the strong, and the rich — and I was none of those.

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Finding a swimming buddy

When I first started to swim in the ocean, it was in a shallow, protected cove halfway up the southern reach of San Francisco Bay. Coyote Point is a good twenty-five miles from the open ocean, well inland of the Golden Gate, facing east toward the tame weather and waters of the Bay’s midsection, exposed to nothing more dangerous on most days than some afternoon wind and the occasional small fishing boat.

Still, when I first contemplated getting into that water, it seemed as wild and daunting as the English Channel. A light breeze ruffled the limestone-gray surface of the water into little wavelets. But the closer I got to the water the bigger those waves looked: Like chop, or rough water, really. I looked closer and noticed little whitecaps forming on some of them. Waves were even breaking on the beach. Tiny surf, but still surf! I wasn’t seriously considering going out in these conditions with no boat to protect me, no surfboard to cling to, no floaty to hold me up, was I?

And who knows what horrors lay under that forbidding surface. The Bay is filled with creatures that are bigger, stronger, faster, and hungrier than I. Seals, sea lions, and sharks are all known to be common in these waters. There have been jellyfish in this cove. Some jellyfish stings can be deadly!

Never mind that the Coyote Point cove is about two to six feet deep at low tide and no more than ten or fifteen feet deep at the highest tide, that the jellyfish here don’t have lethal stingers, that the seals and sharks that swim here don’t bite, and the sea lions don’t wander this far south.

I didn’t know all this the first time I ventured into the water here. For me, I was swimming in (and over) all the mysteries of the deep. And I was doing it alone.

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First swim

How I got started in this open water craziness, ten years ago

DYLAN TWENEY NOV 10, 2022. 6 MIN READ

Listen to the podcast version of this issue.

I’m standing on the edge of the San Francisco Bay in San Mateo, my bare toes gripping the blocky concrete ramp installed a few years ago to help windsurfers get in and out of the water. Before me, the greenish water of the Bay is slightly ruffled by a gentle wind, and in the distance, the city of San Francisco twinkles in the morning haze. 

To my left, just half a mile away, is the north-south corridor of the 101, an endless vein of commuter traffic connecting San Francisco with Silicon Valley. Next to it, the bright horizontal lines of Meta's new Burlingame campus shine out, a clean, expensive-looking set of buildings on the waterfront, where engineers are creating a world of virtual reality, accessible only to those willing to strap on a headset and trade the real world for one made of polygons.

To my right is real reality: San Mateo’s “wild coast,” a low bluff of sandstone topped with eucalyptus. At the foot of the bluff, the water I will be swimming in laps against the rocks. Shorebirds mill about in the water: Coots, scoters, and buffleheads, their patterns of black and white seeming to sparkle as they paddle, dive, and resurface. Somewhere behind me, crows caw at each other in the parking lot.

It’s March, and a chilly wind blowing across my shoulders reminds me not to stand there too long. I walk a few steps into the water, until it’s up to my knees, and then bend down, swirling my hands around in it and splashing some on my face. The water’s about 52 degrees Fahrenheit, or about 11 degrees Celsius — chilly enough to provide a shock to the system when you first get in. 

My swim watch tells me that my heart rate is 82 beats per minute, reflecting my excitement and the reaction to the cold water. The watch also lets me know that it has acquired a GPS signal and is prepared for me to start my swim. Its screen says, simply: Ready.

I take a few deep breaths, and dive in.

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Jumping into writing like jumping into the sea

It’s November, and in the seasonal ebb and return of the San Francisco economy that means it’s time for Dreamforce, the annual tradeshow hosted by Salesforce.com. It’s one of several annual conferences large enough not only to occupy all of the Moscone Center’s three massive buildings, but to spill out into and take over the adjacent street, occupying a full city block of Howard Street. As a demonstration of corporate power’s dominance over civic power in the 21st century, you don’t get much more vivid than this: A heavily used street is closed down and given over to private use, traffic is redirected at great inconvenience and cost, and the police are called in to protect and preserve this now-private space for the duration of the weeklong conference. Plus there is most of a week before given over to setup and a few days after for teardown.

In this privatized city block, Salesforce will erect pavilions, roll out Astroturf, set up food kiosks and stages for entertainment — and all for the benefit of its paying customers. Last year there was even a private “park,” with temporary trees and greenery, with signage that echoed the National Park system’s. At a time when the real National Parks are being starved of operating budgets and their irreplaceable natural wonders are being reconsidered as concessions to be developed by the gods of capital — hotels! amusement park rides! Wi-Fi! — the irony of a miniature “National Park” popping up in San Francisco, but designated for the exclusive use of Salesforce customers, struck me as more than a little ironic.

Yes, Dreamforce brings dollars to the city, and to its hotels and restaurants in particular. Such is the deal: Give us temporary use of your public spaces and in return we will pay you, while those who are paying us will also pay you. 

At least it’s temporary, and the expenses (extra policing, traffic control, etc.) are paid for by Salesforce, so unlike, say, a publicly funded sports arena there is no economic hangover after the circus leaves town.

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November chill

Dreamforce, Zen monks, and swimming as the water gets colder

DYLAN TWENEY. NOV 19, 2019. 5 MIN READ