Dear You:

Little did I know, when I wrote you my first letter in January 2021, that it would take another two years to finish the second letter. Not, mind you, to begin the second—for when I created a new Word .doc to start this one, I discovered eight unfinished letters in The Dinner Party Letters folder. Sigh. Eight.

But while I did type “sigh” there, and while I did periodically feel embarrassed, irritated, while I did chastise myself for overpromising and underdelivering, I had moments of feeling a certain glee. For I was giving myself something I so often find myself wanting to give others, something I so often want others to give themselves—permission. Permission to not have to write a second. goddam. letter. You should write your second letter, Richard, it’s been so long! Who says, I retort. Who says I should? Who decides what is “should” vs. “who cares”?

Last month I read Quit: The Power of Knowing When to Walk Away. It’s by Annie Duke, a former professional poker player. One of the many things I enjoyed about that book is how well she illustrates the human propensity for not quitting, for perseverance. Think of all the virtuous synonyms for perseverance, she tells us. Think of all the books written on resilience, on grit. Conversely, consider quitting.

As readily as positive words to describe perseverance come to mind, so do the negative terms for those who quit, all of which encompass the idea that quitters are failures who don’t deserve our admiration. They are backtrackers, chickens, defeatists, deserters, dropouts, shirkers, wimps, and wusses. They give up and abandon things, waver and vacillate. We consider them aimless, capricious, craven, erratic, fickle, weak-willed, undependable, unreliable, and even untrustworthy.

Or just plain lazy—for example my laziness in failing to manage even two letters in two years.

But, as Duke points out, of course people who have succeeded at something have persevered, by definition. But just because you persevere doesn’t mean you succeed. If it did we’d all be whatever we wanted to be because we just didn’t give up.

It should not, when you stop to think about it, be surprising that it takes a poker player to remind us of this. For all the athletes and political and business leaders who praise grit and despise quitters, it’s a country music singer, Kenny Rogers, who articulates the best retort to them: “You’ve got to know when to hold ‘em, know when to fold ‘em.”

In another letter—if there is another letter, who knows!—I might explore more the universe of sunk cost fallacy and escalation commitment. But for now I want to return to permission, to the emotional side of quitting, to the place where it hurts, to the place of shame. You know what else I haven’t done? I’ve not yet done a single trip to another city to host a out-of-town dinner party. I’ve only had one dinner party in the past six months. I twice bailed on going to Frankfurt for the Book Fair, something I’d done every year from 2001 to 2019. And what I tell myself, what I keep telling myself is, it’s OK. It is OK to not do something, it is OK to change your mind, it is OK to bail, OK to quit, it is OK to not follow through, it is OK to write only one letter when you said you’d be doing The Dinner Party Letters plural.

My coaching clients can feel so stuck. One client comes to me trying to figure out how to grow her business in a declining market. She thinks I’ll be a good coach for her because I happen to be familiar with the industry she is in. She just cannot figure out a path forward. But by the end of the very first session, it’s almost certain she’s making a major career change. By the end of the sixth session she’s giddy, hyper, she’s already started her training (training to be a trainer but I can’t say more than that because of confidentiality which drives me nuts because I’m so excited for her), she is so clearly on her way, the words tumble out of her mouth for thirty minutes, we end the session early because, why not? Why the hell not?

And I can’t give her permission to make that change if I can’t give myself permission to write the next letter whenever-I-want-to-which-might-be-never-NEVER. Which is not in fact how it works, what really happened is that I gave myself that permission-to-not-write-letter because I gave her permission-to-not-grow-her-business. What I do for others, I can actually do for myself. (Physician, heal thyself!)

Thus far, I sound like Mister Permissive, slinging indulgences around, the epitome of decadence. (I put my feet up on the couch after I wrote that line, just to linger awhile in the notion.) Really though, the permission to not do something, to not follow through, to quit, it merely gets us to the staging post. It’s not the endgame. Let’s instead call it a sign that we’ve fought half the battle.

The other half of the battle is, I believe, choices.

Here I am reminded of another recent book, Four Thousand Weeks by Oliver Burkeman. The book comes with the tongue-in-cheek subtitle Time Management for Mortals which suggests it might be a book of “productivity hacks,” tricks to get more done in less time, little mind-ninja stuff that gets you to, say, write a letter every month! Or every week!!

Thank God, it’s none of those things. A giveaway is when Burkeman starts in on the German philosopher, Martin Heidegger—you’re not going to get seven tips to clear the decks by lunch, or breakfast. In particular, he zeros in on Heidegger’s assertion that “our being is totally, utterly bound up with our finite time.” We are time, we are, in Burkeman’s title, “four thousand weeks” (the current average Western lifespan.) To live authentically means fully confronting that finitude. This is in no way morbid; what is morbid is “to indulge in avoid or denial.” Instead we take ownership of our life, and we make choices inside the ineluctable limitations of our life. Only then can we reckon honestly with ourselves. It is the very limitations that give our choices meaning—if we lived forever, yes, we could do everything, but how much would anything really then mean to us. It is the very fact that our time is finite, our choices constrained, that each choice we make has meaning.

One of my favorite films is Wim Wenders’ Wings of Desire. In it, two angels wander the earth since the primordial times—in the timeframe of the film, they wander Berlin, a few years before the fall of the Wall, observing humanity, all the while remaining invisible. They hear our thoughts and seek to give comfort to the afflicted, not always successfully. One day, one of the angels decides he wants to become human, even though that will mean the end of his eternal life. He wants to feel the tangible things, to taste and touch, and also to experience emotion, love and fear and joy.

That’s always been my understanding of the film, largely unchanged through my subsequent watchings. I now realize, however, thirty years after having first seen it, that what he also gets from being human, and mortal, is finitude. That everything now actually matters. That there will only be so many moments and how he spends each moment means something.

And so, for the past two years, I’ve chosen to cook, or read, or run, or stretch, or call a friend, or look out the window at the snow flurries as I’ve done a few times while writing this, or swipe through my phone, or lose myself in Ukraine updates on Twitter, and I’ve also chosen to not write this letter, and all these choices have had weight and meaning. What permission does is remind us that we have choices, and what our limited life span means is that our choices matter.

Today, I decide to not read, or run, or stretch. I decide to write this letter. Because I wanted to. Not because I should write it, not because I set up some structure to guilt myself into writing it, but because today I felt it would mean something to me to write it, and so I began it, and I finished it, and here it is.


The Dinner Party Letters

Belatedly, I’ve decided to start a newsletter though, as I note in the first edition, there’s no news whatsoever, so I’m calling it a letter, the first in a series called The Dinner Party Letters. Sign up at the link; here’s the first in blog post format.


Dear You,


Some of you know me as a theater director turned book publisher turned start-up founder, turned consultant and advisor and public speaker turned agency founder and now, finally, turned coach. Most of you, I think, know some of this history, but not all of it. This monthly letter, in a series I’m calling The Dinner Party Letters, is about what I’ve learned along the way, and about what I’ll continue to learn.

As you can see, it’ll take a little backstory. Bear with me.

When I left my job as publisher of Soft Skull Press in 2009, having been a theater director in the 1990s, I created a blank slate corporation called Cursor. At the time, I knew, or thought I knew, what it was going to do: it was going to be a software platform that would enable a whole new generation of independent publishers. And it would enable countless existing organizations to become publishers. And many existing publishers to sustain themselves. I’m proud of what it did do, which was to contribute to moving the dialogue forward around the intersections of content, community, and culture.

For a while, it became a publisher, and a think tank. With hindsight, what was important was the name. The name was intended to evoke the suspended moment before beginning anew, a moment that for me , when I opened a new blank document on my laptop, paused for one second…and began to type. That moment of fear, possibility, hesitation, decision, indecision, embracing not knowing. The moment between breathing in, and breathing out. The ellipsis. So Cursor became whatever I felt intensely motivated to do.

In this sense, it now lives up to its name, where every day I start anew. ’m now a coach, and my clients include writers, designers, scholars, filmmakers, entrepreneurs (including a health care start-up co-founder and an asset manager), even a diplomat and a cabinet-maker. They come from across the world—the U.S., the U.K., India, Australia, France. I know so little of each client’s world that it is better that I assume I know nothing. I’m a blank page too. My role is to ask questions which the client answers. The truths, the paths, the answers the client seeks, they exist already within the client. These letters will, in part, be about what I learn from my clients as they face blank pages in their lives.

When I am not coaching, though, I am thinking, cooking, reading, gardening, daydreaming, running, listening, watching, stretching, spacing out, indulging, prevaricating, zeroing in. Where I get to combine all of this (except perhaps the running) into one single expereince is by hosting dinner parties. In the past few months, I’ve hosted CoVID-aware dinner parties for typically six or seven people on my deck near the Gowanus Canal in Brooklyn. Those parties are perhaps the most stimulated I ever get. The flow of thought, word, emotion, idea, the activation of all five senses, it is, for me, sublime. It’s the synthesis, especially, that I love, the group of disparate people sober and tipsy, hungry and sated, weaving together anecdotes and jokes, sentiment and snark, winks and nods, belches and farts, sighs and lulls.

In these Dinner Party Letters then (letters, rather than newsletters, since nothing here will remotely resemble actual news), I will take the excitement I experience, the ideas and challenges and discoveries I encounter, from the people I meet and from the people I read, from dinner parties real and metaphorical, and explore them with you. (Email me back, too, if the spirit moves you.)

What does that mean in practice? There will be a letter about fear and poetry; there will be letters about buzzy topics like “context collapse” and “filter bubbles”; there will be a letter called “The Dollar Shave Club and Fifty Shades of Grey”; there will be letters that go into psychoanalysis and the microeconomics of consumer packaged goods, how Gandhi might be best understood as a prankster, the pleasures of being a dilettante, and cooking and gardening and parenting; there will be letters in which I’ll offer opinions I’d never share during a coaching session, and ones where I’ll straddle fences and be hopelessly obtuse.

I also wanted, in this first letter, to try to give you a sense of what subsequent letters might feel like. In other words, what is this letter about? This is something I struggled with—which is mildly terrifying, as I’m going to have to do this every month—but here goes: Why coaching?

If I were to offer one reason why coaching is becoming more necessary, it would be that work is becoming deinstitutionalized. Put another way, it’s the Gig Economy. That term refers not just to Uber or DoorDash or Airbnb but also to freelance designing and writing, to consulting, to adjunct teaching. It refers to the world evoked by phrases like “the CEO of Me Inc.,” “the brand called You,” “do what you love,” “be your own boss,” “side hustles”; it generates advice, manifestos, hand-waving, hand-wringing, and so forth. It’s utopic, it’s dystopic. But a great many people are dealing with it, chasing it, fleeing it, fearing it, embracing it, and it’s nice to have a sounding board as you go through all that. Hence coaching.

But if there’s one thing we do again and again and again in coaching, we ask questions. And as I thought about this letter, and this question of the deinstitutionalization of work that I’ve taken somewhat for granted, I realized I should interrogate it and, at a minimum, try to present something moderately conclusive about the social, economic, political, and cultural factors in this “deinstitutionalization of work”: changes in job security, tenure, displacement, and so forth. In so doing, I realized two things:

  1. The “deinstitutionalization of work” will be one of the ongoing topics of these letters as I continue to explore what I’ve only just started to learn, but it is vast, complex, and way more complicated than “things are getting more precarious.”
  2. We’ve ignored the status quo ante, the “institutionalization of work.” Work was not always the way it was in the 1950s and 1960s. Put in classic link bait lingo: “The gig economy is nothing new – it was standard practice in the 18th century.”


In coaching, the “Yes, and” response, derived from improv comedy, is the norm. In these letters, I’m going to play around with “Yes, but,” the somewhat annoying and smarty-pants mode. In coaching, unlike in psychotherapy, we don’t spend too much time dwelling in the past, but in these letters I shall, because there is so much to be learned from how humans behave. One of the many benefits of the MeToo and Black Lives Matter movements has been the way in which we’re called upon to be aware of unconscious biases, the “snap judgments” we make. I’m going to do my best to be calling myself out in my biases and they are legion, biases not just around race and gender but in all the areas where we rely on heuristics, on mental shortcuts—the availability bias (which causes us to overemphasize recent experience), hindsight bias (I knew that all along), survivorship bias (in which failures, because less visible, are ignored). I invite everyone reading this to help me be alert to where I might fail, to “Yes, but” me.

That said, welcome. More dinner parties to come.




Live the Questions

I did an illuminating (to me) interview with the curious and creative Christina Wallace and Cate Scott Campbell for their podcast The Limit Does Not Exist. Here’s how they describe:

As we continue to navigate the changing landscape of this challenging time, we’re joined by Richard Nash, a coach who specializes in helping creatives become more entrepreneurial, business folks become more creative, and all types of professionals become more comfortable with transitions. No stranger to career zigs and zags, Richard brings his range of theater, publishing, and entrepreneurial experience to our conversation. We discuss doing versus being, why it’s smart to ask stupid questions, and how to rediscover the joy of discovery.


Over the years, I’ve offered so very many opinions about so very many things, here on this site, and elsewhere, and I’ve recently found myself increasingly bored by the sound of my own voice. So, a couple years ago, I began a form of training that has come to be, for me, quite transformative. A training that is about powerful questions, rather than answers. A training that echoes a style of editing I was always drawn to, editing by query. I trained and have been certified as a Coach, as a CPCC, to give me my official designation.

I realize, if there’s one thread through all my work—my life as a theater director in the 90s, running Soft Skull Press in the 00s, launching start-ups and speaking and advising and consulting in the 10s—it’s that I loved helping people rock. Whether as actors, or as writers, or as entrepreneurs, I was helping people to be their maximum selves. It’s often called leadership, though that word tends not to be understood to include those writers and artists who do their thing, leading by means of the cultural artifacts they create.

I help people who identify as creative discover how much more entrepreneurial they truly are (than they think they are); I help people who identify as entrepreneurs and businesspeople discover how much more creative they truly are (than they think they are).

I take, as a motto, the Irish poet Seamus Heaney’s last words: “Noli timere.” “Don’t be afraid.” Fear fucks with us all, and I work to help you put your fears in their place, so you can create and succeed according to who you truly are. Helping you rock. Email me at [email protected] to learn more.

Film is Evil, Radio is Good

Sometimes I let myself go out on a limb. The particular limb I go out on here, is anticipating the end of media. Not just books, but all media, all representation. Replaced by? Telepathy.

Of course, I’m not saying it will happen. But the tension between media and utterly unmediated thought, it’s one that will come. And, in some ways, which I don’t address here, but which all my readers can imagine, it is somewhat upon us.

From the always intriguing Books In Browsers.

When Editors Eat Robots

One way of looking at the political economy of publishing is to look at the labor economics and there’s a rather useful new study from everyone’s favorite consulting firm McKinsey on workplace automation (“The Four Fundamentals of Workplace Automation“) from which we might glean some useful perspective on the future of editing.

Capabilities such as creativity and sensing emotions are core to the human experience and also difficult to automate. The amount of time that workers spend on activities requiring these capabilities, though, appears to be surprisingly low. Just 4 percent of the work activities across the US economy require creativity at a median human level of performance. Similarly, only 29 percent of work activities require a median human level of performance in sensing emotion.


While these findings might be lamented as reflecting the impoverished nature of our work lives, they also suggest the potential to generate a greater amount of meaningful work. This could occur as automation replaces more routine or repetitive tasks, allowing employees to focus more on tasks that utilize creativity and emotion. Financial advisors, for example, might spend less time analyzing clients’ financial situations, and more time understanding their needs and explaining creative options. Interior designers could spend less time taking measurements, developing illustrations, and ordering materials, and more time developing innovative design concepts based on clients’ desires.

And, you know, editors might edit. Actually, though, no, I’m not going to go down the irritating “do-they, don’t-they” of whether editors these days edit or not. (I suspect the answer is, they edited less in the past than it is made out to be, and edit more in the present than is made out to be.) However it is true that many editors have been laid off in the past twenty years and shifted to freelance mode, and it may be that that was the most self-defeating move the industry made in the past twenty years. Because the least automatable bit of the entire publishing supply chain is the editor-as-shrink bit. You attend any self-publishing conference and you don’t hear any shit get talked about their editors, no, the shit-talking is reserved for the marketing and business side.

Further to this, you might enjoy Porter Anderson’s account of a talk I gave in 2014 in Stockholm. (Slides here. Quotes courtesy of Porter’s prodigious ability to live tweet a talk.)

“I changed my title five seconds ago from ‘Editors Beat Robots’ to ‘Editors Eat Robots,’ partially because I don’t believe in neat oppositions of editor versus robot, book versus transmedia, print versus digital. I believe in hybridization, which happens when things get combined. In a certain sense, I could say, ‘Editors Fuck Robots,’ and not in the aggressive sense but in the reproductive sense. What happens when editors combine themselves with robots?”

What is key though is that the business model would need to evolve, away from hit-picking, towards talent support.

“When you understand editing as a service, as opposed to a process of picking products that may or may not sell, your value is defined by how good you are rather than how lucky you are. Which suggests that editors, when they eat robots, when they use tools, when they use data, when they embrace a post-industrial mode, can be the entities that are attracting the value.”

Or, you might say, editors beat publishers.