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 pieces 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 might expect, 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. 

It never in fact became a software platform. For a while, it became a publisher, and a think tank. With hindsight, what was most important was the name. The name evoked the suspended moment before beginning anew, a moment that for me occurred about five minutes ago, 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. I’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 experience 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 delving into the past, but in these letters I shall, because there is so much to be learned from how humans behave. One of the many important and ongoing results 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” or “No, but” me. 

That said, welcome. More dinner parties to come.

Love,

Richard