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.