Look Before You Leap

The sense of danger must not disappear:
The way is certainly both short and steep,
However gradual it looks from here;
Look if you like, but you will have to leap.

~W.H. Auden, “Leap Before You Look,” December 1940

I never wanted to write a newsletter. It seemed too much like doing the one thing I’ve successfully avoided since I finished grad school: having a regular, nine-to-five job. Sure, I’d be working for myself, but that feeling of having to write about one particular subject area, day after day, week after week, month in month out, even when my mind, my inspiration, my curiosity were somewhere far away? It felt like work. Like an obligation.

But when I considered it more closely, I realized something important. It is an obligation. But an obligation to my readers rather than some nameless boss. And that’s exactly what I want. My readers, after all, are the reason I write, day after day, week after week, month in and month out.

I’ve heard a lot of people—many writers I admire—say that when you’re writing, you have to write for yourself, without thinking about anything or anyone else. Harper Lee put it quite extremely: “First of all, you’re writing for an audience of one, you must please the one person you’re writing for. Yourself.” But while I understand the sentiment, I find it quite misleading. Sure, yes, I write for myself. Of course I do. But I also write to be read. I want to share. I want to interact. I want to know that I’m not in an echo chamber of one.

Writing for others doesn’t mean writing to please the world. It simply means writing with the intention of communicating, and communicating well. Kurt Vonnegut has a delightful way of framing the challenge: “Write to please just one person,” he says in his eight rules of storytelling. “If you open a window and make love to the world, so to speak, your story will get pneumonia.” (And he follows that up with making sure you truly communicate: “Give your readers as much information as possible as soon as possible. To hell with suspense. Readers should have such complete understanding of what is going on, where and why, that they could finish the story themselves, should cockroaches eat the last few pages.”)

While I don’t anticipate cockroaches devouring my newsletter—though I am writing this week’s installment from Brooklyn, so anything is possible; but my money is on rats over roaches—I do think Vonnegut’s challenge is a worthy goal. Write for your ideal person. And write so they get it.

Am I up to the challenge? Absolutely not. I don’t have the time or the bandwidth. I have too many other projects—a new podcast; a new book in the works; the World Series of Poker just around the corner. Which is why I opened this first ever edition of The Leap with lines from one of my touchstone poems, Auden’s “Leap Before You Look.” They are lines I quote to myself often: it is never the right time. You never have enough information. The world is one big ball of uncertainty. And yet you have to leap all the same. If it doesn’t scare you, you’re doing it wrong.

“Leap Before You Look”

I say this often, and I’ll say it here once again: nothing is certain, ever. And if you spend all your time looking, gathering confidence, searching for ever-more data, ever-more reassurance that it will all end up ok, you will spend your entire life standing on that cliff. So embrace the sense of danger, of the unknown. Leap before you look. You can always figure it out mid-air. Will I write about social psychology? Decision making? Risk? Cheating (the topic of my next book)? Poker? Poetry? Yes, yes, yes, yes, yes, and yes. Something else? Also yes. I make no promises. I set no expectations. This newsletter will be a window into my brain. And my brain can be one hell of a chaotic place, with myriad projects and ideas all vying for my attention at any given second.

I’m scared and excited to embark on this journey. And I hope you will be here with me for the leap ahead.

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Leave it to me to fail at Vonnegut’s challenge immediately and leave all of the basic details out of this first post. So here they are:

How often will The Leap come out? Once a week. Or so. I hope. I’ll try.

What will it be about? Anything I want to write about. My new pod with Nate Silver, Risky Business, is about risk and decision making—topics I’ve been writing and thinking about for years. (Way back when, my PhD was on self-control and risky decision making!) So I’ll surely be writing about that. My next book is about cheating in games—so you can bet there will be stories of cheating and thoughts about cheating in these posts. I still play poker all the time—and am a member of PokerStars Team Pro—so there will most certainly be poker galore. (The WSOP starts next week, in fact, so I will try to post updates. Nate Silver and I have a summer-long prop bet that we’ll be announcing on our pod this week; stay tuned. And I’m selling action for a few events an no or very little markup, at whichever poker staking site you prefer, PokerStake or StakeKings. No fees in either case.) What I’m reading, what I’m watching, what I’m thinking about, what captures my attention—everything will be fair game. This isn’t a newsletter about any one thing.

What do you get if you’re a free subscriber? For now, until I get into the rhythm of things, all the posts will be free. But I do hope you’ll consider supporting me down the line, if you are so inclined!

What do you get if you upgrade to paid? Access to comments and questions! And once I get going, I’ll be selecting some of these for Q&A posts. Those, along with other bonus content, will eventually be available to subscribers only.

What do you get if you go all-out with a Founding Member subscription (is that what they’re called? I think so?)? Everything you get with a regular paid subscription, my undying gratitude, and eventually, some other benefits. I think I’ll do exclusive Zooms a few times a year for this tier of subscriber, where you can ask me whatever you’d like.

Anything I forgot? You tell me! Comments are open to everyone for this first post, so please let me know if I’ve omitted something important.

I think that’s it. Thank you for being here. Thank you for coming along on the journey. And welcome to The Leap!

“Eeyore was saying to himself, ‘This writing business. Pencils and what-not. Over-rated, if you ask me. Silly stuff. Nothing in it.’” ~A. A. Milne, Winnie-the-Pooh, 1926

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