THE BLOG
06/16/2010 05:12 am ET Updated May 25, 2011

Losing My Book Advance Taught Me to Write

I was given a large book advance in 2005. This didn't sit well with me. It wasn't writerly, I felt, simply to be handed money without having struggled. My reaction was to gamble for about a year.

Gambling was my shtick anyhow. Before Penguin cut me the check--it was for 85 G's, a big and disreputable figure (and that was only the initial installment, payable at the signing of the contract; more would come when I delivered a manuscript the next year)--I'd counted cards for a living. I won money from casinos playing blackjack. With a team of skilled friends I spent five years roaming the country, from Vegas to Reno, from New Orleans to Biloxi to the hellfire of Northern Indiana, through tribal reservations in Kansas, earning decent income and getting barred from over 100 casinos in 15 states.

It was a fun, lawful racket (counting cards may sound illicit; it's not, though you do get shown the door when you're identified), and had the trappings of a marketable memoir.

Fine. I wrote a book proposal and it sold. There were celebratory lunches with my editor and with my agent, but--tellingly?--as I was preparing for the latter, I swallowed an Advil the wrong way and had to get Heimliched by my building superintendent. I showed up at the restaurant looking pale. "What's wrong?" my agent said. I was dicing my salmon into tiny bits, terrified of choking again.

I suppose what was wrong was that everything had happened too easily. It was all about salesmanship and posturing. The writing was expected to be good, of course, but the book in a sense was independent of the prose that would comprise it. Unwritten, it existed already.

And this was inauthentic. This was wrong. A book is the end of a process, not the beginning. I like my authors to have struggled--struggled to develop their insights and the voices with which to pronounce them--because I want books that are urgent. A book should make a new answer to the question of life.

If you start with your answer, you don't need the book.

Therefore, sitting at my laptop, I logged onto Internet poker sites. I meant to write but couldn't. I didn't know how to write or know anything.

Poker is different from blackjack. It's beatable too, but the skills aren't the same, and the mentality is distinct. I wasn't with a team. I was alone. I wasn't playing against loathsome casinos; I was only trying to beat the other players. My motivation was ambiguous.

I was procrastinating, yes, but not concerned about it. My deadline was quite far away. I was losing, but that was all right.

The month my finalized book contract arrived in the mail, I vaporized $2,000. I didn't sweat this at all. It was spring and there were tulips in the parks. I focused more intently on my game and I recovered all the money, as I thought I should. As summer arrived I kept playing. I was doing it most days. I would try to write, get stuck on my third or fourth sentence, log on to PartyPoker or Ultimate Bet, zap $500 or a grand from my checking account to Gibraltar, and roll. I would bet. I would raise. I would raise. I would raise. I would call. I would call. (Good players fold pretty often, but folding didn't stimulate me.) I lost heavily into the autumn.

It was as if I were addicted. How ludicrous! You're a pro, I thought: get it together. Win back the 20 G's, please. Win back the 40 grand, if you would be so kind. I was staying awake for days straight, losing and gnashing my jaws. For months, I pressed on--for a year!

My deadline arrived. I had no manuscript and was down $50,000. I was still a net winner at gambling--plus $700,000 at blackjack--but the story I'd sold had been compromised. Its title was Repeat Until Rich, but, between my online poker losses, taxes on the advance, and living expenses, I had tapped myself out. I was broke.

There had to be a lesson in this. But I didn't know what it was; I couldn't voice it. I wouldn't begin to do that until later, when I'd gotten an extension on my deadline and gotten off poker entirely. Only then, with my story dismantled, was I able to sit down and write it.