For the Win: How Being a Writer is Like Being a Gambling Addict

By Sarah Tomlinson | April 20, 2015 | Tips on Life and Love from Simon & Schuster

I learned to gamble from my father, as he once tried to learn from his mother. In his thirties, my father had lost a lot of money at the track and was in a bad way. Normally he hid his gambling debts from his mother and simply tapped her for regular infusions of cash and wool socks from Sears, both of which he relied on until she passed away in 2002. But this time, he was in real trouble, and so he confessed.

Wordlessly, she accompanied my father to the track where she placed a series of bets, all of which came in, winning my father the exact sum of money he needed. She would not tell him how she had done it, even when he pressed.

He always suspected she’d learned from the New Jersey mobsters she’d dated while working as a hatcheck girl in the Palisades—after she lost her kids to the state and went to prison for child endangerment, and before she got sober, became a nurse, and got my father back from his foster parents. She never went to the track again and would not discuss it, or the boyfriends, with him.

I only went to the track once with my father as a little girl. I might have loved the beauty of the horses, the pretty satin jackets worn by the jockeys, the thunder of the hooves, and the excitement in the announcers’ voices. But I didn’t like this place with its cement block walls, stark bleachers, and short bent men, even though I didn’t fully comprehend that this was my father’s true home now. It had been so, even before my mother left him—largely because of the track—which he only mentioned in his letters to us during my childhood when he could say he’d won.

On our outing, I also watched him place bets without any explanation of the how or why. But I saw him lose again and again. In fact, I never saw him win.

My father placed his first bet at the racetrack when I was six months old. He won $100. Just as quickly, he lost $100. In the decades that followed, he lost three women, including my mother and the girlfriend with whom he had my sister. Five women, if you count my sister and me. He also lost thousands of dollars.

When he finally received the settlement for a lawsuit he’d filed after a car accident that made him unable to work, and then promptly gambled away all of the money on which he’d pegged all of his expectations for five years, he nearly lost his life. He was so distraught that he planned to kill himself. His sister convinced him to go to Manhattan where she was living, and get himself committed to Bellevue, in order to seek entry to the cushy New York state social services program. It was a venture with enough of a wager in it to pull him back from the brink of oblivion.

The story of my relationship with my dad is really the story of his gambling. It’s a complicated touchstone because, as I’m well aware, it doesn’t sound that bad. Many people have survived truly horrific childhoods. And yet, gambling has a very particular impact: the many emotional divots it picks away at in the lives of those who are compelled to do it, and those who stand just outside the bright promise of their obsessive hope—and the dark fallout of its perpetual despair.

Only recently, when my father and I finally started talking about his gambling, and my relationship to him—the gambling, absent father—did I finally see that I had taken up my own form of gambling, having been conditioned by him to hold out hope against all odds.

You see, my father never stopped believing in the track, much as I never stopped believing in him. He kept spinning out promises between us: that he’d see me when his court case was settled, when his back was better, when he stopped gambling. In the years during which he pushed me out of his life, I never really stopped believing in him, but I also started to believe in something else more: my writing. I had no means of making my dad return to me, but I had a no-fail means of becoming a writer: I wrote and things got written.

Through the land mines of my father’s visits and the craters of his absence, I came to know everything there is to understand about gambling, and because it was hard-wired within me, I inevitably took it up as a pastime of my own. This is what I learned about gambling from my father, and through my own literary pursuits:

1) You will lose.
2) In spite of this and the increasing evidence to the contrary, you will expect to win.
3) You will lose again.
4) Just when you are about to give up, you will win enough, little as it may be, to resume hope, and you will be all in once again.
5) Most people will not understand why you do what you do. Those who do, who are compelled by the same compulsions, will be full of legends of those rumored to have won big—examples that keep the dream alive—and superstitions for getting into the winning circle and never, ever losing again.
6) Even with your legends, your superstitions, and your talismans, you will lose.
7) There are techniques you can master that will increase your odds of winning, but even after you learn them, such logic will be trampled by the wild stampede of emotion that accompanies your desperate desire to win.
8) Over the years, you will fall behind others who walk the straight and narrow and punch the time clock and measure their progress with marriage and mortgage.
9) You will vow to stop, but it is in your blood, and you will never stop.
10) No matter what else you gain in life, you will measure everything by the win.

I’m still a writer today, and so I guess, in a way, I’ve beaten the odds after all.