Playing the Odds

Sometimes our lives take us by surprise. There are things that everyone else knows about us – that in fact they take for granted – that we stumble to as something foreign, something that we never really considered. This morning I arrived at the realization that I’m a gambler. This comes as an unexpected revelation; I don’t spend a lot of time in casinos, I don’t have a bookie, I don’t get online and contact Costa Rican betting parlors to parlay the odds on college football weekends. On the one or two occasions that I’ve lost a grand at the craps tables, I about puked. But still and all, opening my eyes to this dreary and cool October Friday in Chicago, I realized that gambling is the way I’ve run my life, ever since I walked out of my father’s house with just the clothes on my back, some thirty years ago, and set out on my own.

A few years after that, I scrimped, kowtowed and connived to open my first restaurant in Tampa, Florida; that didn’t work out so well. Then, deeply in debt, I placed my trust in an acquaintance who told me he had a surefire way to make a pile of much needed cash. Oops. There’s a reason the old saw was constructed about looking closely at things that seem too good to be true. Yes, I’m a gambler but I’d like to think I’ve learned a little since then about hedging my bets.

When the Florida chapter finally closed, I moved to Chicago. Fourteen months in, I left a perfectly good, salaried job, to go to work in a bar. My boss told me I was crazy. Four years later, I owned that bar, Sheffield’s. Now that was a good roll of the dice. We opened The Silver Cloud in ’94 – another Home Run! Then, over the course of the last six or seven years I lost, in succession, a hot dog stand in Omaha, an information services company and an import business that I’m still paying off. None of those, no matter how earnestly conceived, worked out. So what did I do? I opened another restaurant, taking out a huge chunk of equity to make it happen. It’s pretty dicey, and I’m on the hook for a big chunk of dough. But this restaurant will work, I’m sure of it. We’re in a great location, we’ve got a great space, the neighborhood is crying out for us to be there. The catch is we’ve got to be able to hang on until we click. Gamble? Maybe a little.

My friend Marcus Sakey is a talented young author with four novels published and the latest on the way. He and Sean Chercover, another friend who’s also an excellent and published novelist, were at Sheffield’s the other night. They sat in the beer garden and we shot the shit for a while. When I turned to go I realized that I wanted nothing more than to stay there with them, talking about writing and the business of writing. My buddy Craig Gore, in LA, just sold a pilot concept to Fox. We can sit and talk movies all night long. Since it’s already clear that I’m going to gamble with my future, theirs is the table I’m going to be sitting at, working until it’s my turn and the numbers fall my way.

Another legendary chestnut maintains that nothing’s certain but death and taxes. Those of us living in Chicago know all about the taxes thing. I like to think that the death part is a long way off yet, but you never know. Every day above ground is a gift.

Writing’s a journey that never ends, but the best part of life is the journey. We’re all traveling along a long, bumpy road, but it’s better to be traveling than to reach the end. So when I get impatient about the time it’s taking for the new Sheffield’s to get off the ground, or when I fret because my current novel still needs work, I have to remind myself to slow down and enjoy the ride. It’s about the process, not just the results. If you look at it that way, the results don’t seem quite so important, whether we win or lose. Just as long as we’ve got our chips in the game.

— Ric Hess, Oct 23, 03:54 PM

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