I’m staring at two diamonds in my hand and two on the board, with one card still to come. My opponent just placed a bet and is staring daggers across the table at me, as if his scowl could affect my decision. I consider the situation: if a diamond comes out next I will hit the flush and win, otherwise my hand is a steaming pile of crap. Should I call his bet and take the risk, or is the smart move to walk away with what remains of my money and live to fight another day?

Luckily there’s a clear answer to this very common situation, and (surprise!) it’s math.

Time for some quick mental calculation while everyone’s staring at me. There are 52 cards in a deck and I can see exactly six of them: two in my hand and four on the table. Of the 46 cards I can’t see, some are in my opponent’s hand, some have already been folded or mucked, and the majority are still in the deck that’s being dealt. Since I don’t have any information whatsoever about any of these cards, it doesn’t help me to think about these different categories. I just know that there are 46 possible cards that could come out next and exactly 9 of them are diamonds. A roughly 20% chance of making my hand. Not worth it, right?

Hold on a minute. Knowing the odds of success is extremely helpful because it tells me that I’ll win this hand about 1 out of every 5 times I play it (or 4:1 odds against). But there’s one more piece of information I need before either pushing my chips in or licking my wounds. How much did the sucker across from me just bet, relative to the pot? If he made a large bet, I’ll happily fold. Risking a lot on a slim chance of victory is just dumb. If, however, my opponent has made a blunder by betting too little, well then we might just be in business here. Let’s say the pot was already $500 and he just bet another $100. I’d be looking to risk $100 to win $600…and I’d win 1 out of every 5 times. I walk through five example hands in my mind: lose $100, lose $100, lose $100, lose $100, win $600. I come out ahead in the long run and I’m going to take that bet every time. Come on, diamond!

Stressful situations like this at the poker table are rife with opportunity — especially if you’re playing with my friends. Most of them just ‘play from their gut’ or some ridiculous nonsense. It makes it especially satisfying to see that last diamond come out and to hear them marvel at how I knew it would happen. But I didn’t know. I just played the odds. More often than not, a useless card comes out and they guffaw at how dumb my move was as they are scooping up all of the chips and I’m excusing myself to go puke. Regardless of the outcome, I sleep well at night knowing I made the smart move. Over time the chips eventually find their way home to me.

My relationship with the stock market is much the same, really. I place a large number of reasonable bets, knowing that they won’t all pan out. As in poker, the point is not to win hands but to win money.  I continue to collect a bunch of small losses and large gains, watching my portfolio get larger and larger as the years march on. It’s no different a feel than ‘gambling’: I’m still putting my money down on the table because I think I’m observant and astute enough to come out ahead, and I still don’t sweat the inevitable dud.

Due to my good “luck” in the stock market during my early thirties, I found myself in a position to make an even larger bet. I started my own business. As always, I analyzed the odds and carefully considered the risk/reward topography before committing my proverbial chips to the pot. This one was worth a shot.

What came next wasn’t a diamond. It was more like a club.

I’ve struggled for two years with the fallout of that decision. Anger, self-loathing, despair. It’s so easy to retroactively question my decision or to invent reasons to blame myself for circumstances out of my control. At the end of the day, we have to own our choices and play the hand we’re dealt.

Today I started my second business. This one is worth a shot. Knowing that a play like this might work out about one in five times is enough to make it worthwhile. It was basically my entire dating strategy, before I won that whole damn game (2016 champ).

Like poker, life is a game of both skill and luck. All you need is a chip and a chair, and you can start to climb your way up the ladder one decision at a time. Fortune comes and fortune goes. Just because you get a bad beat, it doesn’t mean you made the wrong move.

My problem is that I’m always too many steps ahead. I know that sounds like a humble-brag that’s light on the humble,  but it’s a real problem.  I can’t be here while I’m absorbed in potential futures. My fixation with efficiency and preparedness paralyzes me from doing anything noteworthy. I get overwhelmed by too many variables.

Imagine a world class chess player sits down for a fresh game at a tournament. She surveys her options and starts to reach for her white king’s pawn to move it to e4. It’s a completely standard opening move — more games start with it than don’t.  It allows you to free your queen and bishop and gives you control of the middle of the board. She of course knows all of this, and she knows that her opponent is likely to march his own king’s pawn down to e5 in response. Or possibly his bishop’s pawn in the Sicilian defense. That would be tricky of him. He could even pull out his knight and go with the Nimzowitsch Defense if he’s crazy. He looks kind of crazy, she decides, so she pulls her hand away from the king’s pawn. Better to think this all the way through.

The next option would be to open the game by moving her knight to f3, the good old Zukertort Opening. Of the twenty legal moves on this opening turn it’s one of the most popular, the strategy being to maintain flexibility and get the powerful pieces out early. And what would happen then? In response, the black player may play it safe by moving his knight in a mirrored response or go for a power grab in the center of the board with his queen’s pawn — or even move his bishop’s pawn in an attempt to shoehorn her back into the Sicilian Defense after all. But what kind of Sicilian, open or Najdorf? Fischer and Kasparov built empires on the Najdorf, an unstoppable chain of attacks and reprisals. How many pieces would she lose? What if she lost this tournament using the same opening as Bobby Fischer? Would that mean she’s not as good? Could she face coming home with nothing to show for it?

Suddenly everything on the board is not so black and white. Better to just walk away without making a move at all. This is exactly why I don’t play chess.

I live in a state of disbelief. Year after year I convince myself, in the absence of any evidence whatsoever, that the Cleveland Browns have finally turned it around and could make the playoffs. I did it last year, I did it this year. I promise I’ll do it again next year, reality be damned.

We finally have a quarterback, I say. The offensive line was vastly improved this offseason. We’ve piled up valuable draft picks- that rookie is the real deal! The schedule looks easy. The division looks weak. The fans are thirsty. We finally have a quarterback (for real this time)!

And year after year I sit in stunned disbelief as my optimistic dreams crumble before me, one interception at a time. The rose colored glasses turn a depressing brown and orange as the losses continue to stack up. We haven’t sniffed the playoffs in a decade and a half. We haven’t celebrated a single victory since last Christmas. As of this writing, the team has lost 37 of the past 39 games with no predictable end in sight. This level of ineptitude is frankly unheard of outside of federal bureaucracy or a Three Stooges marathon.

But it will work this time. If Corey Coleman can stay on the field and Josh Gordon can stay off of drugs we’ll have a shot. If Joe Thomas doesn’t retire and Brian Sipe suits up and Lou Groza comes back from the dead. History gives me absolutely no reason to believe, but that just means we’re due. Right?? Hand me my rose colored glasses!

In the scientific world, this behavior is known as confirmation bias- the tendency to interpret information in a way that backs up what you already believe (or desperately want) to be true. You notice all the things that confirm your predetermined hypothesis while simultaneously refusing to see anything that refutes it. It’s honestly not all that different from today’s political discourse, where we fault the “other guys” for acting a certain way but then act oblivious when a member of our chosen team commits the same sin. We make excuses, we grasp for any reasonably logical explanation of why it’s different this time. We don’t notice how our attitudes depend so much on whether there’s an ‘R’ or a ‘D’ next to a name. We just know that our team is the one who will make the world a better place if we can get them in office and keep them there, reality be damned.

But let’s face it. The Browns suck.

How bad are the Cleveland Browns? They won only one game last season (out of sixteen).

Of their last 37 games, Cleveland has lost 33.

I was…

• 30 years old the last time the Browns had a winning season
• 17 years old the last time the Browns won a playoff game
• 12 years old the last time the Browns won their division

I turn 40 this year. It’s been a rough life. Go Browns.

I love me some football playoffs.

The regular season is fun to watch, with all the divisional rivalry and week to week story lines, but let’s admit it: the playoffs are why we’re all here. It’s the measuring stick between a good season and a disappointing one. Just over a third of teams (twelve out of thirty two) are invited to continue their season after the initial sixteen game tryout period- most are politely thanked for their participation and packed away for the winter. This last dance is only for the fighters.

And fight they must. Twelve teams, eleven games. Each playoff game seals the fate of one team’s season permanently. Rookies who have never met defeat so intimately show their young emotions. Veterans start to eye retirement. Old records fall and new highlight reels are born. Periods are placed at the ends of sentences.

It is special because it is so final. It is special because it is sudden and short. In the playoffs we discover what a team is, and nowhere else. There are twelve and then there are eight and then there are four. And then there are two.

Professional basketball teams play 82 games a year, and for baseball it’s nearly double that. If the Cubs lose 14 games in the month of July (they did) it’s not a big deal and they could always make up for it with a lot of wins in August (they did) and go on to finish with the best record in baseball (they totally did). It’s a game of averages, exposing the true value of a team over time. If you think about it, the difference between the best team in baseball and the worst is that the worst wins one out of every three games, and the best wins two. A single day at the park is almost meaningless: just another statistic to throw on the pile for later analysis.

But in football, every game is a big deal. There are only 16 in the entire season and you need to win about 10 of them if you think you’re going to the playoffs. It makes each game feel like a performance art of sorts. Dropping a few in a row can set off the panic alarm among fans and pundits. If you’re a normal team you handle your losses in stride- maybe tell your fans to R-E-L-A-X and then go on to lead the league in scoring.

But not my Browns.

With three games left, we sit at an impressive (though not the good kind) 0-13 record. That’s zero wins and and an ocean of failures. Yikes. If we look back at last season as well, Cleveland has lost 23 of their last 24 games. Obviously that wasn’t counting this year’s four preseason exhibition matches, where the Browns lost…let me look it up…oh that’s right: all of them. If you’re not a football fan you likely don’t appreciate just how historically bad this team is. Someone will write a documentary about this one. Ken Burns is probably licking his chops right now.

The thing is, I just love the goofballs. I can’t be mad. The Cleveland Browns remind me of family and childhood and road trips. I grew up watching them bumble their way through Sunday afternoons and I’ll likely die the same way (soon if they keep losing like this). They serve as a reminder that things don’t always go the way you’d like and you don’t have to win to be loved, but you’ve got to keep pounding away at that wall and at least you’re not a Steelers fan. Hallelujah.

As the weather gets colder I realize that I gave away all of my winter clothes with the lone exception of my hooded Browns sweatshirt. The condolences I receive wherever I wear it are precious to me. They give me an opportunity to remind folks of our team motto: We’ll get ’em next year.

Hope springs eternal. Go Browns.