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We are always playing with the house’s money

I used to be so uptight about everything. I’d agonise over decisions, how to behave, what other people thought of me, what I thought of me, how to live my life "right", how not to make mistakes. The list is longer than that, but those themes have it covered.


As a kid, I remember playing "snakes and ladders" with my older brother (I think it’s "chutes and ladders" if you’re from North America). One hundred numbered squares on a board on the floor. One red and one blue plastic disc to mark which player was where on the board. One 6-sided dice. The first one to get to square 100 from the start on square zero wins. Various scattered cartoon snakes laid in wait for one of the plastic discs to land on the dreaded square, sliding that player back down toward the beginning. Those joy-filled ladder squares which took that player’s marker up toward the winning square. Two boys in home-knitted sweaters and 1970s bowl haircuts, trying their best to win, beat their brother and claim bragging rights. For all of one minute. Until they started to play again.


As each game progressed, the tension rose. In me, at least. I’d hold the dice in my fist a little longer. I’d roll it in there a little longer. I’d will it to land on a good number a little longer. I’d blow into the little gap between my thumb and forefinger for luck. The stakes were high, so all these rituals made sense. Except they didn’t. There was no skill in this game. No strategy. No decision-making. Just luck. I had no say in which number would face up when the dice came to a stop. I don’t think I realised that as a kid. I had to have some kind of say in winning or losing. Nope. None. All I ever had was ‘roll the dice and see what it lands on’.

I first hear the phrase “playing with the house’s money” around 12 years ago. It refers to the idea of going into a casino and play each game with a sum of money the casino gives you at the beginning of the night, for free, to play with. Whatever money remains at the end of the night is handed back to the casino. Then, comparing it to a night at the casino when the same person is playing with the same amount of money, but it’s their own ‘hard earnt’ cash. And they take home whatever money they have at the end – as normal. When I heard this, I could sense the difference in those 2 situations. One would be more fun, with free thinking, free from pressure. The other would be like me playing snakes and ladders as a kid: tense, feeling like there was a lot at stake and a lot less enjoyable.


It made sense, but I didn’t get it. Of course, there’d be a different experience if I were playing with my money compared with the money that was given to me. “So what?” I thought. “How does that help me navigate this thing called life?”


Fast forward to January of this year. I’m a huge American Football NFL fan. Anyone who knows me knows not to try to call me on Sundays after 2 pm UK time from September until mid-February when the NFL season runs. I watch 4 hours of the pre-game show, and then from 6 pm, the Sunday games start until sometime after midnight. If my team, the 49ers, are playing, my neighbours are glad I live in a detached house: I can get a little loud. I watch 2 hours of an NFL News show every weeknight.


As the final 14 teams geared up in January for the playoffs to decide the year’s champion; various views were shared on the chances for each team. One aspect that cropped up by one of the presenters was the notion that one of the teams, the Jacksonville Jaguars, was playing with the house’s money. He went on to say: “No one expected them to make it this far” and “They’re ahead of the rebuilding program they started this year” and “They’ll play loose and will be dangerous to anyone, including teams that are, on paper, better than them”. He had a point. For the previous 2 years, they’d had the worst record of wins and losses in the league.



They’d been bad. And here they were, in the playoffs as one of the 14 teams who had a shot at winning the Superbowl. He also said how much pressure and expectation there was on the teams who had expected to be there and had the best won-loss record.


In listening to this, I shook my head. Playing free or feeling pressure have nothing to do with the past (their won-loss record in the season), nothing to do with the odds of winning set by bookmakers, nothing to do with sports writer’s points of view. That those feelings only ever come from the relationship we have with our thinking in every moment.


The next thing I thought was “Every team is playing with the house’s money. We all are. Always. Throughout our lives”


That thought had such clarity and truth in it. I wondered what made that look so true to me, when until then "playing with the house’s money" seemed, at best, like a nice idea.


I always knew that life has one ending. The same for all of us. I’d been uptight for so much of my life in spite of knowing this inevitable outcome. Every game ends. Every life ends. I’m sure there’s no scoreboard on my deathbed. If there is the meeting with my maker after I cross over and I’m made to look back at my life with the good I’ve done versus the bad I’ve done; I know I don’t have to tally that up every night to make sure I’m on the right side of the equation when I die. My internal guidance system, my "north star" takes care of my doing. I have that sense built into me. It’s how I’m made, and how everyone is made. Yes, I’ve made mistakes, and I’ve been mean at times. I’ll make more mistakes too. That’s also inevitable.


There’s a sentence one of my mentors said to me some years ago that is ringing in my ears as I write this and try to articulate what I’m getting at. “The only risk in life is to feel bad for a while”


I’d spent decades of my life doing everything I could to avoid feeling bad. To avoid disappointment. To avoid self-recrimination if things didn’t go well. Playing small. And hating it.


I forgot that I get over disappointment. 100% of the time. No exceptions.


I forgot that I can not live and avoid feelings. That’s impossible. I forgot that the harder I tried, the more "bad feelings" I had, and the longer I felt them.


I forgot that playing any game means rolling the dice. That the more times I threw, the more sixes would show up. I forgot the statistical fact of that.


I forgot that holding on to the dice longer to avoid falling on the snake (or chute) square meant the ability to play less games. Less of the ups and downs of that game and the bigger game of life.


What is ever at stake in everything I do or don’t do, whether I win, lose or draw? A feeling. A temporary thought-created feeling. A feeling that has nothing to do with my value as a human or who I really am.


In that moment, I remembered the truth: I always was and always will be, playing with the house’s money.

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