I am presently up in Vermont at my father’s house, which is blanketed in a nice fluffy layer of snow. Yesterday I had the great pleasure of playing Scrabble not once but twice, with two of my all time favorite Scrabble opponents: my father and my friend Christyn.

While playing these games I was reminded of one of my most effective life strategies that I learned from playing Scrabble back in my teens.

Christyn and I met when I was 13. She was the cool new girl in 8th grade. Her family had just moved to Vermont from Long Island, NY and she seemed very metropolitan. She wore hip sweat suits and bunchy socks that were strange and stylish looking. She listened to A Tribe Called Quest and all the boys were magnetically drawn to her.

I was emerging from a very awkward braces/bowl cut/dog-showing phase and didn’t know if I could hang with her. But fortunately we managed to become friends… a friendship that has lasted over 20 years.

One of our favorite activities during those teenage years was to go to a coffee shop called Muddy Waters in downtown Burlington to drink coffee and play Scrabble. Muddy Waters is an iconic hippy den with tons of tea varieties in jars and giant chocolate chip cookies and angry Sharpie graffiti in the bathroom about peace and human rights.

If you’re a Scrabble player, you know that a central conflict you often face throughout the game is the question should I play this great letter now? Or wait til next turn to hold out for more points? 

For instance, if you can get an “x” that is worth 10 points, on a triple letter score it’s suddenly worth 30 points. But what if there are no triple letter score spots open and you can put it in an okay spot and only earn 10 points from it – but that’s still the highest points you can get in that turn?

MY policy is this: Always play the best word you’ve got. NEVER shortchange your turn now to hold out for higher points. ALWAYS get the highest points you can with what you’ve got in front of you. Although there might be a few instances where I could’ve earned more by holding out, I believe the sum of steadily playing for the best points I can get each turn throughout the game is higher.

Yesterday when I was playing with my dad, this winning strategy proved itself beautifully. I had two blanks (they can be whatever letter you want, so are rather precious). On my turn, in order to get the highest points possible, I’d have to basically burn both of them. The point count for the word was going to be pretty shitty – like 12 points or something. But it was the highest possibility I could find.

Staying true to my strategy, I did it and dropped the blanks for a meager earning of points. Then on the next turn, the triple word score freed up and with my fresh batch of letters I could spell the 7-letter word “TOUCHED”. I placed “TOUCHED” nicely on the triple word – earning me a total of 52 points. Plus I got 50 point bonus for using all of my letters. Total points for that turn = 102. F#ck yeah!

If I had not been willing to let those blanks go, I would not have been set up to knock it out of the park with “TOUCHED”. Which definitely caused me to win the game.

This is a strategy I literally use ALL THE TIME in my life. I don’t save ideas for tomorrow. I don’t hold out with compliments. I don’t wait for a better moment. I play the best that I’ve got in this moment. And trust that it’ll add up to my highest score in the long run.

Or as Janis Joplin says, in one of me and Christyn’s favorite albums from our teens, “if you got it today, you don’t wear it tomorrow, man! Because as a matter of fact, as we discovered on the train, tomorrow never happens…. it’s all the same fucking day man.”

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