My favorite game as a kid was called Bigger and Better. I seriously doubt it’s still being played by roving packs of unsupervised kids today. The game started with two teams, each given something small and ordinary—like a paperclip or a pen. Then, for an hour, you’d run around asking strangers to trade it for something “bigger and better.” At the end of the hour, both teams would return to compare final objects and see who had traded up the most.

One time we returned after 5 trades pushing an old car. Another time it was a couch. There were a lot of paths to take in Bigger and Better. Sometimes it was only a few long-winded trades, others we dealt in speed and volume. You had to work together and make a team. Who was the smoothest talker in the group? Who was the muscle to move the damn thing down the road? Who could decide which houses to hit up or not— did they have a lot of stuff? Were they willing partners? Would they be inspired or annoyed? Did they need or want what we had? What was the strategy? Bigger and Better might be the closest I ever got to business school.

I loved the unknown. The optimism required. The scramble. The lightness in which we held each object knowing it was about to be traded. The teamwork. The competition. Most of all I loved the possibility. What would happen next? Bigger and better could be anything, anything at all.

I often think about this trade-up game, and it is clear as I have gotten older I seem to have slid into more of a trade-off game. Everything costs something. Time, energy, money, one opportunity means saying no to another, roads not taken. It is no longer asking for something bigger and better. It is a lot more asking “how?”

My dear friend Lynn Casey calls them the cursed hows— when logistics block imagination. Purpose traded for impossibility. Limits set the course. Boo. I am tired of my own limited thinking, health bullshit, protocol, and departments of tradeoffs costing us what connects communities.

Confession. Every month or so I buy a lottery ticket*. I do this for one of two reasons. One— my mom loved the lottery, so sometimes when I acutely miss her I buy a ticket. Some people see their loved ones in sparkles on the ocean, or birds, butterflies, feathers. My mom shows up in lottery tickets. The second reason is that it is a cheap, fast shortcut from feeling stuck to getting back to a mindset of possibility. It is also clarifying to ask myself if I won what would I do? Would I keep the job? Start something new? Where would I invest? Give? Work? Rest? What would I do first? And the wildly revealing question: Who would I tell?

So I trade a couple of bucks to unstuck myself and my mindset, answer some big questions, and push myself out of the “cursed hows”. That isn’t so bad. But I want trade-UPs, not trade-OFFs.

I want to play my life-sized game of Bigger and Better. For me, of course it starts with a pen. So I write. A newsletter. A chapter. A book. A screenplay. Another. Trade UP. Only UP. UP UP UP. Trade-offs get a giant buzzer sound from a failed move on a game show. XXXXXXXXxxxxx. Trade-ups get a DING DING DING. Trade up or not at all. What could be bigger and better than that?

*(I KNOW the lottery is not a smart financial move. It is not my intention. Thanks.)