I have recently become reacquainted with the drama of booking a flight.

It is a fraught decision-making experience. Not only must you navigate existential issues like, “Am I even going to be the same person seven weeks from now? What if I’m not alive? What if I don’t want to go on this trip?”, you also have to deal with logistical ones, plus shifting and unpredictable prices that create a sense of urgency and FOMO. As much as I love travel, I do not love this process.

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When I was a performing songwriter, there was one moment when I was onstage somewhere and thought, “Why on earth should I bare my soul to these people?”

Back then, most of the songs I had written were like the songs I had been hearing singer-songwriters perform for most of my life. They were confessionals about love and romance and adjacent topics. You know, feelings and stuff. This material was so entrenched that I couldn’t seem to write about anything else.

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I was once in a relationship with someone who, I see in retrospect, didn’t like me all that much.

He would point out aspects of my personality or habits, like how long it takes me to leave a party, my sleepiness late in the evening, or my tendency to focus obsessively on a skill I’m trying to master, with a critical eye.

It took me a long time to realize that a lot of the things that he brought to my attention weren’t necessarily defects I had to fix. They were simply traits, neither good nor bad.

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Many of us are used to rules and accept them without question.

For some of us, they make us feel safe and comfortable, like someone’s in charge.

For others, they are begging to be tested, contested, rebelled against, bent, and broken.

Each of these tendencies are valuable and necessary. A society in which everyone is constantly questioning the rules has no peace and stability. On the other hand, a society in which everyone always follows the rules, no matter what they are, veers toward totalitarianism.

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Monopoly is an awful game.

It takes forever to get going and forever to end. It involves too much luck, even without “Free Parking” jackpots.

And once someone starts winning, their victory is irreversible and soon makes the game miserable for everyone, even the winner. It feels icky to be the greedy landlord, riding high on your ill-gotten gains, relentlessly collecting rents in some dystopian Atlantic City where you’ve already bled your tenants dry and sent your own siblings to jail.

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