Look on the Dark Side for a Change

Playing the "And Then What Game" 'til you strike gold.

“Make the best use of what is in your power, and take the rest as it happens.”
— Epictetus, Discourses 1.1

I think I’d have fun as a homeless person.

Before the censorious types string me up for failing to mention the many horrors of street life, hear me out.

We all have fears. Anxieties. Things we would like not to happen.

Since I’m self-employed and there’s no twice-monthly paycheck coming, I could run out of money. Sometimes business is slow. If I look at my bank accounts and see my reserves declining, it doesn’t feel good.

There is a chain of thoughts:

1. I could run out of money.

2. I could lose my home and end up on the street.

3. All this would suck beyond measure. Life would be hell.

This chain has played out countless of times over the last 15 years.

But think of your anxieties, the ones keeping you awake at night. You’ll probably realize there’s a string of assumptions underlying them.

Someone you love dies. A romantic relationship ends and you’re left all alone. Disease strikes and you lose physical abilities or life itself.

These strings usually end with “and then everything sucked forever,” and we tend to leave it at that. Our anxieties sting, so we try to avoid exploring them in detail.

But I find there’s a better strategy — stripping them of power entirely.

Playing the “And Then What Game”:

Think of anything you dread. Consider how it might come to pass, and then what your life would be like once it occurred. What would your day-to-day be like? How would you attempt to make it tolerable?

I play this game with my running out of money anxiety, and I’ve come to realize something — there are elements of being broke and homelessness that sound downright enticing.

I wouldn’t choose to be homeless, but if it was thrust on me I’d be eager to try some things:

• There are food banks and soup kitchens and dumpsters to dive outside grocery stores, and I suspect I wouldn’t starve.

• There’s a big library downtown, and it’s full of books! I could go there and read all day. This is luxury! How many times have I wished for more time to read? It’s also got computers so I could write too.

• I see the fire-and-brimstone bible thumpers on the street, promising eternal torment. I’d like to set up on the opposite street corner and try some things out. Some days, I’d read a Shakespeare play, playing all the parts and hitting the falsetto female voices like a boss. Another day I’d read some of Seneca’s letters to passers-by.

• I’d lean into my inner Diogenes and see what sort of mischief I could get into. The homeless people I see have phones and sometimes even laptops, so I’d start recording Menippean satire Youtube videos and “homeless man V-logs.” Maybe I could be a homeless influencer? I suspect it would be way more popular than this newsletter!

• Maybe from these endeavors I could earn enough money to have regular showers, wash my clothes, and have toiletries, since I prefer not to smell and be dirty.

• I could see if my experiences with virtue hold up to the hardest circumstances. Is virtue really enough for flourishing when times get brutal?

And I could go on. I’m sure homeless life is hard, but it does offer some enticements.

By playing, “and then what games,” with running out of money and all other anxieties, I’m able to render them toothless. They may temporarily rear their head again, but I just remember the chain of “what ifs,” demonstrating that life would be tolerable, and then they deflate.

Virtually all hardship is the same. Each new “disaster” is fate’s opening gambit in the great Stoic invincibility game.

Each is a chance to grow, learn, and overcome. No matter your anxiety, opportunities to be your better self would increase if it showed up.

This realization — that things settle, become tolerable, and joys may be found even “in hell,” — is one of the most calm-inducing thoughts we can bring to bear on life.

Life will go on, we’ll adapt, or we’ll be dead.

I can live with that.

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