How to live a non-boring life

I work a job where I’m surrounded by rich elderly people. For most of them, most things in their life went right. That’s not to say that they never suffered, that their spouses didn’t get cancer or dementia, or that they don’t have the same human capacity to feel pain as the rest of us. 

But largely, the things in their lives went the way they wanted, which is how they ended up at my facility. 

I say this after months of talking to them, being intentional, and listening to their stories. My job is to relate and connect with them. 

But very often, I’m bored to tears listening to them. 

Their stories are largely about living comfortably in various states, vacationing to Italy, and enjoying a steady string of promotions in the corporate world until they retired and came here. It all went right.

Yesterday I was on a run on my normal path. There are often a handful of homeless people along this trail. Probably because it’s minimally patrolled and relatively comfortable in the woods, while not being too far from civilization. 

Often, they’re just asleep in their sleeping bags as I pass by, but last night, I passed a couple who was walking along the path. It looked like they had all of their possessions on their backs or in their hands. Their skin was tanned and their sloppy tattoos were faded by the sun.

And more than any of the people at my work, I wanted to hear their stories. I didn’t talk to them, but I imagined it involved a lot of train hopping and sleeping outdoors and maybe a few fights.

The woman walked with her hand looped through the arm of the man, and it made me curious about how they met. And what is it that makes them so connected that they’d walk like this after so many miles? What traumas have they been through that bonded them?

In the few seconds I saw them, I was more interested in them than any of the people for whom everything went according to plan. Because it looked like many things in their lives went wrong. 

In one of Chris Guillebeau’s recent posts, he said that “The things that go wrong make the best memories.” Think about all the stories you’ve heard where you were dying to hear the end, how it all worked out. Are any of them when everything goes right and there is no peril?

Even the most exciting thing someone could do is somewhat boring when it all goes right. Like, skydiving is a rush for the person doing it, and they may relay their experience of the sensations, but it’s not the same quality of story as something simple that went wrong. “Yah, we went up to 12,000 feet, jumped out, felt the rush, deployed the chute, and made it safely to the ground.” 

It’s the same with travel, if all goes according to plan. You went to Rome, photographed the same historical sites as everyone else, and came home. And you want a Pulitzer?

But think about doing a mundane activity where something went wrong. Immediately there’s a story people want to hear. 

For example, one of my favorite stories is from my uncle, who showed up to clean the grill hood at a Wendy’s, as was his job. But no one had told the two girls closing that they’d be coming at midnight to clean the hoods, so when they used the key to enter, the girls locked themselves in the bathroom and called the cops. 

Within minutes, my uncle and his employee were on their knees with laser sights on their chests. The cops asked my uncle why his zipper was down. Then looked at his employee and asked why his zipper was also down (It was just an unfortunate, hilarious coincidence). Eventually, they contacted the manager and found that they were, indeed, there to clean and not rob the Wendy’s. 

The first time I heard the story I was sucked in and dying laughing. 

Was my uncle doing anything amazing or enthralling like backpacking the Sahara? No, he was cleaning a grill hood at a Wendy’s. But because everything went wrong, the story is the best. 

It makes me wonder about the way we live our lives.

Corporate culture has created a path to cultivate safe comfort so that those in charge can maintain their work force while offering a seamless path from a comfortable hire to a comfortable retirement. You need not take a risk ever again; arriving at the grave will be a simple transition for your soft bones. 

In my life, I’ve made few moves that involved a whole lot of risk and when I look back at the past decade or two, it would be nothing to write a novel about. No film will be made about my 20’s. 

Think about how we’ve been coddled into complacency. 
If you’re entertained, you’re living. 
If you need a boost, treat yourself at the mall.

Really? 

Comfort and entertainment is the highest we can aim for? God gave you this untamed thing called life and the craziest planet in the cosmos and we settle for that?

Of course, I don’t want to end up like the homeless couple — not intentionally, at least — but I also don’t want to make my life decision based on the question, Which option will bring me the most comfort and be easiest?

Would you want to watch that movie? “The story of Stan, the man who chose comfort and most things generally went right until he died.” 

Why not occasionally make decisions where there is a very real possibility that something goes wrong? If it goes wrong, you get a great story. If it goes right, then you advance. Win-win.

There are so many tools that have already been established to sort through these options, like Tim Ferriss’ fear setting, or the Japanese idea of Misogi. 

All of this has been discovered and discussed before, but perhaps it’s time now for us to ask the question, what sort of life do we want? A comfortable one or one worth writing about? The last line of my favorite film is, 

“We’re going to live like we’re telling the greatest story ever told.” 

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