What Makes a Story Worth Telling?

Read to the end for a smart response to last week's Cool Dude Zone

Very quickly before we begin — I am never going to charge for my Substack, but I am really enjoying writing on here, and I feel like if I can get a couple hundred subscribers, I might be able to start doing it more regularly (also I am not employed full-time at the moment so every little bit helps). If you feel like contributing, I would really appreciate it. If not, I still appreciate you reading. Thanks.

A few weeks back I asked in Substack Chat what you all would like me to write about and reader jay (no last name given) asked:

“What makes a story interesting and worth telling to you”

I remember looking at it like the apes in 2001 looking at the monolith, because it was a question that seemed so … familiar and alien at the same time. It took me a minute to make heads or tails of it. I have literally made a career of telling stories, but it is strange to actually try and map what makes a story worth telling.

I mean the first thing is that it’s not the story itself, it’s how the story is told. There are a ton of stories that are worth telling that simply don’t get told because they haven’t found the right narrator. At least half of what makes a story worth telling is how you tell it. But that’s just half of it.

So let’s talk about what makes a good story for me. I think that every story that I have made that I am proud of has all of these elements.

1. Conflict - There has to be some kind of problem or disagreement. It doesn’t have to be between two people — maybe someone is upset that a deer keeps crapping in their yard, or there is a tree branch blocking a perfect view that is just out of reach. Maybe it’s like Modern Times where the conflict is between Charlie Chaplin and the industrialized world. But there has to be some point of disagreement between two things.

2. Stakes - Someone has to care! They don’t have to care a ton, but they do have to care — the conflict of the story has to impact them in some way. One of the most common stories we got pitched on Reply All was “hey, I have been getting email for this person who has a similar email address to mine for years.” Which has conflict, sure, but the impact as so minimal it did not rise to the level of caring. Now if someone reached out and said “hey, I have been getting email for this person who has a similar email address to mine for years, and I am suddenly receiving deeply personal emails from their estranged parents, and I feel like they need to see them,” that feels like at least the kernel of a story to me.

3. Surprise - When we recorded Reply All, we would always record the conversations with one host going in blind. We were so religious about this that we would often kick one host out of pitch meetings while the other did his pitches. Now, surprise can’t just exist as a reaction from a host - the story actually has to carry that surprise. But it’s a huge and important part of an exciting story. Sometimes the surprise makes the story. Take, for example, the story “The Snapchat Thief,” which is a Reply All fan favorites. The initial email for Lizzie was just “my account got hacked and then when I got it back I got a threatening message.” That’s a shitty thing that happened to Lizzie, but on its own it doesn’t rise to the level of a story. But when I started to investigate who might have taken it, and found a barely underground community of teenage hackers and reprobates that frequently break the law cop accounts with usernames like “lizard” and “fuck,” that was the moment it became a story for me.

4. Movement - Starting in one place and end in another. This can mean either actual physical movement — start in one location, end somewhere totally different — or emotional movement — start someplace sad, end someplace happy. This is also a form of surprise sometimes? Sadness in happy moments, silliness in devastating moments, those are both surprising and wonderful. I think one of the personal anecdotes I tell that tends to get the most laughs is about when I got run over by a car. It wasn’t funny in the moment, but man, a lot of people act very silly in moments of crisis like that. And of course that story has movement in that I go from blithely riding my bike down the road to the hospital to and insane recovery that left me forever changed in body and spirit.
   
   There is this excerpt from a Kurt Vonnegut lecture that gets passed around among radio circles like it’s a Rosetta stone for making the perfect story. It’s not quite that simple, but it is a really helpful way to think about what gives a story movement and surprise. If your story crosses that line Vonnegut makes on the X-axis a couple times before it ends, it generally has more heft than one that doesn’t.

5. It’s about something bigger - Again, it doesn’t have to be about something much bigger. But a good story generally says something bigger about the human experience. A good fiction story usually isn’t only about its protagonists - it’s about the systems they live in, or the ways people interact. The same is true with non-fiction. “The Snapchat Thief” is about someone getting their snapchat account stolen. It’s also about the fear inherent in living online, about teenagers becoming self-aware, and aware of the way their behavior impacts the larger world, and how the architecture of the internet facilitates that theft. It shows you something larger than the immediate story whether you realize it or not.

6. Conclusion - This is the hardest one for me, because let’s be honest, almost no story has a tidy ending. There’s a Jawbreaker Song called “Bad Scene, Everyone’s Fault” about going to a local show and running into an old friend. It’s full of heartbreak and observation about feeling out of joint with your music scene and maybe outgrowing a small down, and then it abruptly ends out of nowhere with the line “Then the cops showed up.”

   
   I wish every story could end like that. Unfortunately, endings usually require a bit softer a landing. And somtimes it feels a little manufacuted! A little artificial! I tell a funny story about the time I got run over, and it ends tidily with my recovery. In real life, I still have hardware in my leg and it still hurts all the time. The trauma of that experience will be with me for the rest of my life. But with a story you find some point to leave it that makes sense. It doesn’t have to feel completely wrapped up, or happy or even hopeful. It can feel oppressive, lonely, insurmountable. But it has to feel like it makes sense given everything that came before.
   
   

I have worked with people who have this all down to a science, in that they can look at a story like one would a mountain range and see all the ways it works and ways it doesn’t. That is not me. When a story works for me, I often have a hard time explaining why. It just feels right. But being able to point to all of these pieces, cobbled together over however long I’ve been making radio, has certainly helped me justify certain storytelling decisions and helped me change others.

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Last week I wrote about depression, and what it feels like to talk to someone who doesn’t know depression. I received a very kind message from a reader named Julia Goldman (no relation) that resonated and I would like share part of it (with her permission):

I…don’t think there’s anything wrong with you—I think that the mental health system is broken. I believe that to your point about the two options is flawed, though. It’s not *just* changing perspective or the chemical in balance in our brains—it’s both. It’s both AND putting in the work to rewire our thinking patterns. You mention the “thinking positive thoughts” to prime your brain. To me that’s sort of right, but it’s more of challenging your thought patterns. Noticing those negative thoughts and questioning them. Working down to the root issue and analyzing it. Self awareness and self reflection, accountability and ownership of emotions, feelings, and actions. It’s acknowledging that yes my brain is sad, it’s wired that way, but it can also learn and change. It’s not static.

I think she’s correct that I might have been creating a false dichotomy, and soaking a bit in learned helplessness in a deep depressive episode. But when you’re that deep in the chasm, it’s very hard to have any kind of perspective, and I appreciated her being able to look at it from outside of the chasm and tell me something I know instinctively but always hate to hear — there aren’t really any easy solutions. The only way out is through.

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A big thanks to everyone who joined me on my Zelda stream to raise money for the National Network of Abortion Funds. We closed out the marathon with $3,035 in donations, and it was a lot of fun. For more of me doing incredibly dumb crap live on camera, be sure to follow me on Twitch.

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Here’s the Weekly Jambox. I genuinely thought about just putting this entire Pet Shimmers album in the Jambox because I am crazy over it, but I decided not to. I strongly recommend you check it out though.