Hello friends,

While many were enjoying festive cookouts with family and friends over the long weekend, I spent much of Saturday sitting on my couch, under a blanket (it turned cold in Boston!) trying desperately to work my way out of the 9th circle of story structure hell.

Okay, I'll admit it. The 9th circle of story structure hell does not actually exist. And I'm sure that Dante -- no stranger to story structure -- would be horrified that I've appropriated his allegory in this way.

But when you're in story structure hell, you have a lot of time to consider how your current story structure dilemma compares to other -- less torturous -- conditions.

And so, with no further ado, I present to you: The Nine Circles of Story Structure Hell.

Circle 1: This Story Writes Itself!

I've only had this happen to me once. It was ah-mazing!

The year was 2005. I was covering the World Aquatics Championship in Montreal. It was the height of the Michael Phelps era, and hordes of media had descended on the venue, scrambling to get just one quote from the future most decorated Olympian of all time.

Instead, I had the crazy idea to interview other US swimmers and ask them the world's shortest list of questions.

Who are you?

What is your best event?

What's one thing you can do better than Michael Phelps?

The conceit was so simple, and it was so much fun. I think I interviewed five athletes. And I'd be shocked if the story took me more than 10 minutes to write. It was probably more like 5.

I'm not even exaggerating.

Circle 2: Just Gotta Clean Up the Chronology

There are some magical, wonderful, introspective people who have a story to tell and know how to tell it. These people will give you details and dialog. They'll pause to reflect… without even being asked. They might even wrap the whole thing up in a bow for you.

But there will still be a little work to do. They'll likely tell the story just a touch out of order -- rewinding once or twice to add details they forgot to mention. They'll probably include some details that aren't necessary. And sometimes they'll get a little wordy.

All you gotta do is get everything in order, trim the fat, and replace the wordy bits with some clean narration. Easy peasy.

Circle 3: Clear Chronology, Two Voices

Okay, so imagine the above scenario, but with two people telling the same story.

Now you've gotta decide how to switch back and forth between the two voices while still making sure the story keeps moving forward.

(So, for example, if person A tells you that they walked to the store, person B can mention the name of the store or what they went there to buy -- but they absolutely, positively should not tell us that they walked to the store! They also should not rewind and tell us something that happened before they walked to the store.)

These are often my favorite stories to work on. I love working directly with the audio -- not a transcript -- so that I can make sure I'm picking the most vibrant clips.

Circle 4: Too Many "e" Options

I encountered this problem just this week! I was talking to a pair of producers who are working on a story that I'll be editing. (Hi Sheeba and Kim!) We had previously talked about an "e" structure -- starting the story at a tension point and then rewinding to tell the story from the beginning.

In our first conversation, we picked our "tension point." But this time, as we talked, Sheeba mentioned something she had discovered in her research. Kim and I both had an immediate emotional reaction. The detail was so compelling! And I wondered out loud, should this be the top of our "e"?

The truth is, it might be a terrible idea. Even though its a great moment, it might require too much explanation to really function as the beginning of the story. We might want to hold that moment for later in the piece, to allow the anecdote to really land.

These are all things Sheeba and Kim will need to consider when they sit down to structure the story. But...these are good problems to have. If your story has more than one really great tension point, that probably means you have a really great story!

Circle 5: Way Too Much Great Tape

It is not uncommon for me to identify the audio I absolutely, positively must use in my story...and discover that my story is way too long. Actually, that's usually the norm.

Narrowing down the options can be heartbreaking. We call it "killing your darlings," and sometimes it really does feel like you're committing a crime.

Sometimes, I'll create a "slush pile." These are anecdotes and interview clips that I'm not ready to say goodbye to just yet, but that don't actually fit into my narrative arc. I move them to the bottom of my transcript (or the end of my audio file) and promise myself that I'll find a place for them later.

Most of the time, I never look at them again. I become so enamored with the shape of the story and how everything locks together that I'm able to detach emotionally from that tape and move on.

Circle 6: Great Story. Terrible Talker

This is so, so disappointing. You've found a fabulous story, and the person who can tell it to you just isn't a good storyteller.

This has happened to me many times, but let me tell you about the one time that had a happy ending.

We had been trying for months to schedule an interview with an athlete who had broken a world record. When she finally agreed to an interview, she wasn't willing to go to a studio or have a tape syncer come to her house. So we asked her to record her voice with her iPhone, and I conducted the interview over a scratchy landline.

As we were talking, she would sometimes stop mid-sentence. Or laugh when nothing funny had happened. When I heard her iPhone recording, it was clear that someone was in the room with her, making her self-conscious as she answered my questions.

We had scheduled an hour for the interview, but if I remember right, I was barely able to hold her on the phone for 20 minutes. I hung up questioning whether I had a story at all.

But when I listened back to the tape, I realized I had small nuggets of usable clips. Sometimes they weren't full sentences -- just fragments. But I knew the story well enough that I could fill in the blanks. So, I took a deep breath, stole a few clips from YouTube (shhhh...don't tell the lawyers!) and got to writing.

In the end, it was a pretty decent story. In fact, it won the national Edward R Murrow award for sports reporting that year. Not so shabby!

Circle 7: What's My Actual Story, Again?

If you don't go into your interviews with a plan, you're going to emerge with a jumble of anecdotes and reflections that don't fit together. Finding the plot after the fact is an absolute nightmare. I do not recommend it.

Ignore your impulse to just pick your best tape without thinking about plot. Remember, a narrative isn't a random string of interesting anecdotes.

Instead, look for the moments that connect -- that build on each other and lead to some sort of greater understanding. Focus on those, and not on trying to represent every single tangent you went down during your interviews.

Circle 8: Too Much Analysis, Not Enough Story

Ugh...another common problem that's really difficult to come back from. There are some stories that just need a lot of analysis. Maybe you need to explain the science? Or the politics? Or what's really at stake?

Often, those analysis clips sound sexy. They're full of passion and well-reasoned arguments. They seem compelling...especially if if you just so happen to agree with them!

But here's the thing with analysis. It very rarely changes minds. (Think: every political argument you've seen on social media, ever. Nobody ever says, "You're right! My feelings on this complicated subject have completely changed because you bombarded me with well-reasoned arguments.")

But studies have shown that when people are able to see, first-hand, the impact of that policy, that law, that social norm -- sometimes they actually do change their minds.

As a storyteller, I hope that my stories have this kind of impact. That's why it's easy for me to ignore those "sexy" analysis cuts and make sure I'm focusing on story.

Circle 9: Utter Chaos

(sigh)

This is where I spent my holiday weekend.

Here's what happened…

For the past three months, I've been working on a six-part narrative series. I have interviewed 17 people, and have gathered approximately 20 hours of tape.

I am drowning in tape. Really, really good tape.

(Also, three months is a really short period of time to pull together a six-part narrative series...especially when it takes nearly a month to schedule your first interview!)

The first five episodes focus on the events of one summer in the mid-nineties.

Episode 6 is everything that's happened in the 25 years since.

With the first five episodes, I always felt like I'd have the chance to get to that great anecdote or brilliant concept in a later episode.

And so, anecdotes and concepts got bumped and bumped and bumped until they all ended up in the file for Episode 6.

By the time I sat down to structure the story, I had big plans. I was going to use ALL of these wonderful moments. I'd tie them all together… somehow. And I knew if I could just find a way to make it happen, it would be the most beautiful, most inspiring podcast episode ever made.

I chipped away at it on Wednesday and Thursday. All good.

On Friday, I had set aside the entire day to focus.

First, I procrastinated for a while. Okay, to be honest, I procrastinated for a long while.

Then I stared at the cuts file for a couple of hours.

I felt utterly overwhelmed. How could I possibly fit all of this into a cohesive 30 minute narrative arc?

So, I did the only thing I could think of.

I took a nap.

I've been working from home since March 13, 2020, and never before have I taken a nap in the middle of the workday. But this episode broke me. The idea of making sense of all that tape was just utterly exhausting.

On Saturday, I tried again.

I made a Trello board to try to visualize my story structure.

When that didn't work, I tried breaking the story into chapters. (Sometimes working in smaller chunks helps me make sense of things.)

When that didn't work, I got out my trusty purple pen -- I always think more creatively when I've got a pretty color -- and wrote a list of all of the moments that well and truly NEEDED to be included in the episode.

The only problem is… those moments didn't fit together.

Not at all.

I was still utterly lost in the chaos.

My heart started racing. I felt sick to my stomach. I was filled with dread knowing that I'd never, ever be able to make sense out of all of this.

And then I took a deep breath.

I killed my darlings.

I made copious use of the "slush pile."

I acknowledged that I'd never be able to say everything I wanted to say, and that it was impossible to try to represent the entirety of 25 years in 30 minutes or less.

I focused on story.

I simplified.

I let go of my prior expectations.

I made difficult choices.

This is what we do as storytellers. It's not always easy. It's not always fun. It's very rarely glamorous.

I'm still too close to the episode to know if it's going to be any good. But I'll tell you when it comes out in a couple months. And then, you can be the judge.

Okay, I know I've recommended Jessica Abel's Out on the Wire podcast before, but this week I'm going to point y'all to Episode 7: Dark Forest.

This is my favorite episode from this entire podcast. Maybe my favorite episode of any podcast ever. It speaks to me... and all my insecurities.

I know that very few of you will click on that link. So let me give you the TLDL (too long, didn't listen?) version.

When you're working on something and you're really, really lost and turned around and you just can't seem to work your way out, you're in the dark forest. It's okay. It's actually good.

Because, and I'm quoting Jessica here, "If what you're doing is deep, if it's worth doing, it's going to be hard."