10 Tips That Made Me a Better Storyteller
It starts with the fundamentals.
Pretty much everyone who wants to write has a desire that’s deeper than just writing.
We don’t just want to write. If that were true, I’d have felt that writing safety manuals for trucking companies (one of my first writing gigs) was the epitome of self-actualization.
The truth is that there’s more to writing than just slamming out words on your keyboard. Writing is not just about formatting, word choice, and practice, writing is about having a story to tell and having the skill to tell that story.
Writing is not just about the quality of your content, but the quality of your stories.
Here are 10 tips that have made me a better storyteller over the years.
1. Study stories.
“The hero’s journey” is just the tip of the iceberg.
Here’s a great resource from Big Think, analyzing a lecture by Kurt Vonnegut on “the shapes of stories”.
2. Be a consumer of stories.
As a writer, I tend to become analytical when it comes to stories — sometimes too much so.
At times, I have started to view stories as a math problem instead of as what they are: a wonderful expression of the human experience. I forget that stories are not just something to be “figured out” — they’re something to be enjoyed. Stories are art. Art is a story.
Go to the cinema. Get lost in a novel. Read some poetry. If you want to be a storyteller, never fall too far away from the beauty of stories.
3. Don’t just build plots, build characters.
Charles Dickens is one of the best people to study when it comes to the art of character building.
He created characters like:
Ebenezer Scrooge (from A Christmas Carol)
David Copperfield (from David Copperfield)
Oliver Twist (from Oliver Twist)
Madame Defarge (from A Tale of Two Cities)
And many more iconic characters
Dicken’s ability to create great characters that people love reading about is just part of what makes him a great writer, but in today’s world of short-form storytelling, most storytellers neglect character development. Most storytellers focus on plots and forget about characters.
Don’t be like most storytellers. Develop your characters — even if you’re writing nonfiction.
4. Leave things to the imagination to build suspense and excitement.
“But the entire time, he had been _____”.
Stories are more like real life than we realize.
A lot of people, when building their characters or plots or lessons try to tell you everything. They leave nothing to the imagination.
The problem is, when readers know everything, they get bored. What’s the point in reading about something that you already know about?
In my other newsletter, one of my most popular articles of last year was about moving to Texas. The way the newsletter works, I share stories of my life every week, and I didn’t share that detail about moving until I was literally on my way to Texas with 2 carfulls of stuff.
The article was called “I’m Scared Shitless” and it performed really well.
Granted, I shared the story this way partially on accident — because I was nervous to tell people about my move — but twists and turns from omitted details about yourself make for interesting stories either way.
5. Tell the story multiple times.
I’ve done this in writing and Jiu-Jitsu, but I learned how to do it in my brief (and terrible) stint at stand-up comedy in 2018.
When I did comedy, I’d go out with my small group of comedy friends to 2-3 open mics on a given night. I’d run the same set 2-3 times the exact same way — with small iterations each time. Each time I said a joke, I’d learn different times and places to pause, add a punchline, and other times to just get rid of things that were bad.
I would learn.
In Jiu-Jitsu, when I teach seminars, I do this too. For the last 3 years, I’ve been traveling and doing seminars, but I only really teach one or 2 seminars each year — just different iterations of these same seminars to new audiences.
In writing, I’ve done this as well. I’ve written about tournaments, life experiences, and business lessons in many different ways to many different audiences. Each time I tell the story, it gets a little bit better.
A big part of storytelling is reps.
6. Don’t write like it’s a school assignment. Write how you talk.
I think I’m a decent writer, but I don’t think I am a great “academic writer”.
Academic writing is boring. It’s dry. It’s about weird ideas and vague concepts and it’s not fun to read.
I always try to write things that are fun to read. I write things that I want to read in the style that I would find enjoyable to read. My writing should, if I’m doing it well, sound like how I speak — which is something that has come from years of listening to people speak and reading different people and then forming my own ideas about those people.
The point is your article, essay, book, or whatever shouldn’t sound like homework, it should sound like art or a speech.
Whenever I edit, I read nearly everything aloud so that it sounds almost like how I talk.
7. A big part of storytelling is listening.
The details that you are missing to make your story more interesting are found in the details of the conversations that you are not fully present in.
The way the barista makes your coffee. The way the cashier at the grocery store asks about your day. The way your friend tells you about their heartbreak or failures.
Details for great stories are everywhere — you just aren’t listening enough.
8. Don’t be afraid to romanticize.
I’m currently reading The Sun Also Rises by Ernest Hemingway.
The book depicts life in Europe in the 1920s, and it’s highly romanticized. The characters in the book throw away money. They drink. They sin. They dance.
Their lives are self-indulgent and they aren’t really “great people” (they’re kind of degenerates if I’m being honest), but I can’t stop reading the book. It’s addicting. The romance is addicting. There’s a spice in it.
Other examples of books that have had this effect on me include The Great Gatsby, On the Road, and Kitchen Confidential.
What I think is missing from modern storytelling is that romance or spice. The honesty of indulgence. I like reading about people who just did stuff and just didn’t give too many fucks about the consequences.
Our generation today is hesitant, and hesitancy leads to terrible storytelling.
9. The 24-hour rule.
The more I care about something, the more I adhere to this rule.
If I’m writing something for a client where I’m being paid or if I’m submitting something to a publication, I always follow what Jerry Seinfeld calls “the 24-hour rule”. I use an iteration of this called “the sleep on it” rule.
Sometimes, if I’m on a time crunch, I use the “go to Jiu-Jitsu and take a break rule”.
Either way — there’s a period between writing and editing that needs to take place so that you can view what you wrote with a clearer mind. Without judgement. Without emotion.
Distance yourself from your writing before you edit.
I’ll admit — I don’t always do this. For tweets, Quora posts, and my Grappler’s Diary Instagram posts, I kind of just write, edit, and publish. However, for everything that I want to make as good as possible, I take space between writing and editing.
10. Tell one story, not 7.
Yesterday, I was chatting with my girlfriend, and the subject of my early writing came up. I ended up sending her my first-ever article which I published in November of 2020.
Upon review, I guess the article wasn’t terrible, especially for my first one, but it was an 8-minute read (not too long, about 1800 words) that told a lot of different stories.
I talked about Nietzsche, the movie The Pursuit of Happyness (the one with Will Smith), my own journey with Jiu-Jitsu, and other people’s journeys with Jiu-Jitsu. I talked about teaching, training, competing, self-improvement, philosophy, and more.
When I reread the article, I had a hard time figuring out what it was really about.
If your article is about everything, it’s about nothing. Tell no stories besides the one you’re telling.
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