Storytelling: Are you good at it?

I just finished a complete series re-watch of the TV show Mad Men, and the thing I was struck by most in this viewing was that Don Draper’s character was a masterful storyteller.

Yes, he works in advertising, and it is *his job* to know how to tap into those human emotions, motivations, and aspirations. But he does it with such…finesse.

The thing is: Lots of people tell stories. But few do it well.

I was going back through the interviews I conducted with writers and editors for Yeah Write Club (the much-neglected side project I haven’t revisited in a while because, well, time), and a quote from Bobby Kim, author of This is Not a T-Shirt, reinforced this idea:

Q: Do you think that writing (and writing regularly) has been part of the success you've seen with your entrepreneurial projects? What impact has it had?

A: Of course it has! Everything comes back to the way I communicate and tell stories. Brands and businesses are just conduits for us to connect as human beings. I have an advantage as a writer and as a fan of writing because I can relate to our audience even more effectively.

Makes sense, right? Here’s what you need to know about good storytelling.

Editing is critical.

Have you ever been trapped in a conversation with someone who does not edit him or herself? They share every detail, no matter how non-essential. They go off on tangents. What should be a two-minute anecdote becomes an hour-long epic.

Good storytellers know that in order to capture and hold an audience’s attention, one must edit. This means cutting away all the non-sequiturs and trivial details that distract from the story’s climax and theme, so it only retains the core elements.

When storytelling, ask yourself:

  • Is this detail an essential building block for the story arc I’m building?

  • Will the storyline suffer or become disorienting if I leave/add this detail?

Emotion is required.

Don Draper’s top skill as a storyteller is knowing how to tap into human emotions while telling a story. Time and time again, when pitching an advertising angle, he paints a picture for the client that plucks emotional strings like nostalgia, romantic or parental love, heartbreak, and longing. Why? Because it connects with audiences on a deep, meaningful level.

Stories that tap into emotion and make us feel something register much differently than a quick ad pitch. They make the listener/reader introspective, reflective, and slightly vulnerable. They sometimes even cause a bodily response (like a racing heartbeat, tears, or sweating.)

When storytelling, remember:

  • A good story makes the audience feel something, so if your storyline lacks emotion-based language and scenarios about how you felt in the moment, it will likely fall flat.

  • Your audience should be able to relate to the emotions in your story. If your plotline is too extreme, they may feel out of their range. Adjust as needed.

Tone is everything.

This tip is more related to verbal storytelling, but important nonetheless. Part of Don Draper’s gift when it comes to storytelling is his body language, his facial expressions, and his timing. This clip shows exactly what I’m talking about.

Notice how he pauses between key words. How he touches his chin and uses his hands to reinforce certain lines. How he crinkles his brow when he’s thinking. The personal anecdotes he ties into his pitch that humanize the experience. You can do this in writing with formatting tricks and by developing your personal writing voice.

When storytelling, remember:

  • Pauses, line breaks, and formatting help reinforce main ideas.

  • Inflection and emphasis drive home key emotional aspects of your story.

Good storytelling = engaged audiences.

With social media, millions of newsletters, and the non-stop flood of information that’s hurled at people every single day, strong storytellers are the ones who stand out from the noise. They capture our goldfish-level attention spans and keep us engaged.

A couple of resources I can recommend to help you improve your storytelling abilities:


Quick parting announcement: A new season of the Freelance Writing Coach Podcast has begun! You can listen here (or anywhere you listen to podcasts.) New episodes will roll out every Monday for the next few weeks, so be sure to subscribe so you don't miss any!