Think Like an Artist To Become a Better Storyteller

Posted by in Telling Better Stories

The first time I ever truly connected with a painter was when I saw the Lichtenstein exhibit at the Art Institute of Chicago this past summer.

Crying Girl by Roy Lichtenstein

Crying Girl by Roy Lichtenstein

It’s not that I hadn’t seen famous paintings before, but that I had never seen so many in the same style in room after room, organized in sequential order. Something about seeing a single artist’s near-full body of work as a timeline allowed me to see each painting not as an individual piece, but as a larger part of a cohesive story about the artist’s life, as told by himself.

The exhibit got me thinking about how we can teach people to tell better stories. Lichtenstein’s art legacy is not unique; really, all art is created to tell smaller stories in the context of much larger stories. In fact, the crux of every great artist is figuring out how to be a great storyteller.

So if you are trying to study storytelling so you can tell great stories about yourself, your company, or your brand, it might be beneficial to reframe your mindset and focus on becoming an artist instead. Here’s why:

Artists think in mediums

All stories require a medium and all artists specialize in at least one medium. If you want to be a good storyteller, you need to think in terms of mediums. Then, you can choose a medium with which to communicate your ideas and get really good at it.

Most people who want to be thought leaders in their industry think that they must have a blog. But there are so many other options, many of which thought leaders and storytellers are starting to explore online, and you really only need to be good at one thing to find a fan base.

Back when I worked with Bob Garfield, former AdAge columnist and current host of NPR’s On the Media, we reveled in the fact that no one at SxSW Interactive knew who he was because he didn’t have a blog. But Bob Garfield doesn’t need a blog—he has an accomplished media and journalism career and has built his fan base through that.

You also don’t need to write all your ideas out, and plenty of thought leaders online don’t. For example, Amber Rae shares handwritten notes, ideas, and life advice in the form of Ambergrams. Hugh McLeod dispenses witty life lessons through drawings on the back of business cards. iJustine makes hilarious videos on YouTube. But each of them are still telling stories about themselves.

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Stories can transcend mediums, but they can’t exist without them—so becoming very, very good at communicating in one medium will automatically make you a better storyteller.

Artists put process to storytelling

When you think like an artist, each piece of work becomes a process with a common structure that is defined for the medium. You learn how to better tell stories through that medium by studying the medium itself. Rather than trying to understand how to tell stories (an abstract concept, truly), you can focus your efforts on one form of storytelling, which you can then re-adapt to other mediums as you get better.

So you choose a medium which comes with an accepted structure, and suddenly you have millions of examples of people who are telling stories similarly to how you want to tell your story. This gives you a starting point, because you can look at their work and pick apart what you like and don’t like. You can also look at their work and figure out what is effective and ineffective. Pixar, a company that understands storytelling better than almost anyone else on the planet, lists this exercise at #20 under their storytelling rules.

You’ll also become a better storyteller when you understand the rules of your chosen medium. All mediums have constraints and artists understand that creativity breeds when it has constraints. For example, when Nate Larson and Marni Shindelman decided to use the geolocation data on tweets to photograph perspective, they made up arbitrary rules that allowed them to tell larger stories—like the series they did on people who tweeted with the hashtag #HowToKeepARelationshipWithMe within a 15-mile radius of New York City.

If they had not limited themselves, they would have no story; but now, they’ve been commissioned by Indianapolis International Airport to create a series of photographs based on airport tweets.

Artists mix mediums to create something new

Once you learn the skill set to communicate in one medium, you can cross that with a second medium, which gives you the uniqueness you’ll need to make your storytelling stand out.

Han Solo and I try to squeeze in two outings per week, and one of our recent ones was to go to the Art Institute to see the French Impressionist exhibit where Georges Seurat’s famous large-scale work, A Sunday Afternoon on the Island of La Grande Jatte, was on display. I wanted to see it after another one of our outings where we saw the musical Sundays in the Park With George. The play is probably my favorite play of all time, because it combines music, theater, and painting to tell a single cohesive story whose whole is greater than the sum of its parts. (Also, there is a love story without the story being about love, which always scores points with me.)

Sunday Afternoon On The Island Of La Grande Jatte by Georges Seurat

Sunday Afternoon On The Island Of La Grande Jatte by Georges Seurat

And I love how Austin Kleon, who rose to fame with his Newspaper Blackout poetry, tells stories by deleting rather than adding.

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In a more extreme example of mixed medium storytelling, Flash Rosenberg calls herself an Attention Span for Hire, and uses a combination of her skill sets as a cartoonist, photographer, writer, and performer to produce live-drawings that tell stories through sketches during other people’s speeches, panels, and conversations.

Artists develop a signature storytelling style

We rarely think of the way in which we tell a story, but in truth, it’s as important if not more important that the story itself. The best stories are the ones that no one else on the planet could tell in exactly the same way, and no one else in the entire world is telling stories the way Rosenberg does. If she were just drawing, it wouldn’t be particularly compelling—but she takes her story to the next level by recording her reactions to other’s stories and by incorporating a live element into the story.


Artists are exceptional at figuring out how to be unique, so by thinking like an artist, you will suddenly shift to figuring out not just how to get your point across, but how your work can stand out. Once you make this shift, good stuff starts happening for you in terms of establishing thought leadership, building an audience, and creating better content.

I am still developing signatures in my writing, but I can tell I’m making progress. For example, my signature blog post looks like this:

  • Personal story that seemingly doesn’t relate to topic
  • 3-5 surprising bullet points with at least one unusual example for each
  • A few sentences to tie my points back to the beginning story

Great bloggers like Jon Morrow and Penelope Trunk have built audiences with this post style, because it allows them to inject their personal stories into their content and form emotional connections with their readers.

Almost every thought leader has a signature, and anyone who has ever achieved fame, from writers to musicians to actors to directors to famous oil painters to reality TV stars, has a specific style of telling stories that no one else can do in quite the same way. That’s the new bar for storytelling, and until you get in the mindset of being an artist rather than a blogger, or a CEO, or a speaker, you’ll probably never take your storytelling abilities to the next level.

Artists are experimenters

There is one big caveat to all this that holds people back. Several years ago, I worked for a company where the CEO was so insecure that he refused to approve any content (blog posts, tweets, interviews) that didn’t tell his story in his exact, refined words. As a result, the marketing team didn’t put out much of anything at all, and the company never reached the level of thought leadership recognition it could have.

The reality that companies face, especially with digital and social media becoming a primary vehicle for storytelling, is that you probably won’t completely control your story as it moves through the internet.

In fact, the best way to tell the story you want to tell is to keep repeating it, over and over again in as many different ways as you can so you can drown out other people’s inaccurate interpretations of your words.

This means that to be a great storyteller, you cannot spend a lot of time refining, perfecting, or second-guessing your work because you have to constantly be telling your story in a new, fresh way. It also means that each time you tell your story, you have a new chance to succeed or fail at it. Knowing that you’ll fail some days and succeed others allows you to experiment from the get-go, which will make you a better storyteller.

A great example of this is Seth Godin, who writes short, poignant posts on his blog at least once a day. If you are a regular subscriber, he probably doesn’t wow you each time, and every once in a blue moon he misses the mark completely. But he shows up, and he tries, and he is an amazing thought leader and storyteller because he keeps hammering the same messages home—messages about publishing, building an audience, education reform, and the decentralization of how artists can make a living.

Great storytellers tell new stories every day to get better at it. That’s why I decided that if I was going to take this blog seriously again, I had to write a new blog post every day in the hopes that every once in awhile, something will stick, as long as I bring 100% of my energy to the table each time.

It’s a full-time job, though, because telling stories through a blog is all about telling stories in very small chunks, in between the parts that are useful enough to others that they are willing to read your entire blog post. You have to sneak the stories in.

Bedroom at Aries by Lichtenstein (based on the Bedroom in Arles series of paintings by Vincent van Gogh)

Bedroom at Aries by Lichtenstein (based on the Bedroom in Arles series of paintings by Vincent van Gogh)

And the same could be said for Lichtenstein—he was trying to tell stories about what he saw, his worldview, by parodying mass media, other painters, and even himself in later years. If he was just sharing his worldview with anyone who would listen, he probably wouldn’t have gotten very far. But it was by telling his story little by little, sneaking his story into compelling artwork, that he was able to leave a lasting mark on the world before his death.

Artist's Studio #1 - Look Mickey!

Artist’s Studio #1 – Look Mickey! by Roy Lichtenstein

Which is what you’ll need to do to become a better storyteller—start telling small pieces of your story against a backdrop of something people can care about, until they can’t help but sit up and pay attention.