How do you teach yourself about storytelling? Why is it that some copywriters seem to nail it, while others flounder?
These were the questions I asked myself when I started first started my CAD drafting job in architecture. Fresh out of graduate school, far too many dollars in debt, and stuck behind the drafting table, I listened as clients and ideas moved in and out of the office.
I started to notice the same patterns happening over and over again. Saw brilliant designers and creative urban planners come up with strategies for re-designing cities. Saw tools to change the ways buildings breathed and moved, how people interacted. I saw those ideas crushed, time and time again, under a lack of understanding.
The same things kept happening: during the presentation, ideas weren’t communicated in a way that resonated.
The same things kept happening. During the presentation with the client, the city, or the public agency, the ideas weren’t communicated in a way that resonated — and persuaded. Some people would get caught up in tiny details; others would miss the big picture. Sometimes a great idea got buried under the weight of myopic details.
In addition, your audience has different styles of decision-making. Some leaders make decisions immediately, swept up in ideas and willing to go along. Other leaders need to ruminate and process. Some folks want to believe that they’ve been the ones to come up with the idea.
The art of persuasion and conversation is its own art, its own field.
Knowing how to explain your idea in a way that is compelling, clear, and persuades others to adopt it (and give you money for it!) is no easy task. Tired designers kept arriving at brilliant solutions. They also faced the challenge of explaining themselves. Communication is the art of getting your ideas heard, shared, understood, and adopted. Designing and communicating are separate, but highly related fields.
I began to research communication, persuasion, and storytelling.
Over the past eight years, I’ve read more than 100 books on storytelling, persuasion, copywriting, content marketing, and designing presentations. From Edward Tufte’s books on information design to Joseph Campbell’s The Hero’s Journey, to the neuroscience behind storytelling. This year, I’ve compiled the top 26 books that I think every leader, communicator, thought leader and business owner should read.
This year, if you want to get better at communicating your visions, positioning yourself as a thought leader, and sharing your work in the world, you’ll need to elevate your storytelling, copywriting, and persuasion skills.
“If I ask you to think about something, you can decide not to. But if I make you feel something? Now I have your attention.” — Lisa Cron
If you want to up your game and grow your business, elevate your platform, or become a better storyteller — read these books.
BOOKS ON PERSUASION + COMMUNICATION:
1: Influence: The Psychology of Persuasion, by Robert Cialdini. Influence is a science — it’s not magic; and Cialdini outlines six principles for how people relate to each other, socially, and why tools like reciprocity, scarcity, and liking affect how we interact with each other. It’s also delightfully fun to read.
2: The Elements of Persuasion: Use Storytelling to Pitch Better, Sell Faster, and Win More Business. Stories might seem simple, but understanding how to do them effectively is a skill to master. Maxwell and Dickman show examples of storytelling across every industry, outlining five basic components — passion, a hero, an antagonist, a moment of awareness, and transformation — that form the critical elements of a persuasive story, pitch, or speech.
3: HBR On Communication, by Harvard Business Review. I haven’t picked up an HBR series book I haven’t liked — dense, packed with the latest research, yet distilled into essential tips, Harvard Business Review’s “10 Must Reads” lives up to its name. With essays on persuasion, influence, and understanding conversational style, I learned more about understanding gender dynamics and understanding leadership styles in 40 pages than I have browsing hundreds of internet click-bait links.
4: Trust Agents, by Chris Brogan and Julien Smith. Destined to be a classic. How do people become online influencers? They do more than provide content: they establish valuable relationships, reputations, and utilize media to build trust relationships as leaders and agents in an increasingly interconnected, complex world.
5: How to Win Friends and Influence People, by Dale Carnegie. “You can make more friends in two months by becoming interested in other people than you can in two years by trying to get other people interested in you.” ― Dale Carnegie.
“Often we don’t realize that our attitude toward something has been influenced by the number of times we have been exposed to it in the past.” ― Robert B. Cialdini
BOOKS ON WRITING:
As a writer, my favorite books on writing lean towards the introspective, the habit-building, and the people who devote time to this craft. Here are my favorites:
6: The Artist’s Way, by Julia Cameron. Want to tap into your inner voice? Julia Cameron leads a 12-week program that takes you through all the feelings you have while becoming a maker, a creative, an artist. Yes, you’ll get frustrated. You’ll get mad and stuff from your childhood will surface up. Cameron is here to guide you — and to remind you to play, because play is the outlet and source of creativity. Her “Artist Dates” remind me that exploring the world and documenting my thoughts is exactly what I should be taking time to do.
7: The War of Art: Break Through the Blocks & Win Your Inner Creative Battles, by Steven Pressfield. What holds us back? Ourselves, of course. This pithy and succinct book details the enemy that we all deal with — inner resistance. Resistance shows up in every form, from convincing to conniving to flattering to maddening. How do you overcome Resistance? Simple: show up and work, bit by bit, day by day. Great on a shelf for a little reminder every few days.
“If you find yourself asking yourself “Am I really a writer? Am I really an artist?”, chances are you are.” ― Steven Pressfield
8: Zen in the Art of Writing, by Ray Bradbury. Here are three quotes from this book by legendary Ray Bradbury: “You must stay drunk on writing so reality cannot destroy you.” ― “Every morning I jump out of bed and step on a landmine. The landmine is me. After the explosion, I spend the rest of the day putting the pieces together.” — “Plot is no more than footprints left in the snow after your characters have run by on their way to incredible destinations.”
“You must stay drunk on writing so reality cannot destroy you.” — Ray Bradbury
9: Bird by Bird, by Anne Lamott. A book on writing and life, and all the zany-crazy-personality quirks in between. Fluttering between self-deprecation and frank honesty, Lamott tells the story of the difficulty of writing and getting out of our own way. Humorous at times and painful at others, I have owned this book for more than 10 years and refer to it readily whenever I experience my own writers’ block.
10: Still Writing, by Dani Shapiro. Practical, wise, clever, and funny, Shapiro takes her 20-odd years as a writer and a teacher and tells the story of what it’s like to write. Each chapter is a new essay, a piece of advice, a glimmer into what she’s done. Wise and brilliant.
11: On Writing, by Stephen King. Writers writing about writing is so wonderful — you see their tools, ideas, and childhood and work, all mixed together in a story well told. Stephen King doesn’t disappoint.
12: Show Your Work, by Austin Kleon. This book is about making things, just making them — and about sharing them. It’s time that you promoted yourself in a way that’s authentic and normal to you, and that’s related more to you sharing the work that you’re making (however discomfortable) than it does being a master promoter.
“But now I realize that the only way to find your voice is to use it. It’s hardwired, built into you. Talk about the things you love. Your voice will follow.” — Austin Kleon
13: Resonate, by Nancy Duarte. This book is a foundation for designing visual presentations that have emotional clarity and pull. She diagrams (beautifully!) the Hero’s Journey and the structure of moving speeches, from Martin Luther King, Jr. to Bill Clinton. I’ve read and re-read this book dozens of times and keep a copy at my desk for close reference.
14: Winning the Story Wars, by Jonah Sachs. A lot of books on storytelling are stuffy and academic; this is not. Sachs shows how mass media and brands are failing to tell great stories, and why it’s now a race for businesses to reconnect with the vital ingredients of storytelling — or risk being left in the dust. This book is a clear look at how marketing, business, and storytelling are all tied together.
15: Joseph Campbell: The Hero’s Journey. A seminal work on storytelling, Campbell created the Hero’s Journey, which dissects the structure of great mythologies across religions, contexts, and time. Each Hero has a call to action and proceeds around the mythological clock (or circle) through a number of steps on an adventure from the known world to the unknown world.
16: Wired for Story, by Lisa Cron. “The Writer’s Guide to Using Brain Science to Hook Readers from the Very First Sentence”—Lisa Cron maps out how storytelling works and why we’re wired to listen closely, from hook to structure to finale. Stories ignite our brains in predictable patterns, and knowing the science behind why storytelling works will change your writing faster than any other writing advice might.
17: Improving Your Storytelling, by Doug Lipman. This book looks at the oral history of storytelling and places stories in the context within which they were born. I learned exercises of imagination, detail, and adding environmental cues from this book — and even dabbled in understanding the stand-up, performative aspects of storytelling (whereas most of the other books in this list are focused on narrative and written stories).
18: The Storytelling Animal: How Stories Make Us Human, by Jonathan Gottschall. Humans spend as much as four hours a day in lands of make-believe (if not more). We make up fantasies, read novels, enjoy plays, and live in dream-lands most of the time. Gottschall combines neuroscience, psychology, and storytelling to explain what it means to be a human animal. At it’s core it is what stories have to do with instincts, decision making, survival, and behavior change.
19: A Million Miles in A Thousand Years, by Donald Miller. How do you live a successful story? How does a life become more than a set of random experiences, many of which you don’t seem to have any control over? Donald Miller sets out to write a book about stories, and realizes that his life isn’t very interesting — and doesn’t follow the narrative structure of a story. In this tale, he decides to make his life worth telling, and reveals how story structure works, one lesson at a time.
“And once you live a good story, you get a taste for a kind of meaning in life, and you can’t go back to being normal; you can’t go back to meaningless scenes stitched together by the forgettable thread of wasted time.”
― Donald Miller
MARKETING + UNDERSTANDING MEDIA:
20: Tested Advertising Methods, by John Caples. A primer on all things copywriting and advertising. Originally published in 1978, this book is still a standout example of how to write great copy, headlines, and advertisements. He breaks down the components of advertisements and why some ads sell three times as much as other ads. This is one of the most useful books on advertising. If you’re a copywriter, content marketer, or sales person — you’re in the business of writing headlines every day.
21: Breakthrough Advertising, by Eugene M. Schwartz.Did you know that there’s an urban legend about an elusive book known for it’s legendary advertising copy? Apparently it’s considered a special gift bestowed upon newbie marketers and copywriters. It’s in such demand that this book retails for $300 or more with used copies. Sometimes it can even be found for over $900 on Amazon! Called one of the best books in advertising and recommended by most of the top internet marketers out there today. It digs into the art and mastery of great copywriting. It’s not formulaic — it’s an evolving art, and one that you have to pay attention to and constantly adapt in order to do well.
22: Trust Me, I’m Lying: Confessions of a Media Manipulator, by Ryan Holiday. Blogs, tweets, and social media distort the news like never before. A single malicious rumor can cost a company millions. Products, celebrities, attention? It’s all a game. Ryan Holiday, Marketing Director for American Apparel, takes you behind the spin cycle of creating news. He shows how he consistently and deliberately changed the news cycle and created stories in his favor. Eye-opening and sometimes disgusting, it’s best to know what you’re getting into in today’s media landscape.
23: New Rules for A New Economy: Kevin Kelly. Kevin Kelly, editor of Wired, wrote this book in 1999 — and I still pick it up and re-read it. Offering wisdom about the changing connected world, Kelly suggests that communication is what drives change. Today, connectivity is everything, and “success flows primarily from understanding networks, and networks have their own rules.” He details ten principles of the connected economy and how they play out in business, economics, and life.
24: Positioning: The Battle For Your Mind, by Al Ries and Jack Trout. Trout is considered the father of advertising and a guru of branding, marketing and product management. He brings together elements of psychology and user experience to show how to describe things to the people that matter to your business–your customers. It’s not how you understand what you do; it’s how well you explain it to others, in a way that stands out.
25: Oglivy on Advertising. One of the premier advertising and sales books of all times. Oglivy is a genius. “Ogilvy’s writing is captivating. His work, legendary. His ideas, timeless.” I’ve only begun to dig into the genius in this book, and fully expect to have it dog-eared, flagged, marked, highlighted, and re-read multiple times over.
“Where people aren’t having any fun, they seldom produce good work.” ― David Ogilvy
BONUS — FAVORITE FICTION + NARRATIVE NON-FICTION BOOKS:
I think all great writers need to be great readers. If you’re feeling stuck on technical books, then toss the technical books to the side and pick up a great fiction book. The point of a story is to become absorbed in it. We can pick up great habits by reading good works. (Although a few of the books above, like A Million Miles, Bird by Bird, Still Writing, and On Writing read like narratives).
Some of my recent favorites in fiction and narrative non-fiction are:
- Behind the Beautiful Forevers
- Bend, Not Break
- Brave New World
- The Cuckoo’s Calling
- Ender’s Game
- The Fault in Our Stars
- Fahrenheit 451
- The Fear Project
- The Glass Castle
- The Kite Runner
- Life of Pi
- The Longest Way Home
- The Signature of All Things
- What I Talk About When I Talk About Running
- The Year Without Pants