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The Mess of Your Creative Process Isn't a Problem—It's the Most Important Part
I have bad news and good news: The bad news is creating things always feels like a mess, no matter how experienced or successful you get. The good news is creating things always feels like a mess, no matter how experienced or successful you get. We like to put our heroes up on a pedestal, but
On Current and Future Struggles in the Creator Economy
There’s been a lot of chatter around this lately, maybe because it’s a new year or maybe because there’s a lot of turmoil in the general everything of everything right now. (Some of that is real. Some of that is caused by the nonstop firehose of advertising-supported social media and news media need
My Theme of the Year + My Biggest Note to All My Clients
This piece was originally shared to my newsletter, Playing Favorites. Subscribe for free using the box at the bottom of this page or the big button at the top. Welcome to the first edition of Playing Favorites in 2025, and Happy New Year! Each year, I pick a theme for myself as a kind of North
Whisper
The Snowman was created in 1982. That's three years before Jason was born. Oh, I should explain. I'm Jason. That's my real name. Nice to meet you. Anyway, along came Christina a few years later, and after that, Christmas meant lots of family traditions, wrapped in a familiar if odd feeling: the
"Tell Me About Yourself"—A Framework For Telling Your Story Well
Walking past the room, you would have heard nothing, but all I heard was screaming. To be clear, the room was quite literally silent, and the voice screaming was entirely in my head. But that doesn't make it any less real. I was about to appear as a guest on a podcast for the very first time, and
My Recipe for Great Stories
Before I share my recipe, I need to tell you about a college friend of mine. Let's call him Tim. Because that's his real name. Tim is an Irishman, and I'm Italian. This led to a lot of jokes between us over the years. He'd poke fun at the "olive oil" in my hair (it wasn't), and I'd tell h
Stakes and Brotatoes: Why All Those Awful Business Hucksters Don't Get They're a Joke
It's late, and I should be asleep, but when you're a professional creative, you don't exactly get to leave work at work. Aside from the fact that my office is just a few feet from where I watch Bluey and Mira and Elena with my kids, my job relies on my ability to see the world, synthesize meaning fr
Others Look and Sound Like You. Now What?
Consider the following prompt, the easiest thing you'll be asked all week: "What main topic or topics do I cover in my content?" Now consider the next one, the hardest thing: Remember that others also talk about the same topic(s) as you in their work. Now answer: "Why would a
2 Questions to Get Out of Your Head and into the World as a Stronger Communicator and Leader
They say hindsight is 20/20. What they don’t say is, once you have that clarity of sight, you'll want to close your eyes. Maybe rub your temples. Possibly let your head drop to the table with a satisfying and much-deserved thunk. This was me, all year long. After years of successfully buildi
Do Your Ideas Pass the Permanent Ink Test?
I've hosted something like 800 interviews in my career, spanning a whole heck of a lot of jobs and projects: internships in PR and many more as a sportswriter, personal blog posts written to 12 people, company posts reaching millions, panels I've emceed on stages, webinars and web series and docuser
Be a Thought Leader (It's Not What You Thought)
(Walks up to podium.) (Adjusts microphone.) (Clears throat.) Today, I want to talk about ... thought leaders. (Dives for cover.) (Peeks out from behind podium.) (Stands and brushes shirt off.) Cool, thanks for not throwing stuff at me. Glad you're open to today's idea. Let's cook this tur
If You Want More Passionate Fans, Consider This Subtle Switc
The way most business communicators and leaders try to teach others and earn fans is actually the opposite of what works. Yet we're so convinced of our style, and it's become so common in our community, we don't even see the error of our ways. In short, we keep firing the director. To understand w
Seth Godin Dissects His Signature Story - How Stories Happen #16
In this episode, it's a total treat as the one and only Seth Godin takes us into how he thinks about storytelling and the intersection of strategy and story, and then we hear him dissect a signature tale. Plus, Seth and I trade stories in the back half of the episode—business storytelling nerdery on
The Road Race Problem: Why Growth Is Getting Harder
Justin Moore has a problem. He's a lousy running buddy. Justin is the founder of Creator Wizard , which offers education and community to help influencers win more brand deals. For years, he's has been establishing himself as the Sponsorships Guy in the creator economy. If you identify as being
“Is this ANNything?” Ann Handley and Jay Acunzo Work Out New Drafts
This week, we’re joined by our first-ever recurring guest. The brilliant Ann Handley (WSJ bestselling author of Everybody Writes and globally touring keynote speaker) joins us for a very special episode of “Is This Anything?”, the mini-series, where friends and collaborators join me to work out ne
The Thought Leader's I.P. Pyramid: The 5 Categories of Material Every Powerful Communicator Needs
Back in high school, young baby-faced Jay learned many lessons. I learned how much hair gel was too much hair gel. I learned that puka shells can be worn with every outfit, and I later learned that puka shells should not be worn with any outfit. Also, in physics class, I learned the formula for mo
"We're both the heroes and the villains in our own stories" | Chase Jarvis, Photographer + Entrepreneur + Author
Why is candor essential for a good story? How brutally honest should you actually be in sharing a story with the world? The great Chase Jarvis brings us into his story of self-discovery, with the many twists and turns his professional career has taken, as he works through how to best tell
"If all knowledge is experience, all wisdom is framework" - Laura Gassner Otting - How Stories Happen #12
What is a super-story? And how can you flex yours to fit different audiences, mediums, or conclusions? That’s what we dive into today with powerhouse storyteller, Laura Gassner Otting. Laura takes us into a small story about her first time decorating a Christmas tree with her husband’s family. Init
How to Write and Speak to Ensure Others Care (Lessons from Roy Kent and Seth Godin)
Isaac McAdoo did a bad thing. Of course, it helps that Isaac McAdoo is not a real person and neither was the person to whom he did the bad thing. Let me explain (he says, mimicking a transition line social media posters needlessly use after an opening hook, since the inclusion of any subsequent wor
How I Unf*cked My Marketing: Why Social Media Has Ruined People Who Sell Services
I recently unf*cked my marketing, and I wanted to share a brief explanation. Social media has messed up how many of us who sell services (like me) execute their marketing. One thing that helped me was to ask myself a question: "Do people buy from me, or do they hire me?" If someone buys
"If all knowledge is experience, all wisdom is framework" - Laura Gassner Otting - How Stories Happen #12
What is a super-story? And how can you flex yours to fit different audiences, mediums, or conclusions? That’s what we dive into today with powerhouse storyteller, Laura Gassner Otting. Laura takes us into a small story about her first time decorating a Christmas tree with her husband’s family. Init
Working out a new TED Talk with Author & Journalist Simone Stolzoff - How Stories Happen #11
Go inside the development of a brand new TED Talk, as Jay offers notes to friend Simone Stolzoff on his v1 draft. Simone is the author of The Good Enough Job and a journalist whose writing has been featured in The New York Times, Washington Post, Wall Street Journal, The Atlantic, and more. This
My Favorite Trick to Stronger Ideas & Greater Personal Momentum
Ah, the plight of the majestic hamster on her wheel. There she runs, churning those little legs as fast and furious as she can, working overtime to get nowhere. All hustle, no progress. Doesn't that just describe so much of what the online content space looks like today? Even for those of us who s
"A perfectly competent character is boring" - Nat Eliason dissects his book's prologue - How Stories Happen #10
Telling stories about your life feels fraught. How do you weave together a story that is deeply personal to you and others, contains the right amount of tension without being too dramatic, and feels both gripping and accessible for your audience? In the case of our guest today, Nat Eliaso
What it takes to craft a signature story (Client behind-the-scenes) - Susan Boles - How Stories Happen #9
What should you include or omit to ensure your stories carry your message, resonate with others, and deliver something that could only come from you? That’s the challenge we encounter today. In this special episode, Jay is joined by a favorite client, Susan Boles, to work through a draft
Where to Find Signature Stories to Support Your Message & Grow Your Audience
Among the many things I create in my work, speeches are maybe my favorite. They just get me geek-level excited. Writing is my oldest friend. We're comfortable together. Podcasting is my midlife bestie. We've gotten super close, super fast. But speaking? Speaking is my Hell Yeah friend. (That's t
Ideas that Create Momentum (Are Not the Ideas We're Handed by Others)
My radical non-radical belief is we all have plenty of stories to tell and ideas to share, all of which are better than the typical types of content alleged experts urge us to create. But to unlock and unleash that kind of work requires a mentality shift. You're probably told to "talk to y
To tell stronger stories, understand yourself first - Ryan Hawk & Brook Cupps, Coauthors of The Score That Matters - How Stories Happen #8
Storytellers often face a paradox: to connect deeper externally, you have to turn deeper internally. You have to know yourself and get more honest with how you think and feel than others might be comfortable doing themselves. That often means we have to stop caring what people think of us quite as m
“You have to work against people assuming they know how this goes” - Danielle Bayard Jackson, Author of Fighting for Our Friendships - How Stories Happen #7
How do we compress our lifetime into their runtime? When we’re asked to explain our backgrounds and bios, we need a structure, some practice, and a few anecdotes at the ready. Because our story has to pull triple-duty: clarify who we are, build credibility, and teach whatever it is we’re there to te
20 Truths of (My) Creativity
There's this version of me I often think about, and he brings me back from the brink. When life gets hard, when the kids aren't sleeping or they tantrum regularly, when my schedule gets blown to bits for whatever reason or the news finds a way into my eyeballs a bit too much ... when my work isn't
"I could tell this story in 1950 or 2024 + it would work" - Scott Monty, Exec. Coach - How Stories Happen #6
While everyone scrambles to learn the new trends and act like a futurist, it’s the folks who understand what parts of this work are timeless – because they’re based on human nature – that are most powerful of all. Storytelling is one such thing. It’s been a constant throughout the history
"Words Can Do WHAT?! Are We Serious Right Now?!" - Tucker Bryant, Poet & Speaker - How Stories Happen #5
How do we craft a metaphor that works? More importantly, perhaps, how do we ensure the metaphors we use pivot to the audience to teach them something in their lives or work, without them getting lost? Do we overtly explain the lesson? Imply it? Some combination? It’s a delicate dance, and few do it
Be a Noticer (Your Creativity Depends On It)
It's 2024. It's high time we got some innovation in car horns. (Stay with me, it's gonna get weirder before it gets better.) Look, I don't know about you, but I'm out here every day trying to communicate many more things than this technology lets me. Sure, I can do "beep-beep!" ( hi, fri
"We Congregate Around Emotional Stories" - Rand Fishkin, CEO of SparkToro - How Stories Happen #4
The hardest question to answer when we show up publicly might be the simplest question we receive: “Tell me about yourself.” Who are you? How’d you get here? What’s your story? We then face a choice: we can make the story about us, or we can make it about the thing we’re there to say. We can make o
How to Turn Your Ideas into Visual Frameworks
Throughout May 2024, members of the Creator Kitchen and I are participating in a community-wide creative challenge. We've each picked one goal to accomplish all month long, which must be creation-focused, ambitious, and measurable. We're calling this challenge... MAYking It Happen. (Sigh. I know
"How Do We All Sign Our Work?" - Ann Handley, Author & Keynote Speaker - How Stories Happen #3
When so many people are excited to create a higher volume of content, shouldn’t we think more about what gives our work greater power? That’s what our guest today understands better than most, and she draws that power from everyday moments she hunts out, like a squirrel finding nuts in the yard. Me
"A Story Needs a Job To Do" - Michelle Warner, Business Designer - How Stories Happen #2
Our guest for this episode is rarely online. But when she is, she’s telling small stories with big meaning. Meet Michelle Warner—she’s a business strategist and consultant who architects business models and marketing strategies for clients who sell high-priced services. She also hosts the podcast S