Unthinkable has ended. Please follow my new show, How Stories Happen, in its own feed.

Unthinkable is no longer running new episodes. Listen to the new show, How Stories Happen, wherever you get your podcasts.... more

Hear the trailer for my new show, How Stories Happen, where creators and communicators dissect their stories and drafts, piece... more

The planning fallacy plagues most people, regardless of profession. We under-estimate how long something will take in the near-term, i.e.... more

How do stories really happen?

What's the difference between creating content that others find and consume, and creating things that others adore?

A question to increase the power of your ideas which we're just not asking often enough.

An idea to embrace when you want or need to create, but you sense your work isn't quite where you... more

A holiday tradition on the show. I rewrote a class poem just for our purposes as content creators, storytellers, and... more

Inspiration is everywhere -- if you're paying attention.

Great stories aren't found and reported. They're built and practiced. Effective storytellers know how to imbue any moment with meaning.

Respect creatives. Respect writers. Respect artists. Pay creatives. Pay writers. Pay artists.

In our fourth episode of this mini-series, a prolific creator shares three different possible intros for a powerful new story... more

In our third episode of the mini-series "Signature Stories," we're looking at how a small story can create massive meaning.... more

In our second episode of the mini-series "Signature Stories," we're looking at the making of a tiny but powerful story... more

In a brand new mini-series, we're diving into signature stories from our favorite storytellers. Like Song Exploder but for stories,... more

In this one-shot, we explore taste - what it is, how we define it, and how we can continue to... more

It's our fourth episode hearing from creative people about their internal barriers. Specifically, we'll hear stories and ideas about the... more

The case for focusing on formats, specifics, and following your own interests.

In this one-shot, we explore how to to define quality through creating useful friction, asking 3 important questions, and adding... more

What does it look like to bet your business on resonance, not reach?

In this one-shot, we explore the problems with how "story" is taught, and why rather than focusing on understanding story,... more

In this miniseries called MINI-Series, we’re investigating the little pockets of work that resonate deeply. First up, copywriting and how... more

From a popular video featuring artists Pharrell Williams and Maggie Rogers, an overlooked lesson for doing more meaningful creative work.

We're sharing a favorite from the archives, a classic featuring a New York artist's odd but revealing experiment and the... more

Derek DelGaudio and his one-man show, In and Of Itself, offers a masterclass in how to customize any story we... more

Hrishikesh Hirway, musician and creator/host of Song Exploder, dissects clips from his show. Plus, we explore the overlap of grand... more

How did we arrive at a place where so many creators view AI tools like ChatGPT as a killer robot... more

We celebrate 200 episodes by facing a scary question about the show, then exploring the riddle underpinning every creator's work.

Inside a project, which represents a movement, which represents some hope for reconciling creativity, community, and capitalism.

There's a difference between good storytellers and effective storytellers. Understanding that difference can make all the difference in the world... more

Want to exceed the expectations of your audience? Get ready for a paradox. Maybe the best way forward is, in... more

Nothing is boring. Everywhere around us are small stories with big meaning, if only we'd stop to notice before using... more

Revisiting the eye-opening, ever-changing story of the Savannah Bananas, a small baseball team making a big ruckus.

In a new short-form monologue episode, we explore the world's most powerful storytelling technique.

What if neither working harder or working smarter is the solution? If you're wondering what's even left to try, that's... more

2 Pages with MBS is a refreshing twist on the typical interview show about success in work in life. Recently,... more

In a new short-form, monologue One-Shot, a list of questions to ask when looking to learn from, hire, or collaborate... more

The finale of our MINI-Series, exploring the tiny pockets of creative work that create big emotional responses, with sound designer... more

Part 3 of our MINI-Series, with comedy writer Matt Buechele (The Tonight Show, Netflix).

In our second MINI-Series story, we continue investigating the little pockets of work that resonate deeply. This episode, webcomics and... more

In this new miniseries called MINI-Series, we’re investigating the little pockets of work that resonate deeply. First up, copywriting and... more

This episode we’re exploring our “maker monsters” --  internal barriers which we must wrestle with, befriend, or defeat in order... more

Announcing a new initiative to help you elevate your creativity and see better results from your work.

In a new short-form, monologue One-Shot: In the Margins, Jay reflects on the lessons from one of his favorite childhood... more

One company's mission to increase the signal of the internet, starting by serving writers. In an era defined by egos... more

A story about breaking old habits as you grow, while breaking from conventional wisdom that stifles creativity and leads to... more

The Concept is a new Unthinkable miniseries. Each episode, we explore a single named concept, dug up from science, history,... more

Some people (not you) make excuses for why they can't be more creative with their work. When you hear those... more

The story of when intuition clashes with convention, and how one entrepreneur solved a rather smelly problem in a refreshingly... more

In a new short-form, monologue One-Shot: Rocky, what one of the movie’s most iconic scenes can teach us abound working... more

The Concept is a new Unthinkable miniseries. Each episode, we explore a single named concept, dug up from science, history,... more

The phrase Creator Economy has become inescapable, but there's a looming decision individual participants will need to make which can... more

In a new short-form, monologue One-Shot: why lists often lie, why we love them, and the history of our obsession... more

This week’s episode is an almost surreal, escapist journey into the true story about how the Savannah Bananas became exceptional... more

As the year comes to a close, we’re re-examining how far we’ve come in trying to understand one key concept... more

In a new short-form, monologue One-Shot: My Weekly Constraint and how to address our personal maker monsters.

The story of the most popular YouTube channel about yoga: Yoga with Adriene. Or, really, the business decisions they've made... more

It's our third episode hearing from creative people about their internal barriers. Specifically, we'll hear stories and ideas about the... more

The story of a surprisingly dynamic and captivating idea from a (sometimes) bland and boring space -- and what we... more

In a new short-form, monologue One-Shot: What is the science of resonance and how to we apply it to our... more

We’re back again with our maker monsters and this time we are unpacking imposter syndrome and fear or rejection. Cousins... more

In a new short-form, monologue One-Shot: What we mean by art, and why it matters in the business world.

A transformative idea in how we approach our work in order to resonate deeper: Ask questions Google can't answer.

What makes someone pick you, stick with you, and stick up for you? Your ability to resonate. So how does... more

The planning fallacy plagues most people, regardless of profession. We under-estimate how long something will take in the near-term, i.e.... more

In this new One-Shot (our short-form monologue episodes complementing our larger narratives), I share a term from filmmaking that can... more

This episode we’re exploring our “maker monsters” --  internal barriers which we must wrestle with, befriend, or defeat in order... more

In a new short-form episode, we talk about a fool's errand masquerading as a motivational tool in the workplace.

On this episode, we seek to topple the tyranny of always being right, being certain, and thinking conventionally, and instead... more

It's time to talk about imposter syndrome, mushrooms, and reframing how we view our work so we can get to... more

It's time to revisit an old story, one that may not age well but reminds us of our role as... more

It's time for another short. In this one-shot, let's talk about the BS that stands in the way of seeing... more

Whether you embrace hustle culture and effectively inject the advice equivalent of Red Bull to the brain every day, or... more

What do prolific, thriving creative people have in common that the rest of us don't? It's hard to pinpoint any... more

A special bonus episode: a cross-post of my appearance on Jay Clouse's podcast, Creative Elements. It's the greatest interview/production combo... more

We can't make what matters without facing some resistance -- from our peers, our bosses, our clients, our audience ...... more

In another one-shot episode, we talk about how to evolve as a storyteller in your career across three distinct phases.

A moving mystery story about connection, creativity, and family. This one sticks with you.

How to make your creative process more fluid and your output more prolific.

As we continue to explore this idea of "the next rep," we have to stop and ask the obvious question:... more

Trying something new to ensure more people can go on this journey towards making things that make a difference.

The most inspiring-yet-frustrating quote about creativity -- and the launch of our new exploration on creativity and creative careers. And... more

Today, we wade into some uncomfortable waters, like the problems with experts and expertise (or at least Expert Overload), and... more

Finding best practices isn't the goal. Finding the best approach for YOU is. But if you're going to do that,... more

Years before Sarah Cooper's rise to mainstream fame, she was featured on Unthinkable. (We know this show was REALLY her... more

Tim Urban's blog Wait But Why ignores almost every best practice. Should we? Is it that simple? (Spoiler alert: No,... more

Today, a story made for this moment, about people who were made for this moment.

Today, we go into the Unthinkable archives and revisit the ideas of Jack Conte and Jay Acunzo's shared views on... more

In this episode of "I Made It," one of the world's most sought-after copywriters and writing teachers goes inside the... more