The Great Myth of Brand and Finding a Simpler Understanding

great myth of brand

Conventional thinking says we should grow reach.

Conventional thinking says we should look for more.

Conventional thinking says bigger is better.

Conventional thinking ... is conventional for a reason.

No matter how sound or logical, pervasive or pithy, best practices are lagging indicators, not leading indicators. On my newsletter, Damn the Best Practices, and really in all my work, I've long advocated for a renewed focus on resonance instead of reach. It's not just my little corner of the internet, either. Over the past 6 months, I've gone inside 10 of the world's best B2B organizations to uncover how and why they're prioritizing brand. In this docuseries, Exceptions, I profiled InVision, Zoom, Wistia, Help Scout, First Round Capital, Grado Labs, ProfitWell, Lessonly, Buffer, and Gusto. In talking to both their teams AND their customers, my eyes were opened to a simple fact: Great brands grow by prioritizing resonance instead of reach.

In the end, brand is merely the sum total of every experience others have with you (whether that's "customer experience" or "employee experience"). Every tweet, every email, every purchase, every MOMENT -- it all adds up to create the brand. In other words:

Brand is how others feel about your people.

Period. That's it. It's all about those two things: how they FEEL ... about YOUR PEOPLE.

Again, brand is the sum total of every experience they have. Every experience is created by people. Thus, every brand is built by the collective behavior of your people. That's all this is. We overcomplicate this, and we hide that blunt reality behind words like "company" and "department" and "campaign," but these are merely constructs. They are legal or theoretical entities. The words are shorthand for "the people who work for us." In reality, a "company" is a nonexistent, empty container -- that is, until we, the people doing the work, fill those containers with what we create. Brand is thus the emotional reaction that others have to our stuff that creates a brand.

And today, in this world of infinite choice, we choose to spend time with great experiences. In other words, we choose great brands.

In the business world, we tend to inflate these ideas into more sophisticated-sounding but ultimately meaningless ideas. We think building a brand means launching one-off “brand initiatives,” but in reality, EVERYTHING we do builds the brand.

We chalk up those discrete “brand initiatives” as things that don't drive results, but in reality, a great brand grows inbound results while making it easier to go outbound.

We think “brand” means putting some final polish on something or perhaps launching something fun or “viral.”

In short, the conventional thinking on "brand" is that it's a nice-to-have thing which is all about reach. In reality, it's all about resonance. It's the emotional response others have to our work.

Here’s the bottom line: Every individual has AN experience of our work. The only real question is: Are we being proactive about crafting a great one?

This idea was originally shared to my newsletter. You can subscribe below.

Posted on December 9, 2018 .

Worthy Or Not, Here I Come: The Cure for Imposter Syndrome


My aspirational anchor (the method for setting goals that helps us make more contextual decisions) has long been “to tell the most emotionally resonant stories about work that I can.” This forces me to focus my time and effort on a few things above all else, each of which comes with a tradeoff: stories (not advice), resonance (not reach), and constant improvement (not expertise or any other notion of finality — the “that I can” part of my anchor). My biggest area for improvement is that third part (which is a bit obvious, I suppose, when you consider the third part is “constant improvement.”) 

I don’t know about you, but I often forget to ask myself, “Is this thing I’m creating better than my last?” In my drive to publish, I often release work without ever pausing to consider if I’ve really created the best story about work “that I can.” Instead, I prefer to rely on the number of reps that I put in, because I know I create a ton of stuff relative to the average bear. (Squirrels have me beat though. But they mostly publish clickbait.)

To get better at getting better, I plan to ask myself two questions before shipping my work. They won’t take long to answer, so I can avoid paralyzing myself, but they should be a part of my flow from here onward:

  1. Did I articulate the story’s conflict with enough clarity and emotion? (For those who missed it, here's last week’s email about why conflict matters to story, and how to build your own using the One Simple Story framework.)

  2. Did I tell the story my way? (This means that my quirks, beliefs, and voice must be fully present. I don’t want to create derivative work, nor do I want to create what I think will “work.” If I do either, it’s a sign I ignored the most crucial variable between my context and everyone else’s: me.)

I don’t think I’m alone in struggling with these things, and since I addressed #1 last time, it’s time to tackle #2. What does it mean to do the work "your way" anyway? Isn’t that a scary and vulnerable place to be? What does it mean to be fully present? And, of course, why would anyone care that I did it my way? Am I worthy of their time, attention, and love?

Uh oh. We’re stumbling towards the vast swamp of self doubt, with all its twisting vines of internal debate and the endless croaking of frogs. “Fraaaaud! Fraaaaud! Rippit (up). Rippit (up). Fraaaaud!”

Imposter syndrome plagues a lot of us. But if I’m being honest — and, for once, I feel awkward about being honest — it’s never plagued me.

"ALRIGHT, tough guy,” I hear you thinking. “Nice humble-brag, you greasy-haired egomaniac.” (Not the hair, c’mon…)

Look, it’s not that I’m a single cell better than anyone who DOES feel imposter syndrome. It’s just that the nature of my work has REMOVED the issue entirely. This might sound surprising, given that I’m basically a business personality. What could cause imposter syndrome quite like that line of work? It’s all about ME, isn’t it?

And that’s the issue. It can’t be all about me. It ISN’T all about me. I believe that to remove imposter syndrome — and, really, to do this creative stuff we all do WELL — we have to remove the self.

Hear me out, because I don’t mean “don’t bring your full self to your work.” Just the opposite. We have to bring our full self, but we have to bring it TO the right endeavor. Think of it like this: 

You aren’t the work. You're the vessel for it.

In Break the Wheel, I advocate for a simple switch in how we make decisions. Rather than act like experts, who have all the answers, I propose we act like investigators, who ask great questions. Whereas experts value absolutes, investigators value evidence. It might be helpful to know some generalized theory, but what really matters is asking question after question, finding clue after clue, as the case unfolds. 

Well, if you’re an investigator, then ultimately, your work isn’t about “who you are” but rather “what you’ve found.” You stop focusing on this implied notion of self-importance (“I AM something”) and begin focusing on your investigation (“I FOUND something”). 

When you’re investigator, it’s no longer YOU that must be worthy. It’s what you’ve uncovered. Anyone could have done it. You’re not special. But what you FOUND is. And that’s the work they came to see.

With this simple mental switch, we can beat imposter syndrome. Why are we worthy? Who are we to earn their time, attention, and love? We’re the people who spent meaningful time asking important questions and investigating them thoroughly. We're here to present to them what we found. Let them judge away! They aren’t judging us. You’re judging what we found. We can then step back, away from that thing we found, and stand shoulder-to-shoulder with them to try and see it their way. We shouldn’t feel any more afraid or attacked than if we dug up a rock from the dirt and had someone point out what they see to be true about that rock. That’s not a comment on us. It’s a comment about what we found. 

Who we are still matters, but only so much as it informs our pathway to the work. The person you are is the trusty magnifying glass you can use during your investigation to see the world a certain way. But you still need to pull out that objective truth, and yes, put that truth out there for the world to see or judge.

Ultimately, I think we're all just vessels. Like journalists or detectives, we’re on the case. We ask great questions, and we seek the truth in the world, through whatever we create. 

When someone exhibits imposter syndrome, they continually doubt their worthiness or authenticity, and they live with a persistent fear of being exposed as a “fraud.” When you’re an investigator, however, this seems silly. Fraud? As in, a fake? I don’t even see how that would be possible. How can you fake the fact that I embarked on an investigation? How can I fake this thing I found? I assure you, it’s quite real.

In this era of insta-fame and Insta fame, we aren’t actually the stars of our work. That’s how I can avoid imposter syndrome even though I’m more or less building Jay, Inc. That’s how YOU can avoid imposter syndrome, regardless of what you do. They aren’t here to see us, nor are they really judging us. They want to know what we’ve learned. They’d like an update on our investigation. Work that’s worthy of their time and adoration isn’t created by handing others your answers. It requires that you ask great questions. Every individual alive is capable of doing that. 

Now open your word processor, turn on the microphone, start your design, take your camera on the road, start your company, go for that promotion, or walk through that curtain ... and give them what they REALLY came to see. 

It’s not who you are. It’s what you’ve found.

This post was originally shared to my newsletter, Damn the Best Practices. You can subscribe below.

Posted on December 6, 2018 .

Most Brands Use Data Incorrectly When Trying to Be Creative. Here's How to Avoid the Issue.


In the digital age, we can measure everything. We can measure clicks and views and how many of those views were unique. We can measure exit pages and bounce rates and conversion funnels. We can measure CPC and CPM and CPA.


We can measure (extremely Chris Traeger from Parks & Rec)LITERALLY everything. And because we can measure LITERALLYeverything, we find ourselves buried in data. This can both help and hinder creativity. The difference?

Are you "Aristotelian" or "Galilean" in your approach to data?

It turns out there are actually two ways we can use data, and it doesn't matter if the data in question is qualitative or qualitative. (After all, "data" simply means "information stored for later use." It doesn't mean "numbers.")

In our quest to create exceptional work, we'd be wise to understand both approaches to using data. We'd be even wiser (I'm talking owl with a graduate cap on his head-level wise) to use one of the two in our work.

So what are these two approaches, and which should we use? Ladies and gentlesubscribers, let's meet our contestants...

The Aristotelian Approach

Up first, we have the approach espoused by Aristotle and his followers. A-Stots believed the world was best understood by first seeking theessence of things (what we might call absolutes). 

We can know a rock by knowing the essence of rocks. We can know a river by knowing the essence of rivers. We can know a frog by asking for its license and registration. (Kidding of course. Frogs are notoriously apathetic about proper identification.)

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According to this approach to data, the more we gather information about something, the more we can update our understanding of all versions of that something. We strive to get closer and closer to understanding THE truth. In this way, your brain becomes a sort of filing cabinet. The more we learn about things that exist in the world, the more we can divide and subdivide everything into various categories. Then, when we encounter something that needs interpretation, we merely pull out the right drawer in this ever-growing cabinet in our heads. 

There are two glaring problems with this approach: absolutes (the “essence” of something) and the past (the filing cabinet).

When we approach data with an Aristotelian lens, we plan tomorrow's actions by looking at yesterday's understanding of the world. We cling to absolutes, or as I like to call them, assumptions. In the modern workplace, where many of us face complex problems requiring creative solutions each day, it's dangerous to make decisions based on assumptions. That's where Galilean approaches to data can save us.

The Galilean Approach

Galileo pushed a more modern approach to the scientific method in his focus on testing variables. Whereas Aristotle sought to understand The Truth, Galilean approaches to data require us to seek A Truth. In other words, rather than make decisions based on assumptions, we test, learn, and iterate quickly based on the specifics. 


When we view data with a Galilean lens, we embrace that context matters most. Effectively, Galilean decisions emphasize on firsthand learning, not theory or precedent. Rather than gathering up all the information (absolutes) we need to justify acting, we act to find new information.

As I wrote about in my book, Break the Wheel ("Break the Wheel: The spectacular new book from Jay Acunzo. Get yours now on Amazon!"), it's possible to make decisions with greater clarity and even speed when we make one simple switch: Stop acting like experts and begin acting like investigators. This means we no longer start our thought process by seeking everyone else's answers. Instead, we ask ourselves great questions about our specific context. Whereas experts know absolutes (what works in general or on average), investigators focus on evidence (what works in THIS situation).

Investigators prefer the Galilean approach to data. They realize that the Aristotelian approach hurts creativity. If we must justify every action we take using past precedent, well, we've all seen what happens:

  • The executive joins the company and begins to implement her playbook or hire "her people" without understanding this new team whatsoever.

  • The marketing team publishes list article after list article, bland piece after bland piece, because a famous brand or favorite expert or past moment of success suggests it's "the" approach.

  • A friend bugs you for yet another round of feedback for this new project they're going to launch, they swear.

  • A public speaker performs the exact same 45 minutes with every single speech.

  • ...and more, oh so much more!

In every case, these people build their work on a simple premise: "What worked there and then will work here and now."

Simple, yet faulty. Whether knowingly or (far more likely) implicitly, they're Aristotelian in their approach to data. The data says X. That's the essence. That's the absolute. That's The Truth. 

Cut. Copy. Paste. Ugh.

Don't Market to Vegetarians

Eric Siegel is a predictive analytics expert. While helping an airline brand figure out how to fill its flights more consistently, Eric noticed in the data that vegetarians missed fewer flights. Now, a busy executive or stressed-out marketer might stop there and say, “Great! The data has given us THE answer. We should market to vegetarians."

Thinking more critically and creatively, however, Eric wondered, "Whydo vegetarians miss fewer flights?" (Funny how that pesky question of "why" always slips past us when we just stare at the data.) Why do vegetarians miss fewer flights? Does the essence of a vegetarian include punctuality? 

Well, just think: How did Eric identify these people as vegetarians in the first place? That's not written on their ID, right?

The answer: They requested vegetarian meal options. Ah ha! It wasn't the fact that they're vegetarians that caused them to miss fewer flights. It was the fact that they personalized something about their experience! Whether because they were forced to spend more time with the brand, and thus it was top-of-mind, or because they were looking forward to their experience a bit more than the typical passenger, these people missed fewer flights.

By trying to contextualize an absolute, Eric found a true insight -- an insight on which they could act. Thanks to Eric, they realized,We shouldn't launch a giant campaign to target vegetarians. We should get more people to personalize something about their flights. 

And so they did.

And so they succeeded. 

It may have been cleaner for a chart or graph or statistic to point to THE answer, but remember: Reality is bag of crumbly cookies called Nuance Chip. (Inevitably available as vegan cookies soon...)

Which approach will you take?

Data informs. It doesn't instruct. That's why the need to be data driven is slowly given way to a new phrase among my personal community of tech entrepreneurs: being data informed. That idea hasn't leaked out of the tech bubble much just yet, but I believe it's the better approach to data. I believe it's the Galilean approach, renamed.

Just the phrase "data driven" brings to mind a six-foot, humanoid spreadsheet sitting on a horse-drawn carriage, only WE are the horses. But great work happens proactively, not reactively. When we're data informed, we isolate variables, test, and learn. We insert our own sense of taste and our intuition into the process. (As readers of my book know, intuition comes from the Latin intueri, which simply means "to consider" -- just like any good investigator does.)

If we're data driven instead of data informed, if we're Aristotelian instead of Galilean, then we base our decisions on one fundamental assumption: Our context here and now is exactly like to another situation there and then. In reality, of course, it's not EXACTLY the same. It's ALMOST the same, and considering the differences makes all the difference in the world.

We shouldn't make decisions by shrugging and saying, "Close enough."

Because close enough leads to work that's "good enough."

And "good enough" simply isn't enough ... for us.

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Posted on November 30, 2018 .

How a Simple Experiment at a Picnic Revealed a Universal Workplace Problem | Unthinkable Podcast

unthinkable podcast picnic experiment

Why do we gorge ourselves on holidays? Why do we do ANYTHING that seems mindless? "Because that's how we do things around here."


In this story, the psychological phenomenon that explains this type of decision-making ... and what we need to do to break from it.

Unthinkable is the podcast about questioning conventional thinking to think for yourself at work. The show features stories of people who make decisions that seem crazy, until you hear their side of things. It’s a highly produced, narrative-style show unlike anything you’ve heard from other business or career podcasts.

Listen on Apple Podcasts, Overcast, or wherever you get your shows.

Better yet, get each new episode via email (plus a new original story only found through the newsletter) by subscribing below.

Posted on November 19, 2018 .

One Simple Story: A 3-Step Framework for Telling More Compelling Stories


The following was originally shared via my weekly newsletter, Damn the Best Practices. If you like what you read, consider subscribing at the bottom of this article. I’ll send you my all-time most popular pieces right after.

Pay attention to these four stories, because, yes, there will be a quiz at the end.

Story 1) The itsy-bitsy spider went up the water spout. Out came the sun, and he happily continued his climb.

Story 2) Once upon a time there was a beautiful princess named Snow White. In the nearby forest were some dwarves, somewhere between six and eight of them if I had to guess. One day, a prince came calling for the princess. “Yo, shorty, what’s good?” he said. “I am! I’m good! And so are you, boo.” Then they lived happily ever after. (The dwarves did well, too: paid off their student debt, got a job at the fast-growing FaceScroll, and vested some serious equity before the IPO.)

Story 3) Meet Steve Jobs. He’s a wildly creative dude. Together with his cofounder, Steve Wozniak, Jobs built a computer. “Hey, Woz, you deserve most of the credit. Let’s tell the media that,” he said. “Rad,” said Woz. Then Steve turned to Bill. “Hey, Bill? I owe you a ton of inspiration for lots of this stuff, so I'll give you credit for that too." Bill was pumped. “You’re real neat!” he told Steve. Steve’s company thrived, every employee enjoyed working for him thanks to his pleasant management style, and he was always great father and never got sick and still lives in California today.

Story 4) Our company is revolutionizing the way businesses grow. By combining best-in-breed technology with exceptional service, we help you realize your dreams. Just ask our customers! (Cut to case study video.) "They revolutionized how our business grows. They combined best-in-breed technology with exceptional service, and they helped me realize my dreams."

POP QUIZ! Why do all these stories make me want to press my hand against my cheek and make truly offensive fart noises?

Because they’re awful!

And why are they awful? Because they're all missing something. They're missing CONFLICT. In fact, without conflict, I’d argue these stories aren’t really stories at all. They’re just … statements of fact.

Conflict, or friction, or uncertainty, or drama, or tension, or something, anything at stake … THAT is the most foundational piece of a story. It's what creates the narrative arc that holds attention, resonates emotionally, and inspires action.

Just think about why we call it an "arc" in the first place. Arcs move upward towards a crescendo before sloping back down. What causes that lift? We raise the stakes. Their anticipation grows because they understand that what we're saying truly matters, and they can't wait to hear what happens next.

That's what happens when we insert some conflict. We create a compelling arc:

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Unfortunately, we often fail to add that piece into our stories at any level: our brand, our team, our careers, our content. When we don’t tell an actual story, what happens to our communication?

It falls flat...

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And when what we say falls flat, they flatline. They feel nothing. They remember nothing. They do nothing.

When we fail to tell a story, we become ... nothing. Just a forgettable pitstop in their day, gone once they begin to spend time with something else that truly resonates with them.

With adding conflict, the itsy-bitsy spider merely climbed up a water spout. No worries at all. (Also? No need to sing about him.)

Snow White and the ... I wanna say four? Four dwarves? They began happily and lived happily ever after. No need to think about them ever after hearing their non-story.

Jobs was yet another guy who did well in his career. No lore takes shape.

And then, of course, there's our companies and how we usually communicate. We try to win their attention, to earn their trust, and to make them feel, but all we usually do is deliver statements of fact, void of interestingness, because they're void of conflict.

"Our company is soOoOo awesome. Have ya heard? Just ask our customers! They adore us, let me tell you what! We'll also tell you why ('cuz of all the awesome), and how (by paying us all the monies), and when (always and forever), and where. (Trusted by over 6.9 million companies, across 1,200 different continents, on 78 different planets.)"

Hand, meet cheek…

We need to get better at telling stories -- genuine, worthy, legitimate stories.

Story Structure Made Simple

Last week, I got a great question from a subscriber named Robert Rouse. He’s building a new product, and as a self-described technical guy, he wondered how he could improve his ability to communicate the power behind what he was building.

“I talk about the features, how it's made, pointing out how nothing else today can do what this will do. But that's not a story. It's not personal. No one cares about the features, they care about why the features should exist. How could I break out of thinking in "tech mode" to craft a personal story instead of explaining prototype sketches?”

Bloody brilliant. The key, as I hinted at already? Get bloody. Fight someone, and, if you have to, murder them. C'mon, do it for the story...

I’m kidding! I AM KIDDING! But, look, there’s a reason murder mysteries are so popular everywhere from books to TV to movies to news articles. (Experts predict that by the year Whenever Podcasts Became a Thing, every other show will be required to be a murder mystery.) And why? Because if raising the stakes makes for a great story, then few things are higher stakes than putting a life at stake.

In our work, we don’t need to kill anyone. (2018 Nominee: Least Necessary Sentence Award.) But we do indeed need to add more conflict to the things we say. If we did, suddenly, we’d become great storytellers. In a world where that phrase has become jargon, we'll reclaim it as something worthwhile because we know how to craft things worthy of their time. And yes, we can make this simple, through a three-part framework I call (pause for effect, casually sip coffee while looking you in the eye, start feeling like I’m using too many parenthetical asides in this email, decide that, screw it, I should just tell you)...

I call it the One Simple Story.

In branding, there’s this concept called the One Simple Thing. For years, Coke’s was “happiness.” My business, Unthinkable Media, might claim that every show we create for clients is in some way “refreshing.” I first learned about the OST years ago, and since then, I've wondered how a team turns the idea into ... yanno ... stuff people like? How does the OST turn the theory behind our brand into the actions we take? (That's how I define brand: How others feel about your team's collective behavior.)

Well, to move from idea to action, we can expand a One Simple Thing into a One Simple Story.

Every story contains three fundamental pieces:

  1. Status Quo. This is an agreed-upon belief or state of being. In other words, it's a statement of fact. It is the way it is. This email didn't open with four stories, it opened with four status quos.

  2. Conflict. BUT THEN ... something threatens or changes that status quo. (There's a reason every innovation story seems to use the word "disrupt.") Something is at stake, something just got hard, and we face open-ended questions or problems that need solving.

  3. Resolution. AND SO ... we reach the conclusion of the story. How is that conflict resolved? What is the answer to our big question, or the payoff to the stakes we've raised. The resolution is the better way of the world or the outcome we all seek on our journey together.

Status Quo. Conflict. Resolution. These are the three most basic, most foundational pieces of any story, and way too often, we forget to add the second, and so our audience never journeys with us from the first to the third. Simple? Yes. Transformative? Only if you're communicating with humans.

See if you can feel how much better the "status quos" from earlier become once I add the conflict:

Status Quo: The itsy-bitsy spider climbed up the water spout.

Conflict: Down came the rain and washed the spider out.

Resolution: Out came the sun and dried up all the rain, and the itsy-bitsy spider climbed up the spout again. You go, Itsy! (Yes, we're on a first name basis. We go way back.)

Status Quo: There once was a beautiful princess named Snow White, and like a baker’s dozen of these dwarves.

Conflict: Snow White’s mother dies, and her father remarries this horrible woman. Snow's new stepmom keeps asking her magic mirror on the wall, "Who's the fairest of them all?" When the mirror says Snow White, the stepmom tries to have her killed. But the huntsman fails to do so. Then, stepmom disguises herself as an old woman and convinces Snow White to eat a poisoned apple.

Resolution: The dwarves help Snow White until the prince ultimately vanquishes the evil stepmom and saves the beautiful Snow, because #truelove and #outdatedgendernorms and all that.

Status Quo: There once was a creative guy named Steve Jobs. He wanted to make beautifully designed and simple to use personal computers.

Conflict: He received market pushback, fought with his cofounder, and battled the powerful Bill Gates and Microsoft. He was also a terrible father for most of his life, and very sadly, he contracted cancer and died far too young.

Resolution: Steve Jobs built the most valuable company in history. He eventually mended his relationship with his daughter, inspired a generation of tech entrepreneurs, and delivered some of the most emotional and uplifting words during a commencement speech shortly before his death. Steve Jobs thus became legend.

So what about our story?

Whether it's our brand positioning, some website copy, a speech, a case study, or content we publish in any medium, we're faced with endless chances to tell a better story in our work. But each time we fail to add that second piece of the One Simple Story, we get stuck at the first, the Status Quo. We hand out a bunch of statements of fact, and if there's one thing I know you know, it's that facts don't convince anyone of anything. Stories do. Emotions do.

What if crafted our One Simple Story? What if we let that inform everything we did? Better yet, what if we created a compelling narrative arc from the perspective of the audience?

Our brand might stop looking like a commodity and become the refreshing exception in our niche. Our copy might convert, our speeches might inspire, our case study might actually be worth watching or even sharing (imagine that?), and our content might earn the time and trust we need to achieve all our goals.

Stories are friggin' magic.

Thus, rather than simply claim to be awesome, or best-in-breed, or other abhorrent jargon that prompts my hand and cheek to commence a disturbingly audible dance together, we might instead tell an actual STORY.

In the interest of transparency, here's my organization's One Simple Story. For context, Unthinkable Media creates original series with B2B brands.

Status Quo: As makers and marketers, we want our audience’s attention, and so for years, we focused our efforts on acquiring it.

Conflict: But today, thanks to multiple screens, ubiquitous and instantly accessible content, and endless choice in nearly every competitive niche, the buyer now has total control. They only choose experiences they genuinely enjoy. It is no longer enough for us to simply acquire our audience's attention.

Resolution: We need to hold it. That is our new mandate as makers and marketers. We need to shift our focus from impressions and traffic to subscribers and community. Everything we are trying to achieve becomes possible and gets easier when our audience spends minutes or even hours with us, not seconds. Don't just acquire attention. Hold it.

When we tell our One Simple Story, we also set up a kind of filter. Those who agree with or believe in that story are those we should serve. Those who don't see the world that way aren't worth our time. Best of all, once someone passes through that filter -- once they agree that, yes, this is my story, I'm on board, and I'm feeling you -- we reach a sort of "oh by the way" moment.

At the end of Unthinkable Media's OSS, there's this implied idea that IF you agree with that resolution, IF you want to hold attention, then, oh by the way, there's a type of content you can create with the one expressed goal of holding attention. It's called a show. That's what we make. We make them solely for growth-stage startups and challenger B2B brands, and we make them refreshingly enjoyable. Why? Because the goal is to hold attention.

Let's talk.

Your One Simple Story inspires action because it makes that next step seem utterly irresistible, not because you've gamed any system or hacked your way to a result, but because you genuinely and emotionally resonate with your audience. We crave reach, but we should focus our efforts on resonance. Because then? Oh by the way, you should download our report. Oh by the way, you should subscribe. Oh by the way, you should buy / attend our event / invest in our company / hire me for this job...

Stories. They're magic. Glorious friggin' magic.

Status Quo. Conflict. Resolution. The most overlooked piece is conflict. We don't need to craft any giant hero's journey, either. That individual you're interviewing for your blog or podcast? She’s struggling with something, whether she's an intern, an author, or an industry veteran. Find it. Explore it. Get her thoughts and more crucially her feelings on the subject.

That company you’re building? It exists to solve a problem for the buyer. What is it? Have you described it? Do you own it? Complain about it? Paint a picture of tackling it from the perspective of the customer?

That team or entire industry you’re trying to lead? Something's broken and needs to change "out there." Rally others to fix it. Beyond the jungle is a mountain peak. Bring others on that journey. Advocate for that change. Get angry at what's broken, then have the audacity to do something about it.

What conflict can you include in your story?

We all want to tell a compelling story, no matter what we do or where we work. But too much of what we say falls flat, and as a result, their emotions flatline. We can't continue to keep handing out status quos, pummeling people with statements of fact. The fact is, facts don't change people. Emotions do. So if we can tell a compelling story? My friend, there's nothing we can't achieve.

If we only mastered that ability to insert a little conflict, we'd put back the emotion into what we're saying. In doing so, we might finally deliver something worth spending time with, worth sharing, and worth loving.

We all want others to care about our work, but ask yourself: Are you actually giving them a reason?

Posted on November 15, 2018 .

The Hidden Force Causing Teams to Stagnate (And How to Break Free)


The following is an excerpt from my book, Break the Wheel: Question Best Practices, Hone Your Intuition, and Do Your Best Work. It's available on Amazon in print, Kindle, and audiobook formats.

Jim Mourey is an assistant professor of marketing at DePaul University in Chicago and holds a PhD in marketing and psychology from the University of Michigan. He’s spent his career studying how subtle cues in influence our choices and behaviors. When we spoke, he recalled a pivotal moment in his career that, on the surface, seemed rather innocuous.

In his mid-twenties, as he was exploring the city of Paris, he noticed a woman take a cigarette out of her purse and start smoking. That seems simple enough, but Jim couldn’t stop wondering: why do we constantly make mindless decisions? 

“I’d grown up in a generation in the states where smoking is this horrible, abhorrent thing that nobody should do,” Jim said. “Here was a woman who was non-consciously going through the motions and smoking a cigarette.” 

When something feels easy and familiar to us, why do we seem to abandon critical thinking, even if what we’re doing isn’t a good decision?

It turns out the culprit is a phenomenon known as cultural fluency. 

“In every culture, there are expectations of what’s accept- able and what’s not acceptable,” Jim said. “If something is unfolding in a way that we’d predict it would, that would be an experience that’s culturallyuent. And when some- thing is uent, we don’t have to think very hard about it because the world is happening as it should.” 

On the other hand, when something seems unexpected or different or even counter to conventional norms, that experience is considered culturally “disfluent.” Unfortunately for those who want to think critically for themselves, culture operates in the background. We don’t often notice its effects but are influenced by them when we make decisions. Something that feels culturally fluent becomes more like an automatic behavior than a conscious choice, and that can be incredibly dangerous if our goal is to make the best possible decision in a given situation. 

“Culture guides our behavior on a very subconscious level, so when things feel culturally fluent, we go with the ow, and when they feel culturally disfluent, we stop, hesitate, and think a little bit harder.” This was Jim’s hypothesis. To snap out of any pattern of mindless decision making, you can introduce some cultural disfluency. 

Unfortunately, that might feel rather uncomfortable. Since moments of cultural fluency happen so organically that we hardly notice, moments that are culturally disfluent create some discomfort. In the workplace, that can feel nearly impossible to tolerate. Jim understood this, and he set out to test just how much disfluency a person needs to experience to make better decisions. Naturally, he decided to run a test at his mom’s Fourth of July party, experimenting on unsuspecting friends and family. You know, typical picnic stuff. 

As guests approached the buffet table full of hot dogs, hamburgers, and sides, Jim handed them plates. Half of the group received festive plates covered in American flags and fireworks, while the other half received plain white plates. Without knowing it, these guests had just been enlisted in a psychological test. Because picnic stuff.

Waiting at the end of the buffet, Jim then weighed each of their plates. The results revealed the unseen power of cultural fluency.

“What we found was that people with the Fourth of July plates took significantly more food than the people who got the white plates.” 

Jim surmised that, since the Fourth is an American holiday based on gorging yourself, it felt natural to those guests with festive plates to take more food. Those with white plates, however, were disrupted ever so slightly and subconsciously from the mindless ow of the holiday enough to consider what they were doing. 

Later that year, Jim ran the test again, experimenting once more on his friends and family, this time at a Labor Day picnic. In this iteration of the test, half the guests received white plates while the other half got plates intended for Halloween. As he predicted, people with the starkly out- of-place pumpkins and ghosts on their plates took less food than people with white plates. 

“So taken together, we get at least initial support for this idea that, when there’s a cultural fit, when things are as they should be, people don’t really think. They tend to go with the ow. But when there’s a disconnect, suddenly things are strange. They’re not so strange that consciously we think, ‘Oh, I should take less food.’ It’s just that, for automatic behaviors, we do them less. We hesitate a bit.” 

We hesitate a bit—that line really stood out to me. When our minds urge us to follow a best practice, what if we hesitated just a bit? That would create the necessary space we need to think more critically. According to Jim Mourey, when our minds notice a disconnect between what we expect and what actually happens, even if that disconnect is small, we tend to make more informed deci- sions. Those moments of cultural disfluency awaken our brains to the reality right in front of our faces that we’d otherwise miss as we follow the ow of familiar behavior. In that way, small moments that are uncomfortable can trigger the use of our intuition, i.e., that ability we have to contemplate our environment. Now here’s my question:

What if we could proactively create moments of cultural disfluency? What if we could awaken our intuition on demand?

I think we can, if we’d only master one skill above all others: asking better questions.

By asking great questions of the world around us, we can create some small but necessary distance between us and an expected behavior or flow. That helps us begin to form a more thoughtful answer. In other words, when we act like investigators, we break from cultural fluency to begin thinking more critically. 

“There are people who subsist in the status quo,” Jim said. “These are the people who see the numbers, they’re meet- ing the numbers, and life is good, so they don’t need to change anything. But if you want to be truly innovative, what my research suggests is that this is not the correct approach. If you truly want to innovate and change, you need to break up that ow. This can be something as crazy as redesigning the workspace so it creates an experience of dis uency, or it can be something as simple as traveling.” 

We don’t need to make ourselves unbearably uncomfortable to think more critically about our work. Sure, overhauling your entire workspace could do the trick, but so could a quick trip to a new location, or maybe a plate that looks slightly out of place at the family picnic. Yes, quitting your job to try to build something entirely new and different removes you from the daily flow, but so does simply asking good questions to better understand and test things around you. We need only experience some slight discomfort, and suddenly, we’re paying more attention. Our intuition has been activated. It can really be that simple and small. What matters is that we can see things more clearly, think for ourselves, and make the best decisions for us.

We don’t need to do anything radical to achieve that.

As we established earlier, intuition is the act of considering the world. Thanks to Jim Mourey, we’ve identified what appears to be the biggest barrier to doing so: cultural fluency. However, I actually think that cultural fluency is a symptom. It’s not the illness. Yes, it prevents us from thinking for ourselves, but we aren’t trying to merely think for ourselves. The entire purpose of this journey we’ve taken is to act in better ways. We want to create better work. That may start with making better decisions, but we’re not making these decisions in our heads. They have to inform and change our work each day. So if cultural fluency is the symptom, the blocker to better thinking, then what’s the illness? What is the final barrier between you and taking action?

That's what we explore next...

*   *   *   *

(It's me again. Blog Post Jay.) Knowing about cultural fluency has changed my life. Seriously. I'm in love with the work that I do, and therefore, I can let my aspirations run wild on me. At times, I can let blind aspiration take over for critical thinking. "Blind aspiration," it turns out, can lead to the work equivalent of gorging yourself on the Fourth of July.

Because I'm hungry, and excited, and excitable, and adore creating, and get dopamine hits when people say nice things or when I earn that next show, or speech, or check ... well, I sometimes eschew mindful decision-making for moments of going with the flow based on what one is supposed to do in that situation.

Recently, for example, I was scoping my plans for Unthinkable Media for 2019 in a way that would have been truly detrimental to my happiness if I didn't catch myself. I was setting these aggressive financial goals, which runs exactly opposite to my OWN thinking on how to set goals.

And why? Because driven, ambitious people do such things? Because annual planning means setting huge growth goals? Because "success" means building a staff of people and passive revenue and becoming a zillionaire? 

Yep. Because of that. Because of cultural fluency. 

Instead, I've reverted back to my aspirational anchor. That means thinking about the craft and the process. It means focusing on RIGHT partners (growth-stage startups and challenger brands) instead of the BIGGEST partners (because I find the way most leaders act when they work for massive organizations to be insufferable). I scheduled video chats with subscribers (I'll do more again soon). I switched from mindlessly reacting to what "one should do" to a more proactive, mindful approach to figure out what I should do.

Look, I know this excerpt above wasn't the emotional gut-punch or inspiring story you might have come to expect from me. Maybe you loved it, maybe you didn't, but I am down on my knees (or, at least, reclined on my couch on a Friday night) and I'm BEGGING you: Take cultural fluency seriously. Don't make mindless decisions. All it takes it asking a few more open-ended questions about the working world around you. That's enough to create that necessary cultural DISfluency to the situation to think more critically and make better decisions. (If you need more guidance, that's why I wrote the book.)

I PROMISE you, if you do this, you'll avoid doing things because that's what "someone" in your situation should do, and you'll start down the path towards what YOU should do.

Because that's what matters.

Posted on November 9, 2018 .

Their Work Seems Crazy, Until You Hear Their Side of the Story: Unthinkable Season 3


Season 3 of Unthinkable saw us exploring a wide range of moving, hilarious, and surprising new stories across all kinds of industries: public speaking, consumer electronics, nonprofit and public transportation, software design, CPG, podcasting, beer, blogging, and more. We met a speaker with a man bun and a CEO who prefers PEO — that’s “Poo Executive Officer.” From a safety message the world couldn’t stop singing, to the Procrastination Monkey who couldn’t stop getting in the way, we ventured to the far corners of the business world to dig up stories you’ve never heard and extract insights you’ve never considered.

With each episode, we pushed forward in our journey. As a community, we’re bothered by suck, hellbent on doing our best, and can’t wait to think for ourselves when we’re surrounded by conventional thinking.

These stories inspire us, and their insights empower us.

I’ve been writing, speaking, and creating podcasts for years. Without question, Season 3 is the greatest collection of stories I’ve ever told. I hope you enjoy!

You can also find these stories in the Unthinkable backlogs on your podcast player of choice: Apple, Spotify, Stitcher, Overcast, or wherever you listen.

Posted on November 1, 2018 .

Perfect Isn't the Enemy of Done: Where the Desire for Perfection Really Fits in a Thriving Workplace


This was originally written for my newsletter, Damn the Best Practices. Each week, I share one idea about thinking for yourself at work. The newsletter is for people bothered by all the awful commodity crap out there. You'll find no "hacks" or "secrets," only stories for people who love quality and craft -- like you! 💛 Join free right here.

This week, I'm torn about something we all face. Maybe we can work through it together. I suspect that since you're bothered by commodity work and hellbent on making quality stuff, you struggle with this too.

Here's the deal: When someone says, "Perfect is the enemy of good," or, "Perfect is the enemy of done," this is me:

burn it all down.gif

Burn .... BURN! Thou bringest SHAME upon the House of Creativity! I cast ye out, evil spirits! Be gone, and take thou laziness and thou shoddy craftsmanship with thee, foul beasts! 

(I am nothing if not passionate, thank you very much.)

See, too many people in the business world hide behind pithy phrases like "Perfect is the enemy of good" to justify shipping stuff that's so unbelievably NOT good. And when I see that happen, well, yanno ... fire and brimstone and while we're at it what even IS brimstone?

But last week, one reader helped me realize this stuff's way more nuanced and difficult to parse. Our brief email exchange then unearthed a new thread I wanted to yank on today. 

Last week, in an edition of my newsletter titled "Now what?", I wrote about resetting to first principles to continue this journey we're all on together. A huge part of my writing, and the subject of several email entries including last week's, revolves around this idea that we're battling commodity crap and fighting for better, more exceptional work in our careers, companies, and industries. Naturally, when someone scoffs at the idea of perfect and suggests that "good" or "done" is a superior end goal, I tend to clap back. 

But then Sherene Strahan emailed me from Perth, Australia. Sherene's is a longtime reader and supporter and someone I'm grateful to have gotten to know through this newsletter. (Thanks and hi, Sherene! ) Here's what she wrote me that made me lower my arms and cease all fire and brimstone (whatever that is)...

I'm still developing my own voice in this area [content marketing and business more broadly - Sherene's from journalism and communications] and where you talk in this email about the dross on the internet right now, I felt like you were looking straight at me!!! I'm not where I want to be writing wise, but the only way I can get there is to be bad first. So here's my question: How can we who believe what you believe still push ourselves to get better when we know that, right now, we're probably contributing to more of that sucky stuff?

I mean...

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How much do you love that question?!

How can we aspire to be exceptional but still embrace the only path towards it? Not to mix children's shows too much here, but to quote Jake from Adventure Time: 

"Suckin' at something is the first step to becoming sorta good at something!"

(Adventure Time isn't REALLY a children's show, but I digress...) 

Alright, so: We want to do great work, and the only way to go from where we begin to “great” is to be bad for awhile. Then how are we any different from all that sucky stuff out there? Are we part of the problem?

Well, let's revisit that pithy phrase: "Perfect is the enemy of good (or done)." Why am I constantly calling down fire and brimstone, also known as sulfur? It's because this phrase lacks nuance. It implies that we can't aspire to be perfect AND ALSO ship our work. So, as the saying implies, to motivate ourselves to take action in our careers, we must first remove the desire for perfection.

Pffft. PFFFT!

Then again ... we DO need to ship our work, even if it's bad. We can’t let a desire to be great cripple us to the point of paralysis.

So how can we aspire to perfection (even if it's never something we reach) while still moving forward without delay (even if we aren't creating amazing work yet)? Well, I think the key is to place perfection where it belongs: away in the distance. Then, we can busy ourselves with marching towards it. And the only way to march towards it? Yep. Gotta suck. That’s the first step to being sorta good. And THAT is the first step to being legitimately good. And THAT is the first towards … you get it.

Thus, the real focus shoudn’t be on perfection or action. That’s a false choice. Instead, our focus should be squarely on the driving force behind any thriving career or team: constant improvement.

So, Sherene, the answer is slowly codifying in my mind. Why are you different? Because you took time out of your day to write that email. Why are you any different? Because you were willing to be vulnerable with me, basically a stranger. Why are you different? Because you clearly care. You care about constantly improving. That's what separates you ... and me ... and YOU (yes, you, reading this right now). That's what separates all of us. We may not be doing great work just yet, but we care about getting there. 

Perfection drives us forward. We'll never reach it, but we care about doing the best possible work we can. On the other hand, others who willingly create so-so stuff because “Eh, it works” don't care much at all. Whereas you and I want to maximize the upside, they’re focused on mitigating the downside. They want to put in the least possible effort for the most possible gain.

So, what's the difference between us and them? Intent.

What WE intend to happen is far different than what THEY intend, especially over the long arc of time. As for those receiving our work? I think there are clues they can spot that help them think, “Okay, this project may not be great yet, but it’s trying to be and I appreciate that.”

Take my work in podcasting and public speaking. When someone tries to start their episodes with a cold open instead of droning housekeeping or a glut of calls-to-action ... or when a speaker tries to tell a meaningful story instead of push their "simple secrets for success" … it shows. Both people may execute those things poorly right now, but the signs are there. Like a cook with delicious produce and a prime cut of meat, they started with high quality raw ingredients. They just haven't figured out how to turn that into a great meal yet. But make no mistake: This next dish is gonna be so much tastier than their last.

Outside the working world, as a child, I experienced this in basketball all the time. I was a scrawny, slower player. When you looked at the stats at the end of a game, I wasn’t likely to stand out. I looked so-so at best. But if you watched me play, you could tell I hustled. You could see my jumpshot’s form. You could watch a few moments here and there on defense where I ran to the right places and did the right things. Those all eventually added up to a starting spot on the varsity team in high school. Sure, early on, a fan or two may have thought, “Meh, he’s not so great.” I had to be okay with that, just as you have to be okay with a few others NOT noticing the signs that you have potential in your work. But more often than not, people do notice. Our work offers clues. The narrative that everyone is judging us harshly is in our heads. It’s up to us to ensure that we bring with that terrible thought a better one: I don’t care if they judge me now, because my intent isn’t to be good now. My intent is to be great tomorrow. My focus is constant improvement.

Perfect isn't the enemy of good, nor is it the barrier to done. I just think we're framing the idea all wrong. Aspire to perfection over time, but make sure you're taking one step forward today.

Make the goal constant improvement. Bring the right intent to your work.

"Perfect is the enemy of good" the enemy of great. Keep trying to be great.

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If you enjoyed this entry, you’ll love Break the Wheel: Question Best Practices, Hone Your Intuition, and Do Your Best Work. BTW is my first book, released this past October. Remember: Finding “best practices” isn’t the goal. Finding the best approach for YOU is. We’ve never explored how to do that, which is why I wrote the book. It’s available in print, ebook, and audiobook versions now >>

Posted on October 29, 2018 .

5 Promises to Myself (And You) After My Third Year as a Professional Keynote Speaker


In my third annual installment of keeping myself accountable — and trying both to be transparent and to rally others to do so — I’m continuing my personal battle against BS in my industry. But first, my annual confession, because the nature of this post makes me truly uncomfortable: I realize this post is largely about me. While I write personal stories often, my goal is to do just that with my writing: Tell stories, not laud my work. If I talk about myself, I have to earn that right over time with you, and sharing stories (when they aren’t about others) seems like a good way to do that. So, I’ve given myself permission to write this one article each year to refer to myself almost exclusively.

This post provides the space for me to be introspective about the bigger picture when so much of my time is spent just trying to push the boulder forward. It keeps me centered, and it helps me remember the first principles of why I do this job and what I stand for. 

I’d also encourage other speakers and creators to try this since, let’s face it, this job can warp your sense of self and inflate your ego in a dangerous way. 

Last year, I added a fifth promise to my original four, then graded my progress against each. Now that Year Three is coming to a close, here’s a look at how I’m doing across all five.

2018 Grades

#1: I promise that my Personal Attitude Dial will always be set to “Grateful.”

Public speakers tend to separate into two camps: those who remember this job is a privilege and those who have forgotten. I realized that (and wrote that) last year. But I’ve changed my perspective slightly this year. See, I used to think ego and selfishness caused a speaker to forget just how grateful we should feel to do this work. Now I think it’s more nuanced. Sure, there are those ridiculous speakers you meet who make you go, “Okay, pal. Please just be a human.” But as you slog through endless flights, hotel rooms, and “grip and grin” photo opportunities, it can definitely cause even the most gracious and warm of individuals to forget just how AMAZING this job really is.

Resetting your attitude to Grateful is paramount. It not only makes the work and the speaker more enjoyable for all people involved, it grows the business! Ever hear of the word “heliotropic”? I hadn’t either, until I started to research for my next book. Then I uncovered this notion that organisms tend to move towards the light. So, be the light. Be GRATEFUL. Always.

2017: B-

2018: A

I started by giving myself a B+ but, screw it, I’ve been all-in on gratitude the entire year. Events outside my work actually inspired this: Several friends endured hardships like the loss of a parent or trying times as parents themselves. On the positive end of the spectrum, my parents both turned 60 this year, and while my dad underwent successful surgery, they’re both in good health. My wife and I celebrated 5 years of marriage and 10 years together, and this December, we will welcome our first child, a baby girl. Whether through big moments like these or the small moments like an old friend visiting or the dog deciding, yanno, I’d be more comfortable on dad’s lap right now … I became more aware of good things and more focused on gratitude in 2018. I’m proud of that.

As a speaker, I realize each moment I’m introduced before a talk that, holy crap, this is so much fun. I also recognize that millions of people work their entire lives without so much as a thank you from a customer, colleague, or boss. Then there’s us performers. We do 45 minutes to an hour on stage and people literally applaud — TWICE if you count your introduction! I know there are always frustrating things about every job, but given that clap-happy reality, I think most speakers need to keep a lid on it. Be grateful, always. Stay humble, forever. You’re at an event to serve others, and in doing so, your business will be better served too.

Still, even with an A grade here, I can do better. Last year, I committed to scheduling more 1:1 calls with listeners and subscribers. I did a ton of that this year, but I can be more consistent still. Additionally, I have two ideas to set my Personal Attitude Dial to Gratitude … and then break the lever clean off so it remains stuck there. 

What I’m doing to improve: Celebrate great work, and give away more things more often.

Celebrating and giving: Those are my two tenets when trying to improve this promise to myself to remain grateful.

Celebrate great work: Three years ago, I launched a public journey to explore why there’s so much commodity or crappy work being created out there. I set my personal crosshairs on all the hollow tips and tricks, cheats and hacks, and gurus and get-rich-quick-schemes. I railed against all that stuff, trying hard to build the case for a better way of making decisions than clinging to conventional wisdom or trend-hopping. The culmination of that journey was supposed to be my book, Break the Wheel, published earlier this month. (More info | Amazon)

However, as I wrote to my subscribers this week, this journey is far from over. I’m still “bothered by suck.” But I’m now focused more on celebrating people who do great work.

If my first book was about identifying problems, breaking from old patterns, and enacting change, then my next book (and all content leading up to it) should be about what happens when you enact that change. In other words, in my journey to both remain grateful and continue my ORIGINAL journey, I plan to celebrate great work more often. I’m not just fighting AGAINST something. I’m fighting FOR something.

Then, there’s this idea of giving away more things, more often. This includes my time, but that’s such a finite and precious resource to me, so I’m also announcing things like the Break the Wheel Book Scholarship, whereby I give away a book for free to people whose financial circumstances preclude them from buying nice-to-have things like books (email me for details:, and my Buy One, Give One program, exclusively for newsletter subscribers, which I plan to announce soon.

Promise #2: I promise to wedge my brain’s loading dock permanently open.

2017: A

2018: C

I really slacked off on this one, my friend. Hoo boy…

After working really hard last year to attend other speeches at my gigs, as well as to read more and to ask great questions of what I assume I know or assume I’m good at … I lapsed on all that.

I can try to explain why: I wanted to get my non-speaking revenue engine running more smoothly, i.e., building docuseries with B2B clients. Plus, I felt burnt out towards the end of September and into most of October, and I’d attended one too many talks with an open mind, only to leave disappointed at events past.

But those are excuses. My goal is to be a lifelong learner, to always question my own biases and assumptions, and to focus my work on building a thriving BODY of work. To do that, I need to focus on improvement and learning, not simply rest easy knowing I am good at a few things. That’s the path to stagnation. Honestly? It’s lazy. I was lazy.

What I’m doing to improve: Systemizing how I learn

When something feels hard, our choices are simple: Don’t do it, or find a way to do it (which usually means, make it easier). I’ve been trying to make other areas of my business run more easily without my needing to work up tons of energy, like hiring Meg, my Manager of Awesome, and working with Annie, Daniela, Stephanie, and Jordan as editors and producers of my episodes at various times this year. I’ve been looking at how I spend my time, documenting my processes and goals, and trying to hire smart, creative people to assist where I need it. 

I can do the same with my personal development. 

In my case, that means trying two things, one at events, and one in the content I create. (I’m concocting this on the fly right now, so bear with me. I mean that figuratively, as I’m just thinking through this mid-stream, but also literally, as I’m 35,962 feet above Nebraska right now according to this screen on JetBlue.)

  1. At events: I commit to attending one speech at each event that seems like it will push me to be better, either a keynote with a big idea that can change me, or a breakout session about something I know very little about. 

  2. In my content: I promise to get back to publishing Unthinkable episodes. My podcast took a back seat to client work and writing the book all year long, but it was the main vehicle for exploring new stories and aerating/improving my ideas prior to 2018. I need to get back to that, and I think have a system in place for doing so sustainably. I make no direct revenue from this show, but in a very concrete way, everything I do on that show forms the basis of every dollar I earn.

Promise #3: I promise that being impressively nice is the only time I’ll actively try to be impressive.

2017: A

2018: A-

Yes, it’s another A(ish) grade, but mama didn’t raise no jerk. I’m a nice guy. I know that about myself. I struggled with being the “nice guy” in high school and college perhaps, but since entering the workplace, it turns out that being nice is a distinct advantage. (Sad, but true.) So I genuinely love this about myself (and, hey, you gotta love yourself!).

If I’m in danger of being not-so-nice in any way, it’s when I reply to people sending spammy DMs or emails to try and sell me on something. When it’s laughably terrible or super aggressive or feigns saying the right things to trigger a result, not build a relationship … I tend to clap back. But I should have more empathy. We’re all struggling with something. We’ve all learned to do our work a certain way. If I do reply (and maybe I shouldn’t), I should just explain how their obnoxious tactic made me feel and leave it at that. No need to berate or make fun. 

What I’m doing to improve: Remembering my work’s raisin deeter. (Hashtag French?)

The driving impulse behind my work is “make ’em feel.” In a world of superficial content and surface-level interactions, I want to trigger big emotions and big questions in the hearts and minds of others. This could be sappy and cheesy or funny and exciting. This could create questions about your work or questions about your life. I love consuming content that makes you feel, and I love creating it even more. So if I can remind myself of that mantra every day, I’ll be just about the nicest person ever. After all, it’s really hard to be a douchebag when you have a goofy smile on your face at all times 🙂

Promise #4: I promise to never, ever, ever, ever, ever, ever, ever (times infinity) promise others any “secrets.”

2017: B+

2018: B

In my first inaugural Promise post, I wrote the following: 

“Let’s rip the bandaid right off, leaving the hairless red rash of truth behind: THERE ARE NO SECRETS! There’s only hard work done with the right intent. I can’t teach you to be rich. I can’t give you the one thing every successful person knows. I can’t impart THE steps you must follow, no matter who you are or what you’re doing.”

I’ve upheld this in every thing I’ve said or done over the past 12 months. So why did I take a step back from a B+ to a B? Because not only did I make the same mistake I did last year, I literally promised that I wouldn’t do so.

That mistake? I let others package my work as “secrets.” 

Look, it’s not like I’m going to scrunch up my nose, wag an index finger, and whine to a journalist or podcaster kind enough to interview me, “Ah, actually: You can’t call what I’m sharing a ‘secret,’ mmkay?” But I could try two subtle things…

What I’m doing to improve: These two things…

  1. Never share a link to my guest appearances wherein they call anything I said a “secret” in the headline without first writing my own version of that headline. Rather than simply tweet the link as is, I should write something original to qualify what was said.

  2. Bring up this idea more frequently in the interviews I give. When I’m a guest, I can address this notion that there are no secrets in my answers. I shouldn’t correct an interviewer — that’s condescending. But I could espouse my belief that there are no secrets a bit more loudly in my answers.

Promise #5: I promise to always treat my speech like a product.

2017: n/a (new promise I introduced last year)

2018: B+

Great product managers and designers intimately understand the problems facing their audiences, then build their products in iterative fashion to solve those problems. They test, launch and learn. Similarly, great speakers constantly talk to their audiences when they’re NOT on a stage to investigate the problems they want to solve in the world. The key is to own the problem, not profess to have “the” solution. In my world, that means incrementally evolving the same speech constantly based on new insights and feedback, as well as customizing larger parts to fit a given event. 

Essentially, I’ve created a talk that's “modular.” That’s pretty standard practice for regularly touring speakers. I’m hired to address the same problem and share the same insights with each event, but it must be customized to land with a given audience. As a result, my speech has the same spine every time, but I'm able to build an original body around it according to the needs of that specific room. 

“Modular” speeches enable you to unplug a given story or lesson and plug in another one from your research that feels more relevant for those specific attendees. One easy example is my section about finding first-principle insights about your customers to inform your thinking, instead of leaning on generalized advice or ideas from an internal boardroom or industry expert. The “big” module in that section is the story itself. I alternate between two, using the software company InVision for B2B-heavy audiences or attendees from large corporations, and a construction business from Oklahoma for consumer-focused events, nonprofits, SMBs, or other groups with limited budgets or small teams.

The “beats” of both stories are similar: the set-up, the moment I introduce conflict, and so on. But the content itself is different. So that’s the “big” module: the story itself.

But there are also smaller sub-modules contained in this section. It could be as small as a single word I change. For instance, if I were to say “customer” at an A/E/C marketing event (architecture, engineering, and construction), it wouldn’t make as much sense as saying “homeowner” or “client.”

In addition to this idea of iterative improvement and flexible “use cases,” speeches are similar to products in that both improve when they’re receiving regular use. The more you can analyze what works and doesn’t from real-world delivery of a speech, the better it becomes and the quicker you improve. If I only give a speech once, drafting it in my office and delivering it to ZERO attendees ever, I’m actually not serving the attendees in the room as well as I could. I haven’t refined my product for them at all. (So, yes, there’s such a thing as over-customization. IMHO, you owe it to audiences to practice alone and, more crucially, improve your material by pressure-testing it with real audiences. In this way, it’s like being a standup comedian at smaller clubs working to perfect your Netflix special.)

Lastly, products create compounding value for their users, just as speeches should for attendees. The audience should get more value out of a speaker’s big idea and methodology the more they use them. That means speakers shouldn’t share a one-time fix or promise a (gasp) “secret,” nor should the attendee’s exploration of a speaker’s ideas stop when they leave the room.

Great speakers offer (A) additional content to continue the journey with attendees, and (B) the ideas or frameworks from a speech should also contain a certain level of depth. Attendees can constantly revisit and explore and use them in new ways.

When you achieve that level of depth as a speaker, you write the book. There’s enough meat on the bone. When a speaker’s book sucks, I think it’s because they tried to stretch a talk or a series of blog posts too far, and it becomes thin and flimsy. The object was for the author to write a book, not serve the reader by exploring something worthy of exploring in more detail.

So why the B+ for me under this promise to build my speech as a product?

I think I have a ways to go to improve, but I’m reasonably proud of how much I remixed and refreshed my talk this year compared to last year. In 2017, I didn’t change much gig to gig. In 2018, I did fewer gigs. That lower volume helped give me the time I needed to think critically about each talk and customize more material more of the time. (I still grew my speaking business to six figures this year, but I did so by raising my fee and reaching bigger events, not by churning out more talks.)

Writing the book was also an ENORMOUS boost to my “product," because I now have all these extra research and stories and, crucially, a consistent language to speak more clearly and concisely. The book also gives me the confidence to improvise new moments that weren’t part of the usual “talk track” in a speech. That’s because all the material is to top-of-mind for me. Even if I didn’t rehearse a small moment here and there, I can move and change with the room in real-time, which creates a stronger bond and makes me a better servant to those attendees. 

What I’m doing to improve: More of the same

Sometimes, I think the best thing you can do to succeed is keep doing what you’re doing. As my friend Andy Cook, founder of the software startup Tettra, likes to say, “Most of success is just being disciplined and not getting bored.”

Being a public speaker is amazing. 

It’s rewarding. It’s nuanced. It’s hard. But above all else, it’s FUN. And dammit, I want this fun to continue for years and years. 

Whenever I walk into my home office, I’m greeted by a sign on the wall. When I switch the light on, I see a simple idea: “Always do the right thing, even when no one is watching.” 

Whenever I walk onto a stage, I’m greeted by an audience. When they switch the spotlights on, I remember a simple idea: Always do the right thing, especially for the people watching.

THANKS FOR READING! I welcome your comments and ideas. If you want to learn more about my speaking, visit You can also email me at

Posted on October 23, 2018 .

Exceptions: An Original Series Going Inside the World's Most Creative B2B Brands

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“Brand.” What the hell does that even mean?

Is your brand a logo, a tagline, or an ad campaign? Is it the design and color scheme of your website and marketing collateral? Is it that funny YouTube video featuring your employees? (Hashtag CULTURE!)

If you’re like me and have only ever worked in B2B marketing, then “brand” is … complicated. See, for generations, B2B companies ignored the need to proactively build strong brands, preferring instead to win on product competency and by building a big sales and marketing engine. But that’s changing. In today’s world, the buyer has all the power because the buyer faces insane amounts of choice — even in the case of B2B niches. And what do we as humans choose to spend both time and money on? Great experiences.

That’s what brand is: how others experience your company. And since “companies” don’t exist but collections of PEOPLE do, then brand is the emotional response others have to the behavior of your people.

No longer can brand be a dirty word or overlooked idea in B2B. Brand is the moat that you build around the company. Arguably, as more and more products get commoditized and copied (just ask any SaaS business), brand is THE approach to building a thriving company today. Building a people-powered, customer-centric brand is the one defensible thing in B2B today. It makes you exceptional by making you an exception.

So, um … how does that actually work?

Welcome to Exceptions, an audio documentary series that goes inside some of the world’s best B2B companies to understand how and why they’re building exceptional brands. I’m partnering with Drift to bring you this show, because they’re all about putting the human element back into B2B sales and marketing.

Below, you’ll find episodes in a running log for each season of the show. In each episode — which are highly produced with narration, music, and sweet-sounding editing — we review a few things:

  1. What makes the brand exceptional?

  2. What do actual customers have to say? (We talk about being customer-centric in business today, but we never hear from the actual customer. That changes with this show.)

  3. What’s our Big Idea of the week for building our brands?

  4. How does the work of each brand we profile illustrate that Big Idea? (I typically talk to an executive and a practitioner from each company to get two types of perspectives).

  5. What three questions can we ask ourselves, inspired by that particular episode, to create exceptional brands ourselves?

It’s a simple question to ask, really: Do you want to be a commodity in your industry, or will you find and follow what makes your brand … the exception?

Welcome to the show…

Season 1

first round capital exceptions


Posted on October 19, 2018 .