"Creativity" Does Not Mean "Big"


Why do so many leaders scream "INNOVATE!"? Why do so many teams treat innovation like a bunch of random stunts or infrequent, radical changes? It always feels too urgent or too last-minute when we finally evolve. Why? What if there was a better way? What would it REALLY take to make innovation a habit, not a Hail Mary?

We explore that and more in this episode of Unthinkable.

You can subscribe to Unthinkable wherever you get your podcasts, like Apple Podcasts, Overcast, or Spotify. The show is a narrative-style series about conventional thinking at work and the people who dare to question it.

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Posted on July 12, 2019 .

A Simple System CEOs Use to Raise Concerns & Help Teams Do Better Work

max yoder system conflict

"But my boss."

It's the most common objection to doing better work, whether we’re the boss and need to root out problems to solve (which teams may not wish to vocalize), or we’re practitioners trying to communicate with our bosses. Today, we find a communication framework that anyone can use to have difficult conversations — all in the name of doing better work. This system, known as “non-violent communication,” helps people in the workplace do the seemingly unthinkable: turn potential conflict into something objective and simple, instead of emotional and messy.

You can listen to the story using the embedded player below, or read some of the key points beneath that. This episode features Max Yoder, author of Do Better Work, and cofounder/CEO of Lessonly. We address concepts like finding conflict and communicating it, the structure for doing so, the issue with “but my boss” and the lack of control it creates, and the feelings of imposter syndrome that people of all levels often feel (and how to work around it).

You can also subscribe to Unthinkable wherever you get your podcasts, like Apple Podcasts, Overcast, or Spotify. The show is a narrative-style podcast about conventional thinking that forms at work and the people who dare to question it.

The Instant Excuse Plaguing Teams

I give keynote speeches and run a media and education company for marketers. Both of these things require me to raise my hand and say confidently, “I think there’s a better way to grow our careers and companies.” In every single instance of me doing this, however, there’s one pushback I dread from others: “That’s all well and good, Jay … but my boss.”

This comes in other flavors too: “but my team,” “but my client,” “but my…” insert whoever you like. When faced with the prospect of doing better work, even when that prospect is distilled into a helpful framework or practical approach, it’s tempting for teams to cling to the status quo. Often times, there’s one underlying issue: We don’t feel we’re in control.

This lack of control is often in our own heads, at least in part. (Increasingly, too, I think it’s the BIGGEST part.) Over the years, especially when stepping off stages following a talk, I always felt I had to prepare some kind of clever methodology or big, new idea for handling the “but [others we work with]” pushback. Now, I wonder:

How many of us are actually willing to sit down with others and have an honest conversation? How many of us push through conflict successfully, rather than avoid it entirely?

Part of the issue is we lack a system to communicate our way through these tougher chats. We might be the CEO or CMO, or we might be an intern. It doesn’t matter. As humans, we don’t enjoy conflict. We feel isolated, or lost in the details, or wind up too self-serving when speaking — rather than bringing others along with us, inspiring better work because we’re objective in our conversation. We’re here to solve a problem, not start a fight.

Whatever the case, we often avoid conflict not because we haven’t identified the need to push through something (like stale work), but because of the way conflict FEELS — to us, or to others.

In the book, Do Better Work, Max Yoder helps us work through a simple system called non-violent communication. This approach to conflict holds the keys we need to raise our hands internally and say, “There’s a better way. We can get better results. We can serve our audience and ourselves by doing better work.”

This all starts with managers and leaders assuming a different role than top-down instruction givers.

“It’s incumbent on the manager of a team to provoke those conversations,” Max says in the podcast episode. “What am I missing? What am I not seeing? A manager that comes at a situation with a command-and-control style, where they just tell people what they need them to do, that manager is just going to implicitly suggest that THEY know the answer, that they know the way. Humans will respond to that by following whatever they suggest they do without questioning it, and that’s incredibly dangerous because what you’re doing there, is you’re relying on one set of eyes.

“If you have six people on the team, you can multiply that by 6x, but the manager has to set the expectation and the tone that they are willing to be challenged, they want to be challenged, that they don’t necessarily know the way, that they’re making their best guess right now. Everybody’s making their best guess right now. All the time, we’re making our best guesses.

“Some managers hide that fact, because they believe that a leader should know the answer, should be able to dominate life and know the way. I believe leaders should LEARN the answer. If we set a tone that learning the answer is what is real, and what’s expected, then leaders can start asking questions, they can start being more unsure, they can admit what they don’t know. That starts this cascade of behaviors that are incredibly valuable. We start having conversations that we’d otherwise might not have. We start having teammates come to us and point out potential answers that we’d otherwise not have seen, or pointing out potential icebergs ahead that we’d otherwise not have seen, but that all starts with, How is the manager behaving?”

The process of non-violent communication is outlined in more detailed in the episode, but there are two supporting ideas I’d like to discuss in this article that we must first tackle in order to use non-violent communication in the first place. (They’re discussed in greater detail in the episode as well.)

Those supporting ideas are…

1. Using agreements to meet and exceed expectations.

2. Overcoming imposter syndrome.

1. Failure to meet expectations

Because we avoid conflict (which non-violent communication seeks to solve), we rarely know how to address a pattern when expectations weren’t met. Practitioners might massage the data or try to pretend everything is great, when in reality, voicing that there’s an issue might help the team work through it the next time, and thus improve. Meanwhile, leaders who avoid conflict with their peers, their own bosses, or yes, their teams, kick the can down the road, which lets problems fester or even compound.

In short, as Max says, a failure to communicate when we sense conflict prevents us from creating, in his words, “agreements.”

“I’d be frustrated with a teammate, but I’d never have set an agreement with how they should behave, and yet I was still frustrated that they were behaving a different way than I wanted them to.”

He didn’t realize that THAT was the true source of his frustration: He needed someone to do something, and he hadn’t communicated it to them.

“That’s pretty basic, right? But I was comfortable living with the expectations that they should do something and they should just KNOW, instead of going to them and saying, Hey, can we get an agreement that going forward, here’s how we do things? What do you think of that, and do you have any perspectives yourself that you can add in so we can make this something that’s mutually agreed upon?”

Nobody teaches us about getting agreements instead of merely having expectations (and perhaps telling others what those expectations are). Taking it one step further and cementing those agreements — which creates mutual consent and accountability, by the way — can make or break the team’s ability to exceed expectations over time.

“When I finally got agreements from the team, I was like, WOW! My whole world was broken open in a positive way.”

2. Overcoming imposter syndrome

Listen to the full episode to hear how Max and I work through feelings of imposter syndrome, and why it’s a necessary barrier to overcome to address moments of conflict in our careers. We also outline the exact steps needed to deploy non-violent communication, as well as dive into the empowering story behind Max’s career. He’s philosophical about the workplace in the best possible way, and that’s a direct result of his own life and challenges he overcame.

You can also subscribe to Unthinkable wherever you get your podcasts, like Apple Podcasts, Overcast, or Spotify.

Posted on May 27, 2019 .

Unthinkable Podcast: NanaGram Empowers Families to Love Their Elders, One Photo at a Time


Alex Cook's grandfather brightened every room he entered. Now, thanks to Alex, his brother, an old dog, and some lobsters, Tirrell Cook might just inspire every family to brighten the lives of their eldest members.

You can also subscribe to Unthinkable wherever you get your podcasts, like Apple Podcasts, Overcast, or Spotify.

Posted on May 14, 2019 .

Creative Cafe: How to Create an Irresistible Podcast


In the second episode of the Unthinkable podcast miniseries, “Creative Cafe,” I share never-before published thoughts and ideas learned by making this show for three years. (This miniseries features in-depth, behind-the-scenes conversations about makin' stuff.)

You can also subscribe to Unthinkable wherever you get your podcasts, like Apple Podcasts, Overcast, or Spotify.

Posted on May 14, 2019 .

A Small Fiction: What the Tiniest Project on the Internet Teaches us about Creativity


James Miller couldn't bear another day in the office. He was working in data entry, or as he preferred to call it: ugh.

I dunno about you, but my career path is littered with side projects: big ones, small ones, some as big as yer head. (Sorry, couldn't resist. #Coconuts)

Often times, when I got unhappy or restless in a job, I'd tinker on the side. James was no different. A lifelong writer, he felt this ever-present itch that just needed to be scratched. Working yet another day in the ugh industry simply wasn't gonna cut it. So he launched one of the tiniest creative projects on the internet, and the rest, as they say, is history. Or, if you prefer it: POOF! He exploded overnight. Or if that doesn't pop your bubblewrap, I can always just tell you the truth: The very first comment James received was a cheery "This sucks." The years that followed have been just as messy, if a bit more fun.

That's just how it goes in our work, no matter what we do. Things always feel like they're somewhat messy. But I find that if we can look past the mess and complexity and try to make things simple, we can get proactive in what we build instead of reactive. Doing so requires one specific notion -- one that James Miller's story teaches us today.

In our year-long journey to master the art of reinvention, to keep refreshing our work over time in order to never grow stale, things can be, as the kids say, messy AF. They seemed that way for James -- still do, most days. But on those days, he can hold onto two component parts of his work that help him keep things simple, and once he does, he becomes proactive and creative again. He begins to evolve his work again, bit by bit, each and every time. That's impressive enough on its own, but you'll be even more flummoxed when you hear just how compact his project is.

And no, James is not the CEO of a Fortune 100. He's not the founder of an exciting new tech startup either. He won't appear on How I Built This or on the cover of Fortune magazine, and he certainly won't trot onto a stage in front of thousands of people to present his keynote speech, My One Simple Secret to Success (And You Can Too!).

James just felt that familiar ugh. He had a job. He had no time. He had too many ideas. Or maybe he had too few. Or maybe it was somewhere in the middle. I dunno. It's messy. And that's the point. James was able to face the complexity we all face each day and put himself back in control. He found a way to see past the mess to make things seem simple. Breathtakingly, delightfully, magically simple.

I think you're gonna love this story as much as I loved weaving together the parts and pieces. It was a fun edit for me, and I know it'll be an inspiring ride for you.

Hear the story on the Unthinkable podcast below, or subscribe free via Apple Podcasts, Overcast, or wherever you listen.

Unthinkable shares stories of conventional thinking in our work and the people who dare to question it. Each episode is a sweet-sounding, atypical approach to telling business stories and distilling insights that help us question conventional thinking in order to think for ourselves. Entrepreneur called it "one of the hottest podcasts out there." Salesforce called Jay "a creative savant," while Fortune, Forbes, Inc, the Content Marketing Institute, and others have all praised the show's unconventional style and sound.

Posted on March 21, 2019 .

There's Something About the Light


Claude came from a traditional home. His parents expected him to take the usual path many of us imagined we'd take, though we likely didn't control that image. It was built in our heads for us. You know the one: finish high school, attend a good college, declare a safe major, and, upon graduation, receive our neatly packaged box labeled Career.

Everything in its place. Everything under control. But what do we actually control in this life?

As a young boy, Claude wasn't hearing it. He wanted to go to art school, not study economics, nor manage the family business. His mother, as mothers so often are, was strong for her son, defending his artistic aspirations to Claude's father and pledging to support the budding painter should he enroll someday.

A few years later, when Claude was 16, his mother died. The boy began thrashing. Wouldn't you? When we feel helpless, like we just don't control a thing, that seems to be the only logical response. Claude thus ran away from home to live with his aunt. Four years later, something else he didn't choose: He was drafted into the army.

Claude spent seven years abroad, seeing the world, experiencing the sort of vibrant colors and cultures that could inspire even the most timid of artists to paint. Claude was no timid artist, and yet once again, he didn't paint, because once again, he didn't control the circumstances. While in the army, he grew too sick to stand, much less serve, and so he returned home to his aunt. She agreed to watch over him if he agreed to enroll in art school once he felt better. And when he did, he did.

Finally, at long last, everything felt in its place. Everything felt under control.

Of course, it's worth asking: What do we actually control in this life?

Just a year into his schooling, Claude couldn't stand how instructors chose to teach their subjects. It all felt so traditional and staid. But what could he do? That was how it was done. They believed in painting carefully posed objects, people, and scenes. Everything in its place, everything under control. But Claude wondered, what do we actually control in this life? So he left campus, found a mentor, and began experimenting. He went outside, to the real world, where the messy effects of time tends to warp the world around us. There, he captured this reality with broken colors and rapid brushstrokes. Most notably, he studied and documented the effects of time on a given scene, painting the same thing over and over and over again, using a new canvas for each moment the light -- and his emotions -- changed what he saw. He painted a bridge. He painted a sunset. And of course, he painted some water lilies.

Nothing stayed in place. Nothing was under his control. Because, really, what do we actually control in this life?

So often in our work, when we try to create something consistently great over time, we ignore the effects of time. Instead, we prefer to find THE thing that works, then automate it. We want to find the solution and put it on repeat. I agree that when we identify something successful, we should lean into it, but "leaning into it" shouldn't mean more of the same. It should instead become a continual process of discovery to create an ever-more refreshing version of that thing. As time marches forward, changing the world in small and sometimes big ways, we need our work to do the same. This means relinquishing the need for precision, because it's a false sense of control. That absolute, final, perfect solution doesn't exist once we move away from theory and shine that ever-changing light of reality on our work.

"Paint what you really see," Claude once said, "not what you think you ought to see; not the object isolated as in a test tube, but the object enveloped in sunlight and atmosphere, with the blue dome of Heaven reflected in the shadow."

Factors outside our control will forever effect our work. No matter how successful something is right now, it's at risk of growing stale. We don't control that, and so we'd better get busy reinventing our work over time. Consistently great work consistently changes.

Nothing stays in place. Nothing is under our control. Not really. Because what do we actually control in this life?

Fortunately, there is at least one thing. Claude's story seems to offer us that much. We can't control all the variables that change and twist and warp the world and thus our work once we put it out into the world. But we can indeed control how we see the world. Namely, we can learn to see it through different lights. Sure, we didn't ask for THIS set of circumstances. We wish we had more, better, or different. We face boring tasks, repeat tasks, stale tasks. We can't control that. But we CAN control how we view them. We can choose to view them through different lights.

Claude did exactly that. He learned how to see the same things as everyone else ... in slightly new and different ways. Whereas his peers would want the absolute perfect bridge, he painted that bridge as it exists in the real world: ever-changing with the light. That's how he painted every bridge, and sunset, and of course, every water lily.

If the world is ever-changing, and we plan to put something out into the world consistently over time, then our work must also change over time. What we create doesn't exist in theory. It exists in a specific environment. Maybe start with the latter before thinking about the former.

"For me, a landscape does not exist in its own right, since its appearance changes at every moment," Claude said. "But the surrounding atmosphere brings it to life – the light and the air which vary continually. For me, it is only the surrounding atmosphere which gives subjects their true value.”

Later in his young career, when Claude and a few friends wanted to showcase their art capturing the ever-changing world, the traditionalists turn them away. As a result, the group set up their own, independent exhibits. They showcased their in-the-moment paintings documenting how both the artist's emotions and the light could change each version of something. Claude in particular would paint and exhibit the same scene three, four, sometimes eight or nine different ways.

In the end, we are all doing our best to create something that makes sense for the here and now, but this is a fool's errand, as the here and now is ever-changing. The only thing we can do is to act like Claude and create versions of the work. We can keep evolving, keep refining, keep reinventing. Sure, we can create that one thing, paint that one scene, in the way that makes sense to us NOW, but the real key is to do it again, and again, and again, allowing the effects of time to creep into our work. The goal isn't to create a masterpiece. It's to create an ever-changing, always improving body of work.

Nothing stays in place. Nothing is under control. But what do we actually control in this life? We control how we view things. We can view the same-old, same-old in different lights. And, if we understand how time works, we must. We're not static. Life's not static. It's impossible to expect our work to be.

By capturing the literal, Claude reveals the figurative. Literally, the light changes all day, which thus changed how he painted the bridge, the sunset, and of course, the water lilies. But just as the sunlight changed the scene, the passage of time should change how we view something. We may have done the thing seven or 70 or 700 times before, it doesn't matter. We can choose to see it in subtle new ways, to reinvent and refresh what we create over time. I believe that's the only way we'll succeed over time.

Of course, the traditionalists may not be happy with us. They weren't happy with Claude and his friends. In a fateful twist, one art critic dubbed Claude's independent showcase "the exhibit of impressionists." This isn't true art, he claimed. It's so imprecise, so free-flowing and rough. It's a distant impression of the real thing.

Isn't it all?

The critic meant the title as a rebuke of their work, but the young group of independent artists turned the tables. So in April of 1974, when Louis Leroy published his scathing review, that young artist in love with the changing light merely smiled at his friends. He knew: everything we create is indeed an impression. It's our attempt to capture a moment, which is now gone. The only way to get closer to reality is to mimic reality, creating version after version, change after change ... because change is what "reality" really is. The sooner we embrace it, the sooner we can get on with the work. And so the young artist and his friends embraced it. They took a criticism and made it their moniker.

You may not know the group's name -- Impressionists -- but you've likely heard of the young artist. He's the man who always tried to see the world through an ever-changing light, because in truth, the light is ever-changing. So he kept painting version after version of the bridge. And the sunset. And, of course, the water lilies.

Claude Monet.

Posted on March 13, 2019 .

The Paradox of Exceeding Expectations (and How to Do It Regularly)


There's a hotel in downtown Boston that, like almost every hotel in every city, offers a valet service for your car. Pull up, leave the keys, and take your ticket.

On this particular ticket is a number. The number uniquely identifies your car to the man at the valet desk.

Imagine it's later in the day, and you feel like taking a drive over the river into Cambridge. Maybe you want to walk around the campuses of MIT and Harvard or hang out at a local coffee shop, of which there are dozens. (They have an exposed brick surplus in Cambridge, Massachusetts.) Whatever your plans, you decide to drive -- not necessarily the best move, considering Boston's roads make absolutely no sense at all, but hey, I'm not gonna tell you how to live your life.

In your hotel room, you grab your ticket and scan the words printed just below your ID number. "Thanks for using our valet service! Call us with the number above, and your car will be ready in 30 minutes."

And so, you call the front desk about a half hour before you need the car. You expect them to say thanks, the car will be ready in 30 minutes.

But then the man at the valet desk answers.

"34891? Got it. Car will be up in 10 minutes."

It feels like a gift. You were thinking 30, and they said 10. You quickly grab your coat and head down to the lobby where, to your surprise, your car is already idling by the front door. You glance at your watch.

It's been five minutes.

The next day, you again decide to take out your car from the valet service. This time, maybe you'll head down to Boston's South End. (If you ever do, by the way, be sure to eat at SRV. Not only is it one of the best restaurants in all of Boston and my personal favorite, but the executive chef will be appearing on Unthinkable later this year.)

To start your trip to the South End, you once again pick up your valet ticket in your room a full 30 minutes ahead of time. After all, that's their policy, that's what's written on the ticket -- although you don't expect that to be what happens.

The man at the valet desk answers, and this time, you know what he's about to say.

"Okay, so 34891. Car will be up in 10 minutes."

You smirk. You know what's about to happen. Their policy is 30 minutes. They tell you 10 minutes. They deliver in five. That's what you expect will happen.

You quickly grab your coat and head down to the lobby once again.

The car isn't there.


You glance at your watch. It's been five minutes. Okay, maybe it'll be six. You look at your phone. Two more minutes pass. Still no car. You gaze through the revolving door, feeling a burning sensation in your belly. You're kinda pissed off ... for reasons you recognize as completely irrational. Finally, after 10 minutes, the car arrives.

You know you shouldn't be, but you're annoyed. After all: Their policy is 30 minutes. They told you 10. And they delivered in 10. That should feel so refreshing, but thanks to yesterday, it feels frustrating.

Such is the compounding problem of exceeding expectations: As soon as you do, you've changed their expectations.

Every experience comes with a set of expectations -- the expectations we set for ourselves, the expectations we set for others, the expectations others set for us. The problem is, if we exceed them even once, then THAT becomes the new bar we must get over the next time. What was once exceptional no longer is.

It gets worse: This is a process that is largely out of our control. Yes, we know that THIS time, we might not have so much success, but we just can't help ourselves. We believe we will.

And yes, the valet service knows that THIS time, they probably won't deliver the car in five minutes, so they aim for 10, because that is well below the policy of 30 ... except YOU just can't help believing it'll arrive in five thanks to last time. 

It's necessary but far from sufficient to exceed expectations once. You have to do so consistently. Problem is, "expectations" are a moving target. The bar gets ever higher.

So how are we supposed to exceed expectations? Are we doomed to create an ever-higher bar? No, of course not.

But doesn't the valet need to keep delivering the car ever-faster, until it's instant? No, of course not.

Here's something that's well within our control that does indeed allow us to keep exceeding expectations: We can master the art of reinvention.

Not giant pivots. Not overhauls. Not stunts. Not shortcuts. Not random acts of creativity.

Reinvention. A process of consistent discovery designed to produce ever-more refreshing things. The path by which we can exceed expectations -- not by moving the bar higher, then leaping over it, but by constantly changing the rules of this game entirely.

For example, what if, instead of needing to deliver that car ever-faster, the valet service merely needs to create an ever-changing but ever-delightful experience? Wouldn't that exceed expectations? Here's how that might look:

  • The first time you call down, it was enough to merely tell you on the phone that the car would be ready in 10 minutes. You were expecting them to say 30. Now they must deliver the car in 10 minutes.

  • The next time, you now expect 10, even though the stated policy is 30. Why? You experienced the work, which changed the context, which changed your expectations. So this time, it's merely table stakes that they deliver the car in ten. So now, they face a choice: Can they deliver it in five? And the next time in two? Or perhaps, they can change the rules of the game. Instead of a transaction, they build a relationship. "Thanks so much for your patience, Mary! The car will be out in 10 minutes." That's what you expect, but you DIDN'T expect them to know your name. Not a hard thing for a hotel to know about a person: they know which room you're calling from and who is in that room; they identify each car by a unique number. But that tiny little reinvention of the experience makes it better.

  • The next time, you're expecting them to both deliver the car in 10 minutes AND know your name. Perhaps here, they deliver the car in five minutes instead. Or maybe that's impossible, and so they offer you a warm cup of coffee or a nice, gooey chocolate chip cookie. "Thanks for your patience, Mary!"

Consistently exceeding expectations feels impossible. The logical conclusion is that the valet service would merely have your car ready at all times, instantly. But if we embrace that consistently great work consistently changes, we'd stop focusing on the sliding scale of competency and focus on the wide array of ways to reinvent the work.

The goal isn't to find the one thing that works, then keep refining it. The goal is to improve the experience overall. That goes well beyond a single tactic or strategy. That requires consistent reinvention.

Everyone is capable of changing the experience in small ways. Everyone is capable of reinvention.

Posted on March 6, 2019 .

Different Is Better (Unless It's Not)

Different is Better Unless It's Not.png

The year is 1980, and I am ... negative-five years old. But for the purposes of this story, let's say I'm alive and kicking it in my John Hughes-approved outfit. I start my day by pouring myself a big cup of ... Folgers ... coffee ... I guess? ... because the joy that is a row of MacBook Airs shining their white lights against some exposed brick is decades away. I get acquainted with the morning news, not by casting any pods or scanning through a newsletter, but by turning a few crisp pages on that day's print edition. There, I see some alarming things: Mount St. Helens has erupted -- her first in more than 100 years -- clearly signaling the End of Times. The Iran-Iraq war has burst into reality -- clearly signaling the End of Times -- while teens and early-twenty-somethings are obsessing over this new toy called a "Rubik's Cube" -- clearly signaling the End of Times.

Meanwhile, in Detroit, Michigan (forever away from my home via the 1980 transit of choice, the horse-and-buggy), a former executive in this magical “car” industry is about to make the dumbest decision of his life. That executive's name?

John DeLorean.

Today on the podcast, a few short stories of why the ubiquitous advice to be “different” instead of “better” is actually a bit misleading. Then, I find some long lost clarity about why that’s the case — and why I can’t stand all those hacks and cheats out there. (Finally! I have the word to use.) Plus, we go deeper into the dumb decision made by Mr. DeLorean long before his car was immortalized in Back to the Future. (We will also get some amazing ideas for doing things that are different AND good from legendary recording artist and producer Pharrell.)

Just because you’re doing something “different” doesn’t mean it’s gonna be successful. Let’s take a quick journey through history, encounter a few eye-opening examples — some weird and some wonderful — and rethink our approach to creating consistently great things.

It’s Unthinkable 😉

Hear the story on the Unthinkable podcast below, or subscribe free via Apple PodcastsOvercast, or wherever you listen.

Unthinkable shares stories of conventional thinking in our work and the people who dare to question it. Each episode is a sweet-sounding, atypical approach to telling business stories and distilling insights that help us question conventional thinking in order to think for ourselves. Entrepreneur called it "one of the hottest podcasts out there." Salesforce called Jay "a creative savant," while Fortune, Forbes, Inc, the Content Marketing Institute, and others have all praised the show's unconventional style and sound.

Posted on February 27, 2019 .

How the Tech World’s Sticker Company of Choice Helps Rethink Creativity at Work


It's easy to understand why the Octocat is so ubiquitous in the tech world. I mean, just LOOK AT IT:


This adorable little creature is named Mona Lisa, though she's more frequently referred to as Mona, and even more frequently referred to as "GitHub's cat/octopus thingy."

GitHub is a popular developer platform and community acquired by Microsoft for $7.5 billion last year. With a price tag like that, you might assume that their marketing centered on massive ad buys and the brute force tactics that fellow tech unicorns exhibit. And while they surely have a portfolio approach to their marketing, one of their earliest tactics proved vital throughout the companies growth.


They're not alone, either. Alexis Ohanian, the cofounder of Reddit and a veritable tech celebrity, once called stickers, "The soundest investment I've ever made.

And whether it's GitHub or Reddit, your local developer shop or the next global tech giant, there seems to be ONE company behind almost every sticker purchase in the weird, wonderful world of internet startups. But here's the thing: From the outside looking in, they don't look overly creative. Sure, their website has some nice design, they have a clever name, and as you'll hear, they have a strong CEO as their leader. But it's not like they ooze the kind of whimsical tone of voice on social media or the articles and videos and podcasts or even the Octocat-like logo that all feel like requirements to be "creative."

I think NOW is the best time to share this story with you, as I was recently talking to an executive at a cocktail party following one of my keynotes. I'd remarked that creativity was desperately needed in industries beyond tech and media -- places likes finance, auto retail, and healthcare.

He scoffed.

As you'll hear in this story, his definition of creativity was so far apart from my own. Bridging that gap is something I'm desperate to try today on this episode of the show. If we can re-frame what it means to be creative, we might ditch our reliance on Random Acts of Creativity -- or its evil twin, Shortcut Culture. Both are born of the same parents, a sort of union between our need for short-term gains and our belief in finding THE strategy or tactic.

So, let's hear the story about that surprisingly dominant sticker company from one of their cofounders, CEO Anthony Thomas. (Their other cofounder prefers to remain anonymous. I wanted to interview him. I tried to find him online, asking around and everything. But I couldn't find his name -- nor did the company volunteer it. Just another mystery in an already mysterious story about what consistent creativity REALLY requires.)

Hear the story on the Unthinkable podcast below, or subscribe free via Apple PodcastsOvercast, or wherever you listen.

Unthinkable shares stories of conventional thinking in our work and the people who dare to question it. Each episode is a sweet-sounding, atypical approach to telling business stories and distilling insights that help us question conventional thinking in order to think for ourselves. Entrepreneur called it "one of the hottest podcasts out there." Salesforce called Jay "a creative savant," while Fortune, Forbes, Inc, the Content Marketing Institute, and others have all praised the show's unconventional style and sound.

Posted on February 20, 2019 .

This Concept Explains Why Marketers Fail to Consistently Resonate with Audiences

Emotional Decay.png

"I don't understand!" she shouted. "This used to work EVERY time! What is happening?! What are we gonna do?!?! WE'RE ALL GONNA DIE!!!"

Okay, so that's not really what she said.

This calm, cool, and collected friend and I were colleagues on a marketing team years ago. She was responsible for all things direct response, and I was responsible for the content. And her actual words were probably something like, "Uh, Jay? We're not gonna hit our quota this month. I don't get it. We did exactly what we've done a million times before. This should be fine."

But despite those calm, cool, and collected words, I caught a faint whiff of existential dread. (And since we were marketers talking about leads, by "faint whiff," I mean, a skunk wearing a vest labeled "FREAK THE EFF OUT" had just waddled across the office and took out decades of personal angst directly onto my teammate's face.


Here's why she was so distraught. For years, the company had run the same playbook to generate leads. (The name of the company isn't important. Let's call it GrubSnot.)

For years, GrubSnot published multiple blog posts each day to generate traffic, and then pointed that traffic (always a nice way to refer to human beings) to a big, colorful banner beneath the article. This banner would advertise a FREE Ebook, but of course, "FREE" stood for "Form Requiring Endless Entries." Because marketing!

And so, month after month, year after year, BubsCot would rely on this approach. Publish blog posts, point people to an ebook, convert leads on a forced form.

Blog posts >> Ebook. Blog posts >> Ebook. Over. And over. And over. And obviously, over time, our audience decided, "We're over it."

Arguably, this was my biggest failure as a team manager. Despite my best efforts -- or maybe they weren't -- I couldn't convince CubSlot leaders to invest more heavily in longer-term approaches and higher quality content. By the end of my first year there, I was out.

But, I mean, I understand the resistance to change at RubsTot: They'd found their tried-and-true, and just like any company that does, they were beating the ever-loving (Grub)Snot out of it. If they decided to change, well, it would be after it was too late.

Hence the "Uh, Jay?" from my teammate delivered with "WE'RE ALL GONNA DIE!" urgency.

At the time, I struggled to explain this objectively, but now, I realize: We'd reached the Crapping Point.

When Tried-and-True Becomes Tired-and-Terrible

The Crapping Point is one moment on a chart I'll share with you in just a second. I believe this chart can explain the effects of time on any project or company, no matter how exciting or hollow, big or small, well-intentioned or scammy -- and everything in between. My attempt to explain the affects of time on our work is part of a larger, ongoing exploration to understand one question:

What does it take to create consistently great work?

In the business world, shortcut culture seems to be engulfing everyone, while creativity has been twisted to mean Random Acts. Like a stunt double called in to substitute for the real work, we use our creativity to try and manufacture spikes through one-off ideas, rather than create operational approaches to innovation and improvement. As people obsess over the short-term, the need for consistency gets lost, and with it, the ability to create anything unassailable: original, resonant, and enduring.

Two weeks ago, I tried to diagnose the illness. The need to manufacture spikes is a symptom. Random Acts of Creativity are symptoms. What's the root cause preventing us from creating consistently great work? I believe it's stagnation

Even the best creative projects, careers, and companies run the risk of growing stale over time. There is no "set it and forget it." Over time, the resonance wears away, whether that's the resonance we feel when we create the work or the feelings our audience exhibits towards what we create. (BTW, trying to manufacture spikes in the numbers suffers from stagnation even worse than longer-term approaches. After all, what makes a spike is that both the up-swing and the down-slope stand in stark contrast to the line before and after it. In other words, just as quick as the numbers go up, they go down.)

Stagnation is the enemy. That's why, when my former colleague said, "We did exactly what we've done a million times before. This should be fine," she'd actually answered her own question. She just didn't realize it. We'd done the exact same thing a million times before. Yanno that old saying, "Insanity is doing the same thing over and over again and expecting different results"? Well, in our line of work, insanity is doing the same thing over and over again and expecting the same results.

So let's try to regain some sanity here. To do so, it's important to fully understand the problem to then find a solution. Luckily, we can visualize stagnation as one part of a chart showing the resonance of our work over time. The natural decrease in that resonance in the face of time is something I call:

Emotional Decay

When we find something that works, something that resonates for us as the creators and for them as the audience, that thing undergoes a transformation we didn't ask for and probably want to prevent. We can most vividly understand that transformation by thinking about our own reactions to launching A Thing That Worked Real Good. When we create A Thing That Worked Real Good, our reaction to what's happening changes to match the change in resonance.

It goes something like this (follow the red line along with the words below):

"HURRAY! THEY LOVE US! THIS IS AWESOME! WE'RE AWESOME. THIS IS--Oh. Uh. Okay! This is still fine! This is fine! This is fine! This is--oh no. Okay. It's not getting any better. It's just okay. This is not fine. This is not fine. This is--OH GOD, NO! It stopped working! What happened?! This used to work! WE'RE ALL GONNA DIE!"

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I call this process Emotional Decay. The resonance wears away over time. That emotional pull we felt as the creators of the work and our audience felt as the recipients can slowly, or steeply, decay. That is the effect of time on our work.

We can plot different moments we experience on this line, too:

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Once we do something resonant, rather quickly, the audience experiences Nirvana. They think, “This is the greatest thing I’ve EVER experienced! This is how EVERYONE should do this thing! I love this brand so much I want to marry it and have lots of little baby brands with it!"

Or something.

We've all been there: That jaw-droppingly beautiful video. That gripping podcast episode. That unbelievably enjoyable newsletter written by one devilishly handsome author and speaker who would never, ever fish for compliments in his own newsletter.

That kind of work sparks awesome feelings. (I refuse to say "joy." If you don't know why, congrats on leading a more productive life than most humans with a Netflix subscription.)

Once others feel Nirvana with our work, it can carry, begin, or deepen our relationship together ... for a time. Eventually however, we experience the Drop-Off. For instance, we start seeing diminishing returns from the tried-and-true thing, or we begin to check out of the work and look to automate it, or our audience stops feeling all the feels. They still love us, but the spark isn't quite there anymore. No longer unassailable, we're vulnerable to disruption and choice. (Anyone who's ever been in a relationship for awhile knows this feeling. But unlike dating or marriage, our audience doesn't care about hurting us when they immediately move on to the next thing.)

The issue continues: If we don’t do anything to refresh the work, we experience Stagnation. We keep trying the tried-and-true too long; we completely lose interest in the work on a personal level, and it shows; the audience expects more of us after experiencing Nirvana, but we fail to exceed those ever-higher expectations we've created; the market has caught up or changed in a way that renders our once-exceptional work stale.

Eventually, we feel like things are crumbling around us. Every month or quarter is a mad dash to generate spikes in the numbers just to reach quota. Every new trend feels mandatory. Every email from our boss or client feels urgent. We. Lose. Our. Ish.

We've reached ... the Crapping PointI dunno what happened! It crapped out on us!

What was once exceptional has ceased to be table stakes (stagnation), and it becomes downright crappy. That's been the plight of gated ebooks in B2B marketing for awhile now. That will be the plight of nearly anything that works today, unless we keep refreshing our work to succeed tomorrow.

When we refuse to admit we have a problem, we face the reality of Emotional Decay only after it's too late. Then what do we do? Typically, we try to manufacture a spike. We seek a shortcut, a hack, a quick fix. To escape that ever-urgent feeling that comes with the Crapping Point, we just start the whole damn process all over again:

unnamed (3).png

"HURRAY! THEY LOVE US! THIS IS AWESOME! WE'RE AWESOME. THIS IS--Oh. Uh. Okay! This is still fine! This is fine! This is fine! This is--oh no. Okay. It's not getting any better. It's just okay. This is not fine. This is not fine. This is--OH GOD, NO! It stopped working! What happened?! This used to work! WE'RE ALL GONNA DIE!"

"HURRAY! THEY LOVE US! THIS IS AWESOME! WE'RE AWESOME. THIS IS--Oh. Uh. Okay! This is still fine! This is fine! This is fine! This is--oh no. Okay. It's not getting any better. It's just okay. This is not fine. This is not fine. This is--OH GOD, NO! It stopped working! What happened?! This used to work! WE'RE ALL GONNA DIE!"

"HURRAY! THEY LOVE US! THIS IS AWESOME! WE'RE AWESOME. THIS IS--Oh. Uh. Okay! This is still fine! This is fine! This is fine! This is--oh no. Okay. It's not getting any better. It's just okay. This is not fine. This is not fine. This is--OH GOD, NO! It stopped working! What happened?! This used to work! WE'RE ALL GONNA DIE!"

Over and over again, we tell ourselves the same lie: THIS time will be different. But each time, it's not. It's the same schtick, the same slide towards apathy or even animosity from our audiences. This trend or that trend, this guru or that one. It not only continues, it speeds up! It spins wildly out of control until we risk devolving wholly into shortcut culture, obeying each and every ridiculous Business Bro who appears in a YouTube ad in front of a sports car with a wad of cash in his slimy hand.


How to Survive and Thrive Instead

What if we cared less about the spikes and more about the trajectory of the entire line? What if we thought longer term? What if we could avoid the crapping point and use stagnation as a signal to take action? We could do so, if only we responded proactively to Emotional Decay ... before it was too late, instead of after.

That leads me to my fiercest belief about consistent creativity, one that's easy to agree with but hard to implement -- hence my year-long journey to try. My fiercest belief about consistent creativity:

Consistently great work consistently changes.

Creating consistently great work isn't about finding THE thing that works, then putting that on repeat. That ignores the issue of Emotional Decay. Instead, we need a new idea of what "consistency" means. The work itself doesn't repeat -- only the resonance it creates. But to achieve that, to resonate as time passes, we must change the work to make sense in each new moment in time. In other words, to truly avoid stagnation and combat Emotional Decay, we need to refresh the work.

Consistently great work consistently changes.

Does yours?

Posted on February 13, 2019 .