The irony of "what works"

Once we discover “what works,” inevitably, it stops working. Introduce time and competition and expectations to anything, and suddenly, what once felt like a smash hit slowly wears away.

Time: The context changes. Maybe the thing we did no longer makes sense, or maybe we keep returning to the work so much, we’ve stopped caring as much.

Competition: The market saturates. Whatever we did that was a success thanks to its originality no longer feels like a competitive edge as others catch up.

Expectations: We exceeded their expectations once, which is great, except now their expectations have changed. We can’t keep relying on that same thing, because now they just expect it. That’s the paradox of exceeding expectations: Once we do, we’ve changed their expectations.

Whatever the cause, we experience something called emotional decay — the process by which an initial moment of innovation stagnates as others lost interest and we lose results.

It looks like this:

emotional decay

We move left-to-right from the local maximum (the point at which “what works” will return the best results it ever will, because others like it as much as they ever will), to diminishing returns, to stagnation, to this terrible moment where everything feels broken and we panic that I’ve decided to call the crapping point.

As a result of all of this, to get back up to where we once were, we need to “go big.” We jump in a room to brainstorm, hire consultants and agencies to put out fires, or fire people because we don’t have the money to pay them any longer. We have to trend-hop, leaping between ideas sold to us by experts online. We panic-search for the next big thing. It’s an all-out sprint to manufacture the next spike in the numbers.

This is simply unsustainable.

It’s also ironic.

In our efforts to cling to the tried-and-true, we’re trying to mitigate the risk of change. Why try new things when we’ve found “what works” and can keep repeating it? It’s risky to do anything new, exciting, creative, and innovative when we have our playbook and it’s paying off.

Except it’s not. It’s just a question of where the risk occurs, and to what degree.

When we cling to “what works” for awhile, and the effects of emotional decay render the thing stagnant or even obsolete, we then have to execute some kind of massive change to get back up to where we once were. That’s far riskier than making small changes all the time, trying little things when our results feel strongest.

In other words, when things are working is the perfect time to reinvent ourselves — not through big changes once it’s too late, but small and refreshing changes on the status quo made all the time.

If we normally change only after something stops working, what if we changed what was working while it was still working? Maybe then we’d avoid emotional decay. We’d never stagnate and never reach the crapping point.

The irony of “what works” is it’s a shortcut to do work that’s been de-risked. Except it’s fraught with risk. We just don’t see it … until it’s too late.

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Posted on September 17, 2019 and filed under Wrinkles.

Which box do you mean?

The science is inescapable: constraints breed creativity. Creative freedom doesn’t work. Just think for a moment about a project where you have total freedom. Here, I’ll give both of us such a task right now:

Write a blog post about ANYTHING.

Already, we have a few constraints our brains must grapple with:

Write: put your thoughts into complete sentences using the language you know.

A blog post: whatever you picture when you hear “blog post,” you’re now anchoring to that notion of this project.

About ANYTHING: we understand that we should pull from the entire universe of things one could write about, but since we’re incapable of being “one,” and you can only be “you,” you’ll inevitably pull from YOUR list of “anything” — work, hobbies, personal interests, observations from your life, etc.

Without ever naming what we typically think of as “constraints,” our brains have automatically begun constructing the walls of the box.

Next, given that same command to write a post about anything, we move to the obvious constraints that we mindfully seek: When will I write this? Using what app? How long will it be? Any stories or ideas I have percolating? Do I need to submit this to you, Jay? By when? And how?

We are incapable of action when given too much freedom, because complete and total freedom (or how we interpret that idea — the total lack of constraints) literally can’t exist in the creative process.

So when we say “think outside the box,” it’s a sign that we (or, more commonly, the corporate overlord willing to sound so cliche as to say that phrase to begin with) fundamentally do/does not understand creativity. Because it is literally impossible to think outside of all boxes. Our brains immediately begin to construct one the moment we start thinking or doing anything.

Thus, a far better question: When we say “think outside the box,” which box do you mean?

So often, when we yearn for creative freedom, we’re actually yearning for one of two things: We want a different box than the one we’re in, or we don’t understand the walls of the box we’re already in, and so we keep smashing into what feel like invisible walls.

“Think outside the box.” Okay … but which box do you mean?

Do we mean the box where the walls are made up of historical norms at our company? Do we mean the box that fits us into a mold of what someone in our position is “supposed to” act like? Or do we mean the box that shapes who we are as individuals, because I’m quite certain, I can’t demolish THOSE walls? What about the box that helps us understand who we’re serving on the receiving end of our work? Or the wall of our job’s box that has that big painted sign “BUDGET: $5,000; DEADLINE: December 5”? Do we knock that down?

And which box do we build so that we can truly get creative?

When we want to do exceptional work, the science is inescapable: Constraints are our strengths.

We don’t need freedom. We need a better box, or we need clarity on the box we’re in. If you’re a team leader, help the team both understand and agree to the walls of the box. Frustration comes when they dislike the current walls, or run into barriers they didn’t even know where there. Then, crucially, once the box has been made clear: STAY OUT OF THE BOX! Meddling can also lead to frustration and the desire for creative “freedom.”

If you’re an individual contributor, proactively ask about constraints: time, budget, team, inspirational sources, you name it. Help shape the walls of the box. It may seem counterintuitive, but it yields better work, more ideas, and more effective ideas.

Creative freedom doesn’t work. It doesn’t even exist.

“Think outside the box”? That’s missing the truth entirely. Which box do you mean?

— — —

My book contains an entire chapter on constraints and their effects on decision-making in the working world. Through story and science, we explore how to best construct a box that yields exceptional work, outlining the roles that team leaders play and the roles individual contributors play too. For more on that, consider buying Break the Wheel: Question Best Practices, Hone Your Intuition, and Do Your Best Work, on Amazon. Available in print, Kindle, or audiobook form (narrated by me).

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Posted on September 16, 2019 and filed under Wrinkles.

Once we know what the work really is, we can't help but start

A career is just a vehicle for constant improvement: improve ourselves, improve our teams, improve our communities, improve our world. Careers are just the label we use to describe the arc of time that passes, from the moment we started working to the moment we stop working. All they are, really, are vehicles to keep improving between those two moments.

So when we decide that we can’t start doing something, or we need to talk to someone else over coffee to get it right, or find the “best practice,” or get more years at the corporate gig before we launch our own thing, or whatever story we’re telling ourselves, all we’re doing is delaying the inevitable: The work is NOT about being right in theory. It’s about getting in right in reality. It’s about constant improvement, the slow but steady progress forward.

When we delay our first attempt at something new, exciting, and ours, all we’re doing is delaying the start of the improvement process. And if we want to do great work and have great careers, shouldn’t we want to start improving right away, so we can do something great sooner?

When we sit on the idea and agonize and over-research, we’re failing to see what the work really is: constant improvement.

So you may as well start right now.

— — —

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Posted on September 13, 2019 .

Defining your "enough"

A quote has been reverberating around my mind for the past few weeks. I wish I knew who said it (if you do, please let me know?). It goes like this:

“Enough” is a choice you make, not a destination you reach.

Oof. Hits me right in the feels in the best way.

In the drive to build, to grow, to acquire, and to run, I can find myself getting swallowed by searching for that next thing, always. The more I grow in my career, the more momentum I build, the more I realize that nobody — and I mean nobody — arrives at that “next” level and goes, “Yep, this is it! I’m where I need to be.” Instead, they go, “Oh, okay, cool. I’m here now. What’s up THERE though? I’m gonna keep climbing.”

But sometimes, deciding “enough” enables you to focus on the here and now, to enjoy what you’re doing for its own sake, not the results. And a funny thing happens when we do that: we tend to get better results.

My “enough” for my media company, Marketing Showrunners, is to generate enough revenue to support a small team that loves working together and loves serving a small but passionate audience. That’s enough. I’m finding other areas where I’m finding my “enough” too.

For now, I’d simply ask more people to embrace this idea: Enough is a choice you make, not a destination you reach.

(Hat-tip to Paul Jarvis, who wrote the book Company of One and talks often about helping others find their “enough.” Find his book and other works here.)

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Posted on September 10, 2019 .

Are you all about it?

There’s a flower shop near my home that uses a clever sign to lure customers into the shop. It says, “Come on in for a free rose if your name is Samantha!” Each day, they change the name. They’ve done Amanda, Tim, Bryce, Alicia, Tara, Lindsay, and Jason. (I declined my rose, thus sending myself home from this episode of The Bachelor in Rye Brook.)

We see that sign all the time, though it comes in different forms depending on the business. It’s a clever ploy to catch the eye, a pithy statement to acquire a customer, and a get-it-while-you-can deal to prompt an action. But these are just gimmicks, short-sighted approaches to marketing. They don’t change how the business operates.

But they should.

Imagine if that flower shop was all about human connection. They’d use that clever little sign to advertise not JUST that they have flowers (congrats, so do all your competitors), nor that they’re giving free roses to (checks today’s sign) Marie. Instead, if they were all about human connection, they’d use that sign to introduce you to that concept in a short, delightful way, before you tumbled into an entire business that was all about human connection.

They’d show you a slew of products you could personalize for that special someone. They’d follow-up with a touching, non-automated email or phone call or postcard. They’d remember your birthday and your partner’s. They’d hire empathetic people, participate in their local community, and partner with only the warmest of local business owners. Because to them, human connection isn’t a stunt to drive a sale. They’re not interested in whatever “works” before moving on to the next thing. For this business, human connection is the way to operate. They’re all about it.

We keep talking about things like “authenticity” and “customer-centricity,” and we’ve long talked about differentiation. But what we forget is how to turn these nice ideas into action. It doesn’t happen through one-off stunts or clever ploys. It happens everywhere across the business in small ways ongoing.

When an organization allows that core idea to seep into every nook and cranny of the business, those clever signs and messages aren’t gimmicks. They’re a tiny ray of light shining through, and if you decide to look behind the curtain, you’d be positively basking in sunlight. Because it’s everywhere. It’s not a gimmick or an ad. It’s the way they operate.

Whatever you do, whatever your “thing” is, ask yourself: Are you all about it?

Posted on September 10, 2019 and filed under Wrinkles.

Creativity is just a choice among these 5 changes

When we say “creativity,” we seem to uproot ourselves from the work itself in favor of some nebulous, ephemeral ghost that, apparently, can guide us forward. When the goal is to be creative, we like to think that we’re now in the business of creating something from nothing, but we’re never truly able to start from nothing. There’s always a status quo into which we introduce something different.

Okay, so “creativity” is doing something different? But not just “different,” right? I could write this entire post backwards, so you’d have to read it from the bottom up, from right to left. It’d be one hell of a difference. In fact, it’d be different from every other article written in English on the internet.

But does that make it any good? Is that a different anyone actually wants?

No, it’s not enough to just be different. If it were, any stunt we pull would earn us the love and respect of others we wish to serve. We’re not merely seeking to be different. We’re seeking to be different and good, different and welcome. Let’s call that “refreshing.”

Creativity is doing something refreshing compared to the status quo.

So how do we execute on that? Clearly, it’s not to invent something from nothing. It’s not about invention at all. Creativity is all about reinvention — making refreshing changes on the status quo.

There are only five ways we can reinvent the status quo:

1. Reuse: Increase the number of times others encounter something that’s working inside the same experience.

People adore your brand’s podcast host? Great! Give her a monologue. Let her spread her creative wings a little and fly. Give her more airtime, because that’s reusing something that’s working inside the same experience.

(Reusing is probably the most common type of reinvention on the status quo that we rely on, and used all by itself or used too much, it can merely perpetuate a stale status quo. That’s why we need the rest of this list.)

2. Repurpose: Increase the number of times others encounter something, but in a different experience.

People adore your brand’s podcast host? Great! She now hosts a video show, too. She emcees your annual event, or interviews speakers on the showroom floor., That’s repurposing something, moving a beloved element of an experience from one project to a different one.

3. Replace: Substitute something that’s growing stale for a refreshing new element.

Know that lightning round of questions at the end of your show? Yeah, everyone is doing those. We’ve grown tired of hearing them as listeners. Maybe replace it with something else, like an inspirational section of narration summarizing the episode and urging action, or else skip the frills and conclude the interview with gusto. Either way, replace that lightning round: substitute something that’s growing stale for a refreshing new element.

4. Remix: Combine an existing trait or piece of the experience with refreshing new elements.

People love your podcast, and that’s great, but you’re worried they’ll lose interest after 5, 10, 50 episodes done in a similar style. So every quarter, answer fan mail. Every month, launch a special behind-the-scenes episode. Every year, partner with a brand or show that shares our belief system to create a miniseries inside our show. Remix the show.

5. Refine: Remove unwanted pieces of the element of your work in question, or the entire thing.

This is addition by subtraction. Your podcast gets better when you cut a meandering intro style and jump right into the hook, the cold open, the reason people might care. Refine the intro by removing the unwanted pieces. Or maybe the entire brand gets better when you kill the show entirely. It’s sucking up resources, it’s not beloved by others, and it lacked a strategy when you started it. Refine your brand experience by eliminating the show entirely. Remove unwanted parts of a project or an entire project. That’s refining the status quo.

We adore these big notions like “creativity” and celebrate the seemingly ineffable parts of the work. It can’t be explained. They found their answers “out there,” or else they have The Gift.

But really, when it’s time to do the work — which is all creativity really is, in the end — we need to make this big idea more knowable. We need to hold creativity in our hand like a tool, not wander the wilderness in search of “it.”

Creativity doesn’t mean big. It’s just the sum of lots of smaller moments of reinvention, all rolled together. And there are just five ways to reinvent the status quo, five refreshing changes we can make on the status quo: reuse, repurpose, replace, remix, or refine something.

Make one change. Make all five. Just don’t make zero changes.

The great John Cleese once said, “Creativity is not a talent. It’s a way of operating.” The way we operate is a choice, and when we want to be creative, it’s a choice among these five changes.

What will you choose to do?

— — —

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Posted on September 9, 2019 .

But is it practical?

The command to publish practical advice (if we’re to be successful marketers) often leads to a glut of similar stuff: how-tos, tips-and-tricks, ultimate guides, and lists. In the race to get “practical,” we’ve become “instructional.”

But “practical” doesn’t actually mean “instructional.” It just means that it helps others do something, ideally better.

Know what else helps others do something better?

Stories that inspire them.

Concepts that improve their thinking.

Reminders of the fundamentals.

Research into what matters.

Frameworks for navigating complexity.

Anything, really, so long as it’s informed by the reality of what others are trying to do.

When we’re in charge, and we hear that someone else will be writing something for us, or giving a speech, or hosting a show, or creating anything for our audience whatsoever, it’s tempting to say, “But is it practical? Reminder to make it practical!”

That’s fine, so long as we mean, “Make it informed by what those we serve are trying to do.” It’s not fine, however, if we mean, “Make a list of instructions.” It’s too limiting.

When we say practical, we usually mean instructional. And because we’ve lionized the notion of “practical,” we’ve really created a world where instructions reign supreme. What we publish and what we consume both narrow in on whatever can be packaged as a list, instead of whatever can make a difference to what we or what those we serve are trying to do. And it’s the non-instructional stuff which can have deeper impact our work and our lives than any step-by-step lists ever could.

When instructions are all we seek, we not only create a glut of similar content in the world, we limit ourselves and those we serve. We limit how well we can do something.

That’s not very practical at all.

— — —

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Posted on September 8, 2019 .

Consistency is sexy

When most teams hear the call to “innovate,” the work devolves into a stress-fueled, feverish race to manufacture spikes in the numbers. We obsess over finding “what works,” instead of identifying WHY something works, thus equipping ourselves to be proactive, original thinkers. We try trend after trend, endure hype cycle after hype cycle, doing anything in our power to get those spikes. We pull all these random acts of creativity because we don’t have a plan otherwise.

Just gimme those spikes! We need the spikes!

This is maddening. This is exhausting. This is simply unsustainable.

So how can we make creativity consistent, instead of random?

We don’t talk about this enough in the business world, but consistency is sexy.


I mean, give me a brand that really knows how to evolve with me, because I am a grown-ass man. (That’s the worst thing I’ve ever written. Let’s move on.

Consistent creativity doesn’t create one-off spikes. It shifts the trajectory of the entire damn line. (That’s pretty sexy.)

So how DO we make creativity consistent? Is it possible to turn innovation into a habit, rather than a Hail Mary? I believe so, but we need to shift our perspective on what these terms mean, find the first priciples, then re-build our thinking back up from there.

In the following two episodes of my podcast, Unthinkable, we uncover a couple stories and a few helpful frameworks to help us achieve what feels impossible today: making creativity consistent.

These are the two most popular episodes of the show this year, published only a few weeks ago. They have a different style and approach than most of my prior 150+ episodes, and I think you’ll enjoy this short but enjoyable format.

First episode: “Innovation Impossible” (Stream it on your computer, listen on Apple, or listen on Spotify.)

Second episode: “Wrinkles” (Stream it on your computer, listen on Apple, or listen on Spotify.)

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Posted on September 3, 2019 and filed under Wrinkles.

Writing early, writing often

In the last decade, I’ve been ridiculously, laughably lucky in my career. (Have I worked hard? Yes. Were there circumstances I didn’t control that stacked the deck in my favor from my birth onward? Also yes.)

I’ve worked for companies that sound attractive to work for: Google, HubSpot, a VC firm (NextView), a tech startup.

I’ve done things that sound exciting to do for my own business, too: hosting podcasts and documentary series, writing a book, and delivering dozens upon dozens of speeches, sometimes to thousands of people.

I promise you, I feel grateful for it all. Insanely, obnoxiously grateful. But I also promise you: We view “success” all wrong. We lean back, tilt our heads to the sky, and we daydream about doing some of these things I’ve listed, believing that will bring us fulfillment. If only I could work for X brand. If only I could get Y more followers. What it must feel like to get paid to do this cool project, or to hear the applause of people who sit there to watch you speak from a stage!

And honestly? I can say with absolute certainty, beyond a shadow of a doubt, that nothing — and I mean NOTHING — comes close to the joy, the satisfaction, and the pure bliss of tilting your head back down from where its been daydreaming, opening your laptop … and just writing something.

Writing anything.

Writing consistently.


Nothing shapes your thinking better than writing a little bit, day after day. Nothing builds trust — trust in yourself, or the trust others have in you — than committing to typing out a bunch of stuff, regardless of how many people see it, each morning or evening.

You can chase all the “big” ideas of creativity and success that you want, but I can’t emphasize this enough: Nothing will match the benefits of writing, for free, without anyone’s permission, all the time. And once you start doing it a little bit, you’ll start experiencing this bizarre level of bliss, like nothing else in the world can match. It’s your own corner of the internet, and it matters not who else visits. It matters that you’re there quite often. It’s like that street corner you always thought was somewhat beautiful, or the park bench where you can sit and stare at the world, or the backyard view where you feel most at peace.

Writing early, and writing often, is somehow far grander an experience than any of those “big” things we seem to celebrate. I can think of nothing more fulfilling, because I’ve done nothing more fulfilling.

We live in a truly amazing era, where we can all write daily, simply because we want to write — no matter where we live, where we’ve worked before, who has paid us or what amount. We can be famous. We can be unknown. We can be confident, or uncertain, a great writer, or a poor one. It doesn’t matter. Young, old, classically trained, or a wide-eyed novice — each and every one of us can experience the euphoria of starting our days by writing something. Anything. Consistently. All the time. For free.

So what are you waiting for?

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Posted on August 30, 2019 .

First-moment creativity and what to do instead

It’s easy and therefore, if you look around the business world, pretty darn common for people to focus all their creative energies on the first moment people arrive to their work. Whether we create content, build entire brands, deliver trainings, run people through a process — anything wherein someone else is on the receiving end of our work — it’s tempting to focus solely on what happens when people arrive:

Screen Shot 2019-08-27 at 11.30.56 AM.png

Here, people arrive with an initial set of expectations. Naturally, then, our goal is to exceed those expectations.

If we do, it feels refreshing to them. It’s like a gift — the proverbial “surprise and delight.” We’ll call that the thrill of novelty:

Screen Shot 2019-08-27 at 11.31.15 AM.png

It turns out that “surprise and delight” isn’t just pablum. There’s actual science underpinning the desire to deliver something new and refreshing to others — even if most of us aren’t aware of it.

Researchers at the University of Edinburgh revealed that novelty of experience creates long-term memories in the brain. They examined the effects of surprises on students and their ability to remember their math lessons later in the afternoon. For some students, the researchers created a surprise music class they weren’t expecting to take that day. Those students remembered their math lessons which followed far better than peers who had the typical, expected day.

This is a phenomenon called “behavioral tagging.” When we’re surprised, our brains release a hit of dopamine, which helps form memories. Not only do we remember the moment of surprise, however, we remember the moments around it. That’s why students remembered their math lessons in the afternoon following a surprise music class in the morning. When we’re surprised, we remember that experience and those which surrounded it.

This is an evolutionary trait. When our ancestors stumbled upon a patch of delicious berries in the woods, it was rather useful to remember both the berries and the path they walked to arrive there — even if, while walking that path earlier, they weren’t consciously trying to remember it.

And so, when we deliver something to others that creates a thrill of novelty, behavioral tagging sets in…

Screen Shot 2019-08-27 at 11.31.24 AM.png

…and a memory of us forms:

Unfortunately, it’s right here where we tend to lose our way as creators and strategists responsible for experiences. We want to do one thing that feels refreshing and then, once we deem it successfully, we often put it on repeat because, apparently, it can work forever now.

Screen Shot 2019-08-27 at 11.31.35 AM.png

Of course, ONE interaction is never enough. Trust is earned over time. Advocacy requires ongoing commitment. Relationships are formed through deeper engagement.

No, regardless of what we create, results don’t happen thanks to one moment, one interaction with us.

We need a plan for what happens once someone begins to engage with us more deeply. Because as they do, they start to pick out certain traits that make the experience identifiable. In other words, by agreeing to come back or to spend more time with our work, others begin to make sense of it.

Let’s call that process “identifying anchors.” Anchors are the traits of a project or a brand which others can recall and we can control. People identify a few key traits to remember us and to describe us to others (word-of-mouth). They identify those anchors while engaging with our work more deeply than that first moment they arrived. It looks like this:

Screen Shot 2019-08-27 at 11.32.13 AM.png

Crucially, as people identify anchors, it creates a new set of expectations, and this hurts our ability to return to that initial successful thing. What was once refreshing no longer is, and in fact, it grows stale rather quickly.

Screen Shot 2019-08-27 at 11.32.29 AM.png

So, no, we can’t rely on that “first-moment creativity” that created an initial, positive memory of us. This is the paradox of exceeding expectations: once we do, we’ve now changed their expectations. They agree to engage more deeply, which causes them to identify anchors and make sense of our work to know what to expect, and therefore, they think they know what to expect. Their expectations have changed compared to the first moment of interaction.

Sadly, our work often does NOT change, and if that’s the case, if we return too often to the “tried and true,” something called Emotional Decay kicks in. Emotional Decay is the process by which an initial moment of innovation stagnates as others lose interest and we lose results.

The first time they experienced our work, it was thrilling and new. It was refreshing. That created a positive, long-term memory of us. But then that memory starts to fade rather quickly, as they update their knowledge of our work. If we hand them the same exact experience as before, it might feel good, but not as good as the first time. The third time might feel okay, the fourth fine, the fifth a bit annoying, until eventually, over time, they tune out. They loved it. Then felt good about it. Then fine. Then stopped caring. And we PANIC! We try to pull a random stunt to get back up to that initial thrill of novelty, that initial moment of innovation.

And it’s all because we’re changing our work AFTER it’s too late.

We need to get proactive about the tweaks we make to our work. We need to change before stagnation hits. We need to change what’s working while it’s still working. That way, we avoid Emotional Decay. We change things along with their expectations changing. Right as they know what to expect, we add in something refreshing that they didn’t, a tiny change on the status quo. We can call those wrinkles.

Screen Shot 2019-08-27 at 11.33.07 AM.png

If we do that, we can renew their interest in us. Which again creates a thrill of novelty. Which again triggers behavioral tagging, forms a brand new positive memory.

Screen Shot 2019-08-27 at 11.33.16 AM.png

Once again, however, they update their knowledge of us. They think, “Okay, THIS is what I can expect from them.” So once again we add in a little wrinkle. Again they renew their interest in us, again they experience a thrill of novelty, and so on, and so forth. It’s this constant, continual flow of others changing their expectations and us exceeding them by changing what’s working while it’s still working — not through huge stunts, but small yet refreshing changes on the status quo, all the time. Wrinkles that we can add consistently in order to teach others to expect the unexpected from us. Wrinkles that create a sense that we’ve mastered this art of reinvention.

Screen Shot 2019-08-27 at 11.34.58 AM.png

First-moment creativity is never enough. It’s all about consistency.

Consistently great work consistently changes.

Does yours?

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Posted on August 29, 2019 and filed under Wrinkles.