CHAPTER 3

CHIPPING TOWARD YOUR NEXT BIG MOVE

In May 2015, ESPN fired sportswriter, editor, and podcast host Bill Simmons. The company considered him “disrespectful.” He’d argued with his bosses, provoked controversial attention, and even publicly bashed the NFL commissioner. Oh, and then he dared ESPN to fire him over it.

ESPN took him up on that dare and let him go.

It was a $200 million mistake.

Simmons had spent 15 years at ESPN, cultivating fresh journalistic ideas, challenging incumbent thinking about impartiality, and stoking passions with his contentious writing and podcast. Nothing was traditional about Simmons. In addition to his radical use of language, he never minded giving particular attention to his favorite Bostonian sports teams, and he wasn’t shy about his personal life.

Simmons had talked ESPN into giving him substantial freedom to operate his own multimedia website, Grantland, a brand that lived under the ESPN umbrella and specialized in long-form sports journalism.

A few months after ESPN canned Simmons, they shut down the entire Grantland project—it was notoriously expensive, as Simmons demanded only the best writers and editors for the website. From day one, it had struggled to turn a profit. So less than six months after tossing Simmons, ESPN announced they would be retiring his brainchild.

But Simmons believed in the journalism and audience he’d cultivated. So, soon after he left, he resurrected the concept in the form of a new company, The Ringer, which was essentially Grantland 2.0. Simmons kept all his rebellious style, used a similar tone and vibe, and even swiped many of the same ESPN writers and editors he’d previously worked with. But he wasn’t done poking fun at his former employer. In one of The Ringer’s first pieces, Simmons offered his version of the highly publicized breakup he’d had with ESPN. True to form, he held nothing back, even jokingly suggesting that his new media company should be officially titled “F*ck Off, ESPN.”

Today sports fans across the globe tune in to download podcast episodes and articles from The Ringer. Personally, I never miss an episode of his show, The Bill Simmons Podcast, an unapologetic and honest take on sports and pop culture.

Simmons has always been brash and unafraid to challenge, and never has been willing to sit inside the rules. He’s bold. And, even when ESPN bailed out on his concept after four years, Simmons kept going on the same trajectory.

If you’re going to be a Bold One, you’ve got to get a new pair of specs, ones that allow you to see the coming disruption. Not only that, but you’ve got to find a way to hang on to that perspective even when the environment gets rocky, others laugh at you, or no one understands. Let’s get you those new glasses.

YOUR NEW GLASSES

Simmons wasn’t able to disrupt sports journalism simply because he’s a witty writer or podcast host. He observed and accurately dissected the shifting cultural waters in the mainstream marketplace. Then he took his own surfboard and positioned it to catch the waves.

He accurately understood that the world wanted sports media to be more opinionated, open, and real. ESPN, like other sports media outlets, had capitulated to a more traditional sentiment, where “fair” and “unbiased” ruled the day. But Simmons played a hunch, believing that people wanted authenticity, real opinions, and something to challenge their intellect.

In this chapter, we’re going to explore how to avoid the catastrophes of shortsightedness. Particularly, I’m going to help you take some steps outside of where you are currently in your career, whether as a journalist, a barista, or a project manager, to understand the world through a more holistic lens.

We’re going to look at:

1.   THE ILLUSION OF THE CORE. We’ve been told to double down on what we’re best at. So most of us have been focusing all our efforts and development on a select few skills. But to stay relevant, we must understand where the world is going and be willing to move beyond our own “core capabilities” and add new skills and tools.

2.   DENTING THE OUTSIDE. We can expand our perspective and capabilities by simply “chipping away”—placing small bets on ourselves by learning and experimenting. We don’t have to make monstrous moves today, but we must always keep moving.

3.   THE 3% RULE. To be disruptive, we don’t have to invent a new product, service, or method all at once. Instead, we can remix current ideas, process, and technologies, then sprinkle on just 3 percent of our own style to create something new.

4.   WHY IT’S OK TO BE WASTEFUL. The professional world is hyperfocused on efficiency. The problem? We aren’t willing to explore. If we want to discover something new, we must be willing to tinker, explore, and be wasteful.

The aim of this chapter is to equip you with the tools necessary to see the world as Simmons saw it. And that starts by scaling over one specific roadblock: your own core capabilities.

THE ILLUSION OF THE CORE

Illusions work on a simple premise—distraction. A good illusionist forces your focus on what their hands are doing, or on the loud sound that originates in another part of the room, or on an ostentatious painting. The illusionist wants your focus anywhere but where the magic’s actually happening.

For an illusionist, a distraction is the perfect mechanism to dazzle audiences. For the rest of us, it’s the perfect obstacle to disruption. The illusion that captivates many of us in the marketplace isn’t a rabbit coming out of a hat or someone being sawed in half; it’s what I call the “Illusion of the Core.”

The “core” is your supposed awe-inspiring super-ability. We’re told to focus on that “one area” of skills or expertise. Our specialty, our core. For each of us, our specialty may differ, but from the time we graduate college and throughout our careers, we’re supposed to hone our craft, double down, and stay in our lane. The intention may be good, and there’s clearly wisdom in focus, but if we’re not careful, we’ll fall into a trap, one where we hyperfocus only on a niche, missing where the world’s going, or our own unique skill set. We tend to think:

“I’m a journalist, so I write stories.”

“I’m an accountant, so I use Excel.”

“I’m a salesperson, so I talk to people.”

These mental equations make sense temporarily. But they also can get you stuck. A journalist is more than a writer, an accountant is more than an Excel expert, and a salesperson is more than a talker.

Institutions often take the same approach, focusing on their core product, audience, or segment. Again, there’s power in focus. But as we learned in Chapter 2 with the example of the firefighters, a narrow focus on a particular set of tools, methods, or process can actually be problematic. And in this case, not only does this illusion make us biased toward traditional methods (which was the problem with Ebro), but it can also cause us to focus on the here and now far too much, instead of putting on our long-view glasses.

The upside of narrowing your focus on your core is that you can increase a particular set of muscles and capabilities, whether in a technology, a skill set, or a methodology. But the downside is that when we narrow our focus, we think small. And when we think small, we lose sight of the overarching mission. Let me give you an example.

At Deloitte, I once hired someone that another office thought was just a notch too different. As one of the leaders of innovation in our region, I’d earned a reputation for always recruiting top, innovative, and “unique” talent. One day, a senior manager in our Calgary office sent me a message. Apparently, the people there had interviewed someone they liked, but they simply couldn’t hire him because, in their words, he was “too innovative.”

Too innovative? I thought. I had to meet this guy, whom we’ll call Jack.

Once I met Jack, I could confirm—he was different. He didn’t focus on the charismatic selling qualities that most top management consulting firms look for in consultants: At the time, he couldn’t carry a room with his panache, and his argument didn’t always resonate at a deep level. Most interviewers, like my Calgary colleagues, didn’t see a star-power consultant.

But that was the short view. They were missing something else: Jack was wickedly interested in a budding technology, 3D printing. My team, always on the lookout for what’s on the horizon, hired him. We weren’t quite sure what we’d do with him, but he was on the fringe, right where we wanted to be.

He proved to be an invaluable asset. Of course, he brought his unique building capabilities and 3D printing knowledge into our wheelhouse, helping the firm create deliverables that it had never built before.

The other office was too focused on the core of what they did well, and they weren’t willing to look outside it. What Jack did—3D printing—certainly wasn’t a core need for my team; I didn’t quite know how Jack would be valuable, but I’d been on the fringe long enough to know I wanted to be in the room when “different” people succeeded.

A BOLD QUESTION

Innovation starts by asking ourselves a deep question. One that requires a broad view, to get our eyes off our own core and consider the broader marketplace. We’ve got to ask ourselves one deep, scary question:

Where is the world going?

That’s the jump-start, the catalyst to moving outside your core.

It’s not a safe question; in fact, the answer might move us in ways we never thought. Too many people and companies want to take the distraction, the bait, to continue living in the Matrix and believing that the world isn’t changing, and that their core will protect them.

If we want to avoid the ESPN mistake, we’ve got to ask ourselves this dangerous question today.

So let’s ask that question now and shift back to looking at ourselves. Start peeling back the layers in your own career: Where are you burying your head in the sand as the world is changing? Are you focusing too much on what you (or others) have told you is your own core?

As you think through this, keep in mind that authenticity to yourself is key. In fact, it’s vital. What if Jack had said, “I’m a consultant; in the consulting world, to be successful, I need to drop my obsession with 3D printing and refocus on what matters”? If Jack had focused on what was supposedly the most important, central aspects of being a business consultant, he would have missed the wave that he was set up to take. Likely, if he’d diverted his time and energy into becoming a better consultant, he would have probably landed a job with the other team, and mine never would have hired him.

But Jack didn’t get caught up in a narrow, simplified version of himself. Instead, he kept all his uniqueness and his long view. He knew that his unique interests were a particular match for the coming world, and ultimately he never needed to negotiate on that.

So when you ask, “Where is the world going?” don’t abandon what you love; instead, determine how your wildest idea may be the perfect asset to a new revolution.

INCREASE YOUR SURFACE AREA OF EXPLORATION

So how do you avoid getting so focused on what you’re doing that you miss the waves of innovation?

You’ve got to have enough input into your life, enough ideas circulating, and enough channels of information, that there’s a constant flow. You can’t get dissuaded by your role, company, or even country.

To avoid the hypnotic effect of the Illusion of the Core, get comfortable walking into the jungle of uncertainty. Find the fringe and dabble. You know that new decentralized platform or obscure technology that’s made you think This may be the next big thing, but you haven’t really looked into because it’s scary or intimidating? Why not learn about it? Get in the Reddit forums and be part of the conversation. Ask questions; dig in.

Is there a new way of thinking, a new process, a new development method that seems fringe? Read the Twitter threads; listen to the podcasts; be willing to double-click on the strange new technology, the odd social media network, or the intimidating new method. Utilize podcasts, books, YouTube videos, whatever you can. While it may not apply directly to what you’re doing now, you need to have a surface area that always allows for “the new.”

Look in the darkness, and never reject disruptive ideas. The dumber it sounds, the more value there may be. You’ll find that most disruptive ideas that are worth experimenting start in the loneliest places—basements, Starbucks coffee shops, the subreddits, and private Slack groups.

Above all, always consider where culture is going, and what skills, assets, network, and understanding you must cultivate today, so that when tomorrow’s fringe culture arrives—and it will—not only will you be unsurprised, but you may just be part of it.

PLAY THE HUNCHES

While Simmons had his eyes wide open to the cultural moment of the internet, he wasn’t exactly sure how it was going to play out. Likewise, my team didn’t know exactly what we’d do with Jack, but we knew we wanted him.

If you’re going to disrupt, to innovate, you’ve got to be willing to execute on the hunches.

What if you bet on that hunch you’ve had for a while about how consumer behavior is going to change? Maybe your team’s been marketing in a specific way to a specific demographic, but your gut is telling you that there’s a bigger market in a different age group or a different category. Maybe you’ve had a hunch, for a while, that you need to develop a partnership with a rising star—an employee or a business—that’s doing some creative things in the market, but you haven’t reached out because your own built-in fears said, That’s not my core. Well, overcome that reaction, and play your hunch. Reach out; make the partnership; change the game. If you’re wrong, you’ve just exercised your muscle for the next innovation.

DENTING THE OUTSIDE

In 2022, I had a few consulting sessions with Walmart executives. Remember, this company has been wildly successful since its founding in 1962. I was brought in to help consult on one of its future innovation strategies. Explaining to the folks at a 60-year-old retail company that they need to look outside their core of inexpensive retail at brick-and-mortar isn’t exactly an easy sell. But I still made the move.

I inched them into the idea, without dropping a bomb. Instead of telling them to make insane moves immediately, I told them to think small and just start making little moves outside their core. I encouraged chipping, learning, understanding the broader marketplace and cultural shifts. I explained that they could experiment later, and eventually, once a certain experiment started working, they could take a leap.

In my talks, I call this process “denting the outside”: a subtle chipping away at the outside of your own core of expertise. The goal is to eventually break through to connect yourself and your skill sets with the jet stream of disruption. Disruption is all about becoming the Bold One, the lone base jumper in a plane full of traditionalists. But—and here’s the key—you don’t base-jump before you learn how to skydive. And you don’t skydive without taking a class. It’s baby steps all along the way.

In your career, you take where you are today, and you start inching outside your core, denting it, slowly chipping away.

Making the move into a full-time innovation strategist and speaker wasn’t an overnight accomplishment for me. If I’d told my wife one night over pillow talk, “Hey babe, I’m going to quit my job as a 12-year veteran employee tomorrow to start advising companies on disruption,” I probably wouldn’t be writing this book. Even if I weren’t scared to make the move, she would have been.

So I just dented: I moved from accounting into consulting within my own institution, Deloitte. There I started stretching my innovation wings. From that position, I started speaking on innovation outside my company. When I had some proof of my ideas, I was able to convince my wife of my plan to branch out on my own. This bore some risk, but I wasn’t betting our entire financial future.

It works the same way with your bosses, and with an entire organization. If you’re interested in a new space, and you think your team, department, or company should consider altering its course, go get some real-world experience; then come back and show people. “I really think Web3 is going to make a splash. Here’s a small side project I’ve been tinkering on . . .” is a lot more persuasive than trying to convince a team of traditionalists that because some kids in their garage are really onto something, they should change their entire course today.

If you want to dent the outside, you’ve got to get past the immune systems—yours, and others’.

In summary, start small. To bypass the immune system problem—of yours or anyone else’s—make mini-bets. Movement is the key, not perfection. You don’t need to constantly take insane bets, but you do need to be constantly exercising your innovation muscle. Specifically, there are two keys that can help you begin to execute as quickly as possible:

KEY 1. THINK ABOUT THE NEXT RING

In the 1930s, a Russian psychologist named Lev Vygotsky started developing a model based on his interactions with children. He posited that there are three areas of a learner’s abilities:

1.   WHAT IS KNOWN. This is the center ring, what you already know how to do quite well. This circle represents what a learner can do without help.

2.   ZONE OF PROXIMAL DEVELOPMENT. In the second ring, a learner can complete tasks with help, and the assumption is that this zone will eventually become part of the learner’s core.

3.   WHAT IS UNKNOWN. In the outermost circle lies what is unknown, that a learner would have a hard time completing even with help, as this area is entirely outside the person’s understanding.

If we think about moving adjacent to our core, we can often start to make moves without having to jump to what’s totally unknown. Simmons went from writing to podcasting at one point, a big jump, but not a crazy one. It’s an adjacent skill, incorporating his brash personality and partiality to biased storytelling. Cardi B went from stripping to reality TV, but in between, she used her Instagram—a visual venue, like exotic dancing—to gain an audience. With an audience, reality TV makes sense. There she started talking and gaining support for her latest hot venture, rap. Cardi B was always moving, but she wasn’t always betting the farm. She was moving adjacent to her current skills, enlarging—and eventually disrupting—her entire core. It’s the dance between boldness and utter brashness.

If you’re a software engineer who wants to be a writer, start with technical writing. If you’re a general contractor who wants to get into software, why not start by developing a scheduling app for your team? Small, adjacent moves gain buy-in, and they’re often the easiest, quick wins.

KEY 2. DEFAULT TO TEAM STRATEGY

Once you’ve convinced yourself to take chances, convincing others to join you is generally the next move you should make. While branching could be the best-case scenario for some (or at some point), in many cases, the best outcomes include a Bold One collaborating with a company.

Yes, Simmons made $200 million. But ESPN hasn’t since totally collapsed. It still owns sports and has an audience size that Simmons, even now, could only dream of. What if they’d worked together? How much more successful could they both be today? With ESPN’s network, reach, and decades of hard-earned name-brand recognition and Simmons’s creativity and boldness, their combined output could have exceeded $200 million.

I did eventually leave Deloitte, but I loved my time there, and I still have contacts in the firm I work with today. And remember: to become the godfather of the PlayStation, Kutaragi never had to leave.

Don’t default to leaving. Default to collaborating.

YOUR NEW CORE

When we open our eyes to the processes, methods, and technologies others are using, we can often see efficiencies and breakthroughs that we can bring into our own core competency and, in turn, disrupt our industries. That’s one alternative, but it’s almost the lowest-level alternative. When you dent outside your core, you may just discover something so profound, so interesting, and so compelling to you, that you aren’t just going to bring it inside your core. You’re going to make it your new core. And that’s perhaps the largest reason everyone must dabble on the outside: You don’t know yourself well enough until you move outside your comfort zone.

You may rediscover your own capabilities. Previously, you were a salesperson, but after you dent the outside, you find out there’s more to the story. Yesterday you were an editor, but after denting, you know there’s something else more powerful inside.

The world’s waiting. Don’t wait to dent outside your core.

THE 3% RULE

One way to innovate is to simply remix.

A remix in innovation is exactly what it is in music: a reorganization of ingredients already produced. You reformulate them, and then add in your own flare to create something just new enough that it’s innovative, but just classic enough that it’s possible. You wondering, How much of my own flare do I need to add to call it innovative? Well, it turns out, there’s an exact number: 3 percent. It’s a concept developed by the late Virgil Abloh, creator of the high-fashion label Off-White.

“Three percent is intentional . . . experimental. . . . It’s a parting from the structures designed to inhibit or constrain,” he wrote in Domus 1060. “Three percent gave us Picasso in his African period. In the same way that it gave us J Dilla and the hip-hop movement that raised me.”¹

Abloh was the first African American to become an artistic director at a French luxury fashion house (Louis Vuitton), and apparently his 3% Rule took him there. Few industries rely on appearing “fresh” as much as Abloh’s, but by looking at the world only slightly differently, he put giant holes inside of handbags and turned graphic tees into high fashion. Time named him as one of the 100 most influential people on earth.

It turns out, 3 percent is just enough.

You can find examples of how Bold Ones have executed the 3% Rule everywhere; they remix prior innovations with just enough of their own style to create a modern disruption. To land on the moon, humanity flew through thousands of years of breakthroughs in computing and in our understanding of gravity and the universe. Neil Armstrong’s famous “small step” line was truly prophetic: Take a small step today that builds on the greatness of others.

Here are two ideas to help you foster a “3%,” small-step mentality.

1. COMBINE TECH, PROCESSES, AND MARKETS

Maybe you’re a healthcare professional, and you stumble on cryptocurrency. Is there a way you can combine healthcare and crypto to do something disruptive in patient privacy? Perhaps you’re a regional marketing manager and you stumble on the Agile process used in software—is it possible to apply this methodology to re-create marketing campaigns? If you’re a social worker who understands that the world is becoming more data-driven—is there a way to connect data to your community to address domestic violence?

2. LOOK OUTSIDE TO SOLVE INTERNAL PROBLEMS

Henry Ford stole the idea for his famous assembly line from a meatpacking warehouse. More recently, Steve Jobs stole the idea for his world-renowned Apple store layout by witnessing a Ritz Carlton hotel lobby.

What’s going on outside your company and your industry that you could utilize? The connections are not always obvious at first, and they don’t have to be. When Kara Goldin, founder of Hint Water, broke off from Silicon Valley after creating a $1 billion segment of AOL’s business, she brought her former skill set of collaboration. When she couldn’t find the chemical answer she needed to change the way infused water stays fresh, she looked around and asked questions, knowing someone would help her. The industry was averse to collaboration, but Goldin was from tech, where collaboration abounded. Sure enough, she found someone willing to share an idea on how to infuse water with natural flavors and maintain freshness.

In your current role, if you’re facing a problem, is the exact tool, methodology, or process you need found outside your role, in another marketplace? If you’re a factory manager, learn from technologists. If you’re a project manager for app development, look to what’s going on in mechanical engineering; if you’re a graphic designer, maybe your next breakthrough will be found by studying an assembly line.

WHY IT’S OK TO BE WASTEFUL

In business, we’ve grown accustomed to the “zero-waste” mantra. It’s encoded in our ethos.

As far as sustainability is concerned, I get it. But when the zero-waste philosophy drips into the way we think about our time, energy, money, and resources at a business, there’s a costly side effect: Without waste, we destroy the possibility of innovation.

Waste is essential to innovation, because experimentation is essential to innovation.

The path of the status quo is very efficient. It’s a deeply outlined, guarded, and well-trodden path from one end of the forest to the other. We all know where to start, and how to get to the end, efficiently, without wasting a single movement. But innovation requires a jaunt down off the trail, to find “something else.” Often we don’t even know what we’re looking for. You just know it’s in the woods, somewhere.

In 2021, Beeple sold his magnum opus, an NFT mosaic of thousands of small squares, for more than $69 million. The mosaic, entitled Everydays, is a purely digital file, composed of 5,000 squares of artwork. The sale crushed all previous records for NFT sales, and it was the first time a large auction house had auctioned purely digital artwork. But Beeple’s move wasn’t a steady, incremental climb. He was making small squares every day, then putting them into a larger collage.

On the one hand, it was a purely wasteful venture. On the other hand, it made him millions.

If he had had a boss, I wonder if they would have told him to “stop being wasteful.”

Lionel Messi, one of the greatest soccer players in history, said it like this: “It took me 17 years and 114 days to become an overnight success.” Readiness for a big innovation requires constant practice on smaller ones; in other words, you’ve got to experiment—and be a little wasteful. Kick the soccer ball around.

The inherent problem with experimentation is that, most of the time, you’re actually losing, or at least not gaining. Messi wasn’t getting a percentage of his success in down payments. Beeple wasn’t seeing a small amount of his eventual $69 million. More like it’s all a seeming waste, then a sudden smash hit.

You find success by traveling along a trail of failures. Be willing to make numerous mistakes in search of that one big hit. Try, fail, laugh, get up, and move on.

Grantland struggled in its infancy to make money. ESPN was seemingly justified in shutting it down. But Simmons resurrected the idea, because he wasn’t just thinking about tomorrow’s profits. He was considering the distant future. He was engaging with the undercurrents that were building, that no one could yet see.

In a world of ESPNs, be a Bill Simmons.

SECRETS OF THE BOLD ONES