April 16, 2026How Boundaries Drive Creativity with Sheri Jacobs

Most people think creativity needs room to breathe. Give people more options, more tools, more freedom, and the ideas will come. But what if that assumption is exactly what’s been holding your team back?

I’ve spent years working with some of the most dynamic minds in the speaking world, and one of the patterns I keep seeing is this: the teams that produce the most original, high-impact work aren’t the ones with unlimited resources or open-ended briefs. They’re the ones who know exactly where the edges are. They understand their constraints, and they use them as a launching pad rather than a leash.

That’s why my conversation with creativity keynote speaker Sheri Jacobs stopped me in my tracks. Sheri is the bestselling author of The Unexpected Power of Boundaries, the Founder and CEO of Avenue M Group, and a researcher who has surveyed more than half a million people across more than 300 organizations. She’s also an award-winning wildlife photographer whose images from Antarctica to Zambia prove that her philosophy isn’t just theory. It’s lived, practiced, and tested in some of the most demanding environments on earth.

In this conversation, we get into why innovation usually dies under too much freedom, how a simple three-rule framework at Bank of America produced one of the most successful savings products in recent memory, why jumping to AI before you’ve defined your goal is one of the most common creative mistakes leaders make today, and how a tennis lesson turned into a masterclass on failure, recovery, and momentum.

If you’ve ever told your team to “be creative” and watched them freeze instead of fly, this one is for you.

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Creativity Thrives Inside Constraints, Not Despite Them

There’s a moment Sheri describes from her very first photography trip to the Arctic that I think most leaders will recognize immediately, even if they’ve never picked up a camera. She arrived with every lens she owned, every piece of gear she could carry, every option available to her. And when the moment came to shoot, she froze completely. Too many choices. No clear direction. The opportunity passed while she stood there sorting through her bag.

That story isn’t really about photography. It’s about what happens when we confuse access with clarity.

We do this in organizations constantly. We give people more tools, more platforms, more pathways, and then wonder why output slows down, decisions take longer, and nobody seems to move with any real conviction. What feels like empowerment is often just noise. And creativity, real creativity, doesn’t come from noise. It comes from knowing exactly what you’re working within.

Sheri’s research makes this case clearly. The most creative people and teams she’s studied don’t operate in open fields. They operate inside well-defined spaces. They’ve decided in advance what they’re trying to accomplish, which tools are available, and what’s off the table. That clarity doesn’t kill inspiration. It focuses it.

This idea challenges one of the most persistent myths in creativity: that limits are the enemy of originality. In reality, limits are what make originality possible. When everything is available, nothing is chosen. When choices are narrowed, people commit. And commitment is where real creativity work begins.

The most important distinction Sheri draws here is between the “what” and the “how.” What is your goal, your purpose, the outcome you’re trying to produce? The how is the process, the experiments, the methods, the failures along the way. She argues that what should be fixed and clear. But the how should stay flexible, open, and exploratory. That’s where creativity actually lives.

So if your team is stuck, the first question isn’t “are we being creative enough?” It’s “have we defined the what clearly enough?” Because without that anchor, creativity has nowhere to land.

The Bank of America Innovation Story Every Leader Needs to Hear

One of the most compelling examples Sheri shares is the story behind Bank of America’s “Keep the Change” program, and it’s worth unpacking in detail because it illustrates her framework better than almost anything else I’ve come across.

Bank of America wanted to help customers save money. That was the goal. The what. What they didn’t do, and this is the key, is tell the innovation team how to build it. They didn’t say “create an app” or “design a new product line.” Instead, leadership gave the team three constraints: use existing technology, don’t require customers to change their spending behavior, and make the experience completely frictionless.

Three rules. That’s it.

Within those boundaries, the team created a program that rounds up every debit card purchase to the nearest dollar and automatically moves the difference into a savings account. No new habits required. No new technology to build. No friction for the customer. The solution was elegant precisely because the constraints forced elegance. There was no room for complexity. Every over-engineered solution got cut because it violated one of the three rules.

The result became one of the most successful savings products in the company’s history.

What’s powerful here isn’t just the outcome. It’s the process. The constraints didn’t limit the team’s thinking. They focused it. They removed the noise, the tangents, the distractions, and the “wouldn’t it be cool if” conversations that eat up creative energy without producing results. They created a channel, and the team’s creativity flowed through it.

This is what Sheri means when she says that innovation accelerates when leaders define the edges instead of removing them. You’re not removing creativity from the equation. You’re removing the friction that prevents creativity from doing its best work.

For event professionals, team leaders, and anyone building something new, the takeaway is immediate. Before your next brainstorm, ask: what are the three constraints that define this project? What’s in bounds? What’s out of bounds? What’s non-negotiable? Set those rules first, then let the creativity run.

Why Legacy Rules Are Quietly Killing Your Best Ideas

If the Bank of America story is about constraints that unlock creativity, then this part of the conversation is about the flip side: constraints that were once useful but have quietly become the enemy of progress.

Sheri calls these legacy rules. They’re the invisible walls that don’t show up in any policy document but shape almost every decision a team makes. Things like “we’ve always done it this way” or “we don’t build for that audience” or “that program worked before, so we keep running it.” These rules often made perfect sense when they were created. They existed for good reasons. But organizations change. Markets change. Audiences evolve. And the rules don’t always evolve with them.

What’s dangerous about legacy rules is that they don’t announce themselves. They operate in the background as assumptions, as defaults, as the starting point for every conversation. And because nobody questions them, they compound. One outdated assumption layers on top of another until the whole culture is shaped by thinking that no longer applies.

Sheri’s point here about creativity is both practical and a little uncomfortable: success can be a terrible teacher. When something worked in the past, we hold onto it. We attribute the win to the strategy, the format, the structure, the program. And we keep repeating it, even as the conditions that made it successful quietly disappear. The past success blinds us to the present shift.

The practice she recommends is simple but demanding: conduct regular boundary audits. Look at the rules you’re operating under, both the official ones and the unspoken ones, and ask whether each one still serves the goal. Not “did it used to work?” but “does it still work now?” If the answer is no, it’s time to update or remove it, even if it feels uncomfortable, even if it was someone’s big success from three years ago.

For leaders working on thought leadership or building organizations that want to stay ahead, this is one of the most important creative disciplines available. The ability to question your own past wins, and to update the rules accordingly, is what separates teams that adapt from teams that slowly become irrelevant.

AI Overload and the Real Creativity Cost of Jumping to Tools Too Fast

I’ll be honest: this part of the conversation hit close to home. Because I see it everywhere right now, and I suspect you do too.

Someone on a team gets excited about a new AI tool. They jump in immediately, start generating outputs, and within an hour they have content, ideas, frameworks, and outputs. They felt that their creativity efforts panned out. But when you look at the work, something feels off. It’s generic. It could have come from anywhere. It doesn’t reflect the organization’s real expertise or point of view. Because the tool was used before the thinking was done.

Sheri draws a direct parallel between this and her Arctic photography experience. She went in with too many lenses, no clear artistic goal, and a mindset of “I’ll figure out what I want once I’m shooting.” The result was paralysis and mediocre work. The gear didn’t save her from the lack of direction. It amplified it.

The same is true with technology in general and AI in particular. These tools are genuinely powerful. But they’re most powerful when the person using them has already defined the outcome, identified what their own expertise and perspective should contribute, and is using the tool to support and accelerate a direction they’ve already chosen, not to replace the thinking entirely.

Her recommendation is to pause before you open any tool and answer two questions: what am I actually trying to accomplish, and where does my own knowledge and experience fit into this? Those two questions force you to define the what before you reach for the how. They make the tool a servant of your thinking, not a substitute for it.

This matters especially for business leaders and teams building in the future of work landscape, where AI is no longer optional and the competitive advantage isn’t access to tools. Everyone has access to the same tools. The advantage is the quality of the thinking you bring to those tools. And that quality begins before you ever open the app.

Failure Rules, Dollar Limits, and the Culture That Makes Experimentation Safe

One of the most practical frameworks Sheri shares is what she calls “failure rules,” and I think it’s one of the most underused tools in organizational leadership.

Here’s the problem she’s trying to solve. The people closest to your customers, your front-line staff, your team leads, your field reps, are usually the ones who see the real opportunities. They hear what customers are struggling with. They notice what’s broken in the process. They have ideas about what could work better. But they don’t act on those ideas because they’re afraid to fail, and they don’t have permission to try.

So the ideas sit. The opportunities disappear. And the organization keeps doing what it’s always done while wondering why nothing changes.

Sheri’s solution is to give people an explicit budget for experimentation. Pick a dollar amount, whatever makes sense for your organization, and tell people: you can spend up to this amount testing any idea, no approval needed, as long as you report back what you learned. The constraint isn’t punitive. It’s liberating. It says: we want you to try things, and here’s exactly how far you can go without asking permission first.

At an online payroll startup Sheri worked with, the leadership team took this even further. They created a “best new mistake” award valued at four times any other company award. Not a prize for trying and not getting caught. A genuine, celebrated recognition of smart experimentation that produced real learning, even if the experiment didn’t succeed. The message it sent through the organization was powerful: learning from what didn’t work is as valuable as celebrating what did.

This kind of environment doesn’t happen by accident. It’s built deliberately, through explicit rules, clear boundaries around risk, and consistent cultural signals from the top. And it’s the kind of creativity infrastructure that turns occasional good ideas into a steady, sustainable stream of innovation.

What Tennis Taught Sheri Jacobs About Mistakes and Momentum

I loved this part of the conversation because it turns out Sheri and I have tennis in common, and her story about picking up the game late is one of the most honest things I’ve heard anyone say about learning, failure, and the very human impulse to quit when something feels hard.

Sheri started playing tennis later in life, after decades as a marathon runner. She was fit, disciplined, and competitive. She expected to be decent. Instead, she was, in her words, terrible. And it didn’t just frustrate her: it shook her. She’s a high achiever. Being bad at something in front of other people is genuinely uncomfortable for people like that, and she’s honest enough to admit it.

She wanted to quit. The feeling of repeated failure was too much. But instead, she developed a practice that she now applies to everything: pause, reflect, and reset.

After a string of bad shots, she stops. Steps back. Takes a breath. Looks at what’s happening. And then makes one small adjustment, not a complete overhaul, not a breakdown of everything she did wrong, just one small change for the next attempt. She also gave herself explicit permission to not win every point. The goal shifted from “win” to “get the ball in and work the point from there.” That narrower target, that smaller constraint, made the game more manageable and more improvable.

What she describes is a habit of mind that any leader working in high-stakes, high-pressure environments can borrow directly. Mistakes are inevitable. The question is never whether you’ll make them. The question is what you do in the moment after they happen. Do you spiral? Do you quit? Or do you pause, extract the learning, and redirect your energy toward the next shot?

The reset ritual she describes is deceptively simple. But it’s one of the most powerful tools available for anyone trying to build something new, especially when things inevitably go sideways. And when it comes to entrepreneurship and creativity, things always go sideways.

Fewer Lenses, Better Work: The Discipline of Saying No

By the time Sheri reached her eighth wildlife photography trip to Africa, something had changed. She’d learned her lesson from the Arctic. She didn’t haul everything she owned. She brought two camera bodies, three lenses, and a specific artistic intention. Not “get great shots.” Something more specific than that, a clear visual goal that would guide every decision she made in the field.

The difference in her work was immediate and dramatic.

While other photographers were shooting everything, firing off hundreds of frames to capture every possible angle of every possible moment, Sheri was waiting. She knew what she was looking for. She could recognize when a scene was or wasn’t aligned with her intention. And when the right moment came, she was ready for it in a way that “shoot everything” photographers simply can’t be.

She captured images on that trip that she still considers her best work. Not because she had the best gear, though her equipment was excellent, but because she had the clearest direction. Saying no to the extra lenses created the space for yes to mean something.

This is, in essence, the entire philosophy behind Sheri’s book and her work with organizations. Constraints, boundaries, deliberate limits, aren’t the opposite of creativity. They’re the precondition for it. When you say no to enough things, the yes you’re left with becomes extraordinary.

For women leaders, best-selling authors, and anyone navigating the constant pressure to do more, add more, and stay current with every new platform, tool, and trend, Sheri’s message is a rare and welcome counterpoint. The path to your most original work isn’t through more. It’s through less, chosen deliberately and defended consistently.

Applying Boundary Thinking to Events, Teams, and Creativity

I want to spend a moment here thinking through what this means practically, because I work with event professionals and organizations every day, and I see this play out in real time constantly.

Event planners, in particular, live inside a world of infinite creativity options. Every year brings new formats, new tech, new platforms, new audience expectations. The pressure to innovate is real. But so is the risk of innovation for its own sake, adding things because they’re new rather than because they serve the experience you’re trying to create.

What Sheri’s framework offers is a way to cut through that noise with clarity. Before you build your next event, your next campaign, your next team initiative, ask yourself: what are the two or three constraints that should guide every decision here? Not “what could we possibly do?” but “what are we actually here to accomplish, and what rules should govern how we get there?”

That shift from infinite possibility to bounded purpose is where creative energy finds its focus. It’s where the customer experience becomes cohesive instead of scattered. It’s where teams stop debating everything and start building something. And it’s where the most memorable, distinctive work comes from, not from adding more, but from committing to less with greater conviction.

Sheri Jacobs, as a keynote speaker, brings all of this to life with the kind of storytelling and original research that makes people not just think differently, but act differently. If you’re building an event around innovation, leadership, or the future of work, she’s the kind of voice that moves rooms. And she has the data, the stories, and the lived experience to back it up.

There’s something rare about a speaker who has tested their ideas not just in boardrooms and research labs but in the field, literally, across Antarctica and Zambia, with a camera and a clear intention. The same philosophy that made her a better photographer made her a better researcher, a better strategist, and a better guide for the leaders she works with.

That’s the real power of boundaries. Not that they keep you small. But that they show you, precisely and clearly, how far you can actually go.

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