An American Bison standing on the middle of a road
An American Bison standing on the middle of a road
#playtowin

Pitching, Leading, Growing? Play to Win, Not to Worry

By
Paul Kiernan
(4.9.2025)

We’ve all had those moments. You walk into a room with something you need, something you’re ready to ask for, and the air hits you before you even say a word. Tension. Mood. Something’s off. The vibe has shifted, and your once-clear plan now feels like a trap waiting to spring.

Don’t Play the Obstacle: What Acting Can Teach Us About Leadership and Business

We’ve all had those moments. You walk into a room with something you need, something you’re ready to ask for, and the air hits you before you even say a word. Tension. Mood. Something’s off. The vibe has shifted, and your once-clear plan now feels like a trap waiting to spring.

This is the moment right before the scene begins. It could be a conference room, a kitchen, a hallway—any space where someone has to make a choice. In acting, we call this the moment of intention. You enter a scene with a want, a goal you’re after. But rarely—if ever—is that want handed to you. There’s always something in the way. That’s the obstacle.

Now, here’s where things get interesting. A lesser actor might walk into that moment, feel the tension, and freeze. They might think, “Well, I won’t get what I want, so why even try?” And in doing so, they stop playing the scene. The moment collapses. Nothing happens. It’s dead space.

But a good actor? They do the opposite. They play the want. They read the room, listen with their whole body, and adapt their approach. They find new tactics, new ways to pursue the goal, all while the obstacle pushes back. And that tension—that collision between the want and what stands in the way—is where the magic happens. It’s what makes a performance electric. We lean in because we want to know: how are they going to get what they want?

It turns out, this idea doesn’t just belong on a stage. It belongs in business meetings, leadership conversations, creative pitches, career decisions—anywhere you have to move through resistance to get to something that matters. And yet, so often, people in professional settings “play the obstacle” without even realizing it. They walk in, sense resistance, and retreat. They silence themselves before they’ve even tried.

But what if we approached these moments like actors do? What if we stopped letting the obstacle define our behavior and instead started playing the want with clarity, with creativity, with belief?

That’s what this blog is about. An acting lesson that’s really a life lesson. A scene study for the boardroom, the pitch meeting, the leadership challenge. Let’s raise the curtain.

What It Means to ‘Play the Obstacle’ in Acting

In acting, a scene is always built on two foundational elements: what a character wants, and what’s in the way of getting it. The character wants love, forgiveness, power, safety, a second chance—something they care about deeply. And in front of that want stands an obstacle: another character, an uncomfortable truth, a secret, a rule, a fear, a social expectation. The tension between the two is what gives a scene its heartbeat.

Now, here’s where actors often go wrong—especially when they’re new or unsure. They walk into the scene and focus on the obstacle. They let the block become the performance. They stop playing what they want and instead play the reason they can’t have it.

When that happens, the scene stalls. The character doesn’t fight, doesn’t pivot, doesn’t act. They retreat into defeat before the moment has even begun. That’s what it means to “play the obstacle.” It’s the acting equivalent of throwing in the towel—often without even realizing it.

Let’s make it real.

Picture this: A teenage boy walks into the kitchen to ask his mom if he can borrow the car. He’s got a date—his first date ever. Not just any girl, either. The one he’s been crushing on for months. Everyone at school knows. The pressure’s enormous. He walks in, ready to make his move—and finds his mom angrily slamming pots around. She’s upset. Maybe at him. Maybe at something else. He doesn’t know yet.

Now, if he “plays the obstacle,” he freezes. He assumes she’ll say no. He tells himself it’s pointless. He walks back out. Scene over.

But if he plays the want, something else happens. He sees the mood, but doesn’t let it stop him. He listens. He adapts. Maybe he asks what’s wrong. Maybe he offers to help. Maybe he tries to make her laugh. He uses tactics—because he still wants the car. He’s actively trying to navigate around the obstacle in front of him.

And now? We, the audience, are invested. We’re leaning in. We feel the stakes. Will he get the car? Will he say the right thing? Will he blow it? The scene is alive.

That’s the difference. Playing the obstacle kills action. Playing the want—through the obstacle—creates it. The same principle applies when you walk into a meeting with a bold idea and sense resistance in the room. Do you freeze and back down? Or do you listen, adapt, and keep playing what you want? That moment in the kitchen isn’t so different from the boardroom. The stakes may change, but the scene plays the same.

Image, chest up, of Michelangelo's The David

David vs. Goliath: A Classic Case of Not Playing the Obstacle

You don’t have to be a theater person to understand the power of this idea. Just look at one of the most famous underdog stories ever told.

When David stood before Goliath, he didn’t play the obstacle. Everyone else on that battlefield had already done that. They looked at Goliath—the size, the armor, the undefeated streak—and backed away. They saw the obstacle and believed it was unbeatable. And so, they played the obstacle. They chose inaction. They chose fear.

But David? He played the want. He wanted to protect his people. He believed the fight mattered. And he believed—deeply—that he could win. Not because he was stronger, not because he had better weapons, but because he saw a path through. He had skill. He had a slingshot. He had conviction.

He didn’t ignore the obstacle. He saw it clearly. But he didn’t become defined by it.

This is why that moment endures—not just as a story of faith or courage but as a case study in pursuit. David enters the scene to act. He enters to win. He adapts his tactics to fit the challenge in front of him but never loses sight of the want.

That’s what we’re talking about.

And this doesn’t just belong in ancient history or Sunday school. We face Goliaths every day. They look like high-level clients, gatekeeping executives, complex market forces, budgets, timelines, egos, and inner doubts. The obstacle is real. It can be massive.

But if you walk into a moment and let the obstacle speak louder than your want, then Goliath has already won. You’ve surrendered before you’ve begun.

David didn’t play the obstacle. He stepped forward. Sling in hand. Aim steady. Want clear.

What Playing the Obstacle Looks Like in Business (H2)

You’d think we’d be better at this by the time we’re in the workplace. After all, we’ve all been taught to be proactive, to take initiative, to lead. But then something happens. We enter the scene. We feel resistance. We sense tension. And suddenly—we start playing the obstacle.

It sounds like this: “They’ve already made up their minds.”

“This client always shoots ideas down.”

“I’m not senior enough to speak up.”

“This market is too competitive.”

“My boss doesn’t really listen anyway.”

These aren't just passing thoughts. They become choices—even if we don't realize it. Choices to hold back, to stay small, to not try. And just like the actor who walks into the kitchen, sees Mom is mad, and walks right back out, we let the obstacle win before we’ve even begun to play the scene.

It shows up everywhere. A promising employee doesn’t pitch their idea because they assume it won’t go anywhere. A team backs away from a bold strategy because the client “isn’t ready” for it. A leader delays a hard conversation, assuming it’ll just create conflict.

No one’s yelling “cut,” but the scene has stopped. The stakes are still high, but the action is gone. And just like onstage, the audience—our colleagues, our clients, our teams—starts to tune out.

Playing the obstacle in business might look calm on the outside, but it’s driven by fear, doubt, and resignation. It’s the slow erosion of momentum. It’s a quiet surrender dressed up as caution.

And here's the real danger: the more often we play the obstacle, the more natural it starts to feel. It becomes habit. Culture. “That’s just how we do things here.” And suddenly, a company or a career full of possibilities becomes a graveyard of scenes that never got played.

But it doesn't have to be that way.

A black pug dog looking  with desire at a pie on a table

What It Means to Play the Want in the Workplace

If playing the obstacle is surrender, playing the want is commitment.

It’s stepping into the room, reading the resistance, and still choosing to act. Not blindly. Not forcefully. But actively. With intention, clarity, and adaptability. Just like the actor in the kitchen, a professional who plays the want doesn’t get scared off by the first frown or furrowed brow—they get curious, creative, and strategic.

Playing the want in business is not about being pushy. It’s about staying engaged. It’s about recognizing that your goal matters and that there are always tactics to try—even when the terrain is rough.

Maybe you're the junior team member with a fresh idea. You know it could make a difference, but the room is filled with higher-ups, and the energy is... skeptical. Playing the obstacle means shrinking. Playing the want means refining your pitch, reading the moment, building an ally beforehand, and asking the right question that tees up your idea. It’s movement, not muteness.

Maybe you’re the founder of a small startup trying to carve out space in a crowded market. You could look at the Goliaths around you and bow out. Or you can lean into what makes you different, what problem you solve better, what story only you can tell. You can play your want—your vision—through the noise.

Maybe you’re a leader facing a team that’s frustrated, burned out, or resistant to change. You could take that as a wall. Or you can take it as a cue to listen more deeply, to shift your approach, to find the shared want that reconnects everyone to the work.

Playing the want doesn’t mean you ignore the obstacle—it means you don’t let it lead. You let it shape your tactics, yes. You let it inform your choices. But your focus stays on the want.

That’s what makes you active. That’s what makes you watchable. That’s what creates change.

And maybe most importantly, playing the want is how you stay connected to why you showed up in the first place. It’s how you remember what mattered to you before the obstacle entered the room.

Why This Acting Lesson Matters for Leadership

Leadership is, in many ways, a kind of performance. Not in the sense of being fake or theatrical, but in the sense that leaders are always stepping into moments where people are watching, listening, and taking cues. A leader’s presence sets the tone. Their choices shape the scene.

And like an actor, a leader is constantly navigating obstacles—personalities, timelines, resistance, pressure from above, pressure from within. The room is never perfectly staged. The lighting is rarely ideal. The script, if there is one, is loose at best. But the scene still has to be played.

This is where the lesson matters most.

Leaders who play the obstacle become passive. They rationalize inaction. They point to why something won’t work instead of asking how it might. They wait. They defer. They stay safe. And slowly, their teams start doing the same. The culture that forms is one of hesitancy and caution—a workplace where nothing truly daring ever gets off the ground.

But leaders who play the want change the dynamic.

They read the room and act anyway. They stay in pursuit. They shift tactics when needed but never lose sight of the vision. And because they’re active, the people around them become active too. Teams lean in. Ideas flow. Risks get taken. Progress happens—not because the obstacles disappeared, but because someone kept playing the scene.

A great leader doesn’t just tell people what to do—they model what it looks like to stay engaged when things get hard. They play their want with presence, purpose, and adaptability. And that gives others permission to do the same.

Leadership isn’t about pretending the obstacles aren’t there. It’s about making a choice not to let them be the story.

Jellyfish under the surface of the ocean

Under the Surface: The Stakes Aren’t on the Page

A good actor knows the script is just the starting point. The lines are there, yes—but the real work begins with the choices made underneath those lines. The backstory, the emotional history, the private stakes that never get said out loud—that’s what fuels a performance.

It’s not written in the script that the teenage boy’s date is with the most popular girl in school. Or that it’s his first date, ever. Or that everyone knows and he’s terrified of blowing it. That’s the actor’s job. To raise the stakes. To imagine what this moment means, what’s riding on it, and to let all of that simmer beneath the surface while still keeping the action focused on the want.

He doesn’t walk into the kitchen saying, “This is my one shot at not being a loser.” He walks in and says, “Can I borrow the car?” But the energy underneath—that’s what makes it matter.

As the possibility of Mom saying no becomes more real, the pressure mounts. He can’t afford to give up. He tries new tactics. He listens more carefully. He works the moment with everything he’s got. And we, the audience, feel it. We know this is about more than transportation. It’s about identity. Confidence. Social standing. Maybe even survival in the fragile world of teenage reputation.

That’s the actor’s work. Raising the stakes, silently, and letting those stakes guide how the want is played.

And in the workplace? It’s no different.

Most of the time, we don’t say what’s really at stake. We don’t say, “If this pitch fails, I’m worried I’ll never be taken seriously again.” Or, “If I don’t lead this well, maybe I’m not cut out for this role.” We just say the lines: “Let me walk you through an idea,” or “I’d like to revisit our team structure.”

But underneath, there’s something deeply personal happening. That meeting, that presentation, that conversation—it might be a crossroads. A chance to prove something. To be heard. To be respected. To move forward.

When we play the want, fueled by those unspoken stakes, we show up differently. We’re more alive. More intentional. More present. People sense it—even if they don’t know exactly why.

And just like in a great performance, they start to care. They start to root for us. Because we’re not just saying the lines. We’re playing the scene.

Summing Up: Play the Scene, Not the Problem

Obstacles are everywhere. That’s not the problem.

The problem is when we start playing them—when we let the resistance, the risk, or the fear become the star of the scene. When we retreat from the moment instead of stepping into it with intention.

Whether you’re an actor or a strategist, a student or a CEO, your job isn’t to pretend the obstacle isn’t there. Your job is to stay in the scene. To pursue the want. To adapt, to listen, to respond—to keep moving.

Playing the want is how things change. It’s how ideas break through. It’s how moments become turning points. Because when you stay connected to what you want—and why it matters—you bring people with you. You pull focus. You create action.

At ThoughtLab, we don’t play the obstacle. We play the scene. When challenges show up—and they always do—we don’t back away. We listen harder. We raise the stakes. We get creative. We find a new tactic. We stay in pursuit of what matters: smart ideas, bold work, and meaningful outcomes.

Because we believe every moment is a scene worth playing. And if we’re in it, we’re showing up to win.