Image credit: NewAfrica
We were two high school kids shooting hoops in my driveway when one sentence changed the course of my life.
My friend Anish looked over and said: "What if we ran the play ourselves?"
He meant the Indian community theater productions we'd both grown up watching. Every year, the adults in our community organized elaborate shows for Holi and Diwali. Both of us had theater backgrounds. We'd been in the shows. We knew how they worked.
At the time, it felt like teenage overconfidence.
Looking back, it was one of the most important leadership lessons I ever learned, because what looked like immaturity was actually a skill. The ability to stay curious before the objections load. To move before you're certain. To ask "what if we could?" before experience teaches you to ask "but what if we can't?"
Most adults have lost that skill. Most change initiatives pay the price.
The Part Nobody Puts in the Business Plan
Here's what I remember most about that moment: We didn't sit down and write a business plan. We didn't identify stakeholders. We didn't schedule a planning meeting to discuss the planning meeting.
We went inside and pitched it.
That same afternoon.
The time between "what if we could?" and "let's go ask" was basically zero.
And we pulled it off. We ran productions. They were good. Neither of us pursued a career in acting (though my improv background was close), but Anish went on to build a remarkable career that involved being a White House Fellow, initiating a healthcare coalition in Los Angeles to better serve patients, and being the CEO of a hospital during COVID. In my recent podcast interview with him, he mentioned that he thought some of our crazy antics and ideas as high school kids help shape his approach to things even now, as the second in charge of the Los Angeles County Department of Public Health.
I've thought about that afternoon a lot over the years, especially now that I work with leaders navigating organizational change. Because I think I finally understand why we moved so fast.
We didn't know enough yet to talk ourselves out of it.
Why Ignorance Was Our Superpower
That's not a knock on us. It's the point.
We were teenagers. We hadn't accumulated enough experience to generate a convincing list of reasons why it was a bad idea. We didn't have the mental library of "here's how things like this tend to go wrong." We couldn't immediately picture ourselves standing in front of a disappointed crowd.
Basically, we didn’t have a preloaded arsenal of “yes, buts” in our head. Instead, our brains went somewhere else:
- What if this is fun?
- What if we can actually do this?
- What if we're good enough?
Adults don't usually start there. Adults start with the objections.
- What if it fails?
- What if I look stupid?
- What if people think I overstepped?
- What if I'm wrong? What if this is harder than it looks?
We call that “wisdom,” and sometimes it is. Sometimes it's just “better excuses.”
What Anish Did Decades Later (Same Instinct, Bigger Stage)
On my podcast, Anish talked about how those same teenage instincts showed up decades later in his career. When he was building his healthcare coalition, people around him thought the goals were unrealistic. The scale was too ambitious. The obstacles were too significant.
He said “Yes” anyway. He figured it out after.
That gap — between deciding to try and knowing exactly how — is where a lot of great things get built. It's also where a lot of good ideas go to die, because someone with enough experience explained all the reasons it wouldn't work.
What's Actually Happening When Your Team Goes Quiet
When an organization announces a change (a reorg, a new technology rollout, a shift in leadership or values) the people on that team aren't sitting around imagining what could go right. They're running the loss calculator in their heads.
What am I going to lose control of? What skills that I've spent years building won't matter anymore? Will I still know what I'm doing? Will I still be good at this? What about the relationships I've built? The routines that work for me?
Nobody tells them to do that. It just happens. It's what experience teaches you to do.
And look — that instinct isn't wrong, exactly. It's self-protective. It's rational. But it's the enemy of change.
This is something I've come to believe after years of working with leaders on exactly this problem: The biggest obstacle to change in most organizations isn't resistance. It's apathy.
Resistance is loud. Resistance shows up in meetings, pushes back in conversations, gives you something to work with. Apathy is quiet. It sits in the middle of the bell curve. It nods along in the all-hands and then goes back to doing things the old way; not out of defiance, but out of a deep, unspoken belief that it's probably not worth the energy.
That apathy is often the residue of too many "yes, but" responses that never got resolved.
The Two-Word Choice That Shapes Every Change Initiative
“Yes, And” versus “yes, but.”
These are the two responses available to any human being encountering something new.
"Yes, but" is the response born of experience. "I hear what you're saying, BUT here's why it won't work. Here's what we tried before. Here's what the risks are. Here's why we should wait."
"Yes, and" is the response of someone who hasn't yet learned to default to no. "I hear what you're saying, and what if we tried this? AND what could we build from here? And what becomes possible if this actually works?"
Neither is always right. The problem is that most organizations are set up to reward compliance and punish (or at least limit) creativity - especially when it doesn’t work.
The teenager in my driveway didn't have enough experience to fully appreciate how the yes, but response worked. So he skipped it. And that turned out to be his advantage.
This Isn't About Pretending the Risks Don't Exist
I'm not suggesting we all pretend to be 16 again and abandon risk assessment. That's not the idea.
The idea is that experience is supposed to make us better at navigating the world, not just better at generating reasons to stay still.
When Anish and I said yes in that driveway, we weren't being reckless. We were being curious. There's a difference. Reckless ignores the risks. Curious asks: What if the upside is worth it? What if we try small first and see what we learn? What if the answer to "is this possible?" is actually yes, and we just haven't found out yet?
That's "Start Small" - one of the core principles of the YES AND framework I've built my work around. Big transformation rarely starts with a perfect plan. It starts with a small, curious yes. A willingness to begin before you fully understand where you're going.
My friend didn't have a fully formed plan when he decided to build that coalition. He had a belief that it mattered, and a willingness to take the next step.
That's how most things that actually matter get started.
Three Questions Worth Sitting With
What is one idea you've talked yourself out of in the last year because you "know too much"?
Where is your team defaulting to “yes, but,” and is it because they see a real problem, or because change feels like loss?
What's one small experiment you could say yes to this week, before you've fully figured out whether it'll work?
The driveway moment wasn't transformational because we had a great plan. It was transformational because we didn't wait to have one.
I wonder what you're waiting to find out before you start.
Dr. Anish Mahajan was my recent guest on the podcast. We talked about healthcare, leadership under pressure, and how the instincts you form early in life show up when the stakes are highest. You can find it here; it's worth a listen if any of this landed.
I help executives leading change turn apathetic teams into excited ones — through the YES AND Framework, experiential programs, and the improv-based principles in my upcoming book, Say "Yes, And!" to Change, launching late April. Email me now if you’d like to chat…