Curiosity, Courage, and the Future of Innovation with James Schoen
If you’ve ever felt behind in a world that’s changing faster than you can process, you’re not alone.
In my latest episode of The Why Not Podcast, I sat down with James Schoen—Senior Product Marketing Manager at Square, former Google strategist, entrepreneur, husband, and father—to explore what innovation really looks like when it’s lived out daily.
James doesn’t just talk about change—he builds it. And through our conversation, one message stood out clearly: curiosity and courage are the twin engines of growth.
Comparing Yourself to Who You Were Yesterday
We started with a quote from Jordan Peterson:
“Compare yourself to who you were yesterday, not to who someone else is today.”
James reflected on how freeing that mindset can be. Early in his career, he said, comparison was constant—between classmates, coworkers, and friends climbing the corporate ladder. But as time passed, he realized the only meaningful competition was with himself.
“Your career and life are long. It’s a marathon. Happiness comes when you’re progressing—when you’re better today than you were yesterday.”
That line hit home. Progress, not perfection, is where fulfillment lives.
Lifelong Learning: The Habit Behind Momentum
When asked what habits helped him move from uncertainty to momentum, James didn’t hesitate: a love for learning.
He described leaving a stable corporate job to chase a startup idea, learning AI and coding along the way. With no formal training, he used ChatGPT to build advanced website functionality—something developers had quoted him thousands of dollars for.
“AI might not replace my job,” he said, “but the person using AI will.”
That mindset changed everything. When he later joined Square, he was already ahead of the curve—helping lead AI enablement across their marketing organization. What started as curiosity became a career-defining advantage.
Curiosity as the Path to Happiness
James’ philosophy on happiness is refreshingly grounded. He shared research from his background in positive psychology, explaining that people often chase comfort when what they really crave is problem-solving.
“Happiness isn’t the absence of problems—it’s having the right kinds of problems to solve.”
That hit me. We think we’ll be happiest when life is easy, but meaning actually comes from the work of learning, building, and improving.
It reminded me of finishing my MBA—not the degree itself, but the fulfillment that came from the process. The late nights, the challenge, the push forward. That’s where satisfaction lives.
Building Trust Through Simplicity and Sacrifice
When we shifted the conversation toward leadership and marketing, James shared powerful lessons from his time at Square.
He explained that building trust—especially in financial services—starts with clarity and sacrifice. You build trust when people see that you’re willing to do what’s right, even when it costs you something.
“At Square, our focus is simple: how do we give time back to small business owners?”
He described a scenario that stuck with me—a single mom running a cupcake shop who finishes her bookkeeping between 10 p.m. and midnight. Square’s mission is to simplify her life, not complicate it. Every product decision is filtered through that lens:
Will this give time back to the customer?
If not, they don’t build it.
That level of intentionality builds something more valuable than brand awareness—it builds trust.
Balancing Data and Empathy
Coming from Google, James knows data is powerful. But he also knows its limits.
He shared a story about Square’s early days when the company created its now-famous card reader. At first, small business owners weren’t interested—they didn’t think they needed to accept credit cards. Then one florist lost a sale because a customer only had a card. That moment shifted everything.
“They weren’t looking for a credit card reader,” James explained. “They were looking to make the sale.”
That insight reframed Square’s mission—not as a hardware company, but as a company that helps small businesses make the sale.
The takeaway? Data tells you what’s happening. Customers tell you why. The best leaders listen to both.
Courage Over Perfection
We ended our conversation talking about decision-making—the kind of paralysis that can come from too much data or too many opinions.
James summed it up perfectly:
“Done is better than perfect.”
Innovation doesn’t wait for perfect timing or flawless plans. It rewards the people who move—who act, learn, and adjust along the way.
Final Thoughts
James reminded me that innovation isn’t just about technology or speed. It’s about curiosity, courage, and a commitment to keep growing—both personally and professionally.
When you stop comparing and start learning, stop defending and start listening, stop waiting and start acting—that’s when innovation actually happens.
🎧 Listen to the full episode:
Curiosity, Courage, and the Future of Innovation | The Why Not Podcast
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Noah Cisneros 
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