Career success is often framed as a series of deliberate, optimized moves. But at a recent event hosted by Columbia Business School’s Jerome A. Chazen Institute for Global Business, Josie Natori offered a more realistic perspective: the most meaningful careers are designed over time, shaped by curiosity, experimentation, and a willingness to embrace uncertainty.
Moderated by Lulu C. Wang ’83, Founder and CEO of Tupelo Capital Management, the conversation spotlighted Natori’s career and the principles that have guided her through nearly five decades of entrepreneurship, from navigating change to building the Natori Company.
The discussion, co-hosted by The Hub, came as part of the Chazen Institute’s Sir Gordon Wu Distinguished Speaker Forum, and Natori is a current Lulu C. Wang Asian Business Leader.
A Non-Linear Path
Before her name became synonymous with an iconic global fashion brand, Natori’s career spanned seemingly unrelated worlds. A child prodigy pianist in the Philippines, she later majored in economics at Manhattanville College and joined Merrill Lynch, where she rose to become the firm’s first female Vice President of investment banking.
Yet after nine years on Wall Street, she walked away.
“I was bored,” Natori said. “The challenge wasn’t there.”
What followed was a period of exploration. She evaluated opportunities ranging from franchising to importing goods before an unexpected entry into fashion—sparked by embroidered garments from her native Philippines—set her on a new path. What began as a small, unplanned experiment grew into a lifestyle brand rooted in craftsmanship, artistry, and cultural identity.
Throughout the conversation, Natori emphasized that what others might perceive as liabilities—being Asian, being a woman, coming from outside the fashion establishment—became some of her greatest strengths. Identity, Natori noted, when paired with confidence and performance, can be a powerful strategic asset.
“I always said my biggest asset is being a woman and second, being Asian,” Natori said. “Even on Wall Street, I felt that I was different and that—to me—was an asset. I was called strong and small and terrible. But I used that to my advantage, actually.”
Creativity Meets Discipline
Natori is widely celebrated for her creative vision, but she credits her financial training with providing essential discipline. That balance of artistic intuition anchored by business rigor proved critical as her company scaled.
In the early years, she admitted, “ignorance was bliss.” Free from industry conventions, Natori approached lingerie as fashion at a time when the category was largely static. That instinct helped Natori stand out. Sustaining the business over decades, however, required operational focus, adaptability, and difficult financial decisions.
Creativity, she explained, has always remained central. Drawing on her musical training, Natori described design as an ongoing process of variation and refinement that never repeated the same note in quite the same way.
Building Through Change and Uncertainty
The retail environment Natori entered nearly 50 years ago has been fundamentally upended. Department stores have consolidated, direct-to-consumer competition has intensified, and supply chains have become increasingly volatile.
“In 48 years, this is the hardest climate—without a doubt—that I've ever seen," Natori said, citing tariffs, margin pressure, and shifting consumer behavior.
Yet adaptation has been constant. The company’s e-commerce platform—developed under the leadership of her son, Ken Natori—proved essential during the pandemic and remains a key source of insight into consumer preferences. Over decades, the brand has navigated shifts from formalwear to casualization, from wholesale dominance to digital engagement.
Her message to entrepreneurs was to understand that passion is essential, but realism matters. Entrepreneurship can be deeply rewarding—but it is also demanding, unpredictable, and unforgiving.
AI, the Human Advantage, and Designing Forward
Natori reflected on how artificial intelligence is reshaping retail and design. At Natori, AI is already embedded across the company’s research, e-commerce, marketing, and customer service, helping accelerate cycles and improve efficiency.
Still, she was clear about its limits, noting that technology is a tool—not a replacement—for intuition and experience. AI can generate options and insights, but creativity, taste, and judgment remain human strengths. In an AI-enabled world, curiosity and the ability to question outputs are becoming more—not less—valuable.
Natori returned to the idea that careers and businesses are built through exploration rather than certainty. Not every step needs to be planned. Not every talent needs to be monetized immediately.
In a world defined by rapid technological change and global uncertainty, her message was optimistic. Opportunity, she suggested, still exists, but it favors those willing to embrace who they are, and keep learning.
