In an exclusive interview with CanadianSME Small Business Magazine, we sit down with Sheena Yap Chan, Wall Street Journal bestselling author, keynote speaker, strategist, and host of The Tao of Self-Confidence podcast. With over one million downloads and 800+ interviews, Sheena is a powerful voice for women seeking to lead with authenticity and courage.
Interview by SK Uddin
Sheena Yap Chan is a Wall Street Journal bestselling author, keynote speaker, strategist, and award-winning podcaster renowned for her expertise in elevating leadership and self-confidence through media. She is the founder and host of the acclaimed podcast, The Tao of Self-Confidence, where she interviews women about their journeys to self-confidence. With over one million downloads, her podcast ranks among the top 0.5% most popular shows globally and features over 800 interviews, including conversations with celebrities and eight-figure CEOs.
Sheena’s influence extends beyond podcasting. Her debut book, The Tao of Self-Confidence: A Guide to Moving Beyond Trauma and Awakening the Leader Within, published by Wiley, is a Wall Street Journal and Publishers Weekly bestseller. It is also recognized as one of the top 20 best self-confidence books of all time by Book Authority, the world’s leading site for book recommendations.
Her second book, Bridging the Confidence Gap, also published by Wiley, continues her mission of empowering women by addressing the barriers to confidence and leadership. Her work has been featured on prominent platforms such as MindValley, FOX, NBC News, and the Manila Times.
Sheena is dedicated to closing the gender confidence gap through her training and programs, aiming to elevate women into leadership roles across all industries. She has delivered impactful speeches for organizations like Live Nation, NASA, and UKG, sharing her insights on self-confidence and leadership.
Your journey from feeling invisible as a young immigrant to becoming a bestselling author and global speaker is incredibly inspiring. What key moments helped you turn self-doubt into confidence, and how do you guide other underrepresented women to do the same?
The sudden passing of my aunt was the wake-up call I didn’t expect. It made me ask myself: Am I really living, or just existing? I realized I didn’t want to reach the end of my life full of regrets. That moment pushed me to stop playing small and start showing up for myself — and others.
Growing up in Toronto, I never saw anyone in the media who looked like me. That lack of representation made me feel invisible. Today, I constantly show up to help underrepresented women feel seen and heard — because I know what it’s like to feel like you don’t belong.
I use my platform, programs, and products to help women build confidence, own their stories, and take up space — unapologetically. Whether it’s through my podcast, courses, or community events, I’m committed to creating tools that empower others to do what I once thought was impossible: believe in themselves.
With over 1.3 million downloads and hundreds of stories shared, what are some of the most surprising or powerful lessons you’ve learned from your guests on overcoming imposter syndrome and stepping into inner leadership?
The most powerful lesson is that imposter syndrome doesn’t mean you’re broken — it means you care. Nearly every woman I’ve interviewed, no matter how accomplished, has felt like she didn’t belong at some point. The difference? They didn’t let that feeling stop them.
One surprising insight is how many of them reframe imposter syndrome as a signal for growth. It shows you’re stretching beyond your comfort zone. Another is the role of community — hearing “me too” can be incredibly validating. These stories prove that leadership doesn’t require perfection. It’s about choosing to believe in your impact, even when your inner critic is the loudest voice in the room.
You’ve said confidence is a skill, not just a mindset—especially important in fast-moving industries like tech, AI, and Web3. What daily habits or strategies do you recommend for women to bridge the confidence gap and thrive in these spaces?
Confidence is built through action, not just thinking. That’s why I live by the “ready, fire, aim” mindset — take the step, then course correct. In industries like tech, AI, and Web3, waiting for perfection will keep you behind. Progress happens when you move, not when you hesitate.
Another big piece is failing forward. We’re told the U.S. is 10–15 years ahead of Canada in tech, and one major reason is mindset — they embrace failure as part of growth. In Canada, we tend to avoid it. But failure isn’t the opposite of success — it’s the path to it. Every stumble teaches you something that brings you closer to mastery.
Daily, I recommend doing one uncomfortable thing and tracking your small wins. Confidence compounds when you act, learn, and repeat. The women who thrive in these spaces aren’t the ones who get it perfect — they’re the ones who keep showing up.
Representation is at the heart of your mission. How have your own experiences with cultural identity and media shaped your leadership approach, and what advice would you give organizations aiming to build more inclusive, empowering spaces for women of color?
Growing up in Toronto, I didn’t see women who looked like me in leadership, on screen, or in spaces of influence.
That lack of representation made me feel invisible — like success wasn’t made for someone like me. It deeply shaped how I lead today: by showing up as my full, unapologetic self and creating space for others to do the same.
Visibility is power. That’s why I consistently show up — on stages, online, in conversations — to change the narrative and remind others that they belong too. The more we see diverse women in leadership, the more permission others feel to step into their own power.
For organizations, real inclusion starts with listening, investing in diverse talent, and creating environments where women of color don’t just have a seat at the table — they have a voice. Representation isn’t a checkbox. It’s a culture shift. When women of color are seen, valued, and celebrated, the impact is generational.
You reached major milestones in your 40s—what message do you have for women who feel bound by timelines or fear it’s “too late”? Any final advice for small and medium-sized business leaders working to build more confident and inclusive teams?
It’s never too late to rise. I published my bestselling book, spoke on global stages, and built a platform after 40 — and I’m just getting started. The idea that success has an expiration date is a lie we’ve been sold. Your life doesn’t end at 30 or 40; it evolves.
To women feeling “behind,” I say: you’re right on time. Your story, experience, and perspective are exactly what someone needs to hear today.
For small and medium-sized business leaders: confidence and inclusion go hand in hand. Create cultures where mistakes are safe, feedback is shared, and leadership is modeled at every level. When your team feels seen and trusted, they don’t just perform — they thrive.
Disclaimer:
The views and opinions expressed in this interview are those of the interviewee and do not necessarily reflect the official policy or position of CanadianSME Small Business Magazine. The content provided is for informational purposes only and should not be construed as professional advice. CanadianSME is not responsible for any actions taken based on the information provided in this interview.
