What would you do differently if you knew you were only 10 failures away from your dream?

In this episode of the Lowcountry Life Design Podcast, host Benjamin Lee sits down with College of Charleston alumni Dakota Kate Isaacs, a brand builder, storyteller, mentor, and leader whose career has taken her from Charleston to the forefront of the global beauty industry.

Dakota shares how landing 12 internships before graduating helped shape her willingness to experiment, take risks, and stop waiting for permission to pursue what she wanted. She opens up about the successes that built her career, but also the failures, setbacks, burnout, and unexpected challenges that taught her some of its most important lessons.

The conversation explores what it means to "fail fast," why authenticity matters more than presenting a perfect version of yourself, and how radical honesty can help you discover what you actually want from your life. Dakota also shares how her definition of success has evolved and why her purpose today is simple: to become the person she wishes she'd had earlier in life.

In this episode, you'll learn:

• Why experimentation can help you discover what you want by first discovering what you don't want
• How changing your relationship with failure can change your relationship with risk
• Why the "boring" work of discipline matters when building something that lasts
• How radical honesty and authenticity can help you identify your why
• Why routines, rituals, and intentionality can protect you from burnout
• How mentors and "expanders" can help you see possibilities you can't yet see for yourself
• Why relationships and asking for what you want can create unexpected opportunities
• How a simple gratitude practice can change the way you experience success
• Why sometimes the person you've been waiting for to change your life is you

From being fired from a company she helped build to eventually returning and helping lead one of America's top prestige skincare brands, Dakota's story is a reminder that the moments that feel like failure in real time may eventually become part of something much bigger.

Whether you're a student beginning your career, a professional navigating change, or simply someone wondering what's possible next, this conversation challenges you to stop waiting for the perfect opportunity, take the risk, learn from what doesn't work, and keep moving toward the life you want.

Because if you knew you were only 10 failures away from your dream, how would that change what you're willing to try today?

Connect with Dakota Kate Isaacs

Follow Dakota and explore more of her work:

Dakota Kate Isaacs on Instagram: @dakotakisaacs

The Big Sister Playbook: Follow on Instagram and subscribe on Substack for Dakota's writing, insights, and lessons on ambition, career, personal growth, and designing a life you love.

The Playbook Podcast: Listen on Spotify and Apple Podcasts for more conversations and insights from Dakota and The Big Sister Playbook.

Ingredients by The Ordinary: Look for Dakota's upcoming coffee table book celebrating the story and rise of The Ordinary.

The Big Sister Playbook on Substack:
Read The Big Sister Playbook

The Playbook Podcast on Spotify:
Listen to The Playbook Podcast