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Bold Moves · Jul 7, 2026

Why "Self-Made" is a Lie: Every Bold Mover Needs a Mentor

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Kristen Rocco · Bold Moves

Oprah had Maya Angelou. Bill Gates has Warren Buffett. Meryl Streep has Jane Fonda. Margaret Cho had Joan Rivers.

There’s no question that mentors can be the literal key to helping you soar to new heights, strategically pivot, navigate difficult situations, make important connections, sponsor your work, and much more. They can also be a soft place to land with wisdom and guidance to keep you moving forward when things don’t go your way. A powerful mentor-mentee relationship embodies the metaphor of the wind beneath your wings.

Yet, for us in the United States, it’s easy to fall into the go-it-alone mentality. American values are deeply rooted in individualism, self-determination, and meritocracy. We are fed a steady diet of the traditional American Dream: the idea that upward mobility, freedom, and success belong to the individuals who work the hardest and possess the will to succeed.

But while that ideal makes for a beautiful aspiration, it ignores a fundamental reality: success is interdependent, not independent.

It’s a collective effort, built on the shoulders of those who have come before us. We need people willing to reach down to share advice, speak our names in rooms when we’re not there, and prepare us for the road ahead when our own blind spots obscure the obstacles.

“Alone we can do so little; together we can do so much.” – Helen Keller

Your vision, your clarity on the impact you want to make, your motivation, your resilience - these are individual factors that you must bring to the table. But to help you navigate your bold moves journey, mentors illuminate the path.

As my guest Kanika Chadda-Gupta beautifully puts it: There’s no such thing as “self-made.” Success only happens when you have a dedicated network scaffolding and supporting you along the way.

Throughout her career, Kanika has intentionally sought out mentors who fundamentally changed her trajectory. Early on, NBC’s Willard Shepard advised her to make her mark globally before she became a television reporter for CNN International in India. Years later, former Hello Sunshine CEO Sarah Harden helped her navigate the strategic growth of her own award-winning media platform, That’s Total Mom Sense.

Mentors can come in to advise at a pivotal moment when you face a specific challenge, or it can become a more formal, structured relationship. We go deep in this interview on the latter because that’s the hardest to develop, and Kanika has cracked the code.

In this episode, she shares how mentorship has propelled her bold moves and what she’s learned from cultivating these relationships. She gets past the clichés to give tactical, real-world answers to the questions we are all actually asking:

  • How do you approach someone you admire to become your mentor?

  • What’s the best way to structure the mentor-mentee relationship to ensure it’s purposeful, actionable, and strategic?

  • What advice would you give to women on how to approach mentorship in a way that feels authentic, confident, and relationship-driven rather than transactional?

  • How can a mentor help propel your bold move?

This conversation delivers the practical blueprint for working with a mentor who can propel you forward.

Let’s be mentors for each other right here in this community. Comment with one piece of advice a mentor has given to you that’s truly illuminated your path. I read and reply to them all.

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Watch now 👇, or if you’re on the go, listen to this episode, “Why 'Self Made’ Is a Lie: Every Bold Mover Needs a Mentor. How to Find One and Make It Count” on your favorite podcast app, including Spotify, Apple, Amazon Music, Pandora, and more.

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Read the original on kristenrocco.substack.com

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