Black Entrepreneur Experience Episode 529

Guest: Shakila Stewart | Build Unshakable Confidence & Lead With Presence

Host: Dr. Frances Richards
Date: December 18, 2025

Main Theme / Purpose

This episode features Shakila Stewart—confidence and presence coach, founder of Walk This Way Movement and Chin Up, You Got This—who shares her journey from aspiring artist to acclaimed coach and author. The conversation centers on building unshakable confidence, leading with authentic presence, and the profound ripple effect of empowering oneself and others, particularly Black women and youth. Shakila and Dr. Frances discuss business, personal growth, overcoming adversity, and creating lasting social impact through entrepreneurship and legacy.

Key Discussion Points & Insights

Shakila’s Story: From Self-Doubt to Confidence Leadership

• Early Aspirations and Challenges ([02:50])

  • Dreamed of being on television, model, and actress, but lacked confidence growing up.
  • "I didn't have the confidence to match those goals. But it wasn't until I was 26 years old and my mother passed away... I discovered a strength in me that I didn't know I had." – Shakila Stewart

• Turning Point: Family Responsibility and Founding Walk This Way

  • Inheriting responsibility for her 10-year-old brother after her mother's passing unlocked resilience and leadership skills.
  • Created Walk This Way Movement to help women overcome fear and build self-esteem through posture, presence, and perseverance ([03:30]).

Impactful Client Stories and Social Ripple Effects

• Transformative Workshops with Youth ([04:58])

  • 10-week confidence and leadership workshop for girls in Chicago ended with a showcase.
  • A student's revelation about making her unsmiling mother proud highlighted the impact of confidence work on families.

• The Power of “Chin Up, You Got This” ([05:50])

  • College student, grieving her mother, found hope from Shakila’s book cover.
  • Inspired Shakila to create Chin Up as a nonprofit.

The Essence of Walk This Way Movement

• Movement Name and Family Legacy ([09:44])
  • Inspired by her great-grandmother’s journey—physically unable to walk but nevertheless moving her family to a better life.
  • "Walk this way isn't just about walking with your legs, but having a mindset and using your tools to walk toward a better future." – Shakila Stewart

Personal & Entrepreneurial Growth

• Family, Resilience & Faith ([11:13])

  • Taking guardianship of her brother was difficult but instilled perseverance, leadership, and the importance of community.

• Grounding Habits ([14:12])

  • Reliance on scripture (Isaiah 60:17), faith, journaling, workouts, and family support for alignment.

• Motivation for Entrepreneurship ([15:33])

  • Inspired by Barack Obama’s presidency, created empowering T-shirts and merchandise, which led to an entrepreneurial career.

• Funding the Mission ([16:58])

  • Capital raised through targeted fundraising, strategic networking, and leveraging impactful events.

Values, Coaching, and Building a Legacy

• Faith-Driven Decision Making ([19:05])

  • Guided by prayer, alignment with values, feedback from trusted coaches.

• Selecting (and Being) a Coach ([20:13])

  • "See if they are successful in the area where you want to be successful... see if their values and goals line up with where you want to go." – Shakila Stewart

• Legacy and Daily Impact ([21:00], [21:34])

  • Goal: Inspire everyone to walk into rooms with their “chin up,” knowing their value.
  • Impact through daily digital encouragement and small acts like giving genuine compliments.

Overcoming Adversity

• Surrendering to Purpose ([22:31])

  • During setbacks in Los Angeles, found that true fulfillment wasn’t from external dreams but from surrender and purpose.
  • "I had to surrender what I wanted for what God wanted for me." – Shakila Stewart

• Practical Steps for Inner Work & Combating Imposter Syndrome ([25:42])

  • Encourages writing feelings, creating positive affirmations (“I am, I can, I will”), and practicing daily self-love.

Lessons & Reflections on Entrepreneurship

• Biggest Leap ([27:28])

  • Moving to LA for her dreams—even at personal and professional cost—paid off and ultimately enriched her life.

• Outgrown Beliefs ([28:54])

  • Healed from childhood beliefs of being unworthy due to adoption. "I have so much joy now... Even if your parents didn't raise you, you can still have joy and fulfill your purpose in life."

• Internal/Mental Shifts for Business Growth ([30:08])

  • Learning to charge for work; recognizing value and setting boundaries.

• Unconventional Strategy ([31:05])

  • Strategic volunteering for access and networking, leading to book endorsements and major connections.

• Leadership Humility ([32:26])

  • Apologized for accidentally reinforcing negative stereotypes to students. "The power of words—you can break a spirit or build one."

Wisdom, Legacy, and Rapid Fire Q&A

• Advice to Younger Self ([35:54])

  • "You're gonna get there. You're going to do more than what you dreamt or imagined. You are a powerhouse..."

• Wisdom for the Journey

  • Profit first mindset: Don’t give services away for free—value your contribution ([30:08]).
  • “You have to do the work. People think self-love is easy. You’ve gotta work at it.” ([26:18])

• Rapid Fire Highlights ([37:13])

  • Morning ritual: Prayer
  • Life-changing book: The Coldest Winter Ever
  • Most instructive failure: Turned down an engagement
  • Dream dinner: Oprah or Jay Z (to discuss youth empowerment)

Notable Quotes & Memorable Moments

• On Confidence:
  “When you enter any room, you walk in that room with your chin up knowing that you are valuable and that you bring value to every room.” – Shakila Stewart ([21:00])

• On Purpose:
  “My fulfillment in life wasn’t going to come from my dream coming true. It was going to come from Him.” – Shakila Stewart ([24:00])

• On Teaching & Apology:
  “I broke their spirits... and I immediately, like the next day, had to apologize.” – Shakila Stewart ([32:26])

• On Strategic Networking:
  “I did a lot of volunteering with intentionality because it got me in rooms with people in high-level positions.” – Shakila Stewart ([31:05])

• Advice for Confidence Building:
  “Start with I ams... I am beautiful. I am amazing. If you say these simple things every day, you will eventually start seeing change in your life.” – Shakila Stewart ([26:18])

Timestamps for Key Segments

• Introduction & Shakila’s Backstory – [01:44] to [04:34]
• Client Impact Stories – [04:58] to [08:30]
• Why “Walk This Way” – [09:44]
• On Raising Her Brother & Family Lessons – [11:13]
• Staying Grounded – [14:12]
• Starting in Entrepreneurship – [15:33]
• Funding the Business – [16:58]
• Personal Values & Coaching – [19:05] to [20:47]
• Legacy & Impact – [21:00] to [22:21]
• Overcoming Giving Up – [22:31]
• Advice for Inner Work – [25:42]
• Biggest Leap & Wrong Beliefs – [27:28] to [29:57]
• Business Mindset Shifts – [30:08]
• Breaking Industry Rules – [31:05]
• Leadership Mistakes – [32:26]
• Personal Monologue: Legacy and Mother – [34:02]
• Advice to Younger Self – [35:54]
• Rapid Fire Round – [37:13]
• Connect & Final Thoughts – [40:02]

Ways to Connect & Learn More

• For leaders, women, entertainers: walkthiswaymovement.com
• For youth, parents, educators: chinupyougotthis.org
• Books available: Amazon, walkthiswaymovement.com, chinupyougotthis.org

This episode is a must-listen for anyone looking to build confidence, cultivate resilience, and walk a purposeful path—not just in entrepreneurship, but in all areas of life. Shakila Stewart’s journey and insight offer actionable wisdom and inspiration for aspiring leaders and caregivers alike.