Vanessa Joy: What If Success Wasn’t the Goal After All?

21st Century Entrepreneurship

Vanessa Joy is a photographer, creative entrepreneur, and mother of two—and we spoke about what happens when a relentless drive for business success collides with a long-buried childhood dream. Known for building multiple thriving businesses and being the primary breadwinner in her family, Vanessa shares how a spontaneous trip to Kenya reframed everything she thought she knew about fulfillment, purpose, and legacy.

At the heart of this conversation is a bold emotional shift: from executing perfectly calibrated workflows to creating something that finally felt meaningful.

“All I’ve been doing is building businesses and feeding my family, and yet this one thing I dreamed about as a child—I never did it.”

We traced her entrepreneurial journey back to a rebellious teenage choice in a high school guidance counselor’s office—a reluctant decision to take photography to please her mom. That single act of people-pleasing set the foundation for five successful businesses.

But the real turning point came much later, standing in a Kenyan village, camera in hand, realizing that the children she photographed lived without clean water—and without complaint.

“There was a fly right on her eyeball… and the baby wasn’t even blinking. That’s when I realized—this isn’t fake. This is their life.”

Vanessa speaks candidly about guilt, ambition, and the emotional armor many entrepreneurs wear. Her realization? Building businesses is not the end goal—it’s the vehicle for something greater. The trip inspired her to start a nonprofit, launch a fundraiser using her art, and finally fulfill her childhood promise to fund a well.

“Maybe that was the goal the whole time… to build businesses so I could do the work I’ve always wanted to do.”

Key themes we discussed:

• The emotional cost of ambition and high-functioning entrepreneurship
  
• How childhood dreams can quietly shape adult purpose
  
• Philanthropy through business: the power of anonymous giving
  
• Turning burnout into meaningful creation
  
• Why success without emotional fulfillment often feels empty

Key takeaways:

• A powerful reminder that your most meaningful work may not feel “efficient”—but it will feel alive.
  
• Giving doesn’t have to be loud to be transformative.
  
• Your past (even your people-pleasing moments) can plant seeds for unexpected purpose.
  
• Systems and workflows build business freedom—but freedom is just the beginning.

This episode is for anyone wondering whether chasing "more" is still serving them—or whether it’s time to make space for what truly matters.