Reconnect, Reflect and Celebrate 20 years with Fiz Olajide

In 2025, Transition Enterprises LLC marks its 20th anniversary! Over the past two decades, I have had the honor of working with some of the most talented and inspirational leaders around the world. It has been a privilege to be in service to something greater than myself, helping others tap into their inner wisdom and make bold choices.  

To commemorate this milestone, my dear friend Fisayo “Fiz” Olajide, an acclaimed filmmaker and creative executive, turns the lens on me. Together, we explore my journey—where it all started as well as the stumbles along the way.  

Whether you've been part of this ride from the beginning or are just joining now, this series is a reflection on pain, joy, transformation, and the power of trusting your inner wisdom.  I’m excited to share the triumphs, challenges, and defining moments from the past 20 years.

About Fisayo “Fiz” Olajide
Fiz is a filmmaker and creative executive whose work bridges corporate innovation and cinematic storytelling. As the Director of Brand Design for X, she leads brand strategy and design, shaping a visionary identity for one of the world’s most influential platforms.  

Join us as we celebrate, share and look ahead to the future!

(5:20) Who was Jeanie before starting Transitions Enterprises and the Warriors and Work platform?  (10:58) What were some of the philosophies that resonated with Jeanie when she first got started?  
(14:57) How did Jeanie find her first clients? What were those first years like?  
(15:56) How would she describe her brand and how has it evolved over the years?  
(17:55) Jeanie shares how she views intuition and discusses the power of pausing?  
(21:00) Were there moments of self-doubt and show did Jeanie navigate them?  
(24:13) Jeanie discusses a time when she thought about quitting and shares how she pulled through?  
(27:46) What are some of the things Jeanie would see (business opportunities and clients) that she found didn’t align with her?  
(29:10) What stories comes to mind where Jeanie saw incredible transformations of clients and business colleagues.  
(32:42) What are some of the biggest trials that Jeanie has overcome during her career?  

Connect with Fisayo “Fiz” Olajide 
https://www.fizolajide.com/   

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