The Art of Reinvention: Finding Fulfillment Beyond the Norm with Roger Osorio

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Table Of Contents

We're delving into the profound topic of reinvention, exploring how to pursue our passions, even when it means taking a leap of faith.

In today's interview, I had the privilege of sitting down with Roger Osorio, a remarkable individual who embodies the essence of reinvention. We unravel his personal journey from a corporate job to becoming a math tutor and eventually a teacher. Roger shares his insights into the transformative power of finding fulfillment and happiness in one's work, even if it means diverging from the conventional path of financial success.

He stresses the importance of taking small steps and running experiments in our lives to test different paths. Roger encourages us to discover what brings joy and fulfillment, emphasizing that it's okay to challenge societal norms and redefine success on our own terms.

Throughout the conversation, Roger advocates for considering our unique circumstances and values when making decisions about our careers and overall happiness. His wisdom resonates as a guide for anyone seeking a more meaningful and fulfilling life.

So, without further ado, let's dive into this enlightening conversation with Roger Osorio on reinvention and the pursuit of passion.

But before we do, make sure to learn more about Roger and his incredible journey by visiting his website at You can also connect with him on LinkedIn at

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  • (2:30) Roger's call to reinvention and what did that call sounded like
  • (6:24) What was missing and what actually fulfilled Roger
  • (7:25) Roger's first BREAK moment
  • (9:25) How Roger determined his path
  • (12:52) Roger and his friend going through similar BREAK moments at the same time and how they supported each other
  • (15:36) How Roger pursued the best version of himself
  • (20:16) How Roger's parents and friends responded to his career change
  • (24:12) How Roger became a teacher and the roadblocks he encountered
  • (32:30) The power of belief
  • (36:10) Guiding angels - what they are and how they impacted Roger
  • (37:32) The possibility of outcomes greater than we can imagine
  • (41:33) Flexible goals
  • (44:58) How do you figure out what lights you up? How do you keep that belief flywheel going?
  • (53:29) Helping others lead with happiness
  • (1:03:46) Resilient thinking
  • (1:12:31) The moment Roger realized he needed to commit to reinvention
  • (1:30:10) The biggest thing Roger had to unlearn


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