Skip to content

Listen on: 

Share it: 

Are you struggling to rekindle the spark in your career? 

It’s not uncommon to get caught in the paradox of perpetual growth, but living your life striving to achieve vague goals of more success and more money can often lead you away from what you loved about your job in the first place. Randi Roberts understands that frustration and shares her story about how she left her dream job to create her dream life. After 30 years of climbing the corporate ladder, Randi found herself surrounded by what she wanted but lacking what she truly needed…passion and purpose. Randi shares how she engineered a slow reinvention from corporate to entrepreneur.

Navigating workplace dissatisfaction can feel like a daunting task. In this episode, Randi details how you can get clear on your goals to build a career that supports your financial needs and personal passion. While jumping ship to another job may be tempting, you risk bringing that dissatisfaction with you to your new position. Instead, Randi encourages you to hit the pause button, to zoom out and dissect the very essence of your dissatisfaction. By delving into the depths of your risk tolerance, financial aspirations, and professional dreams, you’ll emerge armed with the clarity needed to forge a path that resonates with your core values.

With Randi’s arsenal of expert insights and actionable strategies, you’ll embark on an exhilarating journey of self-discovery and empowerment. Picture a future where frustration morphs into fertile ground for personal and professional growth. Tune in now and unlock the secrets to crafting a career that resonates with your soul. Your journey begins here.


Introduction [00:00]

From Corporate to Entrepreneur [02:00]

Engineering Your Exit [05:30]

Defining Your Risk Tolerance [11:00]

Contemplating Your Departure [22:00]

Addressing The Root of Discontent [30:00]

Creating Your Own Timeframe [36:00]

Fulfilling Careers. Happy Life [42:00]

Are you yearning for more than just the 9-to-5 grind?

Do you dream of turning your purpose into a business that allows you to prioritize what truly matters—family and impact?

Are you wondering, “Do I have what it takes to transition from corporate to a fulfilling entrepreneurial journey?”  Well, it’s time to find out!

Take my Reinvention Readiness Quiz and discover if you’re ready to reinvent yourself as a purpose-driven entrepreneur. Don’t let another day pass wondering what could be. Uncover your potential and step confidently towards your dreams.

Embark on your journey. Reinvent. Thrive.

Learn more about Randi Roberts:


Subscribe to the Fulfilling Career Happy Life channel YOUTUBE »

Download the Career Satisfaction Assessment »

Stay Connected with Roger Osorio and The School of Reinvention: 

Website ?: 

Subscribe to the Podcast : 



Roger’s Book : The Journey To Reinvention: How To Build A Life Aligned With Your Values, Passion, and Purpose (


“What are you going to need? What does success look like? And define that for yourself so that you know when you’re there! So that you know there’s a risk as an entrepreneur of trying to do too many things, trying to work 24/7 and we may actually cost ourselves the very thing that we’re seeking by going into this entrepreneurial world.” [18:30] -Randi Roberts