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407: Does Your Career Align with Your Values? with Regina Lawless, Author of Do You: A Journey of Success, Loss and Learning to Live a More MeaningFULL Life

Regina Lawless is an inspiration. She is a recent empty nester, founder of Bossy & Blissful, a community for black women executives and business owners, and author of Do You: A Journey of Success, Loss and Learning to Live a More MeaningFULL Life.

After graduating with her BA in communications from California State University-Sacramento, Regina got her first job in human resources at Target. After about 8 years in retail HR, she did a stint in banking, then moved to the airline industry, and in 2016 she pivoted to tech. This led her to Meta, where in 2020 she became the head of diversity, equity, and inclusion (DEI) at Instagram. About 6 months into that role, her husband of 21 years, Al, passed away unexpectedly. This life-changing loss set her on a journey of healing and rediscovery inspired by her late husband’s last text message to her: “Do you, babe. Don’t worry about anything else.”

Through that journey, she realized that she had learned some lessons the hard way that could really help others. So, in 2023, she left corporate America, launched the community she was looking for, Bossy & Blissful, and wrote her first book that outlines a five-part framework she has developed to help you live a “MeaningFULL Life”.

In this episode, Alan and Regina discuss why she wrote the book, what she hopes people get out of it, the state of DEI today, and what life is like on the other side of corporate America. Regina also talks about how her childhood impacts the work she is doing today, the double-edged knife of constant connectivity without real community, the way Gen Z is rolling back the clock, and what the loneliness epidemic could mean for employers. 

In this episode, you’ll learn:

  • How the death of her husband changed everything in Regina’s life
  • Practical ways to navigate grief and start finding yourself again
  • What the loneliness epidemic could mean for employers

Key Highlights:

  • [01:55] Thriving as a new empty nester
  • [03:15] Regina’s path
  • [05:05] What inspired “Do You”?
  • [06:25] Tips for grieving
  • [09:10] How do you “do you”?
  • [12:50] Navigating fear around making the leap
  • [16:50] What’s it like to leave corporate America?
  • [20:50] The current state of DEI
  • [25:05] From NoCal to the Burbs
  • [29:00] Don’t be afraid to “do you.”
  • [30:30] The AI portion of the show
  • [31:40] Back to flip phones!
  • [34:15] The loneliness epidemic 

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