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How to effectively communicate across generations with Jessica Stollings


The Happiness of Pursuit Podcast – Episode #35

How to effectively communicate across generations with Jessica Stollings, President and Founder of ReGenerations.

Have you ever been in a meeting with a boss, or colleague that is much older (or much younger), and you just can’t seem to get your point across? No matter which angle you try to take there seems to be this wall that neither side can break through.

This is exactly how Jessica Stollings started her career. When she launched her career, she couldn’t understand the lack of feedback she was looking for from her boss, and when she did get feedback it made her seem as if she was a complete failure. That led to a unique journey where she would spend an hour a week, which spawned from a Starbucks Gift card from a friend, to do research into the challenges in communication between generations.

What amazed me about Jessica’s story is how she took a personal struggle and turned it into a business.

What you will learn on this episode of The Happiness of Pursuit Podcast:

  • How listening can help bridge the communication gap
  • The value of committing 1 hour per week to discovering your passion
  • The importance of being discipline (week after week)
  • Why understanding how generations communicate can have a huge impact on your career

How to connect with Jessica Stollings:

Jessica Stollings on The Happiness of Pursuit Podcast

Website: and
Twitter: @JessStollings, @ReGenerations
Instagram: @jessicastollings,

Doug Foley
Doug Foley is a podcast host, content marketer, and problem solver. He is also the youngest of 7 brothers and sisters, a proud father of 2, and is on a mission to help people find their passion, take action, and build the life they want to live. He frequently writes about entrepreneurship, personal development, and motivation.
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