
Letting Go: Roy DiNicola on Losing His First Wife and Learning to Lean on Community
01/29/23 • 41 min
It was during one of the most difficult times in his life that Roy DiNicola learned about the importance of community, and the importance of letting go of those things we cannot control.
In the spring of 2008, Roy and Holly DiNicola had been happily married for 14 years and were raising their three young boys, Ryan, Casey, and Owen, in Hopkinton, MA, just outside of Boston. When Holly received a cancer diagnosis, their community rallied around them and stepped in with kindness, large and small.
As Roy and Holly became overnight experts on the range of treatment options for Holly’s metastatic breast cancer, their community sprang into action: cooking meals, shuttling the boys to school and sports practices, managing home renovations, and sending positive thoughts and prayers. In order to share updates on Holly’s progress, Roy created an online journal called “The Fight of the Irish.” It also became a place for Roy to express his love and admiration for his wife’s courage and dogged determination.
Holly’s initial prognosis was good. After just over a year of surgeries, treatments, and medications, Holly persevered. In July 2009, she was declared cancer free and back to living her life at full speed. Roy shut down the online journal.
Two years later, in November 2011, Holly developed a cough that she just couldn’t shake and her speech became impaired. The cancer was back. It had metastasized to her brain, lungs, and bones. Over the next 3 1⁄2 years, Holly fought valiantly. In October 2014, having exhausted all available FDA-approved and experimental drug trials, Holly made the difficult decision to forgo further medical treatment. On February 10, 2015, with family by her side, Holly passed away.
Several months later, on the occasion of spreading Holly’s ashes in Ossipee Lake in New Hampshire, Roy sent one last post, poignantly writing, "In dying, she showed me how to live.”
This is a heartfelt and beautiful conversation; we are beyond grateful to Roy for sharing with us. We know you will feel the same.
Support this podcast by subscribing and reviewing!
Music is considered “royalty-free” and discovered on Audio Blocks.
Technical Podcast Support by: Jon Keur at Wayfare Recording Co.
© 2022 Silver Linings Media LLC. All Rights Reserved.
Support this podcast by subscribing and reviewing.
Music is considered “royalty-free” and discovered on Audio Blocks.
Technical Podcast Support by: Jon Keur at Wayfare Recording Co.
© 2025 Silver Linings Media LLC. All Rights Reserved.
It was during one of the most difficult times in his life that Roy DiNicola learned about the importance of community, and the importance of letting go of those things we cannot control.
In the spring of 2008, Roy and Holly DiNicola had been happily married for 14 years and were raising their three young boys, Ryan, Casey, and Owen, in Hopkinton, MA, just outside of Boston. When Holly received a cancer diagnosis, their community rallied around them and stepped in with kindness, large and small.
As Roy and Holly became overnight experts on the range of treatment options for Holly’s metastatic breast cancer, their community sprang into action: cooking meals, shuttling the boys to school and sports practices, managing home renovations, and sending positive thoughts and prayers. In order to share updates on Holly’s progress, Roy created an online journal called “The Fight of the Irish.” It also became a place for Roy to express his love and admiration for his wife’s courage and dogged determination.
Holly’s initial prognosis was good. After just over a year of surgeries, treatments, and medications, Holly persevered. In July 2009, she was declared cancer free and back to living her life at full speed. Roy shut down the online journal.
Two years later, in November 2011, Holly developed a cough that she just couldn’t shake and her speech became impaired. The cancer was back. It had metastasized to her brain, lungs, and bones. Over the next 3 1⁄2 years, Holly fought valiantly. In October 2014, having exhausted all available FDA-approved and experimental drug trials, Holly made the difficult decision to forgo further medical treatment. On February 10, 2015, with family by her side, Holly passed away.
Several months later, on the occasion of spreading Holly’s ashes in Ossipee Lake in New Hampshire, Roy sent one last post, poignantly writing, "In dying, she showed me how to live.”
This is a heartfelt and beautiful conversation; we are beyond grateful to Roy for sharing with us. We know you will feel the same.
Support this podcast by subscribing and reviewing!
Music is considered “royalty-free” and discovered on Audio Blocks.
Technical Podcast Support by: Jon Keur at Wayfare Recording Co.
© 2022 Silver Linings Media LLC. All Rights Reserved.
Support this podcast by subscribing and reviewing.
Music is considered “royalty-free” and discovered on Audio Blocks.
Technical Podcast Support by: Jon Keur at Wayfare Recording Co.
© 2025 Silver Linings Media LLC. All Rights Reserved.
Previous Episode

Going For It! Executive Coach Cindy Wolpert on Discovering Her Passion and Finding the Courage to Follow It
We are excited to kick off a new season of This is My Silver Lining with Executive Coach, Cindy Wolpert. Cindy is the founder of Results-Based Coaching (RBC) Associates. She works with business leaders across all levels of seniority to maximize their leadership potential, manage successful transitions, and realize their professional goals. She is a creative and thoughtful innovator who is known for bringing calm to the chaos.
Cindy tells us about starting her entrepreneurial journey during the lockdown in March 2020 - moving beyond the fear, building her reputation as an independent coach - there is so much power in being really honest with yourself and pushing yourself into uncomfortable positions.
Prior to founding RBC Associates, Cindy held various product development, operational and HR roles in the Fortune 100. She has first hand experience with the challenges of managing through business and budget cycles, navigating office politics, and harnessing the opportunities that her clients face. This gives her a real edge and makes her an invaluable asset to their advancement.
Cindy found her passion for coaching and leadership development as a client herself. In one of those, “you can make money doing this?” moments, Cindy realized that nurturing the personal and professional development of other leaders would give her the greatest career satisfaction. She threw herself into the deep end of the pool and learned all that she could about coaching, created opportunities to coach at work, and got certified. Prior to leaving corporate America, she led an internal executive coaching practice at Fidelity Investments where she served as the lead executive coach for executives and had responsibility for the certification and development of over 175 internal coaches globally.
As many of you enter the annual review cycle, consider career changes or pound the pavement for a new job, grab a pen and a notebook and prepare to be inspired. We know you’ll come away from this conversation with practical tools and perspectives to consider the career adventures that lie ahead.
Episode Links and Resources:
Cindy Wolpert
The Power of Habit: Why We Do What We Do in Life and Business
Support this podcast by subscribing and reviewing!
Music is considered “royalty-free” and discovered on Audio Blocks.
Technical Podcast Support by: Jon Keur at Wayfare Recording Co.
© 2022 Silver Linings Media LLC. All Rights Reserved.
Support this podcast by subscribing and reviewing.
Music is considered “royalty-free” and discovered on Audio Blocks.
Technical Podcast Support by: Jon Keur at Wayfare Recording Co.
© 2025 Silver Linings Media LLC. All Rights Reserved.
Next Episode

Blame Lewbert: Maria Stewart on How She and Her Husband Parented Their Children through His Battle with Brain Cancer using Love, Honesty and Humor
In Part Two of this three-episode series (listen to Part One here), we speak with Maria Stewart about finding the strength to support her husband as he lost his battle with brain cancer, embracing the help being offered by friends and family, and ensuring that her children could rely on their family “Power Unit” throughout this incredibly difficult chapter in their lives.
In 2010, Maria’s husband, Kevin Stewart, who was then 48 years old, was diagnosed with an aggressive form of brain cancer. Maria and Kevin had three children, ages 10 and 8 year old twins. Maria shares the good advice she received: the children are part of this story. She involved them in making decisions about hospice so they understood that they were part of the process. This empowered them to come through the experience with the knowledge that they could trust her to tell them the truth.
The outpouring of support from friends and family was incredible, but somewhat overwhelming. Maria tells us that asking for help was made easier by a few close friends who could coordinate efforts and make sure their family got what they needed.
Going through this experience, Maria recognized that without resources, it would have been nearly impossible to care for her husband and navigate the complexities of the healthcare system while also caring for her children and trying to fulfill obligations to her full-time job.
Suppose you have listened to Part One of this series, where we speak with Roy DiNicola about the experience of losing his wife to cancer. In that case, you might have gathered that eventually, Roy and Maria find their way to one another. But that is a story for another day.
Episode Links and Resources:
Big Tree is Sick: A Story to Help Children Cope with the Serious Illness of a Loved One, Nathalie Slosse (Author), Rocio Del Moral (Illustrator)
The List of Things that Will Not Change, Rebecca Stead
Glioblastoma - Mayo Clinic Overview
Glioblastoma Multiforme - American Association of Neurological Surgeons
Who is Lewbert from iCarly?
Support this podcast by subscribing and reviewing!
Music is considered “royalty-free” and discovered
Support this podcast by subscribing and reviewing.
Music is considered “royalty-free” and discovered on Audio Blocks.
Technical Podcast Support by: Jon Keur at Wayfare Recording Co.
© 2025 Silver Linings Media LLC. All Rights Reserved.
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