That Greenwich Life

Dorothy Cascerceri Simone
  • 5.0 (56)
  • PERSONAL JOURNALS
  • UPDATED WEEKLY

Hi, I'm Dorothy, a reformed celebrity gossip girl and mom of two living That Greenwich Life in the suburb of Greenwich, Connecticut. Once upon a time, I was a red carpet reporter and tabloid magazine editor in New York City, appearing on all your favorite TV shows spilling the secrets of the stars. But now, I'm using my storytelling power for a purpose far greater than gossip. My own traumatic journey to motherhood and late-stage pregnancy loss taught me that we're all dealing with hard stuff. And it's that shared experience that bonds us together more than we realize.You don't need to live in Greenwich or even locate it on a map to join me every Thursday. All you need is a love for stories that are real, raw, and remind us just how resilient and connected we all really are. Now let's get started.

  1. Ep 10, Season 2: Why We’re All Burnt Out and What To Do About It - A Season Finale Reflection

    FEB 2

    Ep 10, Season 2: Why We’re All Burnt Out and What To Do About It - A Season Finale Reflection

    In this final episode of Season 2 of That Greenwich Life - dont worry I’ll be back for Season 3! - I’m solo and tackling burnout, nervous-system overload, and why constantly being “busy” has become the default — even when it’s costing us our peace.  We are living in a moment of constant overload — mentally, emotionally, and digitally. Our brains were never designed to take in this much information: endless notifications, nonstop content, and the pressure to always be doing more. This conversation is an honest reflection on slowing down in a world that rewards productivity, multitasking, and optimization. I’m unpacking why multitasking isn’t the badge of honor we’ve been taught it is, how information overload is draining our energy, and why learning to work smarter — not harder — starts with discernment around our time and attention. If you’ve been chasing the next opportunity, juggling too many things at once, or feeling stretched thin despite loving what you do, this episode is for you. I’m exploring the idea of single-tasking, letting go of the glorification of “busy,” and creating space to actually be present — not as a luxury or failure, but as a necessary practice. Because we can’t keep going at this pace. This episode is an invitation to pause, slow things down, and reconnect with what actually allows us to show up as our best, most grounded selves. Thank You to My Sponsors:  • RMA of New York — our Season 2 Presenting Sponsor and leading fertility care provider  • Jack Rabbits Gymnastics and Soccer Club — a beloved children’s movement and enrichment space helping kids build confidence, coordination, and joy through play  • Room for Paws Pet Resort — a trusted, full-service pet resort providing exceptional care and peace of mind for families and their furry family members Let’s Connect! If this episode inspired you, please follow, rate, and review That Greenwich Life so more women can find these conversations. Follow me on Instagram @DorothyOnTV  and check out my website www.DorothyOnTV.com for all updates and TGL merch. And watch this full episode on my Youtube Channel.

    1h 2m
  2. Ep 9, Season 2: Bending Beyond Limiting Beliefs, Sobriety and The Power in Accepting We Are All Powerless - with Special Guest Sarah Sadie Newett

    JAN 26

    Ep 9, Season 2: Bending Beyond Limiting Beliefs, Sobriety and The Power in Accepting We Are All Powerless - with Special Guest Sarah Sadie Newett

    Long before we consciously think about it, we’re already making choices. How much to push. When to stay quiet. What feels possible — and what feels off-limits. Most of those decisions aren’t random. They’re guided by beliefs we’ve been carrying for years, often without realizing where they came from. This episode of That Greenwich Life is an invitation to slow down and examine those beliefs — especially the ones LIMITING us. So many of the limits we accept as “just the way things are” aren’t rooted in truth at all. They’re inherited, learned, and reinforced until they feel immovable. But they don’t have to be. My guest, Sarah Sadie Newett, is the founder of SSN, an award-winning movement practice studio in Westport that has built a deeply devoted community of people who return week after week — not just for physical results, but for transformation. She has decades of professional experience as a dancer and aerialist and has performed alongside artists including Lady Gaga, The Roots, and Lil’ Kim. She has collaborated with major wellness and fashion brands such as Max Mara, Alo Yoga, Rhone, and Beyond Yoga.  Through movement and her own journey of sobriety, Sarah helps people challenge long-held assumptions about their bodies and abilities, creating space for confidence, trust, and possibility. Whether working with athletes, creatives, mothers, or high-performing professionals, her clients consistently leave feeling capable of far more than they imagined. This episode is about more than physical flexibility or strength. It’s about what becomes possible when beliefs change — not just in thought, but in practice.  Because when your beliefs evolve, the way you move through your life evolves with them. Thank You to Our Sponsors:  • RMA of New York — our Season 2 Presenting Sponsor and leading fertility care provider  • Jack Rabbits Gymnastics and Soccer Club — a beloved children’s movement and enrichment space helping kids build confidence, coordination, and joy through play  • Room for Paws Pet Resort — a trusted, full-service pet resort providing exceptional care and peace of mind for families and their furry family members Let’s Connect! If this episode inspired you, please follow, rate, and review That Greenwich Life so more women can find these conversations. Follow me on Instagram @DorothyOnTV  and check out my website www.DorothyOnTV.com for all updates and TGL merch. And watch this full episode on my Youtube Channel.

    1h 1m
  3. Ep 8, Season 2: When Life Changes the Plan: Navigating Uncertainty and Redefining Giftedness with Special Guest Julie Vincent

    JAN 19

    Ep 8, Season 2: When Life Changes the Plan: Navigating Uncertainty and Redefining Giftedness with Special Guest Julie Vincent

    Some seasons don’t just stretch you — they quietly change how you see your life, your health, and the future you thought you were moving toward. And it can happen in an instant when one piece of news changes everything.  The hardest part may seem like the moment you receive the news, but the long stretch of not knowing that follows can be even harder: the endless appointments, the unanswered questions, and the quiet fear that hums beneath the surface while life keeps moving forward .  You’re still parenting, working, showing up, and trying to stay hopeful… even when everything feels uncertain. On this episode of That Greenwich Life, we’re talking about what happens when life hands you something you never planned for — and how you find your footing again when the ground underneath you shifts. My guest, Julie Vincent — @IamJulieVincent on Instagram - is a mother, advocate, and the founder of The Gifted Life — who shares her deeply personal journey of navigating her daughter’s rare genetic diagnosis - followed by her own – and the years of uncertainty and the emotional toll of living in the in-between.  Through her story, we explore how answers, even when they’re hard, can become a turning point — and how choosing presence, truth, and self-trust can change everything.  It’s a conversation about optimism over panic, truth over denial, and learning how to live fully — right where you are. Thank You to Our Sponsors:  • RMA of New York — our Season 2 Presenting Sponsor and leading fertility care provider  • Jack Rabbits Gymnastics and Soccer Club — a beloved children’s movement and enrichment space helping kids build confidence, coordination, and joy through play  • Room for Paws Pet Resort — a trusted, full-service pet resort providing exceptional care and peace of mind for families and their furry family members Let’s Connect! If this episode inspired you, please follow, rate, and review That Greenwich Life so more women can find these conversations. Follow me on Instagram @DorothyOnTV  and check out my website www.DorothyOnTV.com for all updates and TGL merch. And watch this full episode on my Youtube Channel.

    1h 3m
  4. Ep 7, Season 2: Soul Contracts + Breaking Cycles of Generational Trauma with special guest shamanic healer Eve Kerwin, the White Buffalo Woman

    JAN 12

    Ep 7, Season 2: Soul Contracts + Breaking Cycles of Generational Trauma with special guest shamanic healer Eve Kerwin, the White Buffalo Woman

    Last week on That Greenwich Life, we opened a conversation so many of us have been carrying quietly for years — the shame, confusion, and emotional exhaustion of family estrangement. And the messages that poured in made one thing unmistakably clear: you are not alone. So in this episode, we’re continuing that conversation — and going deeper - because estrangement doesn’t usually begin with one explosive moment, one argument, or one final breaking point. It often begins inside toxic family systems — patterns we were born into, roles we never chose, and cycles that stretch back farther than any of us realize. In this episode, we explore generational trauma, and to help us unpack all of this, I’m joined by Eve Kerwin, also known as The White Buffalo Woman — a shamanic healer I found in the middle of one of the darkest seasons of my life. In a single session, she helped me make sense of my past, offered clarity around profound loss, and gently opened my eyes to what might still be possible in my future (which she SO ACCURATELY PREDICTED!) — when hope felt completely out of reach. Eve Kerwin has worked with clients around the world for decades, guiding them through grief, trauma, ancestral patterns, and spiritual awakening. Drawing from intuitive healing, soul work, and Akashic wisdom, Eve offers a deeply compassionate lens on why we experience the relationships and challenges we do — and how healing can ripple far beyond one lifetime. Thank You to Our Sponsors:  • RMA of New York — our Season 2 Presenting Sponsor and leading fertility care provider  • Jack Rabbits Gymnastics and Soccer Club — a beloved children’s movement and enrichment space helping kids build confidence, coordination, and joy through play  • Room for Paws Pet Resort — a trusted, full-service pet resort providing exceptional care and peace of mind for families and their furry family members Let’s Connect! If this episode inspired you, please follow, rate, and review That Greenwich Life so more women can find these conversations. Follow me on Instagram @DorothyOnTV  and check out my

    1h 4m
  5. Ep 6, Season 2: The People We Grieve Who Are Still Alive - A Deep Dive into Estrangement with special guest Bianca Jade

    JAN 5

    Ep 6, Season 2: The People We Grieve Who Are Still Alive - A Deep Dive into Estrangement with special guest Bianca Jade

    Listener Note: This episode includes discussion of suicidal ideations.  There are some conversations we avoid because they’re heavy and complicated - and because they bring up shame, grief, and questions that don’t have easy answers. This episode is one of those conversations. But I’m not avoiding it any longer. This week on That Greenwich Life, we’re opening the door to a topic so many people are living with quietly: family estrangement. Not the dramatic version people assume — but the slow, painful unraveling that happens when relationships meant to feel safe begin to feel harmful, draining, or deeply confusing. And this can also apply to friends who feel like family – or at least used to. My guest this week, Bianca Jade - @BiancaJade on Instagram -- is a TV host, content creator, and leading beauty, health, and lifestyle influencer who has openly shared her infertility journey and path to motherhood with a level of vulnerability and authenticity that has helped countless women, men, and families—including me personally. She has appeared on major outlets including the Today Show, CBS Morning News, Dr. Oz, and regional affiliates across the country. If you’ve ever felt torn between loyalty and self-protection…If you’ve ever questioned your own reality because “they’re family”…If you’ve ever carried grief for a relationship that never became what you hoped it would or one that went from feeling safe and familiar to unsafe and unfamiliar…this episode is for you.  Thank You to Our Sponsors:  • RMA of New York — our Presenting Sponsor and leading fertility care provider  • Constantino’s of Greenwich - our episode sponsor for the easiest dinners weeknights or weekends and don’t miss their homemade ice cream that my kids BEG me for!  Let’s Connect! If this episode inspired you, please follow, rate, and review That Greenwich Life so more women can find these conversations. Follow me on Instagram @DorothyOnTV  and check out my website www.DorothyOnTV.com for all updates and TGL merch. And watch this full episode on my Youtube Channel.

    1h 19m
  6. Ep 5, Season 2: Reinvention, Identity Shifts + Finding What’s Next — with special guest Sharon Macey

    12/22/2025

    Ep 5, Season 2: Reinvention, Identity Shifts + Finding What’s Next — with special guest Sharon Macey

    This week’s episode is for every woman who has ever looked at her life — the career, the home, the relationships, the routines — and quietly wondered:How did I get here… and what do I actually want next? We’re diving into the subtle identity shifts that happen over time — the ones we don’t always see coming. The ones that show up after motherhood, after loss, after burnout, after you’ve held everyone else together for so long that you suddenly realize:I don’t feel connected to myself anymore - and I want more. And in this episode, I’m sitting down with someone who understands reinvention in a way that feels both comforting and electrifying: Sharon Macey — host of the podcast “Mom To More,”  who has devoted her work to helping women return to themselves and figure out their next chapter. Together, we explore: the quiet ways women lose their sense of identitythe “stuck” feeling that so many of us try to push awaywhat reinvention actually looks like — in real time, not the polished versionThis conversation is grounding and honest and full of those moments where you suddenly feel less alone — the kind that remind you your second act doesn’t have to look like your first. You are allowed to want more, and you are allowed to discover parts of yourself you haven’t met yet. This episode feels like exhaling — and maybe even like the very beginning of your next chapter. Thank You to Our Sponsors:  • RMA of New York — our Presenting Sponsor and leading fertility care provider  • Constantino’s of Greenwich - our episode sponsor for the easiest dinners weeknights or weekends and don’t miss their homemade ice cream that my kids BEG me for!  Let’s Connect! If this episode inspired you, please follow, rate, and review That Greenwich Life so more women can find these conversations. Follow me on Instagram @DorothyOnTV  and check out my website www.DorothyOnTV.com for all updates and TGL merch. And watch this full episode on my Youtube Channel.  Until next week - don’t just live your life, LOVE it!

    1h 4m
  7. Ep 4, Season 2: Why Some Female Friendships Feel So Complicated — And What You Can Do About It with special guest Julia Dzafic of Lemon Stripes

    12/15/2025

    Ep 4, Season 2: Why Some Female Friendships Feel So Complicated — And What You Can Do About It with special guest Julia Dzafic of Lemon Stripes

    This episode opens the door to a conversation so many of you have been whispering about, DM’ing me about, and trying to navigate quietly on your own:how female friendships shift in midlife and especially in motherhood — and why it feels so confusing. If you’ve ever found yourself wondering why you don’t talk to your friends the way you used to,why coordinating even a 15-minute coffee feels impossible,why some relationships feel stronger than ever while others suddenly feel misaligned,this episode is going to feel like a deep exhale. I’m joined by creator, author, and mom-of-two Julia Dzafic aka @lemonstripes whose honest conversations about motherhood, mental health, and the messy and beautiful behind-the-scenes of life resonate with so many women. Together, we unpack not just how friendships change as life piles on — but why they do. We talk about the shrinking bandwidth every mom feels, the guilt that creeps in when you’re stretched too thin, and how to tell the difference between a friendship that needs nurturing - and one that has quietly run its course. Make sure you listen to the full episode because toward the end, we also get a special cameo from licensed therapist, author and my best friend, Alison Seponara aka @Theanxietyhealer who you have seen on the show before. She shares her clinical take on why so many women experience this shift, what friendship “misalignment” really means, and how to navigate the emotional layers of these transitions with more clarity and compassion. It’s honest, validating, and the conversation we all need. Thank You to Our Sponsors:  • RMA of New York — our Presenting Sponsor and leading fertility care provider  • Constantino’s of Greenwich - our episode sponsor for the easiest dinners weeknights or weekends and don’t miss their homemade ice cream that my kids BEG me for!  Let’s Connect! If this episode inspired you, please follow, rate, and review That Greenwich Life so more women can find these conversations. Follow me on Instagram @DorothyOnTV  and check out my website www.DorothyOnTV.com for all updates and TGL merch. And watch this full episode on my Youtube Channel.  Until next week - don’t just live your life, LOVE it!

    1h 3m
  8. Ep 3, Season 2: The Untold Mental Toll of Perimenopause — And Why You’re Not Imagining a Thing - with special guest, author Lauren Tetenbaum

    12/08/2025

    Ep 3, Season 2: The Untold Mental Toll of Perimenopause — And Why You’re Not Imagining a Thing - with special guest, author Lauren Tetenbaum

    This episode opens the door to a conversation so many women have been craving: the mental and emotional side of perimenopause — the part no one prepared us for. If you’ve been waking up at 3am, feeling overstimulated, forgetting words mid-sentence, wondering why you don’t quite feel like yourself anymore —  this episode is going to feel like a deep breath. I’m joined by therapist and author Lauren Tetenbaum, whose new book Millennial Menopause is helping women understand what’s happening in their minds and bodies during this transition. Together we unpack not just the physical symptoms we were never taught about — but the emotional toll that comes with it and how important it is for women to pay attention to their mental health at this time of life. We also talk about why so many women feel dismissed by doctors, what real support should look like, and how to advocate for yourself during this chapter of life. It’s validating, eye-opening, and incredibly grounding. It’s an episode you don’t want to miss. Thank You to Our Sponsors and Partners  • RMA of New York — our Presenting Sponsor and leading fertility care provider  • Constantino’s of Greenwich - our episode sponsor for the easiest dinners weeknights or weekends and don’t miss their homemade ice cream that my kids BEG me for!  Let’s Connect! If this episode inspired you, please follow, rate, and review That Greenwich Life so more women can find these conversations. Follow me on Instagram @DorothyOnTV  and check out my website www.DorothyOnTV.com for all updates and TGL merch. Watch this full episode on my Youtube Channel.  Until next week - don’t just live your life, LOVE it!

    58 min
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5
out of 5
56 Ratings

About

Hi, I'm Dorothy, a reformed celebrity gossip girl and mom of two living That Greenwich Life in the suburb of Greenwich, Connecticut. Once upon a time, I was a red carpet reporter and tabloid magazine editor in New York City, appearing on all your favorite TV shows spilling the secrets of the stars. But now, I'm using my storytelling power for a purpose far greater than gossip. My own traumatic journey to motherhood and late-stage pregnancy loss taught me that we're all dealing with hard stuff. And it's that shared experience that bonds us together more than we realize.You don't need to live in Greenwich or even locate it on a map to join me every Thursday. All you need is a love for stories that are real, raw, and remind us just how resilient and connected we all really are. Now let's get started.

Information

  • Creator
    Dorothy Cascerceri Simone
  • Years Active
    2024 - 2026
  • Episodes
    55
  • Rating
    Clean
  • Copyright
    © 2024, That Greenwich Life, All Rights Reserved
  • Show Website
    That Greenwich Life

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