Mom With a Mic: Dorothy Cascerceri Simone on Infertility, Courage, and Reclaiming Her Voice

Mom With a Mic: Dorothy Cascerceri Simone on Infertility, Courage, and Reclaiming Her Voice

From Mom To MORE® | Midlife Reinvention for Moms by Sharon Macey

March 30, 2026 · 46 min · Episode 59

About this episode

Dorothy Cascerceri Simone discusses her journey through infertility and how motherhood has influenced her career and personal ambitions.

In this episode of Mom to MORE®, Sharon Macey welcomes media personality, podcast host, and storyteller Dorothy Cascerceri Simone, the voice behind That Greenwich Life. Dorothy has worn many professional hats including celebrity journalist, television host, producer, live event emcee, luxury travel writer, and now podcast host and auctioneer. In this honest conversation, Dorothy shares how motherhood reshaped her ambition and led her to create an intentional hybrid mom life, designing her work around her children while still pursuing creative opportunities that energize her. She also opens up about her infertility journey, including multiple miscarriages and a late stage pregnancy loss. Tune in for a candid conversation about resilience, reinvention, vulnerability, and redefining success in motherhood and career. [00:00] Introduction [02:14] Dorothy's "intentional hybrid mom" approach to work and motherhood [05:05] Why motherhood came at the perfect time in her career [09:18] Finding her voice through podcasting [14:35] Her infertility journey and late-stage pregnancy loss [18:02] Breaking the silence around miscarriage and infertility [22:23] Lessons learned from hardship and…

People in this episode

Host: Sharon Macey

Guest: Dorothy Cascerceri Simone

Topics covered

  • infertility
  • motherhood
  • resilience
  • career reinvention
  • vulnerability

Keywords

  • infertility
  • miscarriage
  • motherhood
  • podcasting
  • career success
  • resilience
  • vulnerability

Mentioned in this episode

Organizations: That Greenwich Life

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