You don't know what you don't know

Sunday, December 28, 2025

In this episode of Navigating Eldercare, host Laura Daniels sits down with Esther Pipoly, the founder of Loss of Life Advocates (LOLA). Esther shares her deeply personal journey of losing both her father and husband in the same year, which inspired her to create a service that "triages" the chaos of life transitions. Together, they discuss the importance of pre-planning, the practical hurdles of settling an estate, and why "you don't know what you don't know" until a crisis hits.

Chapters

00:02 – Introduction to Navigating Eldercare Host Laura Daniels introduces the mission of the show: providing expert insights and practical solutions for families and professionals navigating the elder care journey.

00:20 – Meet Laura Daniels and Care Advocates Laura shares her background as a guide for families transitioning from hospitals or rehab to senior living, emphasizing her role in finding assisted living, memory care, and community resources.

01:17 – Guest Introduction: Esther Pipoly and LOLA Introduction of Esther Pipoly, founder of Loss of Life Advocates (LOLA). Esther discusses how she turned personal tragedy—the loss of her father and husband in 2014—into a mission to help others.

02:39 – The Reality of "Not Knowing What You Don't Know" Esther describes the overwhelming technicalities she faced after her husband’s death, including frozen bank accounts, business closures, and fighting for life insurance, which took 840 days to settle.

04:05 – What Does LOLA Do? A deep dive into LOLA’s services. Esther explains that they act as "quarterbacks" for any type of loss, from the death of a loved one or pet to the loss of a job or a dementia diagnosis.

06:45 – Building a Team of Trusted Partners Esther discusses her network of vetted professionals, including estate lawyers, funeral directors, real estate agents, and palliative care specialists who help families through the "business side" of grief.

08:31 – Common Misconceptions About Pre-Planning A discussion on the cultural taboos of discussing death and the common mistakes people make, such as failing to style bank accounts correctly or rushing to call utility companies before receiving a death certificate.

10:59 – First Steps to Getting Your Affairs in Order Esther recommends using a "Playbook" to organize life infrastructure (financials, banking, and real estate) before meeting with a lawyer to draft a will.

14:19 – Business Succession and Legacy Planning The importance of having a plan for small business owners. Esther shares how unexpected disability or death can leave a business in shambles without updated beneficiary and operational plans.

15:47 – The Emotional Side of the Business Esther offers advice for those overwhelmed by practical tasks. She explains how LOLA takes over the "actionable items"—like calling employers or schools—so the family has the space to actually grieve.

17:38 – Post-COVID Shifts in Grief and Loneliness A reflection on how the pandemic changed society's view of death and the rising "epidemic" of loneliness and secondary trauma.

19:51 – Success Story: A Journey of Closure Esther Pipoly shares a moving story of a client named Michelle, illustrating how professional support during a husband's terminal illness allowed the family to focus on their children and eventually find a new beginning.

23:45 – The Future of LOLA and Closing Remarks Esther shares her vision for cloud-based playbooks and palliative care partnerships. Laura provides contact information for both Care Advocates and LOLA.

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