Women's Money Wisdom

Episode 271: Estate Planning Made Manageable with Rachel Donnelly


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What really happens when someone passes away—and are you (or your family) prepared to handle it? In this episode of Women’s Money Wisdom, Melissa Joy, CFP®, sits down with Rachel Donnelly, founder of Afterlight and author of Late to Your Own Funeral, to unpack the messy, often overwhelming world of death administration.

Rachel shares her personal story of becoming executor for both her parents’ estates—while working full-time and raising young children—and how that experience inspired her to build a business helping others avoid the same chaos. Together, Melissa and Rachel dive into the real work that goes beyond writing a will: handling assets, updating beneficiaries, navigating probate, and keeping bills paid when no one’s watching.

They discuss why so many women delay estate planning, the hidden landmines (like untitled assets and digital accounts), and how you can start untangling this intimidating topic with simple, practical steps. The conversation also tackles how to bring up these sensitive issues with family, why “co-anything” can backfire, and how to avoid turning a loved one’s legacy into a logistical nightmare.

Key Takeaways:

  • Estate planning isn’t just about legal documents—it’s about full asset management and communication.
  • Women are more likely to delay estate planning, often because they don’t know where to start.
  • Probate horror stories highlight why comprehensive planning matters.
  • Digital assets (social media, crypto, email) need to be included in your plan.
  • Choose roles (executor, trustee) carefully—co-roles can create more problems than they solve.
  • Even imperfect action now is better than procrastinating and risking chaos later.
  • Having the tough conversations with family now can save heartache and confusion later.

Whether you’re starting from scratch or fine-tuning your existing plan, this episode will give you the confidence to take action—because death is inevitable, but an administrative nightmare doesn’t have to be.

Learn more & connect with Rachel:
Website: www.myafterlight.com
Instagram: @myafterlight
LinkedIn: Rachel Donnelly
Book: Late to Your Own Funeral

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https:...

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Women's Money WisdomBy Melissa Joy, CFP®

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