November 19, 2025

How to Talk to Aging Parents About Decluttering (Without the Family Drama) with Jeannine Bryant (Ep 284)

48 minutes

Learn how to approach aging parents about decluttering, navigate sibling emotions, and prepare for estate sales with compassion, clarity, and less clutter this holiday season.

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Resources Mentioned:⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Get all the links and resources at wannabeclutterfree.com/284⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Connect with Jeannine Bryant

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⁠⁠⁠Jeannine's Website⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Follow Deanna Yates, the host of Wannabe Clutter Free on:

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⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Get my children's book: Lenora and Her Super Duper Messy Room⁠⁠⁠⁠⁠⁠

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The holidays often bring family, memories… and stuff. If you’ve ever looked around your parents’ house and thought, “Someday we’ll have to deal with all of this,” this conversation is for you.

In this heartfelt episode, rightsizing expert Jeannine Bryant joins me to talk about how to compassionately approach decluttering with aging loved ones.

We cover:

How to start tender conversations without conflict

What to do when siblings have stronger emotional attachments

The truth about estate sales and what to expect

How to start early, so decluttering feels peaceful instead of pressured

The questions to ask around the Thanksgiving table to spark connection, not guilt

Whether you’re helping your parents downsize, sorting through family heirlooms, or simply preparing for future transitions, this episode will help you navigate it all with grace.

Time Stamps:

00:00 – Welcome & Thanksgiving week reflections

02:00 – What “rightsizing” really means (and why it’s different from downsizing)

05:00 – The emotional side of letting go and facing mortality

08:00 – When keepsakes shift from comfort to burden

10:00 – Separating love, memories, and stuff

13:00 – Why your kids don’t want your stuff (and that’s okay)

16:00 – How to talk with siblings who attach emotions to things

18:00 – What to keep, what to display, and what to release

23:00 – Family conversations to have during the holidays

27:00 – How estate sales actually work (and what to expect)

33:00 – The hidden cost of “saving everything”

36:00 – Practical right-sizing tips to start now

39:00 – Donate early, not later — why it matters

41:00 – Clutter-free gifting and experience-based holidays

42:00 – Rapid fire: What clutter-free means to Jeannine

44:00 – Key takeaways + gratitude for our loved ones

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Music: Fresh Lift by Shane Ivers - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.silvermansound.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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We’d love to hear how you’re applying the strategies discussed in this episode. Share your stories and tips with us on social media (@wannabeclutterfree). Don’t forget to subscribe for more insightful episodes designed to make your busy life a bit easier.

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By Deanna Yates | Professional Organizer, Decluttering Coach, Wannabe Minimalist

4.5

364364 ratings

November 19, 2025

How to Talk to Aging Parents About Decluttering (Without the Family Drama) with Jeannine Bryant (Ep 284)

48 minutes

Learn how to approach aging parents about decluttering, navigate sibling emotions, and prepare for estate sales with compassion, clarity, and less clutter this holiday season.

****************

Resources Mentioned:⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Get all the links and resources at wannabeclutterfree.com/284⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Connect with Jeannine Bryant

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠Jeannine's Website⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Follow Deanna Yates, the host of Wannabe Clutter Free on:

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Get my children's book: Lenora and Her Super Duper Messy Room⁠⁠⁠⁠⁠⁠

****************

In this heartfelt episode, rightsizing expert Jeannine Bryant joins me to talk about how to compassionately approach decluttering with aging loved ones.

We cover:

How to start tender conversations without conflict

What to do when siblings have stronger emotional attachments

The truth about estate sales and what to expect

How to start early, so decluttering feels peaceful instead of pressured

The questions to ask around the Thanksgiving table to spark connection, not guilt

Whether you’re helping your parents downsize, sorting through family heirlooms, or simply preparing for future transitions, this episode will help you navigate it all with grace.

Time Stamps:

00:00 – Welcome & Thanksgiving week reflections

02:00 – What “rightsizing” really means (and why it’s different from downsizing)

05:00 – The emotional side of letting go and facing mortality

08:00 – When keepsakes shift from comfort to burden

10:00 – Separating love, memories, and stuff

13:00 – Why your kids don’t want your stuff (and that’s okay)

16:00 – How to talk with siblings who attach emotions to things

18:00 – What to keep, what to display, and what to release

23:00 – Family conversations to have during the holidays

27:00 – How estate sales actually work (and what to expect)

33:00 – The hidden cost of “saving everything”