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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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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