The Downsizing Roadmap Podcast
Welcome to The Downsizing Roadmap Podcast, your go-to resource for navigating the emotional and practical challenges of downsizing. Whether you’re helping a senior loved one transition to a smaller space, embracing minimalism, or simply looking to simplify your life, this podcast offers expert tips, heartwarming stories, and actionable advice to guide you every step of the way.
Join us as we share insights, interview trusted vendors, and explore real-life journeys of letting go and moving forward. Tune in to find inspiration, solutions, and support for creating a lighter, brighter future.
Subscribe today to make downsizing manageable—and maybe even fun!
Meet Your Hosts:
Jodi Rosko and Heather Fisher
Realtors and Downsizing Specialists
The Rosko Group
Keller Williams Community Partners
https://downsizingroadmap.com/
The Downsizing Roadmap Podcast
54. 10 Decluttering Questions That Actually Work—Including the ‘Would You Buy It Again?’ Test
When the decision feels emotional, overwhelming, or stuck—sometimes it’s not about trying harder. It’s about asking better questions.
In this episode of the Downsizing Roadmap Podcast, we walk you through 10 powerful decluttering questions that cut through guilt, obligation, and uncertainty to help you move forward with more confidence. From the “Would I buy this again?” test to prompts that challenge identity, obligation, and emotional clutter—these questions will help you get unstuck when “keep or toss” just isn’t cutting it.
You’ll learn:
- When to use each question during the downsizing process
- Why some questions work better for sentimental or inherited items
- How to apply these questions room by room
- How to shift your mindset from guilt to progress
Whether you're sorting through a full house or just starting to pare down, these tools are here to help. You don’t have to be ruthless—you just need a better way to think about your stuff.
🎧 Listen now and keep a notepad handy. One of these questions might just be your breakthrough.
Links Mentioned:
🔗 Get our free downsizing resources and guides at https://downsizingroadmap.com
🔗 Want more support? Schedule a consult with our team. https://downsizingroadmap.com/contact/
Follow & Share:
💌 Know someone stuck in their downsizing process? Forward this episode or share it on social—these questions are meant to be used.
If you enjoyed this episode, don’t forget to Follow our show so you never miss a new one. We’re here for your downsizing questions — on the podcast, in your community, and when you’re ready to move. As Realtors®, we can connect you with the right specialists to make your next chapter smoother. We’d love to hear from you!
📧 Email us: info@downsizingroadmap.com
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🌐 Learn more: www.downsizingroadmap.com
Let’s simplify, declutter, and create space for your next chapter—together!
