10 Questions to Ask When Deciding What to Keep, Donate, or Toss

Downsizing or decluttering a home full of memories can feel overwhelming. Whether you're helping a loved one transition into a new space or simplifying your own surroundings, it’s not just about getting rid of “stuff” - it’s about honoring a life’s journey while preparing for a new chapter.

At Simplifying Your Life, I support seniors and their families through every step of this process. These ten thoughtful questions can help you sort through belongings with confidence and care - so you can make space without losing what matters most.

1. Do I use this regularly - or has it just been sitting here?

If it’s collecting dust, chances are it’s no longer serving a purpose. Let this question guide you in deciding if the item adds value to your day-to-day life.

2. Would I buy this again today?

Imagine you're seeing the item in a store right now. Would you pay money for it again? If not, it may be time to let it go.

3. Is this item tied to a memory or a sense of obligation?

We often keep things out of guilt: gifts we never used, heirlooms we don’t actually like. Remember: memories aren’t in the things—they’re in your heart.

4. Do I have duplicates or something similar that serves the same purpose?

Too many casserole dishes? Multiple winter coats? Pick your favorite and donate the rest to someone who could really use it.

5. Does this fit the life I’m living now - or the one I lived years ago?

Our needs and lifestyles change. Hold onto items that support your current stage in life, and release what belongs to the past.

6. Is this something my family will want - or something I assume they’ll want?

Ask! Adult children often appreciate the gesture but may not want or need inherited items. It’s better to have the conversation than to assume.

7. Would someone else benefit from this more than I do?

Sometimes the best way to honor an item is to pass it along to someone who will love and use it. Donating can be deeply rewarding.

8. Is this item in good condition, or is it time to toss it?

Broken appliances, stained linens, or outdated electronics aren’t helping anyone. Recycle or dispose responsibly when items have passed their prime.

9. How will I feel about this item tomorrow or next year?

If you're unsure, set it aside in a “maybe” box. Revisit it after a few days with fresh eyes. Often, clarity comes with time.

10. Am I keeping this item out of love or out of fear?

Letting go can feel scary, especially when things represent people or moments we’ve cherished. But releasing clutter doesn’t erase love, it creates room for what’s next.

Need a Helping Hand?

Decluttering and downsizing don’t have to be done alone. I am here to support you and your loved ones with compassionate organizing, move coordination, and companion care.

Whether you're preparing for a move or simply want to create a calmer space, I can bring peace of mind and a plan that works for your family.

📞 Let’s talk about how we can help. Contact me today for a free consultation.