How to Make Downsizing Decisions You Won't Regret

A practical guide for rightsizing your home and your life.

by Cathy Borg

✅ STEP 1: Start Your Downsizing Decisions - Walk Through & Evaluate

Before packing anything, take a quiet walk through your home with a pen and paper. This first step in making smart downsizing decisions requires no pressure to purge yet — just observe and evaluate.

Ask yourself:

• Will this fit comfortably in my next home?

• Will it match my new space or lifestyle?

• Do I truly want this, or am I keeping it out of guilt or habit?

• Have I used this in the last 5 years?

• Would I take this with me if I had to move tomorrow?

✏️ Tip: Keep three columns: YES, NO, MAYBE. Label by room: Kitchen, Bedroom, Living Room, etc.

✅ STEP 2: Smart Downsizing Decisions - Sort the “NO” List

When you're ready to start letting go, label 4 boxes. These clear categories help streamline your downsizing decisions:

• 📦Donate

• 💲Sell

• ♻️Recycle

• 🎁Distribute (to friends/family)

Start in low-use areas like guest rooms, storage closets, or the basement — quick wins boost your motivation.

✅ STEP 3: Paced Downsizing Decisions - Sort in Manageable Chunks

Downsizing takes more energy than you expect. Don’t try to do it all in one day.

Plan short, focused sessions:

• Set a timer (15–60 minutes)

• Focus on one room or one closet

• Take breaks — downsizing fatigue is real

✏️ Tip: Do the tough decision-making when you're fresh, not at the end of a long day.

✅ STEP 4: Tough Downsizing Decisions - When You’re Not Sure What to Do With Something…

Ask:

• Do I love it, need it, or use it?

• Does it support the life I want to live now?

• Could a photo or small keepsake preserve the memory instead?

Try this simple body check:

✏️ Tip: Hold the object. Close your eyes. Breathe.Do you feel a lift (keep) or a slump (let go)?

✅ STEP 5: Final Downsizing Decisions - Get Stuff Out — Fast

Once items are sorted, remove them quickly so you don’t second-guess yourself.Put boxes straight in the car, not back in the hall!

If you need help:

• Use a junk removal or donation pickup service

• Try an online auction (like MaxSold) for selling items fast

• Ask family members to take what they’ve claimed — soon

💡 BONUS TIP: Don’t Let “Maybe” Pile UpStill stuck? Store your MAYBE items in a marked box. If you don’t miss them after 30 days, chances are, you’re ready to let them go.

You Deserve a Fresh Start

You’re not just moving things — you’re making space for the next chapter.

Let that guide your choices. You don’t need to keep it all. You just need to keep what matters most

About the Writer

Cathy Borg is a partner at In and Out Organizing, serving the Greater Toronto Area. She specializes in helping adults 50+ and their families declutter, downsize, and navigate life transitions with less stress and more clarity. With over a decade of experience, Cathy combines practical strategies with compassion and respect, ensuring every project feels manageable and meaningful.

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Need Help?

We help families across the Greater Toronto Area with compassionate, practical support for:

• Decluttering & organizing

• Downsizing & moving

• Estate clearing

📞 Call Brad at 416-859-0518 for a free consultation📧 info@inandoutorganizing.ca🌐 inandoutorganizing.ca