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Why Buying & Selling at the Same Time Can Feel Impossible (And What to Do Instead)

Buying and Selling at the Same Time? You’re Not Alone.

You want to scale up or scale down. Either way, you're not just doing one real estate transaction — you’re doing two.

And that? That’s a juggling act that most people are never properly prepared for.

The Real Problem Isn't What You Think

Most of the people I speak with assume the problem is:

  • Not enough listings. (Really means nothing has caught your eye)

  • Prices are too high. (What’s available isn’t worth the asking price to you).

  • It’s a bad time to move. (There’s a lot going on in your life or what’s available isn’t worth the effort required).

But the real issue? No one showed you how to move smart.

3 Shifts That Make All the Difference

1. Sequence Over Speed 💡
Trying to buy and sell “at the same time” is chaos. You need a sequence: sell with a flexible closing, secure a short-term rental if needed, or leverage your financing to buy first.

2. Financing Isn’t Just Mortgage Rates 💰
Have you reviewed your home equity options? Talked to a broker about bridge loans or HELOCs? A solid financial strategy changes everything.  (Side note: at the time of this blog there is still the threat of tariffs and navigating new trade agreements and interprovincial trade barriers).

3. Clarity = Confidence 🧠
If you’re not sure what you want in your next home, how will you know when you find it? My workbook walks you through how to define your “right size.”

Want to See How It All Comes Together?

I created a free guide, House-ology’s Right Sizing.  You can download it here house-ology.ca/right-sizing.html

If you're thinking of moving, let’s talk strategy before you make a mistake that costs you time, money, or peace of mind.

Michelle ✌🏾

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🏡 Buyers, Is It Time to Scale- Up?

“More Than Space: What’s Driving Your Next Move?”

🔎 Space Is the Excuse, But Not the Reason

Most people think they’re scaling up because they’ve “outgrown” their condo. But that’s not the full story. You’re not just craving square footage—you’re craving a lifestyle that reflects where you’re going, not where you started. Maybe your kids need outdoor space. Maybe your in-laws are staying longer. Or maybe you just want to exhale without hearing your neighbour’s microwave beep. Whatever it is, it’s not just a move—it’s a milestone.

🧠 Emotional Clarity = Strategic Clarity

The truth is, most bad real estate decisions happen when we skip the emotional work. If you don’t know what emotion is driving your move—whether it’s anxiety, guilt, aspiration, or pure exhaustion—then you’ll look at listings that don’t align with your life. I often see buyers misread their motivation and end up with homes that impress on paper but underwhelm in real life. Clarity upfront saves chaos later.

📈 Your Finances Should Match Your Future

Scaling up isn’t about pushing your max pre-approval. It’s about investing in a home that will meet your family’s next 5–10 years. Does it support the commute you're about to have? The new school you're eyeing? A second income stream like a rental suite? If your budget doesn’t reflect your future goals, you’re just decorating a detour.

🗝️ Choose Your House Like You’d Choose Your Life

A house is not a status upgrade—it’s a lifestyle structure. When you begin with that in mind, the filters you use shift. A mudroom might matter more than a formal dining room. Proximity to trails may beat proximity to downtown. You stop searching with a list of rooms and start searching with a list of needs.

💡 Consider This:

  • Is your “why” based on discomfort or desire?

  • Are you buying a home for your future self—or for your current stress?

  • Could renting for 6 months help you buy smarter?

✅ Mini Checklist:

  • Write down 3 non-negotiables for your next chapter

  • Define your real lifestyle needs vs. wish list

  • Review your mortgage pre-approval in light of long-term changes

  • Journal how you want to feel in your next home—start there

You don’t need to have it all figured out today.
You just need to be clear enough to make choices that align with your life—not your pressure.

Talk soon,
Michelle Babb, Broker of Real Broker Ontario
House-ology™ | Simultaneous Moves, Simplified™
Book a 15-Min Clarity Call →

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This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.