The 5 Biggest Downsizing Mistakes I See (And 3 Beautiful Benefits That Follow)

When I sit down with people who are considering downsizing, I don’t just see square footage and storage bins — I see real lives in transition. Some of these transitions unfold with ease, excitement, and clarity. Others are full of avoidable heartache and frustration. Over the years as a Downsizing Specialist on the North Shore of Vancouver, I’ve started to recognize patterns: the most common missteps that slow people down, and the surprising wins they experience once they finally make the move.

Let’s walk through the five biggest downsizing mistakes I see — and then the three biggest benefits families consistently tell me they’re grateful for afterward.

1. Waiting Too Long

This is the number one hesitation I see: people put off downsizing until a crisis hits — a health scare, a fall on the stairs, a financial stress point, or a loved one who suddenly can’t live independently anymore. When downsizing is reactionary rather than planned, both the emotional load and the financial pressure spike.

By contrast, planning ahead gives you time to make thoughtful decisions — instead of rushed ones.

And you’re not alone in your reasons for considering a move. According to Statistics Canada, among Canadians aged 56 and older who moved, the top reasons were reducing housing costs (27.3%), being closer to family (19.1%), and health considerations (12.7%). It’s that last one — health and mobility — that I see most often.

2. Collecting Too Much Stuff

Clutter isn’t just a physical problem — it’s a psychological barrier. I see people hesitate to even start the downsizing conversation because they’re overwhelmed by what’s in their basements, garages, closets, and attics.

Here’s the kicker: in a recent Canadian survey, more than 70 percent of Canadians said they were bothered by clutter in their homes, and many don’t know what to do with it or feel too overwhelmed to begin.

That emotional load — combined with sheer volume — can paralyze decision-making. But small chunks of sorting, paired with the right support, quickly create momentum.

3. Not Knowing Where to Start

This often shows up in two ways:

• “Who do I call first?”

• “I don’t want to burden a real estate agent yet.”

I hear both of these more than you’d think. Without a clear first step, people freeze.

When you work with a downsizing specialist from the beginning, you get that roadmap:

• What professionals you’ll need (organizers, estate sale advisors, movers).

• What costs to expect.

• A step-by-step plan so you know why you’re doing each thing, not just what you’re doing.

And sometimes people simply don’t ask for help because they don’t want to feel like they’re “not capable.” That’s normal. But it’s also exactly why guides and specialists exist — to lighten that load and make the process empowering instead of overwhelming.

4. Skipping a Detailed Financial or Estate Plan

Downsizing isn’t just about the space you live in; it’s about the life you want next. Too often, families focus only on the home sale and forget to align that with retirement cash flow, taxes, estate planning, and long-term financial security.

A fee-for-service financial planner, like those at Parallel Wealth ( www.parallelwealth.com ) or similar firms, can help map out a clear picture of your retirement needs versus your downsized lifestyle goals — so you’re not left guessing whether the move gives you the freedom you imagined. This fee-for-service option provides an expert in retirement and estate planning outside of the bank or wealth management firm that you invest with and can provide a clear path for the timing of downsizing, tax strategies, the start of Canadian benefits and how to legacy plan with your estate wishes in mind.

When you treat your downsizing as a strategic financial step — not just a real estate transaction — the confidence and clarity that come with it are transformational.

5. Not Taking Time to Dream

People spend decades dreaming about what they did with their homes — family dinners, kids’ rooms, holiday gatherings — but far fewer imagine what they might do next.

Downsizing isn’t the end of a story; it’s the beginning of a new one. I’ve seen clients light up when they start to picture a kitchen they love instead of a basement they dread. Or an art studio instead of a garden shed. Or travel plans instead of weekend chores.

A little dreaming — early and often — makes the whole process feel purposeful instead of burdensome.

3 Surprising Benefits People Tell Me They Wish They Had Experienced Sooner

Even with all the hesitation and emotional tug, once clients settle into their new space they often tell me the same thing:

1. “I Wish We Had Done This Sooner.”

People often underestimate how much better daily life feels in a well-right-sized home — until they finally experience it. A smaller home doesn’t mean less life; it often means better life.

2. New Hobbies and Passions Emerge

One of my favourite trends? People trade time spent maintaining space for time spent enjoying life. I’ve seen clients discover pottery classes, painting, weekend travel circles, new exercise interests, and even writing projects they’d tucked away for years.

Concerned that he may not thrive without tinkering in the garage? A new found interest in cooking may emerge and replace that hobby with a new one!

Instead of spending weekends mowing lawns and fixing gutters, suddenly there’s time for the things that feed the soul.

3. A Newfound Sense of Freedom, Peace of Mind, and Joy

This one echoes across generations and personalities: downsizing gives people breathing room — literally and figuratively.

Financial peace of mind, less physical upkeep, mornings without a million chores, evenings that feel restful instead of rushed — that’s not just convenience. That’s a quality-of-life upgrade.

If you’re standing at the downsizing crossroads, know this: with the right plan, support, and mindset, what feels daunting today becomes the launchpad for a more joyful, intentional tomorrow.

If you want to talk through where to start or how to make a plan that feels good — I’m here to help.

Shelley Hird
North Shore Realtor® and Downsizing Specialist
604.209.4855
www.shelleyhird.com