For years, we thought we knew exactly how our story would go.
We’d raise our kids in the suburbs of Toronto, work hard, build equity, and one day — someday — retire to our cottage on the lake. That was always the plan. The cottage was our endgame: sunsets on the dock, quiet mornings with coffee, maybe a pontoon boat (for Jenny - Dean hates them) and no commute.

But ten years ago, “someday” showed up early.

When Life Decides You’re Ready (Even If You Don’t Feel Like You Are)

Dean’s company was cutting jobs, and his name was on the list.
At the same time, I was burning out in corporate life. Long days, endless meetings, a schedule that never seemed to match the life we actually wanted to be living.

We could have panicked. We could have waited it out, found another corporate job, told ourselves retirement wasn’t that far away. But instead, we did something most people would never dream of:

We sold our family home in Scarborough, packed up our lives, and moved to our cottage on Balsam Lake full-time.

Everyone thought we were making a mistake.

“You’ll Be Back Within a Year.”

That was the chorus from friends, neighbours, even family.

“You’ll get bored.”
“The winters are too long.”
“You’ll miss the convenience.”

And honestly? In the beginning, we weren’t sure they were wrong.
There were moments of doubt: plenty of what have we done? conversations. Adjusting to small-town rhythms after years in the city takes time. The house was smaller. The winters were quieter and felt longer. Grocery shopping meant planning ahead and checking your list - twice.

But the stress; the constant rush and noise; started to melt away.

What We Found Instead

Something shifted when we stopped chasing the “right time” and started living the life we actually wanted.

• The kids had more freedom. There was room to explore, to bike, to swim, to breathe.

• We had more flexibility. Time to be present for school events, community activities, and lazy afternoons on the dock.

• The lake community that had always been our summer escape slowly became home.

The move we made out of necessity turned out to be the best decision of our lives.

The Myth of the Perfect Time to Downsize

If you’ve ever told yourself, “We’ll wait until the kids finish school,” or “We’ll downsize when the market’s better,” you’re not alone. Most homeowners in Ontario do exactly that. They wait.

But here’s what we discovered: There’s no perfect time to downsize.

Waiting for certainty often means waiting forever.
The yard work doesn’t get easier. The repairs don’t stop. The maintenance doesn’t slow down. And the longer you put it off, the harder the move becomes, both emotionally and physically.

What Downsizing Really Means

Downsizing isn’t just about selling a house or finding a smaller one.
It’s about choosing the lifestyle that fits who you are now, not who you were when you bought the home.

For us, that meant:

• Less space, but more calm.

• Fewer chores, but more freedom.

• Less stuff, but more time to actually enjoy life.

It meant letting go of what was no longer serving us. Not just our things, but our routines, our commutes, our constant feeling of “busy.”

We didn’t downsize because we had it all figured out.
We downsized because we realized we didn’t want to keep waiting for a life we already knew we wanted.

When You Know, You Know

If you’re starting to feel that pull. You know, the quiet sense that your house feels heavier than it used to... pay attention.
That’s how it starts for most downsizers in Ontario.

You look around and realize:

• The guest rooms sit empty most of the year.

• The yard feels bigger than you can manage.

• The stuff you’ve accumulated no longer fits the life you want to live.

You might not be “ready,” but readiness isn’t the goal. Clarity is.

And sometimes, clarity comes when life gives you a nudge. Or, in our case, a shove.

The Lesson: It’s Not About Timing, It’s About Trust

Looking back now, we can see it clearly: we didn’t move too soon. We moved right on time.

Because downsizing isn’t just a financial decision. It’s an emotional one.
It’s about trusting that you’ll figure things out on the other side, even if you can’t see the full picture yet.

Moving early gave us more than a new address. It gave us:

• A sense of balance we hadn’t felt in years.

• A community that feels like home.

• Time: to live, to breathe, to actually enjoy the life we were working so hard to reach.

Thinking About Downsizing? Start Here.

If you’re considering downsizing your home in Ontario, whether it’s before retirement or simply because your priorities are shifting, start with small steps.

• Get clear on your why: What’s driving your decision?

• Look at the how: What kind of lifestyle do you want next?

• And remind yourself: There’s no perfect time. There’s only your time.

Our story isn’t about luck. It’s about letting go of the fear that you have to have it all figured out first.

Because when you make a move that aligns with your life, not just your finances, everything else falls into place.

Watch Next: Downsize Your Home in Ontario — Selling Made Simple

If you’re ready to take the next step, we’ve put together a video series that walks you through exactly how to make downsizing easier. From decluttering and staging to pricing and planning your next move.

Watch the full playlist: [Downsize Your Home in Ontario: Selling Made Simple]