Published April 6, 2026

It's All Downhill From Here... So They Say

Author Avatar

Written by Brandon Hebert

Brandon Hebert - Reflection Era

It's All Down Hill From Here... So they Say


Alright, this is not your standard real estate article. Apparently turning 40 puts you in your “reflection era,” so here we are. Looking back, none of this really felt like a plan at the time… but it all connects now.

I grew up in Pickering and got my first real introduction to real estate early. At 19, I bought my first home from my grandparents as they were downsizing. It was an end unit row house in Leslieville, right on the edge of the Beaches. I made it work by negotiating a down payment with my parents and renting out part of the home to classmates. Looking back, that was the start of my understanding of real estate, long before it became my career.

I went to school for graphic design, marketing, and advertising, graduating in 2008. Not ideal timing, given the recession. With limited opportunities, I started my own design business. Many of my clients were Realtors, and it did not take long to realize the marketing could be better. That idea pulled me into real estate and still drives how I approach homes today.

At 24, I got my license, sold my home, and then left to travel. I got bit by the travel bug and never really shook it. More than anything, it gave me perspective. Seeing how differently people live and what “home” means in different places has stayed with me. When I came back, I got back into the market. A condo in South Etobicoke with a partial lake view led to a pre-construction stacked townhouse with a rooftop terrace facing the water. Each move built on the last, eventually leading to a detached home, becoming a landlord, and experiencing real estate from multiple angles.

Looking back, there has always been a pattern. From the Beaches to the west end, I kept finding my way back toward the water. This year marks my 16th year in real estate. For a while, life felt like it was moving quickly and lining up well. Then 2019 happened. One of our favourite years. Somewhere between the Raptors winning and us finding out we were going to be parents, everything shifted in the best way.

We left the city to be closer to family in Durham. As our family grew, space became tight. Before our third arrived, we made the move. After plenty of drives along the waterfront toward Port Hope, passing through Newcastle and saying “maybe one day,” that day finally came. We found the right place in the Port of Newcastle and made the move just in time.

Now we are here, and we love it. The community, the pace, the people. Our kids are happy, and we have felt welcomed from day one. If you see us at the park, on the trails, or along the boardwalk, say hi. We are always up for meeting new people.

So that is the story so far. From Pickering, to Leslieville, to a few stops along the way, and now to Newcastle, always finding our way back to the water. Not a bad run to 40. It hasn’t all been easy, but that’s what makes it worth it.

Reflection era… more like appreciation era.


Brandon Hebert
The Hebert Group
416.949.7529

Brandon Hebert

Categories

Buying, Selling, Downsizing

|

home

Are you buying or selling a home?

Buying
Selling
Both
home

When are you planning on buying a new home?

1-3 Mo
3-6 Mo
6+ Mo
home

Are you pre-approved for a mortgage?

Yes
No
Using Cash
home

Would you like to schedule a consultation now?

Yes
No

When would you like us to call?

Thanks! We’ll give you a call as soon as possible.

home

When are you planning on selling your home?

1-3 Mo
3-6 Mo
6+ Mo

Would you like to schedule a consultation or see your home value?

Schedule Consultation
My Home Value

or another way