The final of our four interviews with the It’s Your Move team is Jake Caldwell, who has had a no less of a varied background than his teammates. You may find out a thing or two about Jake’s past when you read below. He could not be more rooted to the community here in Kingston, nor more committed to finding the right path for his life and work. Jake sends a word of encouragement out to everyone at the end of this interview, for anyone similarly seeking authenticity and enjoyment in their life!


Meet Jake Caldwell.

Jake, you have an interesting background. Tell us about that and what drew you to Real Estate?

It’s true that it wasn’t a straight path for me. I guess Real Estate was always something I loved even as a kid. I remember looking at glossy magazines of luxury houses even when I was really young. When my parents were selling their house, I remember being really interested in the process. It was a funny house, especially for Smith’s Falls, kind of a California-style bungalow. I remember their Real Estate agent sitting at the table trying to come up with a good description of the place, and I piped up, “It’s deceptively large.” There was a silence and the whole room stared at me and kind of laughed and that became part of her blurb about the house.

But yes, I didn’t just grow up and become an agent right away. Actually, I first got a diploma from the School of Business at St Lawrence College, in Marketing, but I ended up more or less hating that! One afternoon, I sat down on the couch and was kind of thinking “great, now what?” After a few minutes of sheer terror I grabbed a piece of paper and a pen and started writing. “What’s important to me?” “what do I want to do before I die?” You know, the Big Questions… I don’t know why, but building my own home suddenly jumped out at me as something I knew I had to do before I died. I didn’t even own a hammer at the time though! I realized pretty quickly that if I was going to achieve that goal I was going to have to make some pretty drastic changes. So that realization led me into the SLC Carpentry program, and then from there to the Heritage Carpentry from Algonquin College, the Perth campus. I loved that, and continued with that for almost a decade working for Mark Peabody for the majority of the time.

Then I got married and Anne and I had Evelyn, and my goals shifted. My back was getting worse and I wanted to be able to provide for my family long-term so I talked to my Dad. He and I have always been close, but we think differently so conversations with him almost always prove to be helpful/insightful. He suggested I look into Financial Advising, and after a year of that we founded Caldwell Wealth & Estate Advisory together, in the Woolen Mill. Advising wasn’t for me but I enjoyed helping with managing and staffing, and eventually sitting in on meetings with my father and his clients.

Two things happened after about three years. One, it dawned on me that I would never enjoy financial advising as much as my Dad did! And two, I knew what made me excited: it was a mix of sales, homes, architecture, and space. All of those elements were in Real Estate. I guess I would say that my background in carpentry taught me about houses and building, but the four years with my Dad prepared me for Real Estate and taught me about client relationships.

It does sound like you covered all the bases! So it wasn’t a specific house or home that you fell in love with?

Not really, it was the concept of creating a structure that would be a home, and that the bricks and mortar of a place could be given life by the occupants. I loved that aspect, but I love that about a variety of homes I’ve encountered, and worked on.

When you’re 90 and looking back on your life, what will be your definition of success?

Ha, this sounds like a conversation with my Dad all over again! Well, I guess just knowing that I did my very best for each and every client I worked with. I know it may sound hokey, but I would consider my life successful if people know that I care about them…about their hopes and dreams for their house and how that would affect their lives, their marriages and kids. I guess, looking back on my own life so far, I would say that that is something that is deeply important to me, that people are excited about their life. I think the right career, even if that means making radical changes is really important and making radical changes about where they live or how they live is really important. It is possible to wake up and feel excited about the life you’re living. Not everyone knows what that looks like, and sometimes it can be a circuitous route to the right life, like mine was! But you only get one life, so don’t ever settle for “good enough.”

Jake’s is always available to chat, if you ever want to soak up some of that encouragement firsthand. Call 613.449.6588 or email