From 65 to 50: How I Discovered My Real Retirement Date

I want to tell you about two meetings with my financial planner, separated by exactly one year. The first one made me question everything I’d ever assumed about retirement in Canada — the timeline, the number, the whole picture. The second one made it real.

The First Meeting (September 2024)

It was supposed to be routine. Annual check-in, review the accounts, nod at the graphs, leave feeling vaguely responsible about my financial life. That was the plan. I walked in with no agenda. I walked out with a question I couldn’t shake. What if I’ve been assuming things about my future that were never actually true? I didn’t do anything dramatic with that question right away. I drove home. I made dinner. I opened a bottle of red wine. And then I opened my laptop.

The Rabbit Hole

Here’s what you need to know about my brain: when it finds something interesting, it doesn’t let go. I have ADHD, which means hyperfocus is both my superpower and my sleep schedule’s worst enemy.

That night, one question led to a spreadsheet. Which led to another spreadsheet. Which led to a budget. Then four budgets. Then four budgets with three withdrawal rate scenarios each. Then a colour-coded comparison table. Then it was 2am.I was running numbers. Scenarios. What if I saved more? What if I spent less in retirement? What if I didn’t retire in Canada at all?

The number I kept solving for — the age at which this all became mathematically possible — kept getting smaller. I started at 53. Then 52. I kept refining, kept pressure-testing, kept running it again from a different angle expecting to find the flaw. I didn’t find the flaw.

The Moment It Became Real

At some point in those months of late nights, the math stopped being abstract. It attached itself to a real place. I’d been researching cities — cost of living, climate, quality of life, healthcare, tax implications. And somewhere along the way, I found myself pricing out an actual life in Plovdiv, Bulgaria. A good life. A quiet, unhurried, sun-drenched life, with excellent food and a remarkably low cost of living.

The number that made that life possible — the portfolio size I’d need to sustain it comfortably — was around $550,000 to $618,000 CAD, shifting as my thinking about where to land evolved.

I looked at my timeline. I looked at the number again. And then I noticed something else. The year the math pointed to was also the year a significant personal chapter of my life would be closing — the kind of transition that would naturally free me to go wherever made sense. The financial door and the personal door were opening at the same time. That felt like something worth paying attention to.

The number I kept landing on was 50.

The Second Meeting (September 2025)

I walked into my planner’s office a year later with a very different kind of agenda. I had done months of work, spreadsheets, four retirement budgets, and a number for four different lifestyle scenarios — strangely, not one of them was in Canada.

I’ll be honest; I watched her face the entire time she was reviewing my projections. Every expression. Every pause. I was looking for one thing in particular: a very specific facial response that had haunted me since our first meeting.

I didn’t get it.

Instead, after a few minutes of silence, her eyebrows lifted.

“Your numbers do work,” she said. “With a lot of assumptions on the tax and overseas living.”

There it was. Not a guarantee. Not a green light with no caveats. A qualified, measured, professional confirmation that the math was sound — if I was willing to do the work to validate the assumptions.

I was already doing that work. I’ve been doing it since the night I opened my laptop with a glass of red wine and a question I couldn’t let go of. Whether the final date turns out to be 51 or 54, or somewhere in between — I knew in that moment it was going to happen. One way or another. This blog is how I’m figuring out the details.

Note: At the time of writing this post, 50 was the number I kept landing on. The math has continued to evolve — follow along to see where it lands.

Nothing on this site constitutes financial advice. I’m sharing my own journey — please do your own research and consult a professional before making financial decisions.