I Could Have Retired at 50. Why Did I Keep Working Until 55?

For years, I had one goal in mind: retire around 50.

When I finally reached 50, I didn’t retire.

It wasn’t because I hadn’t saved enough or because my retirement plan had fallen apart. I was financially ready. I simply wasn’t ready to stop working.

So, I kept going for another five years. In August 2026, at 55, I finally called it a day.

Why the delay? It turns out that being able to retire and actually wanting to retire are two different things.

Financially ready, but not in a hurry

By the time I reached 50, I had spent many years saving, investing, and building wealth. I had a plan, understood my expenses, and felt comfortable with where I stood financially.

But I was also enjoying my life.

I worked remotely, which gave me the flexibility to travel while continuing my career. For around five years, I spent weeks or even months at a time in different countries, including Thailand, Colombia, Vietnam, the Philippines, Egypt, and Mexico.

It was a pretty good arrangement. I could work during the day and explore somewhere new when I finished. I wasn’t exactly suffering.

And honestly, why rush into retirement when you are already enjoying some of the freedom it offers?

Travel helped me figure out where I wanted to retire

Working remotely while travelling also gave me a chance to test different places as potential retirement destinations.

A holiday can make almost anywhere look perfect. Living somewhere for a few weeks is a different story. You start thinking about grocery stores, transportation, internet, healthcare, safety, and all the other exciting things that don’t usually make it into holiday photos.

I learned that no single place has everything.

My ideal retirement destination would have good weather, be safe and walkable, offer great food, and have a reasonable cost of living. Being close to a beach is a definite bonus. Good healthcare and infrastructure matter too.

I also discovered that I enjoy slow travel much more than rushing from one tourist attraction to another. I would rather spend a month getting to know a place than visit ten cities and need another holiday to recover.

Those years helped me understand what I wanted retirement to look like. They also gave me confidence that I didn’t need to settle on just one destination.

Making sure the numbers worked

Enjoying life was important, but I wasn’t going to walk away from a career without checking the finances properly.

I reviewed my retirement plans with a financial adviser. We looked at my expected expenses, income, and different financial scenarios. The conclusion was that my money should last for the rest of my life, even under the less favourable scenarios we considered.

My planned retirement budget is around $100,000 a year after tax, covering everything.

That’s my personal number, based on my lifestyle and plans. It isn’t a magic retirement formula, and it certainly won’t be the right amount for everyone.

The important thing was knowing what I needed, having a plan to fund it, and being comfortable with the risks.

I didn’t want to retire and spend the next 30 years worrying about whether I could afford lunch.

What will I actually do all day?

This was another question I wanted to answer before retiring.

I had seen people retire and struggle with what to do with their time. After years of working, having every day free can sound wonderful. But eventually, even sleeping in gets a little boring.

I already enjoyed scuba diving, fishing, swimming, golf, exercise, and meditation. I made time for these activities while I was still working, partly to make sure I genuinely enjoyed them and wasn’t just imagining a perfect retirement.

The plan is to spend most of the year outside Canada, keep our home base here, and return for the summer months.

More travel, more time outdoors, more exploring, and fewer meetings that could have been emails. Not a bad retirement plan!

Why I finally retired at 55

There wasn’t one big event that made me retire. It was simply the right time.

I had reached the financial position I wanted, had a good idea of how I wanted to spend my time, and felt ready to move on.

Looking back, I don’t regret working those extra five years. I enjoyed the flexibility, the travel, and the income. More importantly, I didn’t feel forced to retire just because I had reached an age I had picked years earlier.

Financial independence gave me the choice. I could keep working, change direction, or stop altogether.

That’s what I think FIRE is really about. It isn’t necessarily about retiring as early as possible. It’s about having enough financial freedom to decide how you want to spend your time.

For me, that time has finally arrived.

Freedom and peace of mind. That’s what retirement means to me.