Ep 185 - 5 Retirement Regrets Canadian Retirees Confess After 65 (Even Millionaires)
In this episode of Your Retirement Planning Simplified, Joe Curry explores five of the most common retirement regrets Canadians experience, from underestimating healthcare costs to not having a written retirement income plan. Learn practical strategies to stress-test your retirement plan, manage inflation, and avoid the financial surprises that can derail retirement confidence.
Key Takeaways
Many retirees discover retirement looks different than expected. Inflation, lifestyle drift, and helping family members can quietly increase spending over time.
Healthcare in Canada isn’t completely free. Dental, vision, medications, private diagnostics, and home care can create meaningful out-of-pocket costs later in retirement.
Monthly expenses often end up higher than planned. Inflation and lifestyle realities frequently push spending above what retirees initially projected.
“Surprise” expenses are often predictable categories. Home maintenance, accessibility renovations, travel insurance, and outsourcing household work should be built into the plan.
Having assets isn’t the same as having a retirement plan. Even affluent Canadians often lack a coordinated strategy for income, taxes, investments, and estate planning.
Insights Worth Sharing
“Most retirement regrets aren’t about picking the wrong investment — they’re about real life being messier than the plan.”
“Healthcare in Canada isn’t completely free, and retirees often discover that the hard way.”
“Inflation doesn’t stop just because you retire.”
“Many so-called ‘surprise expenses’ aren’t surprises at all — they’re just costs that weren’t modeled in the plan.”
“Having enough money isn’t the same thing as having a retirement plan.”
Resources
Ontario Securities Commission Retirement Research
Government of Canada – CPP and OAS Information
Avoid These 5 Costly Retirement Regrets with a Smarter Income Plan
Most people picture retirement as a well-earned reward after decades of hard work. More time for travel, hobbies, and family. Less stress and fewer financial worries. But when I speak with retirees - and when we look at the data from Canadian surveys - a different story often emerges. Not necessarily a bad one, but one that’s more complicated than people expected. In fact, many retirees share the same handful of regrets. Let’s walk through five of the most common retirement regrets Canadians experience, and how better retirement income planning can help avoid them.
1. Retirement Didn’t Look Like They Expected
Nearly half of retirees say their retirement lifestyle looks different than they imagined. Often the issue isn’t investments - it’s real life. Inflation increases the cost of living. Spending slowly creeps higher over time. And many retirees end up helping adult children or supporting grandchildren more than expected. This is why retirement planning shouldn’t rely on a simple straight-line projection. A good plan stress-tests your retirement income against inflation, market volatility, and changing lifestyle needs.
2. Healthcare Costs More Than Expected
Canada’s public healthcare system covers a lot - but it doesn’t cover everything. Many retirees underestimate the cost of dental care, vision, hearing aids, prescriptions, and private diagnostics. Home care support can also become a significant expense later in retirement. Even if travel and recreational spending declines with age, health-related costs often increase. A realistic retirement income plan accounts for these potential out-of-pocket expenses.
3. Monthly Spending Was Higher Than Planned
According to research from the Ontario Securities Commission, almost one-third of retirees report higher monthly expenses than expected. The reason usually isn’t overspending. It’s incomplete planning. Many people budget for groceries, property tax, and utilities, but forget about helping family members, travel, hobbies, or inflation over a 20- to 30-year retirement. When retirees finally have time to enjoy life, they often discover the lifestyle they envisioned costs more than expected.
4. “Surprise” Expenses Keep Appearing
Home repairs, vehicle replacements, travel insurance, and accessibility renovations often catch retirees off guard. But these aren’t truly surprises. Roofs wear out. Furnaces fail. Bathrooms eventually need updating. And as people age, they may need to outsource tasks like lawn care or snow removal. A strong retirement plan treats these as inevitable categories rather than occasional surprises.
5. Having Money Isn’t the Same as Having a Plan
One of the most surprising findings from Canadian studies is that many affluent retirees still lack a coordinated retirement plan. Even among households with over $1 million in investable assets, fewer than half have a detailed retirement strategy. A true retirement plan coordinates investment withdrawals, RRSP and RRIF strategies, CPP and OAS timing, tax-efficient investing, and estate planning into a single roadmap. Without that coordination, retirees may face unnecessary tax bills, income gaps, or financial stress.
The Bottom Line
Most retirement regrets don’t come from making a single bad financial decision. They happen when real life turns out to be more complex - and more expensive - than the original plan assumed. The solution isn’t perfection. It’s thoughtful planning and regular stress-testing.
Learn more about our retirement planning process at MatthewsAndAssociates.ca.