No one wants to look back on their retirement and feel like they missed something important. But ask enough retirees about their experience, and you’ll start to notice a pattern.
It’s not always the big financial missteps or the bad investment decisions that sting the most. Often, it’s the things they didn’t do—the conversations that didn’t happen, the planning that came too late, or the opportunities they let pass by.
We spoke with retirees and combed through national surveys to understand the most common regrets people have once they leave the workforce. More importantly, we’ll walk through how you can take simple, proactive steps to avoid those regrets yourself.
This one comes up again and again. Many retirees say they didn’t take retirement planning seriously until their late 50s or even early 60s. By that time, it can feel like you’re playing catch-up—especially if you haven’t been consistent about saving or if your lifestyle expectations are high.
What you can do now:
Start where you are, not where you wish you were. Take a look at your current expenses, savings rate, and retirement account balances. If you don’t already have a financial plan in place, this is the moment to get one. A good plan can help you map out how much you’ll need, what you might need to adjust, and what’s still possible—no matter your starting point.
It’s easy to assume that once you hit 65 and qualify for Medicare or similar programs, healthcare becomes a non-issue. But many retirees are surprised by how quickly out-of-pocket expenses add up. Things like dental work, hearing aids, prescriptions, and long-term care aren’t always fully covered.
What you can do now:
Build healthcare costs into your retirement budget. Consider a Health Savings Account (HSA) if you’re still eligible—it can help you save for medical expenses tax-free. It’s also worth looking into long-term care insurance and understanding what’s covered by your provincial or national healthcare system versus what isn’t.
Many people hang onto the family home well into retirement, thinking it’s the right choice emotionally or financially. But larger homes often come with higher costs, more maintenance, and unnecessary space. Several retirees told us they wished they had made the move earlier—when it felt like a choice, not a necessity.
What you can do now:
Think about whether your current home still fits your lifestyle. Could you relocate to a more affordable area? Would a smaller place free up cash for travel or experiences? Downsizing isn’t just about reducing costs—it can also lighten your mental load and give you more freedom.
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You’re not just combining lives, you’re combining financial histories too. That means two sets of habits, two credit scores, two levels of experience with saving and spending, and maybe even two very different definitions of what a budget is. Start with a full picture of where you both stand. Talk through your income, your debts, your savings, and your everyday money habits. This is not about shaming each other or keeping score. It is about being transparent so you can build trust and avoid surprises later.
Even if you are walking straight into a new job, there could still be a delay before the first paycheck. And if you are switching industries, going back to school, or starting a business, that cushion matters even more. Aim to save three to six months of essential expenses. More is better if your next move is unpredictable. This is not a forever thing. It is just enough to keep you afloat without leaning on credit cards or panic.
We get it. You’ve just inherited a house and the first instinct might be to do something, anything. Sell it. Move in. Light a sage stick and start redecorating. But here’s your permission slip to pause. There’s no trophy for rushing big decisions while juggling emotions and funeral casseroles. Unless the home is in foreclosure or there’s some urgent financial emergency, take a minute. Sit with it. Breathe. You’ll make better decisions once the dust settles a bit.