June 19, 2025
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鈥檒l start to notice a pattern.
It鈥檚 not always the big financial missteps or the bad investment decisions that sting the most. Often, it鈥檚 the things they 诲颈诲苍鈥檛 do鈥攖he conversations that 诲颈诲苍鈥檛 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鈥檒l 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 诲颈诲苍鈥檛 take retirement planning seriously until their late 50s or even early 60s. By that time, it can feel like you鈥檙e playing catch-up鈥攅specially if you haven鈥檛 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鈥檛 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鈥檒l need, what you might need to adjust, and what鈥檚 still possible鈥攏o matter your starting point.
It鈥檚 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鈥檛 always fully covered.
What you can do now:
Build healthcare costs into your retirement budget. Consider a Health Savings Account (HSA) if you鈥檙e still eligible鈥攊t can help you save for medical expenses tax-free. It鈥檚 also worth looking into long-term care insurance and understanding what鈥檚 covered by your provincial or national healthcare system versus what isn鈥檛.
Many people hang onto the family home well into retirement, thinking it鈥檚 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鈥攚hen 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鈥檛 just about reducing costs鈥攊t can also lighten your mental load and give you more freedom.
鈥
