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.
Retirement isn’t just about money—it’s about purpose. Many retirees find the transition away from full-time work surprisingly difficult. Without a plan for how they’d stay active, engaged, and socially connected, some fell into boredom or even depression.
What you can do now:
Start asking yourself what you want your day-to-day to look like. Do you want to volunteer? Travel? Pick up a hobby? Maybe even work part-time or consult? Retirement is a huge lifestyle shift, and the more intentional you are about how you’ll spend your time, the more fulfilling it will be.
Retirement impacts more than just you. Whether it’s decisions about living arrangements, legacy planning, or caregiving roles, not having the right conversations ahead of time can lead to tension—or worse, regrets that are hard to fix later.
What you can do now:
Make time to talk with your spouse or partner about your shared vision for retirement. If you have adult children, keep them informed about your plans, especially if they’ll be involved in any financial or caregiving decisions. You don’t need to have all the answers, but clear communication now can prevent a lot of stress down the road.
No one can plan perfectly. Life happens, and retirement rarely plays out exactly how we expect it to. But when we listen to those who’ve been through it, we get the chance to learn from their hindsight—and use it to shape better outcomes for ourselves.
Avoiding regret doesn’t mean avoiding risk. It means making thoughtful, informed decisions today that support the life you want tomorrow.
If you’re ready to take the next step in your planning, we’re here to help with tools, guidance, and resources designed to make it easier.
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This summer, we are skipping the burpees and giving your finances a glow-up. Four weeks. One challenge per week. Less stress. More savings. And yes, you can do it from a beach chair.
We’d all love to be whisked away to a private villa in Sicily or Bali where someone brings us espresso and warm pastries on a balcony with ocean views. But for most of us, a “big vacation” has to fit into the same budget that also pays for groceries, car insurance, and that unexpected vet bill.
Welcome to the world of loud budgeting, doom spending, and a whole new way of thinking,, and talking — about money.