Every year, over 2,000 Canadians are asked a simple question. If you could go back and change one financial decision, what would it be?
They’ve been running this survey for eight years now. Eight years. And Canadians keep naming the same regrets, in almost the same order, every single time.
I’m going to count down all ten. The six that show up in the data, the three I see running my financial planning practice that no survey captures, and at the very end… my own biggest financial regret. Which is probably not what you’d expect from a financial planner.
#10: Not Buying a Home
The data comes from FP Canada’s 2025 Financial Stress Index. Let’s start at the bottom.
Only 6% of Canadians say their biggest financial regret is not buying a home when they could have.
Six percent. In a country where housing dominates every dinner conversation, every election, every comment section…
And yet when you actually ask people what they regret most? It barely registers.
I think a big part of that is control. A lot of people who didn’t buy… couldn’t. It wasn’t really a choice. And people tend not to regret things that were never up to them.
#9: Not Getting a Better Education
8% of Canadians say their biggest regret is that they wish they’d gotten a better education. And this one’s less about the diploma on the wall and more about the earning trajectory it set. The Bank of Canada found that the wage premium for a university degree has been declining for 20 years. It went from 63% in 1997 to about 53% by 2018. A big part of that is supply. More graduates than ever, competing for jobs that don’t necessarily require their credentials. Meanwhile, demand for skilled trades has grown.
So when someone at 50 says “I wish I’d gotten a different education”… it’s not always that they wish they’d gone to university. Sometimes it’s that they wish they’d gone to trade school.
#8: Not Pursuing a Better-Paying Job
9% regret not pursuing a better-paying job. The comfort trap. Staying somewhere because it’s stable, not because it’s optimal.
And here’s the Canadian version of this you might not think about. Public sector golden handcuffs. A defined benefit pension is an incredible thing. But it can also keep you in a role you’ve outgrown for a decade longer than you should be there.
Public sector workers retire about two to three years earlier than private sector workers, which tells you the pension is doing its job. But the people who regret it aren’t the ones who stayed for the pension. They’re the ones who stayed for the pension and nothing else.
#7: Overspending
11% regret overspending. And look, nobody wakes up one morning and decides to blow through their money. A lot of the time, it’s slower than that. You get a raise. Six months later, your baseline has shifted. New car. Nicer dinners. Slightly better everything. You never made a decision to spend more. It just… happened.
That 11% is actually down from 14% in 2024. Fewer people regret overspending. Which might be the most lifestyle creep thing I’ve ever heard.
These are the kinds of regrets I help people avoid every day at Blueprint Financial. Whether you’re figuring out when you can actually afford to stop working, or you’re a business owner who needs an exit strategy that doesn’t leave money on the table, we build plans around your specific numbers. Not rules of thumb. If you want to talk it through, there’s a link below to book a free discovery call. Build the life you want, with the right Blueprint.”
#6: Not Investing Enough
20% regret not investing more, earlier, or more wisely. This number has been rock steady at 19 to 20% for four consecutive years. It doesn’t budge.
And it’s almost never “I picked the wrong stock.” It’s “I didn’t start.” The money was there. It just sat in a savings account because they were waiting for the right moment. A dip. A correction. Some signal. And the market just… kept going without them.
Here’s what that costs.
$500 a month in a TFSA at a conservative 7% return. Start at 25, by 65 you’ve got roughly $1.3 million. Tax free. Start at 35? About $610,000. You just lost $710,000 by waiting ten years. Start at 45? $260,000. You contributed $120,000 and only doubled it.
#5: Not Saving Enough
And then the big one from the survey.
21% of Canadians say their biggest regret is not saving more or starting earlier. Three years running at exactly 21%. The single most cited financial regret in the country.
And here’s what makes it worse. Canada’s household savings rate right now is only 4.7%. That’s the national average. If you’re in Ontario, it’s around 1.7%. British Columbia? 0.6%. For every dollar of disposable income, BC households are saving less than a penny. The two most expensive provinces to live in, and the ones saving the least.
Those are the regrets the surveys capture. But in my years of financial planning, I wanted to share some of the regrets that keep my clients up at night.
#4: Retiring Too Late
The average Canadian retires at 65. And most people assume they’ll have decades of good health ahead of them. But Statistics Canada just released updated numbers on something called health-adjusted life expectancy. It measures how many years you can expect to live in good health. Not just alive. Actually healthy enough to do the things you planned.
At age 65, that number is 15.3 years. So the average 65-year-old has about 15 good years left. That sounds like a lot… until you realize you’ll probably spend the first two or three figuring out what retirement even looks like. And then the knees start going. The energy dips. The travel gets harder. Your real window for doing the things you actually saved for is narrower than you think.
And yet I’ve sat across from clients who did everything right. Maxed every account. Hit their number. And then kept working for three, four, five more years. Because they didn’t feel ready. Because the number felt like it should be bigger. Because work was their identity and they didn’t have a plan for what came next.
And then something changed. Their spouse’s health. Their own energy. A trip they kept postponing that eventually became impossible.
You’d think the opposite of “not saving enough” is “saving too much.” It’s not. The opposite is saving enough and then not stopping. The money was ready. They weren’t. And by the time they were, the window had already started closing.
“If you’re thinking about how to keep more of what you’ve saved, we put together a free guide: 5 Proven Strategies to Save More on Taxes in Retirement. Grab it at:
👉 https://blueprintfinancial.ca/retirement-tax-saving-guide
#3: A Poorly Planned Business Exit
If you own a business, this one’s for you.
Only 9% of Canadian small business owners have a formal succession plan. Nine percent. And yet 76% plan to exit within the next decade. That’s over $2 trillion in business assets about to change hands with almost no planning behind it.
Here’s what’s at stake. There’s a lifetime capital gains exemption of $1.25 million on qualified small business shares. That can shelter a massive chunk of your sale from tax. But it doesn’t just happen. You need the right corporate structure in place years before you sell — holding company, share reorganization, asset purification. And CRA has a 24-month lookback: at least 90% of your company’s assets need to have been used in active business at the time of sale, and 50% for the two years before that. You can’t clean it up at the last minute.
If you wait until there’s a buyer at the table, you’ve already missed the window. And the regret isn’t “I didn’t build a good business.” It’s “I built a great business and left hundreds of thousands on the table because I never planned the ending.”
#2: Underestimating The Complexity of Leaving Canada
When you leave Canada and give up tax residency, CRA treats you like you sold most of your investments at fair market value on the day you left. It’s called a deemed disposition. Your TFSA, RRSP, and Canadian real estate are excluded. But everything else — non-registered investments, shares in a private company, crypto, foreign property — CRA wants their cut before you go.
And then there’s the RRSP trap. If you cash out your RRSP as a non-resident, the default withholding tax is 25%. And here’s the part that catches people off guard: even if you’ve moved somewhere with a tax treaty, lump-sum RRSP withdrawals usually don’t qualify for a reduced rate. In most cases, you’re still paying that full 25%
People assume moving abroad is like moving provinces. It’s not even close. It’s a full taxable event. And if you don’t plan for it, you can lose tens of thousands on the way out the door.
If this applies to you, or if you’re even starting to think about it, I did a full breakdown of departure tax in another post.
#1: My Personal Biggest Regret
Alright. I told you I’d share mine.
My biggest financial regret has nothing to do with a tax strategy I missed or an investment I should have made.
Conclusion
We all make mistakes. I try to view it as data, rather than regret it.
Here’s the thread that runs through every single one of these. They all felt small in the moment and enormous in hindsight. The thing about financial regrets is they don’t announce themselves. They accumulate quietly until one day you look back and realize the decision was already made.
If any of this hit close to home, don’t wait until the decision becomes permanent. Talk to someone — a planner, an advisor, or a professional who can look at your situation before small issues turn into expensive mistakes.
That’s exactly what we help Canadians do at Blueprint Financial. There’s a good chance at least one of the issues in this article applies to your situation right now.
If you’d like to find out what that means for you, explore our financial planning services.
And if you want more practical insights on taxes, retirement, and smart financial decisions, join our free financial newsletter.
The best financial decisions are usually made before you have to make them.
