Imagine asking a room of 70-year-olds what they’d do differently with money. The same five regrets come up, almost word for word — and every one of them was fixable decades earlier.
Picture it: a community hall, thirty folding chairs, thirty Canadians in their seventies with a lifetime of paycheques, mortgages, and surprises behind them. You ask one question — “What do you wish you’d done differently with money?” — and something strange happens: they all start describing the same five mistakes.
This is a composite, not a real survey — but the regrets are real. They’re the ones that surface in every retirement study and every honest conversation with someone who’s run out of runway. Nobody in that imaginary room says “I wish I’d bought a bigger TV.” They talk about time, habits, and small decisions that compounded — for them or against them.
Here are the five regrets, in the order they come up most often — and, more importantly, the fix for each one that you can apply now, while time is still on your side.
Regret #1: “I Never Started Investing. I Just… Didn’t.”
The story: This is the most common regret by a mile, and the saddest, because it was never about money — it was about inertia. “I kept meaning to look into it,” says our composite 70-year-old. “Then I was 40. Then 50. The money sat in savings the whole time. I did everything right — I saved! — and it still wasn’t enough.”
She’s describing the stillness tax: $50,000 left in a savings account for 20 years grows to roughly $55,000, while the same amount invested at a hypothetical 7% annualized could compound to roughly $193,000 — about $138,000 of growth that never happened, purely because the money never got its assignment. (Full math in our companion piece on the TFSA vs RRSP $50,000 rule.)
Nobody in the room lost their savings in a market crash. That’s the irony — the people who feared investing didn’t avoid losses; they chose the slowest, quietest loss available.
The fix you can apply now: Open a TFSA at a beginner-friendly brokerage (Wealthsimple and Questrade are common Canadian starting points), set up an automatic monthly contribution — even $50 — into a broad, low-cost index ETF, and leave it alone for decades. You don’t need to understand everything first; you need the account to exist. The 70-year-olds in our imaginary room would trade an awful lot for the compound years you’re holding right now. (General education, not personalized advice.)
Regret #2: “Every Raise Disappeared Into a Bigger Life”
The story: “I made $35,000 at 25 and $95,000 at 55,” says the man in the third row. “And somehow I was still living paycheque to paycheque at both ends. Every raise bought a nicer car, a bigger place, better vacations. I wasn’t reckless — I just… expanded. My savings rate at 55 was the same as at 25: basically zero.”
This is lifestyle inflation, and it’s the reason high earners go broke just as reliably as low earners: if spending rises in lockstep with income for 30 years, your wealth at the end is roughly the same as someone who earned half as much and saved the difference. Income is what you earn; wealth is what you don’t spend.
The cruelest part: none of the upgrades made them happier for long. The nicer car felt normal within months. Psychologists call it the hedonic treadmill — satisfaction resets, but the spending doesn’t.
The fix you can apply now: Bank half of every raise. When your income goes up, automatically redirect at least 50% of the increase to savings or investments before your lifestyle adjusts — you never miss money you never got used to having. A $4,000 raise with half banked is $2,000 a year in new savings, every year. Do this three or four times across your career and you’ve quietly built the retirement fund your 70-year-old self will thank you for. For the full playbook, read How to Stop Lifestyle Inflation.
Regret #3: “My Money Sat in the Wrong Account for Decades”
The story: “I had a TFSA,” says the woman by the window, a little defensively. “I opened one in 2009 when they started. I just… kept cash in it. I thought the account was the investment. Nobody told me I had to actually buy something inside it.”
Heads nod around the room. This regret has two flavors. Flavor one: keeping long-term money in a regular savings account instead of a TFSA or RRSP, paying unnecessary tax on growth for years. Flavor two — more common than you’d think — is opening the right account and then leaving it in cash, earning next to nothing, while assuming the tax shelter was doing the work. The shelter only protects growth; it can’t create it.
The fix you can apply now: First, check what your TFSA and RRSP actually hold — log in today and look. If the answer is “cash” and the money is for long-term goals, that’s a stillness-tax situation wearing a tax-shelter costume. Second, learn the basic division of labour: TFSAs are generally flexible and great for long-term wealth building; RRSPs give you a tax deduction now and are built for retirement. The full breakdown with real numbers is in TFSA vs RRSP: The $50,000 Rule for Canadians. The account is the container; the investment is the contents. You need both.
Regret #4: “I Had No Cushion When Life Hit — and Life Always Hits”
The story: The room gets quieter for this one. “The layoff came at 47,” says one man. “Six months, no work. We put everything on credit cards — the mortgage payments, the groceries, all of it. We were still paying off that stretch at 60.” Another woman: “My husband got sick. I cut my hours to care for him. There was no backup plan because we’d never made one.”
Here’s what the 70-year-olds want you to understand: it’s not a question of whether an expensive surprise arrives, but when. And without an emergency fund, every surprise gets financed at the worst possible price: high-interest debt, exactly when your income is lowest.
The debt from one bad year can shadow you for a decade. Credit card balances at ~20% interest don’t just sit there; they grow while you’re trying to recover, turning a six-month crisis into a five-year repayment plan. Several people in our imaginary room trace their thin retirements not to low lifetime earnings, but to one uninsured stretch in their 40s or 50s that they financed with plastic and never fully escaped.
The fix you can apply now: Build an emergency fund of 3–6 months of essential expenses in a separate high-interest savings account — separate being the operative word, so it doesn’t quietly become vacation money. Start with a mini-goal: $1,000 as fast as you can, then one month of expenses, then keep going. Automate a transfer every payday; even $75 per paycheque gets you to $1,950 in a year without a single decision. For the full how-to, read 5 Reasons You Need an Emergency Fund.
Regret #5: “I Ignored the Small Leaks — Fees, Subscriptions, and ‘Just $12.99′”
The story: “I want to laugh about this one, but I can’t,” says the last speaker. “I paid 2.3% a year on my mutual funds for thirty years because my advisor was a nice guy and I never asked what it cost. And the subscriptions — I was paying for three streaming services I hadn’t opened in months. Death by a thousand $12.99s.”
Small leaks compound just like investments do — against you. On a $100,000 portfolio growing at a hypothetical 7% before fees, paying 2% a year in fees versus 0.25% costs a six-figure sum over 25 years, because every dollar paid in fees is a dollar that stops compounding for decades. The 70-year-olds didn’t feel the fees leaving; they felt the smaller balance arriving.
Subscriptions and micro-spending work the same way in reverse: they don’t feel like decisions at all, which is why they survive every budget. Three forgotten subscriptions at ~$13 a month is nearly $500 a year — money that could have been an extra TFSA contribution, compounding quietly in your favour instead of a streaming company’s.
The fix you can apply now: Do a 30-minute money leak audit this weekend. List every subscription and cancel what you haven’t used in 30 days. Then check the fee on every investment you own — look for the MER (management expense ratio). If you’re paying over 1% on a basic diversified fund, know that lower-cost index alternatives exist, often under 0.30%. You don’t need to become a fee obsessive; you just need to ask the question once. (Our 10 Saving Money Hacks That Actually Work has nine more leaks to plug, each with the math.)
Common Mistakes Younger Readers Make With These Regrets
Mistake #1: Treating this as a “someday” list. The entire theme of the room is that someday never came. Every regret above was fixable with a 20-minute action — opening an account, setting up a transfer, checking a fee — that got postponed for years. If reading this article doesn’t produce one concrete action today, it’s entertainment, not education.
Mistake #2: Trying to fix all five at once. Overhauling your entire financial life this weekend leads to burnout by Wednesday. Pick the regret that stung most while reading — that’s your starting point. One system, run for a month, then add the next.
Mistake #3: Assuming high income will solve it. Regret #2 exists precisely because income doesn’t solve it. The differentiator was never the salary; it was the savings rate and the systems. A $60,000 earner who saves 20% builds more wealth than a $120,000 earner who saves nothing — the math doesn’t care about your job title.
Quick Answers to Common Questions
I’m in my 20s or 30s — is it really not too early to think about this? It’s the best time. Every regret in this article is, at its core, a regret about wasted time — and time is the one asset you currently have in abundance. A dollar invested at 25 has roughly twice the compounding runway of a dollar invested at 35. Your 70-year-old self is begging you not to waste the decade you’re in right now.
I’m in my 50s — is it too late? No. The math is less generous than at 30, but every year of better habits still counts — and the non-investing regrets (emergency fund, fees, lifestyle inflation) pay off at any age. The worst response to “I wish I’d started earlier” is to keep not starting.
Which regret should I fix first? The emergency fund (Regret #4) comes first — investing while one surprise away from credit-card debt is building on sand. Then start investing (Regret #1), even small. Then plug the leaks (Regret #5), check your accounts (Regret #3), and set up the raise rule (Regret #2). That’s a complete system, built one layer at a time.
Do I need a financial advisor for any of this? Not necessarily to start. The fixes above — emergency fund, automatic TFSA contributions to a low-cost index ETF, a subscription audit — are all DIY-friendly. An advisor can help with complex situations, but don’t let “I need professional help” become another way to postpone the 20-minute actions. And if you do hire one, ask what they charge — see Regret #5.
Final Thought
Here’s the thing about the room of 70-year-olds: none of them needed brilliance. None of the five regrets required genius to avoid — just a savings account with a purpose, an investment account that actually got funded, half of each raise set aside, and the occasional glance at fees. The bar was never high. It was just early, and early is the part you can’t get back.
You are, right now, someone’s “younger self.” So pick one regret — the one that hit hardest — and fix it this week. Twenty minutes. One action. That’s the whole difference between the people in the chairs and the people who never had to sit in them.
Start with the habit that funds everything else.
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Happy Budgeting!
Stanley
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