Most people spend more time planning a two-week vacation than they do confirming whether they are actually ready to retire. That is not a criticism. Retirement planning is genuinely complex, and the stakes are high enough that it is worth slowing down before you hand in your notice.
This checklist is not about whether you have saved enough. It is about whether you have done the thinking required to turn your savings into a reliable, tax-efficient income for the next 25 to 30 years. These are the ten things worth confirming before you stop working.
1. You Know Exactly Where Your Income Will Come From, Year by Year
Not roughly. Not “from my RRSPs and CPP.” Exactly.
A retirement-ready income plan tells you the specific dollar amount coming from each source every year: RRIF, TFSA, non-registered accounts, CPP, OAS, defined benefit pension, LIF, or any combination of those. It shows your gross withdrawals, the estimated tax on each, and what actually lands in your account after everything is accounted for.
If your answer to “where will my income come from next year” is a general wave at your portfolio, that is a sign the plan needs more work before you retire.
2. Your CPP Timing Has Been Properly Modeled
Taking CPP at 60 versus 70 is not a trivial difference. The gap in monthly payments between those two ages is $1,175.95 per month at the maximum level, and roughly $626 per month for average earners. That is permanent, for the rest of your life, and indexed to inflation.
Before you retire, this decision needs to be modeled against your full income picture, not decided based on gut feeling or what a friend did. The right answer depends on your health, your other income sources, your tax situation, and whether you have savings to bridge the gap while you wait. A Canadian who reaches 65 in good health has an average life expectancy of roughly 84 for men and 87 for women, which means most healthy retirees will live well past the breakeven age for deferring. But that is a general statement, not your answer. Your answer requires proper modeling.
3. You Understand Your OAS Clawback Risk
Old Age Security is worth roughly $8,900 per year at age 65 in 2026, growing with inflation over time. Over a 25-year retirement, that adds up to well over $200,000. It is worth protecting.
Once your net income exceeds $95,323, the CRA recovers OAS at 15 cents for every dollar above that line. RRIF withdrawals, CPP, pension income, and even the gross-up on eligible Canadian dividends all count toward that threshold. TFSA withdrawals do not count at all.
Before you retire, confirm whether your planned income in the years you collect OAS will push you above that line, and if so, whether there are structural changes (pension splitting, account sequencing, RRSP drawdown timing) that can protect your entitlement before it starts getting clawed back.
4. Your RRSP Drawdown Strategy Is Designed, Not Defaulted
The default for most Canadians is to leave the RRSP untouched for as long as possible and convert it to a RRIF at 71, then take only the minimum withdrawal each year. For most people, that default is not optimal.
The years between retirement and age 65 (or 71 if you work longer) are often a window of relatively low income. Drawing the RRSP down strategically during those years, at a lower tax rate, shrinks the eventual RRIF balance and reduces future mandatory withdrawals that could otherwise push you into higher brackets or trigger OAS clawback later. Converting to a RRIF at 65 rather than 71 also unlocks pension income splitting with a spouse and the $2,000 pension income tax credit.
If your plan is simply to leave the RRSP alone until the government forces your hand, confirm with an advisor whether that is actually the best path or just the path of least resistance.
5. Your TFSA Is Built Up and Protected
The cumulative TFSA room in 2026 is $109,000 for anyone who has been eligible since 2009. That is a significant tax-free pool, and in retirement it becomes one of your most valuable tools.
TFSA withdrawals do not show up on your tax return. They do not affect OAS clawback calculations. They do not push up your effective tax rate. In a well-designed retirement plan, the TFSA acts as a flexible buffer: use it in higher-spending years (a big trip, a renovation, an unexpected expense) without triggering tax consequences, and replenish it in lower-spending years.
Before you retire, confirm your TFSA is as large as it can reasonably be, and that your plan does not drain it too early. Depleting it in the first few years of retirement to “pay less tax now” is one of the most common and most costly DIY planning mistakes.
6. You Have a Cash Wedge in Place by Account Type
Market downturns happen. They are not rare events. A retiree who is forced to sell investments at a loss in a down market to cover living expenses locks in that loss permanently. The cash wedge strategy protects against that.
The idea is straightforward: keep 2 to 3 years of planned withdrawals from each account type in safe, non-market assets. If your plan calls for $30,000 per year from your RRIF, roughly $90,000 of your RRIF should be sitting in cash or cash equivalents. This gives you the flexibility to leave your invested assets alone during a downturn and wait for recovery before drawing them down.
One important detail here: the cash needs to be in the right account. Cash sitting in your TFSA does not help you if the plan requires withdrawals from your RRIF. The wedge must align with where the withdrawals are actually coming from.
7. Your Portfolio Is Aligned with Your Withdrawal Plan
Once you know the sequence and amount of your planned withdrawals, your portfolio structure needs to reflect that. This is often where the gap between a savings mindset and a retirement income mindset shows up most clearly.
In accumulation, the focus is on growth. In decumulation, the focus shifts to reliably generating the income your plan requires without being forced into bad timing decisions. That may mean holding more stable assets in accounts you plan to draw from soon, and keeping growth-oriented investments in accounts with longer time horizons like your TFSA.
Before you retire, confirm that your portfolio and your withdrawal plan are actually talking to each other.
8. Your Estate Documents Are Current
This one is easy to defer and surprisingly common to get wrong.
Before you retire, confirm that your will is current and reflects your actual wishes. Confirm that your power of attorney is in place and that the person named is still the right choice. Then go account by account and confirm that beneficiary designations are up to date on your RRSP, RRIF, TFSA, and life insurance policies.
An outdated beneficiary designation, like one that names a deceased person or an ex-spouse, routes those funds back through your estate. In Ontario that means probate fees of 1.5% on the value above $50,000, paid before anything reaches your beneficiaries, plus delays and legal complexity that the right designation would have avoided entirely.
This takes a few hours to review and update. It is worth doing before you retire, not leaving it as something to get to later.
9. Your Plan Has Been Stress Tested
A retirement plan that only works if markets cooperate and nothing unexpected happens is not a complete plan.
Before you retire, run at least two stress tests. The first: what happens if investment returns only match inflation (roughly 2 to 2.5%) for the first decade of your retirement? Can you still sustain your income without running out of savings? The second: if one spouse passes away earlier than expected, is the surviving spouse financially okay? CPP survivor benefits cover up to 60% of the deceased spouse’s pension. OAS does not transfer. A defined benefit pension may have a survivor option or may not. These details matter and the answers should be in your plan before you need them.
If your plan has never been deliberately broken to see where the cracks are, it has not been fully tested.
10. You Know What You Are Retiring To, Not Just From
This one is not about money, but it belongs on this list because it affects everything else.
The retirees who struggle most, even those who are financially well-prepared, are often the ones who planned their exit from work in great detail but gave almost no thought to what comes next. The commute is gone. The routine is gone. The built-in social structure of work is gone. And if there is nothing specific to replace it, that freedom can turn into restlessness or isolation faster than most people expect.
Before you retire, have a real answer to the question: what am I actually going to do with my time? Not a vague one. A specific one. Hobbies, travel, volunteering, part-time consulting, time with grandchildren, whatever it is. The financial plan works best when it is funding a life you have genuinely thought about living.
Putting It All Together
Retirement readiness is not a single moment. It is the result of a set of decisions made deliberately, in advance, while you still have time to adjust them.
Going through this checklist honestly before you stop working is not about finding reasons to delay. It is about walking into retirement with confidence that the financial side is properly handled, so you can focus on everything else.
If several of these items feel unclear or unresolved, that is not a reason to worry. It is a reason to sit down with a retirement income specialist before you hand in your notice. A few hours of planning now can make a significant difference across a retirement that could easily last 30 years.