Pre-Retirement

The 5-Year Pre-Retirement Checklist for Canadians

July 19, 2026  |  7 min read

The five years before you stop working are the most consequential planning window of your financial life. The decisions made during this period, including when to take CPP, how to draw down registered accounts, whether to pay off the mortgage, and how to structure income in year one of retirement, can add or cost you hundreds of thousands of dollars over a 25-to-30-year retirement.

Most people spend more time planning a two-week vacation than they do planning the financial transition into retirement. This checklist is a starting point for getting serious about the five years that matter most.

Know Your Retirement Income Before You Retire

This sounds obvious but most people do not actually do it. Before your last day of work, you should have a clear projection of your year-one retirement income: the exact amount from CPP at your chosen start age, your OAS amount if applicable, any pension income, projected RRSP or RRIF withdrawals, and any other sources. You should also know your estimated tax on that income.

If that projected income does not cover your planned lifestyle, you need to know before you retire, not after. You still have time to adjust your retirement date, your savings rate, or your planned spending.

The Pre-Retirement Checklist

The five-year window closes faster than you expect. People who build a retirement income plan three to five years before stopping work consistently have more options than those who plan in the final six months. Deferring CPP requires income to bridge on. RRSP drawdown strategies need time to execute. The earlier you plan, the more levers you have to pull.

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Freehold Financial Planning is an advice-only, fee-for-service financial planning practice based in Windsor, Ontario, serving clients across Canada. This article is for educational purposes and does not constitute personalized financial advice.