Retirement decision checks.
Technical rules matter, but the practical answer depends on the household context around them.
| Decision | What to check first |
|---|---|
| Draw registered money | Marginal tax rate, withholding, RRIF minimums, future OAS exposure. |
| Use TFSA/cash | Emergency reserve, tax-free flexibility, large expenses, future contribution room. |
| Sell taxable assets | ACB, capital gains/losses, dividend/interest income, tax-slip timing. |
Five years before retirement is a useful planning window. There is still time to review income sources, tax timing, investment risk, insurance, debt, estate documents, and whether the current advisor setup is built for retirement income.
Key takeaways
- Build a first retirement-income timeline.
- Review investment risk before withdrawals begin.
- Check insurance needs before employment coverage ends.
- Identify documents that will matter for CPP, OAS, pensions, RRSPs, and tax returns.
Who this applies to
Use this when retirement is within about five years and benefit estimates, pensions, savings, debt, insurance, tax records, and account roles need to be organized before the final work-date decision.
If the matter is urgent, legal, tax-filing specific, investment-trade specific, or account-instruction specific, start with the right professional or institution instead of relying on a public article.
The planning issue
- Build a first retirement-income timeline.
- Review investment risk before withdrawals begin.
- Check insurance needs before employment coverage ends.
- Identify documents that will matter for CPP, OAS, pensions, RRSPs, and tax returns.
A five-year retirement checklist should show what to gather, what to decide now, and what can wait before employment income changes.
Example Ontario scenario
A couple plans to retire in 2031. They have not chosen CPP or OAS dates, the RRSPs are growth-oriented, insurance is old, and the tax return has started to include investment income. Five years is enough time to organize the decisions.
The first planning conversation would list the pension, CPP/OAS, tax, insurance, debt, and account records that need to be clarified before the final work-date decision.
Documents to gather
- Latest tax return and notice of assessment
- CPP and OAS estimates or My Service Canada details
- Pension estimate or benefit booklet
- RRSP/RRIF, TFSA, non-registered, LIRA/LIF, and corporate account statements
- Insurance summary and beneficiary information
Keep sensitive documents out of public notes and ordinary email until the office confirms the secure route.
Red flags to slow down for
- Waiting until the final work date to gather pension, CPP, OAS, and account records
- Assuming age 65 is automatic without reviewing bridge income and tax
- Ignoring debt, insurance, employer benefits, or spouse/survivor context
- Changing investments before the retirement-income need is defined
Questions that change the next step
- What decision is actually being made, and what can wait?
- Which facts would change the answer?
- What costs, taxes, fees, or paperwork could appear if action is taken now?
- Who else needs to be involved before anything permanent changes?
- What would a clean next step look like after the first conversation?
Professional boundaries to keep clear
- Financial advisor or planner
- Accountant or tax preparer
- Lawyer for estate documents
- Current pension or account institution
- Insurance professional when coverage is part of the question
Sources checked
- Canada.ca: Prepare for retirement
- Canada.ca: CPP retirement pension timing
- Canada.ca: Old Age Security pension recovery tax
- CRA: RRSP options when you turn 71
Related Stiller pages
- Retirement Income Planning
- Downloads
- Tax Planning & Preparation
- Investment Review & Portfolio Planning
- Estate & Inheritance Planning
Article-specific next step
Build the income map first. If this topic connects to your situation, use the First-Call Checklist or review the Retirement Income Planning page before booking a first call.
