Retiring at Year-End? Your 90-Day Countdown Starts Now

For many of our clients, December 31 is circled on the calendar. Here's what to settle between now and then.

By Jennifer Jackson, Senior Wealth Advisor | The Jackson Group at CIBC Wood Gundy | October 2026

Every fall, our phones get busier. A lot of the people we work with, particularly at 3M, General Dynamics and other large employers across Southwestern Ontario, have picked December 31 or January 1 as their last day. The finish line is finally in sight.

It's an exciting time. It's also the stretch where the most important financial decisions of your working life get made in just a few weeks, usually while you're also training your replacement and planning a farewell lunch.

Here's what we help our clients settle in the final ninety days. You only get to retire once. The decisions in these last few weeks can shape the next thirty years, so give them the time they deserve.

1. Your pension choice

If you have a defined benefit pension, you may be offered a choice. You can take a monthly pension for life, or take the commuted value as a lump sum. This is often the biggest single financial decision you'll ever make, and it's usually irreversible.

There's no universal right answer. It depends on your health, your spouse, your other savings, your appetite for managing investments and how much you value a guaranteed cheque. Be aware that commuted values move with interest rates, that a portion of a large lump sum may be paid out as taxable cash rather than transferred tax-free, and that your election window is limited. Read your package the week it arrives.

2. The timing of your severance and final pay

A retirement date of December 31 versus January 1 can make a real difference on your tax bill. Retiring allowances, vacation payouts and bonuses paid in January land in a new tax year, often one where your income will be much lower. Depending on your years of service, part of a retiring allowance may also be transferable directly to your RRSP, and unused RRSP room can absorb more. Ask HR what can be timed before you sign anything.

3. Your benefits

Find out exactly which health, dental and life insurance coverage continues into retirement, what it costs and what ends on your last day. If group life insurance is ending, decide whether you still need coverage, and whether converting it makes sense, before the deadline passes.

4. Your income map

Your paycheque is about to stop. We build what we call an income map. It shows which accounts you draw from, in which order, and when CPP and OAS start. The goal is for your money to arrive each month like a salary, and for you to pay as little tax as possible over your whole retirement, not just next year. For couples, this includes pension income splitting.

5. Your first year

This is the part people skip. What will you actually do on Monday, January 4? The clients who thrive in retirement usually have a few things planned, such as a trip, a project, a volunteer role or a standing coffee with friends. Put something in the calendar for the first few months. It matters more than you'd think.

Our suggestion

If you're retiring at year-end, or even just thinking about it for next year, book a meeting before your pension package arrives. We know these plans well, and we'll walk through the options side by side with real numbers, so you can make your decision with confidence rather than on a deadline.

You've worked hard for this. Let's make sure the landing is a smooth one.

Warmly,

Jen

"Wealth isn't just about your money. It's living along the way."