When AI Gets Your Retirement Wrong
- Jordan Defazio
- Apr 17
- 4 min read
You asked AI when to take out your CPP.
It gave you a confident answer.
But it didn’t ask about:
the rental property
your wife's pension
about your health situation
And yet the answer came out clean, certain, and final.
“Great question! I completely understand your situation. Here's a personalized retirement plan tailored just for you!"
That's the real problem with AI and retirement planning.
It's not that the tool is always wrong.
It's that it's always confident, even when it only has a sliver of your story.
Why AI Sounds Right Until It Isn't
AI is fast, fluent, and fakes sounding like an expert.
It also operates from a fraction of your full picture.
On a recent episode of More Than Money, we asked whether you should be using AI to plan your retirement.
The short answer is for some things it can work but for others it’s unable to.
Because AI can't see what you can like:
Your full income picture
Your spouse's situation
Your estate plans
Your timeline
Your health
A retirement plan built on a sliver of the truth is a plan that breaks in the places you didn't know to check.
What Can AI Miss About Canadian Retirement?
Here are four places where the gap matters most.
1. The OAS ClawbackFor 2026, the OAS recovery tax begins once your net income crosses $95,323.
Above that line, you lose 15 cents of OAS for every dollar.
A withdrawal plan that looks fine in isolation can quietly push you past the threshold.
Without your full picture, AI can't warn you.
2. RRSP and TFSA Withdrawal Order
What’s really crucial is to know what order to use your accounts, because it can impact many
factors.
Get it right - and you can stretch your assets further and protect your OAS.
Get it wrong - and you can pay avoidable tax.
AI can't tell you which order is right without first knowing what your life is like and what your
financial situation is.
3. Pension Income Splitting
Starting at 65, you can split up to 50% of eligible pension income with your spouse.
For many couples, it can help them spare headaches when retirement planning.
But it only works if someone knows how to ask and how to structure it.
4. CPP Timing
Taking CPP early feels safer.
Delaying it to 70 increases your benefit by 42% for life.
The right answer depends on your health, your other income, your spouse, and how long your family tends to live.
AI doesn't know any of that.
But you do.
Trust your instinct on when to rely on it and when to rely on you.
The Things AI Can't Feel
Numbers are the easy part of retirement.
The hard part is everything around them.
The spouse who's anxious about the markets
The adult child who keeps needing help
The parent moving into care
The business you're still half-running
The grief of selling the family home
The quiet question of how many healthy years you have left
No model weighs any of that.
Retirement isn't a math problem.
It's a life problem with math inside it.
What AI Is Actually Useful For
AI isn't useless.
Used well, it's a genuinely helpful assistant.
It can:
Draft budget scenarios
Explain unfamiliar terms
Brainstorm the questions you should be asking
Help you organize paperwork before a meeting
It's a fine research tool.
It's a poor advisor.
Retirement Planning in the Age of the Chatbot
Use AI as a calculator, not a compass.
Check every number against someone who knows the rulebook and the full picture of your life.
Because a plan that almost works, is a plan that eventually doesn't.
At PKAG, we help Canadians build retirement plans that hold up when rules, markets, and life all shift at the same time.
If you have any questions, feel free to contact us.
You can also book a meeting with us and we can go over it in person.
We also have free, no-obligation seminars where we'll discuss AI, tax strategy, and how to stay in control of your retirement plan.
We look forward to hearing from you.
This commentary is intended to provide general information and should not be construed as tax, legal, financial, or other advice. Individual circumstances and current events are critical to sound planning; anyone wishing to act on the information presented should consult with his or her tax, legal or financial advisor.
This information, including any opinion, is based on various sources believed to be reliable, but its accuracy cannot be guaranteed and is subject to change.David Popowich, Faisal Karmali, Leanna Wachniak, Robert Gerrie are Investment Advisors with
CIBC Wood Gundy in Calgary. The views of David Popowich, Faisal Karmali, Leanna
Wachniak, Robert Gerrie do not necessarily reflect those of CIBC World Markets Inc.
CIBC Private Wealth consists of services provided by CIBC and certain of its subsidiaries,
including CIBC Wood Gundy, a division of CIBC World Markets Inc.




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