Episode 75: What Are the Biggest Financial Mistakes People Make 5 Years Before Retirement?

Published July 6, 2026

Five years before retirement is one of the most important planning windows you'll ever have.

In this episode of Money Monday, Darren Devine, Financial Planner with Sun Life and President of Devine & Associates, discusses the critical five-year period leading up to retirement.

For many Canadians, this stage represents a shift from accumulating wealth to preparing income, managing risk, and ensuring all aspects of their financial plan work together.

This episode explores six common mistakes that can impact retirement readiness:
→ Not understanding what retirement will actually cost
→ Assuming retirement income will simply "work itself out"
→ Taking too much—or too little—investment risk
→ Carrying unnecessary debt into retirement
→ Focusing only on investments while neglecting other planning areas
→ Waiting too long to build a coordinated retirement plan

You'll also learn why retirement planning involves much more than account balances. Income strategy, taxes, estate planning, insurance, and risk management all play important roles in creating a successful retirement.

The good news?
Five years before retirement is often the ideal time to make adjustments, test assumptions, and improve your plan while you still have flexibility.

Because retirement should not feel like a guess.
It should feel like a plan.

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Money Monday Related Episodes 

Retirement readiness isn't built overnight. These episodes explore the planning decisions, income strategies, and financial considerations that can help make the transition into retirement smoother and more predictable.

Episode 70: The Retirement Readiness Audit: 5 Questions to Ask
A practical self-assessment designed to help identify potential gaps in your retirement strategy before they become bigger concerns.
Episode 74: How Much Money Do I Need to Retire in Canada?
Understanding your retirement income needs is one of the most important steps in determining whether your current savings strategy is on track.
Episode 56: What Will Your Paycheque Be in Retirement in 2026?
Retirement planning isn't just about building assets—it's about understanding how those assets will generate reliable income when you stop working.
Episode 27: Does Your Investment Strategy Match Your Life Stage?
As retirement approaches, your investment strategy should evolve alongside your goals, timeline, and comfort with risk.
Episode 66: Should You Pay Off Your Mortgage Before Retirement?
Debt management becomes increasingly important as retirement approaches. This episode explores one of the most common questions pre-retirees face.

What Are the Biggest Financial Mistakes People Make 5 Years Before Retirement?

Presented by Darren Devine, CFP®, CLU®, Financial Planner, Sun Life and President of Devine and Associates Financial Services Inc.

Retirement is close enough to feel real… but still far enough away to put things off.
And that’s exactly where some of the biggest financial mistakes happen.

Hello, and welcome to Money Monday, where we help simplify your financial journey. I'm Darren Devine, Financial Planner with Sun Life and President of Devine & Associates. For over 20 years, I’ve been helping families across Ontario plan with confidence, protect what matters most, and stay grounded through life’s financial ups and downs.

When people are about five years away from retirement, they’re often in a really important transition period.

They’re no longer just building wealth for “someday.”

They’re getting close enough that the decisions they make now can have a real impact on how retirement actually looks and feels.

And this is where we often see a few common mistakes.

Mistake number one: Not knowing what retirement will actually cost.

A lot of people have a savings goal in mind, but they haven’t really worked through what their monthly retirement lifestyle will cost.

What will you spend on housing?

Travel?

Groceries?

Healthcare?

Helping children or grandchildren?

Replacing a vehicle?

Home maintenance?

Retirement isn’t just about hitting a number.

It’s about understanding the lifestyle that number needs to support.

Mistake number two: Assuming your income will “just work itself out.”

Many people know they’ll have some combination of CPP, OAS, pensions, RRSPs, TFSAs, or non-registered savings.

But they haven’t mapped out how those pieces will work together.

For example:
Where will your monthly income come from?
When should you start drawing and from which account?
How do taxes fit in?
And will your income be reliable enough to support your spending?

Without a coordinated income plan, retirement can feel much more uncertain than it needs to.

Mistake number three: Taking too much risk—or not understanding the risk you’re taking.

Five years before retirement is usually not the time to be guessing.

Some people stay too aggressive because they feel behind.
Others get overly cautious and move everything into cash too early.
Neither extreme is ideal.

This stage is really about making sure your investments still match your timeline, your goals, and your comfort with volatility.

Mistake number four: Ignoring debt heading into retirement.

Not all debt is equal, but going into retirement with high monthly debt payments can put pressure on cash flow.

This could include:

  • a mortgage
  • lines of credit
  • credit cards
  • car loans
  • or even helping family in a way that strains your own finances

The closer you get to retirement, the more important it becomes to understand what debt you want gone, what debt is manageable, and how it fits into the bigger picture.

Mistake number five: Forgetting that retirement planning is more than investing.

A lot of people focus almost entirely on their portfolio.

But the years leading up to retirement are also the time to review:

  • insurance needs
  • beneficiary designations
  • wills and powers of attorney
  • tax efficiency
  • and what happens if life doesn’t go exactly according to plan

Good retirement planning isn’t just about growing money.
It’s about protecting the life you’re building.

Mistake number six: Waiting too long to make a real plan.

This may be the biggest one of all.

Too many people spend the final years before retirement hoping things will come together instead of testing the plan ahead of time.

Five years out is actually a great time to ask:

  • Am I on track?
  • What needs adjusting?
  • What can I still improve while I have time and flexibility?

Because small changes made now can have a much bigger impact than last-minute decisions made later.

The good news is this:
If retirement is five years away, you still have time.

  • Time to fine-tune.
  • Time to reduce stress.
  • Time to create a plan that helps you move into retirement with more clarity and confidence.

So if you’re getting closer to retirement and you’re not quite sure whether all the pieces are working together, this is the right time to take a closer look.

Because retirement should not feel like a guess.
It should feel like a plan.

Thanks for tuning into Money Monday. Don’t forget to like and comment for more episodes filled with tips to help make your financial journey a breeze. Until next time, I'm Darren Devine, and you can always talk to us today at DevineAndAssociates.ca!

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