Episode 70: The Retirement Readiness Audit: 5 Questions to Ask

Published June 1, 2026

Retirement confidence doesn’t come from guessing.
It comes from understanding how your income, taxes, planning, and long-term strategy work together.

In this episode of Money Monday, Darren Devine, Financial Planner with Sun Life and President of Devine & Associates, walks through five important questions that can help assess retirement readiness and identify potential planning gaps.

Many people assume they’re “probably okay” for retirement — but true confidence comes from clarity, not assumptions.

This episode explores key questions around:
→ Understanding your realistic monthly retirement income needs
→ Stress-testing your plan for longevity and market uncertainty
→ Knowing your after-tax retirement income
→ Reviewing beneficiary designations and estate coordination
→ Maintaining a written retirement plan that evolves over time

Retirement planning isn’t just about building wealth. It’s about understanding whether your income, tax strategy, estate planning, and long-term goals are aligned.

A retirement audit isn’t meant to create fear — it’s meant to create structure, awareness, and confidence.
Because when you understand where you stand, financial decisions become much easier to navigate.

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Related Money Monday Episodes

Retirement readiness is about more than savings alone. These Money Monday episodes explore how income, taxes, longevity, and planning work together to support long-term confidence.

Episode 56: What Will Your Paycheque Be in Retirement in 2026?
Understanding your retirement income sources can help you determine whether your monthly lifestyle goals are realistically supported.
Episode 60: Will You Outlive Your Money… or Will Your Money Outlive You?
A closer look at longevity risk and why retirement planning should account for long-term sustainability.
Episode 61: When Should I Take CPP? 60, 65, or 70?
Timing decisions around government benefits can significantly impact retirement income and long-term planning outcomes.
Episode 65: How Much Tax Will I Pay on My RRIF?
Understanding after-tax income is an important part of building a retirement plan that works in real life — not just on paper.
Episode 52: Do You Have a Written Plan — or Just Good Intentions?
A written retirement plan can help connect your income strategy, investments, taxes, and long-term goals into a coordinated roadmap.

The Retirement Readiness Audit: 5 Questions to Ask

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

Most people say,

“I think I’m on track for retirement.”

But when I ask a few simple follow-up questions…

That confidence often turns into uncertainty.

So today, let’s do something practical.

Let’s run a short retirement readiness audit.

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. I’ve been helping families across Ontario plan, protect, and enjoy their retirement income for over 20 years.

And one thing I’ve learned is this:

Retirement confidence doesn’t come from account balances.

It comes from clarity.

So here are five questions worth asking yourself.

1. Do You Know Your Monthly Retirement Income Target?

Not your savings number.

Not your investment return.

Your income target.

What will you realistically need each month to support your lifestyle?

Housing. Travel. Healthcare. Family support. Taxes.

If you don’t know your income target, it’s difficult to measure whether you’re truly prepared.

2. Have You Stress-Tested for Longevity?

Retirement today can last 25–30 years or more.

Have you tested what happens if you live longer than expected?

Or if markets underperform early in retirement?

Longevity risk isn’t dramatic — it’s gradual.

But it’s one of the biggest risks retirees face.

3. Do You Know Your After-Tax Income?

This one surprises many people.

Your retirement income may come from:

  • CPP
  • OAS
  • Pensions
  • RRIF withdrawals
  • Non-registered investments

Each source can be taxed differently.

The number that matters most isn’t gross income.

It’s what lands in your bank account.

If you don’t know your after-tax monthly amount, that’s a gap worth addressing.

4. Are Your Beneficiaries Current?

Beneficiary designations often outlive intentions.

Have you reviewed:

  • RRSPs
  • RRIFs
  • TFSAs
  • Insurance policies

Do they reflect your current family situation?

These forms typically override your Will.

They deserve attention.

5. Is Your Plan Written — and Updated?

Many people have investments.

Fewer have a coordinated retirement income plan.

Even fewer have a written plan that is reviewed regularly.

Retirement isn’t a one-time decision.

It’s an ongoing strategy.

The Bigger Picture

This isn’t about creating anxiety.

It’s about creating alignment.

If you can answer these five questions clearly and confidently, you’re likely on solid ground.

If you can’t, that doesn’t mean you’ve failed.

It simply means it’s time for structure.

If you’d like to walk through your own Retirement Readiness Audit and see how your numbers align with your goals, we’d be happy to help.

Clarity brings confidence.

And confidence changes how retirement feels.

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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