Episode 76: The First 90 Days of Retirement: What No One Prepares You For

Published July 13, 2026

Retirement isn't just the end of a career.
It's the beginning of an entirely new chapter.

In this episode of Money Monday, Darren Devine, Financial Planner with Sun Life and President of Devine & Associates, explores a side of retirement that many people don't anticipate.

The transition itself.

While retirement planning often focuses on savings, investments, pensions, and income projections, the reality is that retirement is also a significant lifestyle and emotional adjustment.

This episode explores five key areas retirees commonly experience during their first few months of retirement:
→ Adjusting from a regular paycheque to multiple retirement income sources
→ Navigating changes in routine, purpose, and identity
→ Understanding how spending patterns often change in early retirement
→ Managing travel and lifestyle expenses intentionally
→ Avoiding unexpected tax surprises as income sources shift

You'll also learn why even well-prepared retirees can feel uncertain during this transition—and why that's completely normal.

The first 90 days often reveal how your financial plan functions in real life.
When income, lifestyle, and expectations align, retirement tends to feel more comfortable and sustainable.

Because retirement isn't simply about leaving work behind.
It's about building a new rhythm for the years ahead.

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Money Monday Related Episodes

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Episode 58: If You Retired Today, What Would You Keep — or Change — in Your Lifestyle?
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Episode 56: What Will Your Paycheque Be in Retirement in 2026?
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Episode 74: How Much Money Do I Need to Retire in Canada?
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Episode 70: The Retirement Readiness Audit: 5 Questions to Ask
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Episode 49: New Year, New Budget: How Retirees Can Help Beat Creeping Costs
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The First 90 Days of Retirement: What No One Prepares You For

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

Everyone plans for retirement.
Very few people plan for what it actually feels like.
No one talks about the first 90 days.
And those first three months?
They can be the most financially and emotionally revealing of your life.

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 I can tell you — retirement isn’t just a financial event.
It’s a life transition.

Let me tell you about someone I’ll call David.

David retired at 66.

  • He had a solid plan.
  • CPP timing mapped out.
  • RRIF strategy in place.
  • No debt.
  • Healthy portfolio.

On paper? Perfect.

But 60 days in, he called me.
Not because something was wrong.
Because something felt… different.

That brings us to

5 things to consider:

1. The Income Rhythm Shift

For 40 years, David was paid every two weeks.
Then suddenly — no paycheque.
Even though the money was there, it felt strange.

In retirement, income becomes:

  • CPP
  • OAS
  • Pension and
  • RRIF withdrawals

But it doesn’t feel the same as a salary.
That psychological shift takes adjustment.

That’s why structuring retirement income to resemble a predictable “paycheque” can make a huge difference in confidence.

2. The Identity Shift

This one surprises people.

When you stop working, you don’t just lose income.
You lose routine. Structure. Sometimes even identity.

Many retirees experience a quiet question:
“Now what?”

And that can influence spending decisions more than people realize.

Some overspend early.
Others underspend out of fear.

Both are emotional reactions.

3. Spending Pattern Changes

Here’s what often happens in the first 90 days:

Spending spikes:

  • More dinners out.
  • Home projects.
  • Celebration trips.
  • Helping children.

It’s natural — retirement feels like a reward.

But if early spending isn’t coordinated with your income strategy, it can create unnecessary stress later.

4. Travel & Lifestyle Budgeting

Pre-summer retirements often mean immediate travel plans.
But lifestyle inflation can sneak in quietly.

It’s not just one trip.
It’s:

  • Flights, insurance,
  • upgraded accommodations,
  • and extended stays.

    • Planning for lifestyle intentionally — not impulsively — helps keep retirement sustainable.

    5. Tax Withholding Surprises

    This one catches many Canadians off guard.

    When income shifts from salary to multiple sources — CPP, OAS, RRIF — tax withholding isn’t always automatic or sufficient.

    You can end up with:
    A surprise tax bill or too much withheld unnecessarily.
    Adjusting tax withholding early helps avoid unpleasant surprises the following April.

    The Bigger Truth

    The first 90 days of retirement aren’t about spreadsheets.
    They’re about adjustment.

    Financial rhythm. Emotional rhythm. Lifestyle rhythm.

    When those three align, retirement feels smooth.

    When they don’t, even a well-funded retirement can feel uncomfortable.

    If you’re planning to retire this year — or within the next couple of years — don’t just plan the numbers.
    Plan the transition.

    Because retirement isn’t just the end of work.
    It’s the beginning of a completely new chapter.

    And the first 90 days set the tone for everything that follows.

    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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