Episode 78: What Happens If You Retire and Then Want to Go Back to Work?

Published July 27, 2026

Retirement does not always unfold exactly the way you expect.

In this episode of Money Monday, Darren Devine, Financial Planner with Sun Life and President of Devine & Associates, explores a retirement scenario that is becoming increasingly common:

What happens if you retire and then decide you want to work again?

For some people, retirement feels comfortable right away. For others, leaving work can reveal how much they valued the routine, social connection, purpose, or income their career provided.
Returning to work does not necessarily mean retirement failed. It may simply mean your idea of retirement has evolved.

This episode explores:
→ Why retirement does not need to be a permanent or all-or-nothing decision
→ How part-time, consulting, seasonal, or purpose-driven work can fit into retirement
→ How employment income may reduce pressure on retirement savings
→ Why returning to work may allow investments more time to grow
→ How new income can affect taxes and registered-account withdrawals
→ Why emotional readiness matters alongside financial readiness

Going back to work can sometimes strengthen a retirement plan by reducing the amount you need to withdraw from savings and providing greater flexibility for travel, home repairs, or other lifestyle expenses.

However, additional employment income may also affect your tax position and how CPP, OAS, pensions,

RRIF withdrawals, and other income sources work together.
The goal is not simply to ask whether you can return to work.

It is to understand how that decision fits into your broader retirement plan.

Because retirement today is often less of a hard stop and more of a transition into a new phase of life—one that can still include meaningful work on your own terms.

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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 67: How Much Did You Save Towards Your Retirement Last Year?
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Episode 20: Spending vs. Budgeting: Aligning Your Values and Goals to Your Finances
Working again may be less about necessity and more about supporting the lifestyle, experiences, or priorities that matter most to you.

What Happens If You Retire and Then Want to Go Back to Work?

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

Retirement doesn’t always unfold exactly the way you imagined.

So what happens if you retire… and then realize you’re not quite done working?

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.

For some people, retirement feels great right away.

More freedom.

Less stress.

More time for family, travel, hobbies, or simply slowing down.

But for others, retirement can feel a little different than expected.

Sometimes people miss the routine.

Sometimes they miss the social connection.

Sometimes they realize they’d like a little extra income.

And sometimes, after stepping away, they discover they’re not fully ready to stop working altogether.

And the good news is—that’s okay.

Retirement does not have to be an all-or-nothing decision.

More and more people are choosing a version of retirement that looks more flexible:

  • part-time work
  • consulting
  • seasonal work
  • passion projects
  • or going back in a lighter, less demanding role

So what happens financially if you do retire and then decide to work again?

The first thing to know is that going back to work can create opportunity—but it can also affect how different parts of your financial picture work together.

For example, earning income again could:

  • reduce how much you need to withdraw from your savings
  • give your investments more time to grow
  • ease pressure on your retirement income plan
  • or allow you to be more flexible with bigger expenses like travel or home repairs

In many cases, going back to work can actually strengthen your plan.

But it’s also important to understand that added income may affect things like:

  • your tax position
  • when you choose to draw from registered accounts
  • and how different income sources fit together

This is where planning matters.

Because the question is not just,

“Can I go back to work?”

It’s also,

“How do I do that in a way that supports my bigger plan?”

Emotionally, this matters too.

Some people feel embarrassed, like going back to work means they “got retirement wrong.”

But that’s not necessarily true at all.

Wanting to work again does not always mean something failed.

It may simply mean your idea of retirement evolved.

Maybe you want more structure.

Maybe you want more purpose.

Maybe you want to stay active and engaged.

Maybe you just want more options.

Retirement today is not what it used to be.

For many people, it is not a hard stop.

It is a transition into a new phase of life—one that can still include meaningful work, just on different terms.

That’s why retirement planning should never be based on a rigid picture of what retirement is “supposed” to look like.

A good plan should leave room for change.

Room for choice.

Room for the fact that what sounds good at 65 may feel different at 67.

So if you’ve retired and are thinking about working again, or if you’re approaching retirement and wondering whether you may want that option later, that’s a conversation worth having before you make any big moves.

Because retirement is not about locking yourself into one version of the future.

It’s about creating a plan that gives you the freedom to adjust as life changes.

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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