Retire Confidently: 5 Proven Questions to Know

Saving money for retirement is only part of the equation. Many Canadians think they are ready to retire.
However, they often pay unnecessary taxes or struggle to maintain their lifestyle.

Before making this life-changing decision, ask yourself these five questions. Then, answering “yes” to all of them will give you the confidence to retire with peace of mind.

1. Do You Know How Much You’ll Spend When You Retire?

In an ideal world, what does your life look like in retirement? Can you put a dollar figure on that lifestyle?
Many people ask, “How much do people usually spend?” This question is tricky because circumstances vary.

Some key points to consider:

  • Knowing your lifestyle costs is the foundation of your retirement plan.
  • Some clients have $3 million and spend $5,000 per month, while others spend $15,000 per month because they want to die with nothing.
  • Irregular expenses, like home repairs, replacing vehicles, or helping kids financially, also affect your portfolio.

2. Do You Have an Income Plan for When You Retire?

Many Canadians work with a financial advisor but only get investment management. There’s often no plan showing which accounts to draw from first in retirement or how this aligns with CPP and OAS timing.

Key aspects of an income plan:

  • Shows which account you’ll draw from first.
  • Details which investments in each account will be used.
  • Highlights tax impacts over the next 30 years.

Don’t just settle for an investment portfolio. Ask your advisor to help you create a withdrawal strategy so you pay no more tax than necessary.

3. Have You Stress-Tested Your Portfolio?

Markets have done well in recent years, but what if you stop working tomorrow and the market drops? Where will your money come from? Will it last?

Ways to protect yourself:

  • Avoid relying solely on average long-term returns when planning withdrawals.
  • Diversify your investments across asset classes.
  • Use a bucketing strategy: keep some money in cash or conservative investments to ride out market corrections.

4. When Will You Take CPP and OAS?

Many people take government benefits as soon as possible — CPP at 60, OAS at 65 — simply to get the money. That’s not always wrong, but you should know the break-even points.

Factors to consider:

  • Review all options to find what works best for your retirement plan.
  • Early vs. later CPP/OAS impacts withdrawal strategy.
  • Timing affects portfolio investments and potential OAS clawback.

5. Do You Understand Your Future Tax Bill?

Some retirees focus on keeping their tax bill low today. They avoid RRSP withdrawals and live off non-registered or tax-free accounts. While this may reduce taxes now, it can increase taxes later.

Key points to keep in mind:

  • Leftover RRSP funds pass tax-free to a spouse, but may become taxable after the second spouse dies.
  • Poor decisions can cost hundreds of thousands in extra taxes.
  • Planning withdrawals now ensures a tax-efficient retirement.

Final Thoughts

Retirement readiness isn’t just about savings — it’s about strategy, timing, and clarity. When you can confidently answer these five questions, you’re not just ready to retire — you’re ready to enjoy it.

That’s the foundation of our Atlas System — a process designed to help Canadians map out income, spending, and tax strategies so every dollar supports the life they want in retirement.

Watch the full video on YouTube and visit the Trans Canada Wealth Management YouTube channel for more retirement planning tips.

Marc Sabourin is a Winnipeg-based Financial Advisor and Retirement Specialist with Harbourfront Wealth Management. His specialty is working with pre-retirees and retirees who are looking for retirement, investment, & tax advice. 

Disclaimer: The views expressed are those of Marc Sabourin, Certified Financial Planner, and Investment Advisor, and not necessarily those of Harbourfront Wealth Management Inc., a member of the Canadian Investor Protection Fund

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20 Retirement Tips

When entering retirement or having recently retired, these 20 tips should be considered. A thorough retirement plan will touch on all 20.

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