Retirement planning for late starters

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Estimated read time: 11 minutes

Retirement is a deeply personal decision, shaped by financial readiness, emotional preparedness, and life circumstances.

My husband retired in December 2021 after spending two years supporting his team of 20 through the anxieties of COVID-19. The emotional toll was immense, and we both reached a point where retirement became our best choice.

But how do you know when you’re truly ready?

Financial preparedness: Understanding your numbers

Ten years before retirement, we consulted a financial professional, expecting clear guidance on tax planning and investment savings. The $1,000 bill felt steep, especially given how little clarity we gained. Frustrated, we started researching self-help investment resources.

Learning should be enjoyable, and the right resources can make all the difference. Find a video that resonates with you, and take charge of your financial future.

Peace of mind as you age

Planning ahead ensures you maintain financial independence so that you can fully enjoy your retirement. With this goal in mind, your retirement plan should be based on factors unique to your situation like:

  • Your current and desired retirement age
  • Preferred retirement location
  • Expected and unexpected expenses
  • Current savings, investments, and debts
  • Retirement income sources
  • Financial obligations to family
  • Potential inheritance
  • Stability of your partnership/relationship
  • Investment knowledge and risk tolerance.

My dad always said, ‘Avoid retiring with a mortgage, loans, or credit debt.’ I wish I had listened sooner — but life had other plans.

Let me tell you our story…

The right location for retirement

In 2004, we struggled to accept that we couldn’t afford to retire in the cities we loved — Toronto and Vancouver. Moving to a smaller town in our 40s and 50s felt like a loss, even a failure. But looking back, it was the best financial decision we ever made. It helped us rebuild, regain security, and ultimately create a better retirement.

Would you consider relocating in retirement?

It’s never too late to start

We were late starters in the savings game — 40 and 53 when we finally got serious. My partner carried $30,000 in debt, which took five years to pay off. I had another $30,000 and chose bankruptcy — a decision that came with deep emotional weight.

Ego bruised, we tightened our budget, lived below our means, and prioritized every extra dollar toward financial recovery.

I never realized how costly it is to be poor, my partner said.

Finally, we turned our life around…

Once our debts were gone, we shifted gears — saving aggressively and investing strategically. We moved from mutual funds to direct stock market investments. In just 10 years, my Locked-In Retirement Account (LIRA) grew from $44,000 to $500,000. At 71, I converted it into a Life Income Fund (LIF), while my partner—leveraging his tech industry expertise — continued to invest conservatively in my LIF.

P.S. Before we dive into practical retirement tips, consider using a resource for course correction. If you’re a late starter, Resilient Choices (Edward Jones, 2023) is a great place to begin.

When you’re ready, plenty of online tools can guide you toward a successful retirement.

A great place to start is the Canadian Investment Regulatory Organization (CIRO). With 5 simple topics, you can understand your retirement account options and create a plan.

But if you’re looking for advice from someone who started late and still made it work, here are the strategies that helped us build a secure retirement.

Learn what government income is available to you

Start by taking Canada’s 3-minute government quiz to assess your pension eligibility.

Pro Tip: Set up a My Service Canada Account to view your Record of Employment (ROE) online. This will help you estimate how much government income you can expect to receive from Canada Pension Plan (CPP); Old Age Security (OAS); and, if eligible, a Guaranteed Income Supplement (GIS).

Assess your expenses and cash flow

Understanding your current and future expenses is crucial for a secure retirement. We use Quicken for Mac to track our spending and our annual cash flow. This approach ensures that my Life Income Fund (LIF) withdrawals cover next year’s required and discretionary expenses, without jeopardizing our financial future.

In our planning, we accounted for:

  • Actual expenses (e.g. property tax, groceries, utilities)
  • Projected medical expenses
  • Home repairs & maintenance
  • Personal income taxes
  • Travel plans.

Having a clear financial picture helped us make informed decisions and avoid surprises.

Build a back-up plan

Having a backup income plan is smart—especially in case your investment income fluctuates in the future. If your savings are low, ask yourself:
Do I need to save more, invest differently, or earn extra income?

Calculate how long your money will last

We use an Excel sheet to project income and expenses from now until age 100, updating it yearly with actual figures.

Pro Tip: Instead of relying on a single estimate, run different scenarios — best case, worst case, and most likely — to build confidence in your plan.

Protecting the assets your already own

Retirement planning isn’t just about growing your wealth — it’s also about protecting what you’ve built. Unexpected costs, such as medical expenses or long-term care, can quickly drain savings. One option is to use your home as a financial safety net. Downsizing, selling, or even sharing your space with trusted live-in companions can help offset costs.

Don’t forget. Your digital assets need just as much protection as your physical ones. Cyber threats targeting retirees are on the rise, making cybersecurity just as essential as home security. Let’s explore how to safeguard both your financial and personal well-being.

Securing your home for the future

Regular maintenance and upgrades

Keep your home in top shape to prevent costly emergency repairs and maintain its value. Investing in upgrades, such as modernizing kitchen appliances or improving energy efficiency, can significantly increase your home’s appeal to future buyers.

Weatherproofing and emergency readiness

Extreme weather events—floods, storms, and sudden temperature swings—can cause thousands of dollars in damage if you’re unprepared. Protect your home by maintaining proper drainage, upgrading insulation, and ensuring your sump pump is in top working order. Sometimes, a single oversight can turn into a crisis.

Aging in place modifications

Consider renovations that will allow you to stay comfortably in your home longer, such as grab bars, better lighting, or stair alternatives.

Protecting your digital and financial assets

Cyber threats targeting retirees are on the rise, making digital security just as important as financial planning. Here’s how you can safeguard your accounts:

The flood that almost was

Protecting more than just your finances

Taking steps to secure your financial future is crucial — but protecting your home is just as important. Whether it’s cybersecurity threats or unexpected home disasters, a little preparation can save you from major stress and financial loss.

We learned this the hard way when we almost faced a flood that could have cost us thousands.

Here’s what happened…

In April 2022, record-breaking snowfalls, rapid temperature shifts, and heavy rains put thousands of homeowners at risk of flooding.
We weren’t spared.

Water was creeping into our cold room from the cement stairs above. And, our sump pump, instead of directing water away from the house, was cycling it back toward the house. If it failed, we could be facing thousands in flood damage.

With no time to waste, my husband grabbed an rusty old axe from our shed, hacked through our deteriorating wood deck, and rigged an emergency drainage system. It wasn’t pretty. Then, the pump gave out entirely.

With supply chains strained and sump pumps selling out citywide, we barely managed to get one of the last two in stock. Had it not been for the good graces of our neighbor, who called in a favor and had a professional install the new sump pump the same day, we would have been at a high risk of basement flooding.

We had our excuses like everyone else. We were too busy coping with work and eldercare and all the other daily challenges of getting by.

But that summer, we didn’t take any more chances. We reinforced our drainage system, upgraded the sump pump, and made landscaping changes to direct water away from the house. And we added cement housing over our existing stairway to prevent further leaks in our cold room.

Nevertheless, the experience made us realize the importance of maintaining the most important asset we had.

The takeaway

Retirement planning isn’t one-size-fits-all. Whether you start early or make decisive changes later in life, every step forward counts. Our journey wasn’t perfect, but it was ours—filled with unexpected challenges, hard decisions, and ultimately, financial security.

I won’t lie — transitioning from a stable financial situation to the uncertainty of retirement felt risky. The stock market was down. COVID was still a concern for us. Our truck was on its last legs. The snowblower broke. We had just spent over $20,000 on concrete repairs and drainage landscaping. It was not the smooth start to retirement we had envisioned.

But if there’s one lesson we’ve learned, it’s this: regular maintenance and emergency preparedness aren’t optional — they’re essential.

Retirement planning is about more than just money; it’s about peace of mind.
The best time to start planning is now, and the best strategy is one that ensures you can retire on your terms.