Ep 171 - What I Learned From 100 Early Retirees in Canada

Written By Joe Curry

Learn what more than 100 successful Canadian early retirees did differently to make life after work sustainable. Joe Curry breaks down the income systems, bridge strategies, CPP and OAS timing, and flexible RRSP/RRIF withdrawal strategies that turn a portfolio into a reliable retirement paycheck—especially if you’re thinking about retiring before 60.

Key Takeaways

It’s not about a magic number, it’s about a paycheck system.
The early retirees who thrived focused less on hitting a certain portfolio value and more on building a predictable retirement income system—whether through a total return approach with guardrails or an income protection style backed by pensions, annuities, CPP, and OAS.

Bridge years (before CPP/OAS) can make or break early retirement.
Successful early retirees had a clear bridge strategy for the 5–10 year gap before government benefits, using a smart mix of non-registered accounts, strategic RRSP withdrawals, TFSAs, and sometimes part-time work to keep taxes low and income steady.

Flexible withdrawal systems keep taxes and risk in check.
Instead of a rigid “set it and forget it” rule, they coordinated withdrawals from RRSPs, TFSAs, and non-registered accounts to intentionally fill lower tax brackets, reduce future RRIF minimums, and limit OAS clawback while keeping lifestyle spending on track.

Spending plans start with real cash flow, not a line-by-line budget.
They looked at their actual after-tax take-home pay—what truly flows through the household—then test-drove that retirement cash flow before leaving work, planning for forgotten costs like home maintenance and different phases of retirement spending.

Market independence beats market prediction.
Cash wedges, bucket strategies, guaranteed income, and guardrail-based withdrawals all served one purpose: reducing dependence on short-term market returns so retirees could stay invested for growth while knowing their near-term income was protected.

Insights Worth Sharing

“Early retirement success isn’t about a big number—it’s about a reliable paycheck system.”

“Your savings aren’t a trophy to protect; they’re a tool to fund the life you actually want.”

“Bridge years are an opportunity, not a problem, if you’re intentional about taxes and withdrawals.”

“You don’t need to predict markets—you need a structure that makes you independent from them.”

“When you know your true cash flow, the guesswork disappears and confidence shows up.”

Resources

How 100+ Canadians Retired Before 60 — and the Income Systems That Made It Work

Retiring before 60 sounds exciting—until the questions start creeping in. Will my money actually last? What happens before CPP and OAS? How do I pay myself when the paycheque stops?

In this episode of Your Retirement Planning Simplified, I share the patterns I discovered after analyzing more than 100 Canadians who successfully retired before age 60. What stood out wasn’t that they all had multi-million-dollar portfolios. It was that they had systems—intentional retirement income planning—built around how money would flow into their bank account month after month.

Instead of fixating on a magic savings number, these retirees built a predictable retirement paycheck. Some leaned toward a total return approach, drawing from a diversified portfolio using dynamic or guardrail-based withdrawals. Others preferred an income protection style, matching essential expenses with stable sources like pensions, annuities, and future CPP and OAS. Different styles, same goal: confidence that the bills are paid and there’s room for enjoyment.

One of the biggest differentiators was how they handled the bridge years—that 5–10 year gap between leaving work and when government benefits begin. The retirees who made early retirement sustainable didn’t just “wing it.” They combined non-registered assets, RRSP withdrawals in low-income years, and TFSA flexibility. Some added part-time consulting or passion projects—not because they had to work, but because it added meaning and helped fund the plan.

This is where tax-efficient investing really shows up in real life. By intentionally filling lower tax brackets early with RRSP withdrawals, they reduced the risk of large RRIF minimums, higher marginal tax rates, and potential OAS clawback later on. The bridge years became a planning opportunity, not a liability.

Another key pattern: the most successful early retirees really understood their cash flow. Instead of obsessing over a detailed spreadsheet budget, they looked at their actual after-tax take-home pay and acknowledged that almost all of it was being spent. From there, they adjusted for things that would disappear in retirement (RRSP contributions, commuting costs, maybe a mortgage) and made room for what would likely increase—travel, hobbies, and “every day is Saturday” expenses.

Many even test-drove their retirement spending a year or two before leaving work. They lived as if they were already retired, based on their projected retirement income, while they were still earning a salary. That trial run exposed surprises like home maintenance and one-off projects before paycheques stopped.

Finally, they didn’t try to predict markets. They built market independence. That might mean a cash wedge, a bucket strategy that separates “defence” money from “offence” money, or more guaranteed income. Guardrail-based withdrawal strategies helped them adjust spending—up when markets were strong, down modestly when they weren’t—without panicking.

When you pull it all together—income structure, bridge planning, flexible RRSP and RRIF withdrawal strategies, CPP and OAS timing, and a clear handle on spending—you get a framework that supports real life after work, not just a spreadsheet.

Joe Curry
Next

Ep 170 - What Should You Withdraw First: RRSP, CPP, or TFSA?