Ask someone when they plan to retire and you’ll likely hear a number:
“Sixty-five, I think.”
Or maybe, “I’ll keep working until I can’t.”

For a concept as important as retirement, our collective expectations are oddly vague—and deeply rooted in outdated ideas. The truth is, retirement isn’t about age. It’s about freedom. And the earlier you stop thinking in terms of birthdays and start thinking in terms of strategy, the more likely you are to leave work on your own terms.

This isn’t a piece about aggressive investing or ditching your job at 40. It’s about building a retirement plan that makes sense for your lifestyle, goals, and risk tolerance—whether you dream of early exit or simply want to avoid working longer than you need to.

Forget the Age. Focus on the Formula.

The traditional retirement model—work 40 years, collect a pension, spend your golden years on a beach—was designed for a different economy. One with lifelong employment, guaranteed pensions, and shorter lifespans.

Today’s model is more personal—and more complex:

• Fewer guaranteed pensions, more personal responsibility.
• Increased life expectancy (and healthcare costs).
• Career shifts, side hustles, and non-linear income.

That means retirement has less to do with hitting 65, and more to do with answering one question:
Can your money support your life when your work no longer has to?

To do that, you need three things:

1. A target number (not just a date).
2. An income plan that doesn’t dry up.
3. A vision for what retirement actually looks like—because you can’t budget for a blur.

How Much Is “Enough”?

There’s no universal answer. But you can build a framework that fits you.

Start by asking:

• How much do I spend now—and what will change post-retirement?
• Do I plan to relocate, downsize, or maintain my current lifestyle?
• Will I still work part-time, consult, or pursue income-generating hobbies?
• How much risk am I willing to take in my investments, and for how long?

Many people rely on the 4% rule: if you withdraw 4% of your retirement portfolio each year, it should last 30+ years (assuming a balanced investment strategy). So if you want $60,000/year in retirement, you’d need $1.5 million saved.

But that’s a rule of thumb—not gospel. Your number depends on your spending, not someone else’s math.

Building a Portfolio That Pays You

A good retirement plan doesn’t just grow your money—it replaces your income.

That might mean:

• Index funds for long-term, diversified growth.
• Dividend-paying stocks to provide income during retirement.
• Rental properties or passive income streams for stability.
• Annuities to provide guaranteed payments (with caveats).
• Cash reserves to weather downturns without selling investments at a loss.

Asset allocation should evolve over time. What makes sense in your 30s or 40s (growth-heavy, risk-tolerant) may need to shift in your 50s or early 60s toward preservation and predictability.

This is where many people get stuck: they think saving is the plan. But retirement isn’t just about accumulation. It’s about distribution.

Retirement Isn’t a Cliff. It’s a Curve.

The day you stop working won’t be the same for everyone.

Some people ease out gradually—consulting, freelancing, or mentoring. Others go cold turkey and never look back. Increasingly, people retire in phases, adjusting work around life instead of the other way around.

The key is clarity: know what you want your days to look like when the paycheck stops. Travel? Volunteering? Creative work? Time with grandkids?

You don’t need a detailed itinerary—but you do need a vision. Because financial freedom without purpose can feel disorienting. The best retirements aren’t just funded. They’re designed.

Don't Ignore the Human Factors

Health. Relationships. Identity. These matter just as much as your financials—and often get less planning.

• Healthcare costs are rising—and Medicare or provincial plans may not cover what you expect. Build in extra savings or supplemental insurance.
• Mental health and social connection matter. Work is a source of structure and community. Retirement can feel isolating if you're not intentional about staying engaged.
• Purpose drives fulfillment. Ask yourself: what will replace the sense of contribution that work gave you?

Retirement isn't an escape from something. It’s a shift toward something else.

Planning for Succession, Not Just Exit

If you’re a business owner or executive, retirement planning should include succession strategy.

Who takes over? How will knowledge transfer happen? What role—if any—will you play after the handoff?

Too many leaders delay this conversation, only to find themselves rushing it when circumstances force their hand. Build your succession plan early, revisit it often, and make it part of your broader financial and legacy strategy.

Not Just When. Why.

You can set a retirement date, hit the number, and still feel unprepared—because retirement isn’t about flipping a switch. It’s about designing a future that feels worth moving toward.

The earlier you start, the more flexibility you have. That doesn’t mean hustling harder. It means getting clearer:

• About what freedom looks like for you.
• About how you want to spend your energy, not just your money.
• About what it’ll take to get there—and when you’ll be ready to make the leap.

You might still retire at 65. Or 70. Or 55. But if you treat retirement as a strategy, not a milestone, you’ll be doing it on your terms—not anyone else’s.