The Retirement Planning Window Most People Waste (And How to Use It Correctly)

Most people think retirement planning ends the day they retire.

In reality, one of the most important planning opportunities doesn’t even start until after work stops — and it quietly closes a few years later.

I call it the retirement planning window, and it’s one of the most underutilized opportunities I see when working with pre-retirees and newly retired clients.

If this window is used intentionally, it can significantly reduce taxes, increase flexibility, and improve long-term retirement income.
If it’s ignored, many of the best options disappear permanently.

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What Is the Retirement Planning Window?

The retirement planning window is the period of time when someone has:

• Retired from full-time work
• Has not yet started Social Security
• Is not yet subject to Required Minimum Distributions (RMDs)

For many people, this window spans roughly ages 60 to 72, though the exact timing varies.

What makes this period so powerful is one simple thing:

Income is often temporarily lower than it will ever be again.

That creates planning opportunities most people don’t realize exist.

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Why This Window Matters More Than Most People Realize

During working years, income is often too high to implement meaningful tax strategies without unintended consequences.

Later in retirement, income becomes forced:

• Social Security benefits begin
• RMDs create mandatory withdrawals
• Pension income stacks on top

But during this window, income is flexible.

That flexibility allows for decisions that can shape the rest of retirement.

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The Most Common Mistake I See

The biggest mistake I see is doing nothing.

Many retirees assume:

• “I’ll just live off my savings for now”
• “I’ll deal with taxes later”
• “Once I start Social Security, we’ll see where things land”

Unfortunately, by the time Social Security and RMDs begin, many of the best planning opportunities are already gone.

At that point, people are no longer planning — they’re reacting.

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How This Window Connects to Social Security Taxes

This is where many retirees get caught off guard.

Without planning:

• IRA balances remain fully taxable
• RMDs push income higher later
• More Social Security becomes taxable
• Medicare premiums may increase

This is exactly how people walk into the Social Security tax trap without realizing it.

Used correctly, this window can dramatically reduce that outcome.

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Strategies That Are Most Effective During This Window

Not every strategy is right for everyone — but these are the tools that tend to work best when implemented during this period.

Strategic Roth Conversions

Converting portions of traditional IRAs to Roth IRAs during lower-income years can:

• Reduce future taxable income
• Lower the percentage of Social Security subject to tax
• Increase tax-free income flexibility later

This is about control — not avoiding taxes entirely.

Income Smoothing

Instead of allowing income to spike later, withdrawals can be spread more evenly across retirement years, reducing tax pressure and surprise thresholds.

Coordinated Social Security Timing

Social Security claiming decisions should be coordinated with:

• IRA balances
• Roth conversion strategies
• Spousal benefits
• Long-term income needs

Timing matters more than most people realize.

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A Pattern I See Repeated Over and Over

Clients who come to me before Social Security starts usually have far more options.

Clients who come to me after RMDs begin often say:

“I wish I had known this earlier.”

The difference isn’t intelligence or discipline — it’s timing.

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How This Window Fits Into a Bigger Retirement Plan

This planning window isn’t about making one decision.

It’s about coordinating:

• Taxes
• Income sources
• Account types
• Government benefits

When done properly, it creates:

• More predictable taxes
• More spendable income
• More confidence

And fewer unpleasant surprises.

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Final Thoughts

Retirement planning doesn’t end when work stops.

In many ways, that’s when the most important decisions begin.

The retirement planning window is a temporary opportunity — and like most opportunities, it favors those who recognize it early and act intentionally.

If you’re within a few years of retirement or recently retired, this is one of the most important conversations you can have.