Retire Richer: 7 Tax-Smart Moves Wealthy Retirees Are Making Right Now

Retire Richer: 7 Tax-Smart Moves Wealthy Retirees Are Making Right Now


Retirement isn’t just about what you’ve saved—it’s about what you keep.

You’ve worked hard, invested wisely, and built substantial wealth. Now that you’re approaching or enjoying retirement, it’s time to think about preservation—and that starts with taxes.

The wealthiest retirees know this: taxes don’t stop when you stop working. In fact, without a plan, your tax burden in retirement can quietly erode everything you’ve built.

That’s why they work with experts to make smart, proactive moves—right now.

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1. Strategic Roth Conversions

Wealthy retirees are converting portions of traditional IRAs into Roth IRAs before required minimum distributions (RMDs) begin. Why?

  • Pay taxes now at a potentially lower rate
  • Eliminate future RMDs on converted assets
  • Leave tax-free inheritances to heirs

🔁 A Roth conversion can backfire if done without a strategy.
A trusted advisor can help time and size conversions wisely. Find yours →

2. Tax-Loss Harvesting (Even in Retirement)

Don’t let market dips go to waste. Tax-loss harvesting—selling underperforming investments to offset gains—isn’t just for younger investors. Retirees with taxable accounts can still benefit.

Pair losses with rebalancing to keep your portfolio aligned while minimizing taxes.

3. Qualified Charitable Distributions (QCDs)

If you’re 70½ or older and giving to charity, wealthy retirees know that QCDs from IRAs are one of the most efficient ways to donate.

  • Satisfy RMDs
  • Reduce taxable income
  • Support causes you care about—strategically

❤️ Philanthropy with tax perks? That’s smart giving.
Ask your advisor how QCDs can fit into your income plan. Start here →

4. Asset Location Optimization

It’s not just what you invest in—but where.

High-net-worth retirees often place income-generating assets in tax-deferred accounts and growth-focused or tax-efficient assets in taxable ones. This careful placement strategy helps minimize annual taxes and improve overall returns.

5. Filling Lower Tax Brackets

In retirement, income tends to fluctuate. Savvy retirees “fill” their lower tax brackets intentionally—by realizing capital gains, taking distributions, or converting IRA assets—to take advantage of favorable rates before they rise.

It’s the opposite of guesswork—it’s surgical.

6. Estate Planning with Tax Efficiency in Mind

The current federal estate tax exemption won’t last forever. Wealthy retirees are gifting assets strategically now—through irrevocable trusts, family LLCs, and annual exclusion gifts—to lock in today’s generous thresholds.

They’re not just preserving wealth—they’re protecting legacies.

🧾 Not sure if your estate plan is tax-optimized?
Find an advisor who can help align your estate, tax, and retirement plans at Advisor.com

7. Delaying Social Security Strategically

While many claim Social Security as soon as they’re eligible, wealthier retirees often wait. Why?

  • Benefits grow 8% per year after full retirement age
  • Coordinated correctly, delayed benefits can reduce taxes on other retirement income
  • A larger survivor benefit can protect a spouse

This isn’t about delay for delay’s sake—it’s about maximizing long-term income while minimizing taxes.

Your Money, Working Smarter

The most financially secure retirees didn’t get there by chance. They got there by working with professionals who helped them optimize, not just accumulate.

🎯 Whether you're five years out or already retired, a tax-smart advisor can help you keep more of what you've earned.
👉 Compare your top financial advisor matches for free at Advisor.com

Because retiring richer isn't about luck—

It's about strategy. And now’s the time to sharpen yours.