5 Strategic Tax Moves for Boomers to Protect Retirement During Market Volatility

If you’re approaching retirement—or already savoring those years—market volatility can trigger more than just concern about portfolio balances. For Baby Boomers and near-retirees, these market swings feel personal and immediate, not just distant background noise. The real question isn’t just about investment performance: it’s about safeguarding your financial security, cash flow, and peace of mind.

The silver lining? Even in unpredictable markets, there are actionable, tax-savvy strategies you can implement to help shield your retirement lifestyle from unnecessary losses and tax exposure. The focus here is not investment advice, but practical, proven tax and cash flow management steps you control—regardless of Wall Street’s gyrations.

1. Deploy Tax-Loss Harvesting Strategically

If some investments in your taxable accounts have experienced declines, now is the time to consider tax-loss harvesting. This technique lets you realize capital losses to offset current or future capital gains, proactively reducing your overall tax liability.

  • Offset long-term and short-term capital gains
  • Potentially reduce up to $3,000 of ordinary income per tax year
  • Support portfolio rebalancing with minimized tax impact

Remember, tax-loss harvesting is not panic selling. It’s a disciplined, precise tax planning move aimed at maximizing net after-tax performance over time.

2. "Bunch" Deductions for Bigger Tax Savings

With the IRS’s higher standard deduction, many retirees find itemizing deductions less beneficial. However, dollar-cost averaging your charitable contributions or medical expenses across multiple years might mean missing out on significant tax benefits.

Instead, consider bunching charitable donations and allowable medical expenses into a single tax year—pushing your itemized deductions beyond the standard threshold, maximizing your write-offs, and boosting your cash flow. Alternate with the standard deduction in subsequent years if it fits your situation best.

3. Optimize Retirement Account Withdrawals

Market declines underscore the importance of having a coordinated, tax-efficient withdrawal strategy. Avoid selling assets at a loss, but don’t ignore proactive distribution planning:

  • Coordinate withdrawals from taxable, tax-deferred (401(k)s, IRAs), and tax-free (Roth IRAs) accounts
  • Adhere to Required Minimum Distributions (RMDs) if age 73+
  • Mitigate spikes in taxable income to avoid higher Medicare premiums or additional taxes

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Work with a qualified tax preparer on sequencing withdrawals for long-term tax efficiency—especially during market downturns.

4. Evaluate Roth Conversion Windows

Temporary market dips may provide unique opportunities for Roth IRA conversions. Converting tax-deferred assets to a Roth IRA while values are suppressed can help you move assets into a tax-free growth environment at a reduced tax impact.

Key advantages:

  • Future qualified withdrawals are tax-free
  • Diversifies tax exposure in retirement
  • Reduces future Required Minimum Distributions (RMDs)

Note: Roth conversions increase taxable income for the conversion year, so work with a professional to avoid triggering unwanted tax consequences or Medicare IRMAA surcharges.

5. Make Tax Planning a Year-Round Priority

In today’s environment, reactive tax planning isn’t enough. Ongoing, proactive strategies throughout the year are essential for protecting your legacy and liquidity. This includes:

  • Adjusting strategies for changes in income or market conditions
  • Timing deductions and income streams deliberately
  • Staying informed about evolving tax laws and opportunities
  • Coordinating with your tax advisor for integrated retirement and tax planning

The objective: Maximize your after-tax wealth by legally minimizing what you owe—because you worked hard for your nest egg and deserve to enjoy it without unnecessary tax erosion.

Smart Tax Moves Begin with Expert Guidance

At Haley Claypool & Associates, we specialize in helping Boomers and pre-retirees in Newport Beach and beyond build customized tax strategies that adapt to market uncertainty and personal goals. As a seasoned tax preparer and accounting professional, I’m committed to hands-on, tailored service—ensuring each move we recommend is practical and IRS-compliant, supporting a worry-free retirement.

Ready to make the most of your retirement years, regardless of what the market throws your way? Contact Haley Claypool at wendy.claypool@ipersyst.com or call 818-338-8700. Visit our Newport Beach office at 2549 Eastbluff Drive #448 to start building your future with confidence.

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Let's talk. We are here to help!
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