When the market drops, headlines usually focus on buying opportunities—“buy the dip,” they say. And yes, scooping up high-quality assets at a discount can be a smart long-term move. But seasoned advisors know that real planning opportunities often hide in plain sight during volatile markets—and they’re not always about what you buy. Sometimes, it’s about how you plan.

Julie: Turning Market Declines Into Roth Conversion Opportunities

Julie, a high-income executive in her 50s, isn’t trying to time the market—she’s trying to reduce her future tax bill. With her traditional IRA temporarily down in value, we viewed the pullback as a chance to convert a slice of her IRA to Roth while those assets were “on sale.”
By converting depressed assets, she pays taxes on a lower value today, and any future rebound happens inside a Roth account—with no required minimum distributions and tax-free withdrawals for her or her heirs. It’s not flashy, but it’s quietly powerful.

Drew: Gifting Assets While They’re Down (and Letting the Recovery Happen Outside the Estate)

Drew, age 62, has begun thinking seriously about wealth transfer. While the markets felt uncertain, we didn’t panic—we got strategic. He transferred shares of a concentrated stock position into an irrevocable trust for his kids. The timing mattered. Because the asset was temporarily down in value, Drew was able to gift more shares while using less of his lifetime exemption. If the stock recovers in the trust, that growth happens outside of his estate. This isn’t just tax-smart—it’s legacy-smart.

Blake: Turning Losses Into Tax Assets

Blake, a business owner in his 30s, didn’t love seeing red on his screen—but he understood the value of tax-loss harvesting. We combed through his taxable portfolio and harvested a handful of losses that could offset future gains or up to $3,000 in ordinary income annually.
Then, we reinvested the proceeds into similar—not identical—positions, keeping him aligned with his overall investment plan while building a “bank” of future tax benefits. Market turbulence gave us the opening. Planning turned it into an advantage.

Beyond the Headlines

It’s easy to focus on the dramatic stuff when markets drop—buy the dip, sell the losers, brace for impact. But sometimes, the real opportunity is in the less obvious plays: strategic Roth conversions, thoughtful gifting, and tax-loss harvesting. These aren’t just portfolio moves—they’re planning moves. They compound over time, often quietly, in ways that improve outcomes for clients and their families down the line.

At Members’ Wealth, we use volatility as a trigger—not for panic, but for proactive planning. If your portfolio has dipped and you’re wondering what to do, the answer might not be “buy more”—it might be “plan better.”

Planning Strategies to Consider During a Market Pullback:

• Roth conversions at temporarily depressed values
• Gifting depreciated assets to trusts or family members to move future appreciation outside the estate
• Tax-loss harvesting to offset current or future capital gains and reduce taxable income
• Rebalancing portfolios without triggering large tax consequences
• Filling lower tax brackets with IRA withdrawals or conversions before income bounces back
• Reviewing concentrated positions for partial liquidation or charitable planning
• Exercising stock options while valuations are lower
• Strategic contributions to Donor-Advised Funds using undervalued assets
• Estate planning updates to reflect gifting and valuation opportunities

If you're looking for guidance on how to take advantage of any of these strategies during turbulent markets, let's connect. Some of the best financial decisions aren’t made when everything feels easy—they’re made when it doesn’t.

These examples are for illustrative purposes only and do not represent actual client experiences. Individual results will vary based on personal financial circumstances and tax laws.

About the Author – Stu Caplan

Stu Caplan is Senior Wealth Strategist at Members’ Wealth, a boutique wealth management firm that offers a comprehensive approach to serving individuals, families, business owners, and institutions.

The firm’s goal is to preserve and grow its clients’ wealth to endure over time, while thoughtfully evolving its strategy to suit an ever-changing world. With over 20 years of industry experience, Stu and the Members' Wealth team thrive on bringing clarity and confidence to clients' unique situations.

Stu received his MBA from The Robert H. Smith School of Business at the University of Maryland and his bachelor’s degree from the Eller College of Management at the University of Arizona. Stu resides in Bucks County, PA with his wife and two sons. He’s an avid golfer and is thrilled that his boys have embraced the game. He also volunteers his time as a board member of the PKD Foundation and Abrams Hebrew Academy.

To get in touch with the Members’ Wealth team today, I invite you to email info@memberswealthllc.com or call (267) 367-5453. 

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