Can "Losing" Money in the Stock Market Actually be a Good Thing?

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Monday, October 19, 2026

Losing money in the stock market is never the goal. But what if some of those losses could actually work in your favor?

In this episode, Josh Pick and Logan Harris explore how investors can use market declines to potentially reduce taxes without abandoning their long-term investment strategy. They explain direct indexing and tax-loss harvesting, two strategies that can turn individual stock losses into opportunities to offset capital gains.

The conversation also covers how these strategies can create additional flexibility for Roth conversions, help investors diversify concentrated stock positions, and potentially preserve more wealth for retirement and future generations.

It's a look at an investment strategy that was once largely reserved for the ultrawealthy, and why advances in technology are making it accessible to more investors.

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The Retirement Blueprint Show airs every Friday at 4 PM and Saturday at 12 PM on 98.9 FM The Answer. You can also subscribe to the podcast so you never miss an episode.

Investment advisory and financial planning services are offered through Simplicity Wealth, LLC, an SEC-registered investment adviser. SEC registration does not constitute an endorsement of the firm nor does it indicate that the adviser has attained a particular level of skill or ability. Investments involve the risk of loss. Simplicity Wealth Advisors does not provide legal or tax advice. The content provided is for informational purposes only and should not be construed as investment, legal or tax advice. Clients and prospective clients are encouraged to consult with their own legal and tax professionals regarding their specific situations.