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Tax Strategies in a Down Market: Roth Conversions, Tax Loss Harvesting, Gifting, Portfolio Rebalancing

Note: CLE credit is not offered on this program

Recording of a 110-minute CPE webinar with Q&A

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Conducted on Thursday, September 1, 2022

Recorded event now available

or call 1-800-926-7926

This course will outline specific tax and investment strategies advisers should consider in order to guide taxpayers during a bear market. Our panel of investment analysts will provide expert advice on Roth conversions, harvesting tax losses, rebalancing portfolios, and other strategies to take advantage of current events.


Investors can profit in up and down markets; unique planning opportunities are available when the market is down. During a market downturn, RMDs are lower, and choice stocks can be purchased at steep discounts. It is prime time to take advantage of tax-loss harvesting. Individuals can deduct up to $3,000 in losses against ordinary income annually. Stock losses can offset capital gains making profitable redemptions tax-free. Taxpayers need to be wary of wash sales rules. Buying "substantially identical" securities 30 days before or after a loss sale can lead to disallowance of the loss.

Taxpayers considering a Roth conversion could do so with substantial tax savings when the market is lower. However, Roth conversions are wrought with complications. The pros and cons should be carefully weighed before converting. The pro-rata rule for taxing these rollovers could leave taxpayers with unexpected and significant taxes payable. Tax practitioners working with individual income tax clients need to be aware of investment opportunities that are present now in order to properly advise taxpayers.

Listen as our panel of financial planning experts leads you through investment strategies taxpayers should consider during a down market.



  1. Tax strategies in a down market: introduction
  2. Loss harvesting
  3. Roth conversions
  4. Tax-exempt investments
  5. Rebalancing your portfolio
  6. Gifting
  7. Investment opportunities
  8. Retirement contributions
  9. Other considerations
  10. What not to do


The panel will review these and other critical issues:

  • How tax on a Roth conversion is calculated
  • How to avoid wash sale rules
  • How taxpayers can better utilize their estate tax exemption by making gifts during a market downturn
  • What should taxpayers consider when rebalancing their portfolios during a bear market?


Janse, Roy
Roy Janse, CFP, AIF, CRC

Managing Partner
Goldfinch Wealth Management

As the Managing Partner of Goldfinch Wealth Management, Mr. Janse's highest priority is to assist clients as they...  |  Read More

Lawrence, Ashton
Ashton Lawrence, CFP, ChFC, AIF

Goldfinch Wealth Management

As a Financial Advisor at Goldfinch Wealth Management, Mr. Lawrence aims to deliver personalized client care and an...  |  Read More

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