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Understanding When it’s Okay to Sell Investments at a Loss

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Investing in financial markets involves a blend of strategy, timing, and risk management. Among the various decisions investors make, selling at a loss can be a bitter pill to swallow. Afterall, one of the fundamental principles of investing is “Buy Low, Sell High” not the other way around. While this is ultimately the goal of investing and I would to always have a portfolio consisting of 100% winners, in reality, a diversified portfolio will have some positions that win and some that lose. In these cases, there are circumstances where selling an investment at a loss can actually be a smart move. 

6 Circumstances for Selling at a Loss

1. Rebalancing Portfolio

One of the primary reasons investors sell at a loss is to rebalance their portfolio. Over time, certain assets might grow disproportionately compared to others, causing an imbalance in the original allocation and in turn the target risk and reward characteristics. Selling some underperforming assets at a loss allows investors to reallocate funds into stronger-performing or different asset classes, maintaining their desired risk-return balance.

2. Tax Loss Harvesting

Tax loss harvesting involves selling investments at a loss to offset gains from other investments. By strategically realizing losses, investors can minimize their tax liability. Capital losses can be used to offset capital gains, and if losses exceed gains, they can be used to offset taxable income to a certain extent, reducing the overall tax burden.

3. Change in Investment Prospects

Market conditions and the fundamental outlook of companies or assets can change. If an investment’s prospects have significantly deteriorated, selling at a loss might be a prudent move. For instance, a company facing internal issues like management problems or declining market share might not recover its value in the near future. Cutting losses can prevent further erosion of capital.

4. Reevaluation of Investment Thesis

Sometimes, an investor’s initial thesis might no longer hold true due to changing industry trends, technological advancements, regulatory changes, or shifts in consumer behavior. If the reasons for the investment have fundamentally altered, selling at a loss might be the right decision to avoid further losses based on an outdated rationale.

5. Liquidity Needs or Emergency Funds

In certain situations, unforeseen financial needs might arise, such as unexpected medical expenses or a sudden job loss. Selling an investment at a loss could provide the necessary liquidity to address these immediate needs. While not ideal, having accessible funds for emergencies can outweigh the losses incurred.

6. Avoiding Further Downside Risk

Cutting losses at a predetermined level can be a part of risk management. Having an exit strategy can help protect against significant losses in case an investment continues to decline. Sometimes, it’s better to sell at a loss rather than holding onto a declining asset, hoping for a recovery that may never materialize.

While selling investments at a loss can be emotionally challenging, it’s essential to recognize that losses are a part of investing. Making informed decisions based on changing circumstances, portfolio rebalancing, tax considerations, and risk management can sometimes outweigh the short-term discomfort of a loss.

Investors should carefully evaluate their individual circumstances, goals, and the broader market context before deciding to sell at a loss. Seeking advice from financial professionals can provide valuable insights and guidance tailored to one’s specific situation. Ultimately, understanding when it’s appropriate to sell at a loss is an integral aspect of a well-rounded investment strategy.

Steven Gilbert

Steven Gilbert CFP® is the owner and founder of Gilbert Wealth LLC, a financial planning firm located in Fort Wayne, Indiana serving clients locally and nationally. Gilbert Wealth helps clients optimize their financial strategies to achieve their most important goals.