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Balancing Regret and Insight: The Impact of Counterfactual Thinking

Updated: Jan 28

The path of investment can often feel like navigating a labyrinth of choices. Buy, sell, hold, diversify, go for blue chips, take a chance on tech startups - each decision unfolds into a future rife with either profits or losses. Sometimes, the outcomes surprise us. That promising biotech venture crumbles while the traditional manufacturing company flourishes. When facing these unexpected results, the human mind instinctively travels down the road not taken, contemplating the 'what if' scenarios - an exercise known as counterfactual thinking.

Counterfactual Thinking: An Overview

Counterfactual thinking is the process of mentally reconstructing past events by imagining different outcomes or scenarios. In essence, it's the cognitive mechanism behind the thoughts that start with "if only" or "what if." For example, "If only I had bought Tesla stocks in 2010, I'd be a millionaire now." Counterfactual thinking can be either upward or downward. Upward counterfactuals involve imagining a better outcome than what actually occurred, such as contemplating the gains missed by not investing in a successful startup. Conversely, downward counterfactuals consider a worse outcome - a sigh of relief that you didn't invest in that seemingly promising venture that turned out to be a scam.

Counterfactual Thinking in Investing

Counterfactual thinking is a fundamental part of the investment process. It allows investors to evaluate their decisions, learn from their experiences, and ultimately make better-informed choices in the future. For instance, consider an investor who purchased shares in a retail company before the pandemic. The company's shares plummeted as lockdowns were imposed, and the investor incurred significant losses. The investor might use upward counterfactual thinking here, thinking, "If only I had sold my shares before the pandemic, I could have avoided these losses." In contrast, an investor who sold his shares in a pharmaceutical company before it announced a groundbreaking new vaccine may engage in upward counterfactual thinking, saying, "If only I had held onto my shares, I could have made a significant profit." Downward counterfactuals can also play a role in investment decision-making. For instance, an investor who decided to hold onto their shares in an oil company just before the oil prices plummeted might think, "It could have been worse. At least I didn't invest more money in this company."

The Upside: Lessons from the Road Not Taken

Counterfactual thinking allows investors to examine their decision-making process, providing valuable insights and lessons for future investments. It aids in identifying patterns, testing hypotheses, and fostering learning. For example, an investor might realize, "I tend to hold onto stocks for too long," or "I seem to have a bias towards tech stocks." This insight can then be utilized to adjust investment strategies. If an investor finds they often sell stocks just before they peak, they might aim to hold onto stocks for longer. Similarly, if an investor tends to favor a particular sector, they might aim to diversify their portfolio more effectively.

The Downside: The Danger of Overconfidence and Hindsight Bias

Despite its benefits, counterfactual thinking can also lead to dangerous pitfalls for investors. One such risk is overconfidence. Investors might overestimate their ability to predict outcomes based on past events. After all, knowing that Amazon would become a tech giant is far easier in 2023 than it was in 1997. Moreover, counterfactual thinking can lead to hindsight bias, the tendency to view past events as having been predictable at the time they occurred. An investor might say, "I knew I should have invested in that startup," when in reality, the success of the startup was far from certain at the time of the potential investment. This bias can distort an investor's perception of risk and their own decision-making abilities, potentially leading to imprudent investment choices in the future.

Balancing Act: Healthy Counterfactual Thinking

To harness the benefits and avoid the pitfalls of counterfactual thinking, investors should strive for a balanced approach.

  • Embrace Uncertainty: Recognize that investing inherently involves uncertainty and risk. No investor can predict the market with complete accuracy. Instead of dwelling on 'missed opportunities,' focus on the fact that the information you had at the time was different from what you know now.

  • Objective Analysis: Use counterfactuals as a tool for objective analysis rather than regret. For example, instead of lamenting, "If only I had bought Bitcoin in 2010," an investor might think, "Next time I come across an innovative yet risky investment, I'll consider allocating a small portion of my portfolio to it."

  • Avoid Hindsight Bias: Keep a decision journal detailing the reasons for each investment choice. This practice can help prevent hindsight bias by providing a clear record of what you knew and thought at the time of the decision.

  • Downward Counterfactuals: Make use of downward counterfactuals. It's easy to dwell on how things could have been better, but considering how things could have been worse can provide a valuable perspective and foster gratitude.

  • Diversification: Diversification can help manage risk and uncertainty. If you find yourself frequently thinking, "I should have invested in X instead of Y," this might be a sign that your portfolio is not sufficiently diversified. A well-diversified portfolio can mitigate regrets about specific investment decisions.

Counterfactual thinking can be a double-edged sword for investors. On the one hand, it provides valuable insights that can enhance future decision-making. On the other, it can foster overconfidence, hindsight bias, and unproductive regret. Investors who strike the right balance will be well-equipped to use counterfactual thinking to their advantage, learning from the past, improving their decision-making process, and setting themselves up for future investment success.


An interesting fact about counterfactual thinking is that it's not only influenced by the outcome of a situation, but also by how close we were to a different outcome. This phenomenon, known as the "near-miss effect," has been extensively studied in contexts ranging from gambling to sports. For example, investors may experience stronger regret and engage in more counterfactual thinking if they sell a stock, and it increases in value significantly just a day later, compared to if the same increase happened a month later. This happens even though logically, the timing of the increase should not impact the investor's evaluation of their decision. The near-miss effect thus adds another layer of complexity to counterfactual thinking in investing.

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