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Selling investments, particularly in a volatile market like crypto, presents significant psychological challenges. Investors often find themselves dealing with emotions driven by market narratives and the fear of missing out, making the decision to sell difficult. The episode stresses the importance of establishing a clear selling strategy beforehand to remove emotional influences during market highs, when selling might be necessary but the excitement makes it hard to act. By doing so, investors can avoid the pitfall of holding onto assets too long, potentially leading to missed opportunities for profit.