The High-Water Mark Fallacy in Long-Term Investing

December 17, 2025

The High-Water Mark Fallacy in Long-Term Investing

Daly Investment Management we wanted to take some time and share our Daly Investment fact for December 2025. Since 1916, the Dow Jones has made new all-time highs less than 5% of all days, but over that time it is up 279,000%. including dividends. 95% of the time the less you look the better. We know every client has different goals and risk tolerance and nothing is one size fits all but below are some insights into how we manage at Daly Investment Management.

The High-Water Mark Fallacy in Long-Term Investing

One of our Daly Investment investing principles is to discourage investors from focusing on their portfolio's "high-water mark." Using historical market data, at Daly Investment we argue that since markets spend the vast majority of time below their all-time highs, fixating on this metric leads to emotional, short-sighted decisions, and recommends adopting a long-term perspective with less frequent portfolio monitoring for better outcomes

The High-Water Mark Paradox

Here is an interesting fact from Daly Investment. Since 1916, both the Dow Jones and the S&P 500 have been at an all-time high on less than 5% of all trading days. This historical data reveals that for any long-term investor, their portfolio has been below its peak value—or "high-water mark"—for approximately 95% of the time. Despite the market being technically "underwater" from its peak the vast majority of the time, the total return during this period was a remarkable 279,000%. This contrast illustrates the disconnect between the frequent feeling of being below a peak and the significant potential for long-term growth. 

The Pitfall of Emotional Investing by Daly Investment

Focusing on the high-water mark as an emotionally driven and ultimately unsuccessful investment strategy. At Daly investment we warn that investors who constantly check their accounts to see if they have returned to a previous peak are prone to making poor, reactive decisions. This behavior is characterized as a form of market timing, which is contrasted with the more proven strategy of "time in the market." Such constant monitoring and fixation on reclaiming a high-water mark, whether daily or monthly, leads to an uncomfortable and stressful investment experience rather than a successful one.

The Case for a Long-Term Perspective

At Daly Investment we advocate for a disciplined, long-term approach as the solution to the high-water mark fixation. We always recommend to look at one's portfolio less frequently to avoid emotional reactions to normal market fluctuations. Investing is framed as a "long-term game," where patience is key. At Daly Investment we know new highs will most likely be reached again in the future. By detaching from the daily and monthly performance and avoiding the impulse to time the market, investors can have a more comfortable and ultimately more successful experience.

Daly Investment located in Chicago Illinois is one of the premier Fiduciaries in the Chicagoland area. Whether it’s an initial discussion about how to invest for your financial freedom or how to avoid taxation when moving multi dollar portfolios let’s talk (224) 347-2623 or checkout www,DalyInvestment.com, we are happy to leverage our decades of experience to help you towards your retirement and financial goals,no question is too small or too big.