Record Highs and Record Cash Hoards
The S&P 500 has set 27 record closing highs so far this year, according to Forbes. At the same time, money market funds now hold $7.93 trillion, a record, per the Investment Company Institute. This juxtaposition—markets climbing while many investors sit on the sidelines—raises a classic investing dilemma: should you jump in, wade in gradually, or wait for a better entry point?
Forbes frames this as "standing on the deck of a pool," where the water is always cold. The question, it suggests, is not when to get in, but how to commit to a plan.
The Cost of Waiting
The strongest case against waiting comes from a Charles Schwab study, "Does Market Timing Work?," published in 2025. The study gave five hypothetical investors $2,000 a year to invest over a 20-year period ending 2024. The perfect timer, who bought at the exact low every year, ended with $186,077. The investor who put money in immediately on the first trading day each year ended with $170,555. The one who divided purchases into 12 monthly chunks ended with $166,591. Even the unluckiest investor, who bought at the exact peak every year for 20 years, ended with $151,343. Meanwhile, the investor who stayed in cash ended with just $47,357.
Forbes sums up the takeaway: "Staying out of the pool created the biggest risk. That overwhelmed any timing decision."
Record Highs Are Not Red Flags
The fear that record highs signal an imminent crash is common but unsupported by data. J.P. Morgan Asset Management found that since 1950, about 7% of trading days closed at a new all-time high, and nearly a third of those highs became floors the market never fell more than 5% below again. Since 1988, investing only on record-high days produced an average one-year return of 14.3%, versus 11.9% for any random day. Schwab's research finds the market rises 75.6% of the time in a typical 12-month period. As Forbes puts it, "Avoiding highs means avoiding the market."
Lump Sum or Dollar-Cost Averaging?
When you have a lump sum, is it better to invest it all at once or to wade in gradually? Vanguard found that investing a lump sum immediately beat spreading it over three months about 68% of the time from 1976 through 2022. Morgan Stanley's Global Investment Office found the same result with a smaller edge, at most 0.42% a year for its most aggressive portfolio. These findings support the "plunge" over the "wade," but the edge is modest and the decision matters far less than getting invested at all.
The Long-Term Case for Staying Invested
The Motley Fool's coverage emphasizes the historical strength of the S&P 500. The index has generated an average annual total return of about 10% since its inception in 1957. That long-term performance, the argument goes, rewards patient investors who can "tune out the near-term noise"—a phrase used to encapsulate the advice of Peter Lynch that "everybody in the world is a long-term investor until the market goes down."
The Motley Fool also cites John Bogle, Vanguard's founder and creator of the first S&P 500 index fund, who urged investors: "Don't look for the needle in the haystack. Just buy the haystack." This passive approach is underpinned by the index's structural advantage: it is rebalanced each quarter to always include the 500 largest American companies, pruning the weak and adding rising stars.
Acknowledging the Risks
The S&P 500 is not without its downturns. The Motley Fool notes that the index has historically experienced significant drawdowns: 57% from October 2007 to March 2009, 34% from February to March 2020, and 25% from January to October 2022. The Motley Fool attributes these to the Great Recession, the COVID-19 crisis, and the Fed's rate hikes. However, the long-term upward drift has more than made up for these declines.
The Motley Fool also points out that the S&P 500 looks historically expensive at 29 times earnings, above its average price-to-earnings ratio of 20 to 23 over the past three decades. Despite this, the article's tone, built on statistics like the $1,000 invested at the start of 2007 growing to about $7,650 today (versus about $2,500 in a 20-year Treasury), underscores that patience and staying invested are what matter.
Morningstar's 150-year study of market crashes, which includes a "Lost Decade" when an all-stock portfolio stayed underwater for 12 years and 9 months after buying at the top in August 2000, is a real cautionary tale. However, Morningstar also found that 2022 was the only episode in those 150 years where a balanced portfolio (60% U.S. stocks, 40% 10-year government bonds) stayed underwater longer than stocks, at 42 months versus 27. The historical rarity of such a outcome argues for staying invested and, if necessary, rebalancing.
A Practical Framework: Plan, Automate, Wait 48 Hours
Forbes offers a framework that satisfies both the head and the heart. The first step is simply to write a plan. A written investment plan—covering your goals, asset allocation, and risk tolerance—makes decisions systematic rather than emotional. Next, automate your investments. When contributions happen automatically, you sidestep the constant temptation to wait for a better price. Finally, make it structurally difficult to deviate from your plan. Forbes proposes a 48-hour waiting period before you make a change, forcing you to state your new plan and check whether it beats the one you already committed to.
This echoes the behavioral advice drawn from Seneca and Odysseus, as Forbes presses: premeditation of evils and lashing yourself to the mast can protect against the Siren of market timing. The plan takes the decision out of the hands of that weekend worry.
Conclusion: The Plan Is The Point
The evidence, from the data and dozens of studies, converges: getting invested—via a plan, with stomachless automation—is what delivers long-term wealth. Waiting for the perfect moment, or fearing record highs, risks staying on the porch. The pool is cold; it always is. The wise approach is to plan accordingly, jump in, and stay the course.