Investors spend a lot of time thinking about when to invest. Is the market too expensive? Is a recession coming? Should we wait until after the election, the next Fed meeting, or the next correction?

Those are fair questions. Entry points matter, particularly over short periods. But investing is rarely a twelve-month exercise. For most advisors, one of the most common conversations each quarter involves putting new money to work—proceeds from a business sale, a bonus, an inheritance, a retirement distribution, or simply cash that has accumulated on the sidelines. Inevitably, the question comes:

“Is now a good time to invest?”

The answer is rarely as clear as we would like, because no one rings a bell when the perfect time arrives.

Consider the last 30 years. Investors have lived through the dot-com bubble, 9/11, two major wars, the Global Financial Crisis, a global pandemic, inflation above 9%, rapidly rising interest rates, multiple bear markets, four different presidential administrations, and a steady stream of predictions that this time was different.

There has been no shortage of reasons to stay on the sidelines.

And yet, investors who remained invested throughout that period were rewarded handsomely.

What makes that outcome particularly interesting is that the market does not feel consistently rewarding along the way. On any individual trading day, U.S. stocks have historically risen only slightly more than half the time—at 54% based on S&P 500 daily closing returns from 1928-2024.

Stretch the timeline, though, and the math begins to change.

Over the last 30 years, approximately three out of every four calendar years have produced positive returns as measured by the S&P 500. Extend the holding period further, and negative outcomes increasingly become uncommon.

~54% of days positive → ~73% of years positive → increasingly favorable outcomes over longer holding periods.

That is the power of time.

Of course, past performance does not guarantee future results, but as the investment horizon lengthens, the importance of the original entry point begins to fade, the range of annualized outcomes narrows, and compounding becomes increasingly important.

Time does not eliminate investment risk. It changes which risks matter most.

Thirty Years of Reasons to Wait

Looking backward, the long-term rise of the market can appear almost inevitable.

Living through it was anything but.

Technology stocks collapsed. The financial system nearly seized up. The economy shut down during a pandemic. Inflation surged. Interest rates moved higher at a pace many investors had not experienced in decades. Wars, elections, banking concerns, debt-ceiling fights, and geopolitical uncertainty repeatedly dominated the headlines.

At almost every point, there was a perfectly reasonable argument for waiting another six months.

The problem is that six months has a way of becoming twelve or eighteen months.

Despite all of those interruptions, an investment in the S&P 500 over the past 35 years (from 6/30/1991 through 6/30/2026) would have compounded at over 11% annually.

That return was not earned because investors were able to avoid uncertainty.

It was earned while living through it.

Market Timing Requires Being Right Twice

There is nothing wrong with wanting to avoid a market decline. If an investor could sell before a major downturn and reinvest near the bottom, the benefits would be enormous.

There isn’t just one problem, there are actually two.

Successful market timing requires two correct decisions: when to get out and when to get back in.

The second decision may be even harder than the first.

Markets are forward-looking and often begin recovering before the economy—or the headlines—starts looking better. During the Global Financial Crisis, for example, the U.S. stock market reached its bear-market low in March 2009 while unemployment continued rising for months afterward.

An investor waiting for clear evidence that the economy had recovered would eventually have gotten that confirmation. Unfortunately, the market had already moved substantially higher by then.

Being right about the economy is not necessarily the same thing as successfully investing around it.

Missing the Best Days

Market returns are not distributed evenly.

A relatively small number of unusually strong trading days can account for a meaningful portion of long-term wealth creation. Missing only the 10, 20, or 30 strongest days over a multi-decade period can dramatically reduce an investor’s ending wealth.

Here is what makes that particularly difficult: many of the market’s strongest days occur during periods of significant volatility, sometimes surprisingly close to its worst days.

In other words, the periods that make investors most uncomfortable can also contain some of the days they can least afford to miss.

To successfully time the market, an investor would need to avoid much of the downside while somehow remaining invested for much of the rebound.

Possible? Certainly.

Repeatable? That is a much higher bar.

Eventually, Time Matters More Than Timing

Over a one-year period, valuations, economic surprises, geopolitics, interest rates, and sentiment can dominate returns.

Over twenty or thirty years, the original purchase date becomes one small part of a much larger story about compounding.

This does not mean valuation is irrelevant. It does not mean there is never a bad time to invest. And it certainly does not mean markets only go up.

Entry point matters. It simply matters less with time.

Eventually, the question:

“Did I invest at exactly the right time?”

becomes:

“Did I remain invested long enough for the strategy to work?”

That is a very different question—and for long-term investors, probably the more important one.

Waiting Has a Cost

Cash feels safe because the number on the statement does not move around much.

But waiting is still an investment decision.

An investor sitting in cash risks missing additional appreciation, losing purchasing power to inflation, or simply continuing to move the goalposts for when to invest.

Consider the investor waiting for a 10% correction. The correction may eventually arrive—but only after the market has risen 20%.

The investor got the correction he was waiting for and still ended up buying at a higher price.

Valuation can help establish reasonable expectations for future returns. It is far less reliable as a tool for predicting what markets will do next month, next quarter, or next year.

There will always be a reason to wait. The question is whether waiting actually improves the odds of reaching the long-term goal.

When Timing Does Matter

None of this means every available dollar belongs in the stock market today.

Time horizon should be one of the primary determinants of portfolio construction. Money needed next year should not be invested the same way as money intended to fund retirement twenty-five years from now.

Liquidity needs matter. Taxes matter. Valuation matters. Portfolio concentration matters. Most importantly, an investor’s ability to tolerate volatility matters.

Reducing equity exposure because an investor’s financial circumstances or time horizon have changed is fundamentally different from reducing exposure because an investor believes the market is about to decline.

One is financial planning. The other is market timing.

That distinction matters.

Patience Over Precision

There will always be reasons to wait.

Markets will look expensive. Recessions will come. Elections will create uncertainty. Interest rates will change. Wars and unexpected crises will occur. And there will always be someone on television with a very convincing argument for why the next six months will be different.

The last 30 years have given investors plenty of opportunities to be afraid.

They have also given us a useful lesson.

The investor who waits for uncertainty to disappear before committing capital will eventually discover that uncertainty never disappears. It simply changes form.

The perfect entry point is obvious only in hindsight.

Long-term investment success has not historically required finding that perfect moment. It has required something much less exciting—and much harder to stick with:

Participation. Discipline. Patience.

Investors naturally want to find the perfect time to invest.

Given a sufficiently long horizon, the better question may be whether we are giving the investment enough time.

John Wade Therrell III, CFP®, is an Investment Counselor at Leavell Investments. John Wade has been with the firm since 2015 after a successful 10-year career in the banking industry. He earned his CERTIFIED FINANCIAL PLANNER™ designation in 2018 and he became an approved advisor for the NFL Players Association in 2024. John Wade also serves in various leadership roles within the firm, including the Board of Directors and the Executive Committee. John Wade holds a B.A. from Rhodes College as well as a graduate degree in banking from the Southwestern Graduate School of Banking (SWGSB) at SMU. Educational honors include receiving the SWGSB 2015 President’s award. John Wade was also a 2011 member of Mobile’s 40 Under 40 Class and is involved in a variety of civic and business organizations along the Gulf Coast.

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Important Disclosures: The statements and opinions expressed in this article are those of the authors as of the date of the article, are subject to rapid change as economic and market conditions dictate, and do not necessarily represent the views of Leavell Investment Management, Inc. This article does not constitute investment advice, is not predictive of future performance, and should not be construed as an offer to sell or a solicitation to buy any security or make an offer where otherwise unlawful. Investing in securities carries risk including the possible loss of principal. Individual circumstances vary. Past performance is no guarantee of future results.