Ten years ago, several of the smartest advisors extant said that we were going to get a once-in-a-lifetime chance to invest in equities at prices similar to those Warren Buffett paid in 1974. All we had to do was wait for the S&P 500 to fall another 20 percent from 666.

These advisors were almost right. What they didn’t realize was that the moment was right then in March 2009. Like most of the world, they thought, with some justification, that the worst was yet to come. This was after nearly two years of bad news that began in the spring of 2007 with trouble in the housing markets. It got worse with Bear Stearns’ bankruptcy in March 2008 and seemed to hit a bottom with the Lehman Bankruptcy and AIG bailout that September. By March, Goldman Sachs had said the S&P 500 might fall as low as 400.

For Main Street, the recessions of 1973-1974 and 1981-1982 were nasty, but this downturn was of a different order of magnitude. The bailouts of the auto industry and AIG were enormous, but not historic firsts. That precedent was set with the airline bailout after the September 11 terrorist attacks. 

But what are the real lessons for advisors today? Most are trying to invest clients’ money so they can maintain their financial independence over a 30- to 40-year period, not beat some benchmark.

Brad McMillan, chief investment officer of Commonwealth Financial Network, believes today’s narrative about the March 2009 market bottom is missing the point entirely. In the last decade, the S&P 500 has quadrupled and McMillan worries that a smug air of self-congratulation is becoming pervasive among the investor class. Everyone is talking about the trip from bottom to peak when they should be talking about the trip from peak to peak.

McMillan isn't predicting another crisis or bear market. In fact, he expects the stock market—and its associated risks—to keep rising.

But like many, he thinks the 13.9 percent annualized gains for the S&P 500 for the decade ended December 31 are unlikely to be replicated in the next decade. Advisors looking for a better yardstick might want to take a longer, more pedestrian 20-year perspective. Over two decades, the S&P 500 returned 5.63 percent.

Timing the market may be a fool’s errand, but spotting once-in-a-generation bargain prices can at least turn the tables in clients’ favor. That sometimes means defying some of the smartest guys in the room. In early 2003, Bill Gross and Jeremy Grantham agreed that equities were cheap but each had their own, very convincing reasons why they were a long way from the bottom. Grantham maintained bear markets always overshoot—but they had already declined more than 50 percent from their peaks. Just because very smart people have powerful arguments doesn’t make them right.

Many experts believe equities today are reasonably priced. They may indeed be right, but corporate profit margins are at record levels and various valuation metrics, including the Shiller price-to-earnings multiples and other yardsticks factoring in today's low interest rates, are not far from all-time highs. Two years into his first term, a president is boasting about the stock market like a 1950s’ New York Yankee fan or a 1960s’ Boston Celtics fan—and like no leader before him.

“The bull case is that they [profit margins, valuation, multiples] all keep going higher,” McMillan says. And of course, they can. “We’ve seen it before, but how long can it continue?”

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