Many investors like to think of themselves as pretty good market timers, able to consistently buy low and sell high. Some may get lucky from time to time, but those rare successes can lead to delusional over-confidence — “I saw that crash coming!” — along with some form of Dunning-Kruger metacognitive failure. Add to that a dollop of selective retention as to one’s past successes and you end up with a recipe for false belief in one’s ability to jump in and out of markets at the right times.

Those of you who fantasize about being able to sidestep the downturns but still participate in the recoveries should ask yourself these simple questions: 1) What repeatable, not chance-based process would have had you selling equities in late February near the highs? 2) What process would you have followed to buy back in after the 34% collapse? 3) Would you have had the discipline to ignore your instincts to make a timely repurchase near the March 23rd lows? Both ends of that trade are hard to time, emotionally challenging to execute and more costly than many people realize. 

I was reminded of the risks of trying to time the market by a recent column from my Bloomberg Opinion colleague Farnoosh Torabi. Last month, Torabi explained why she was reducing her equity exposure from 81% of her portfolio to 60%, and tripling her fixed-income holdings to 27% in her retirement accounts. For a variety of reasons, not least of which is her age — she has decades before she retires — I would have advised her against those actions.

As someone who has had a decent amount of luck in the timing space — emphasis on the word “luck”  — I am both fascinated and horrified by how timing is done by retail investors. Given 2020’s first quarter sell off and new highs in the third quarter, let’s consider all that goes into attempting to time the market, its emotional challenges and financial costs. 

The Exit: What motivates people to exit equities, in whole or in part? Most of the time, it is emotion. I almost never hear investors say, “Everything is going great, the market and the economy look fantastic. Liquidate all of my holdings immediately!” But that is pretty much what you would need to do to catch the market at a top. It is rarely cool, contemplative analysis about a high probability event that no one else sees. Those are incredibly rare, as is having the personality to manage the process. 

What tends to happen is that as markets fall, the drumbeat of bad news feeds upon itself. Eventually, that leads to panic. Too often, the exit is part of what technical types call “capitulation.” The word means “total surrender” and it usually results in doing whatever it takes to make the pain stop. There’s no shortage of studies showing that strategy is never the recipe for strong market returns. 

The Re-Entry: Getting back in when everyone else wants out is even harder to do. We have evolved as social primates, and our skills in cooperation and group dynamics create a distinct survival advantage. Doing the exact opposite of what your peers are doing requires fighting your most basic instincts. Buying into a panic selloff is much easier said than done. You have a choice of a variety of indicators – technical, quantitative, sentiment, momentum, economic — but none have been shown reliability in nailing the lows.

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