Barry Ritholz has a nice piece on the difficulty of market timing here…
“Still, it points out the challenge of trying to explain day-to-day movements of markets. Therein lay one of the challenges of market timing.
There are other difficulties as well:
Behavior: We begin with where so many things go awry for investors, namely their own inability to be rational and disciplined. To successfully jump in and out of markets, one must rely on a specific set of rules. History informs us that relying on one’s gut or intuition may result in the occasional lucky call, but it is neither reliable nor consistent. Most people tend to succumb to their own physiological responses to losing money by doing whatever to just makes the pain stop. Easy trades are rarely lucrative ones.
Contrarian: There is a two-fold challenge to making a contrarian market call. The first is that most of the time, markets more or less get it right. Markets are kinda sorta eventually efficient. All of the various clichés you hear — “wisdoms of crowds; don’t fight the tape; the trend is your friend” — is essentially an acknowledgement that pricing is mostly rational.
The second challenge is in precisely identifying when market participants have morphed from a crowd to a mob, exhibiting either extreme fear or extreme greed. But that’s what a good contrarian timer has to do.
Every Cycle Is Different: How have the dominant elements this cycle — high-frequency trading, the rise of indexing, ultra-low rates, quantitative easing, exchange-traded funds, etc. — impacted markets? I have some ideas, but nothing I really want to wager money on. It surely would be helpful to timers to understand how these and other elements impact market moves.
Don’t misunderstand what “It’s different this time” actually means: It refers to the trading error that fails to recognize human behavior is immutable and unchanging. However, market structures, investing products, firms and even trading tools do evolve and change. Don’t confuse the two.
Clustering: Perhaps the biggest challenge is that the best and worst days tend to come close in time. The reason for this is that big selloffs or huge rallies lead to wildly overbought or oversold conditions. The rubber band gets stretched too far and has to snap back.
Given the relative proximity these big days have on the historical timeline (see below), and how often these occur back to back, there is little room for error. Getting most but not all of the timing right could lead to missing the big recovery or getting caught in a damaging selloff. That has the potential to seriously impact returns.
https://www.bloomberg.com/view/articles/2017-09-06/the-fickle-fortunes-of-market-timing
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