First time I heard about left and right side trading. [LOL]  

Usually the terms I am aware of is momentum trading and value investing. Trend following or contrarian investing. 

In order not to mix up the directions, I will just comment in terms of momentum trading and contrarian trading. 

Momentum trading focuses on identifying new trends early and ride the trend for as long as possible until hit set targets or before reversal of trends. 

Contrarian trading focus is on identifying Reversal patterns, usually after bull runs or bearish plunges. Then trying to plan early start to new trend or have additional buffer. 

Personally, over the years I realised that trend following doesn't suit my style. 

Trend following can't start early without clear signals and by the time clear signals are in, potential profits could have already been lost up to 20-30%. If set too low a target, after deduction of the initial 20-30% that was missed out and after commissions, there isn't much to earn, will end up becoming some form of scalping. If the target is set too high, there is a risk of reversals before that happening. It's very tricky to be both practical yet not too optimistic. 

As such, I don't like to chase trends and I especially do not like market highs especially all time heights. Gives me the jitters. Never know how high can it go, or when will it reverse. Trading indicators are almost useless when the markets are irrational, which is more often than not. 

I will usually prefer to go against the trend. I especially love to sell calls on weak stocks on rallies and sell puts on strong stocks during plunges. The rationale is that overtime, markets will eventually wake up And become rational. During that time, markets will revert to their true value. 

The risk in going contrarian is 

1. it is going against where the masses are going. Expect cold water to rain down on the trades when we share. There will be many bashing for popular shares, especially when calls are sold on weak stocks. There's no counter to this, unless we dun share trades or just shut out the noises. There are times whereby I rather not share trades due to the amount of hate received. Not worth the noise for some measly tiger coins. 

2. Catching falling knives is another issue.

This is particularly bad when sell offs starts.

When markets are irrational, sell offs can continue until it's totally mind blowing. Cos fear controls investors, contrarian buying when strong stocks fall will cause us to lose sleep.

There will always be the what if I am wrong, what if the stock doesn't recover. There will be lots of self doubt. 

1 way is to enter small. Do not go all in. Split entry points and average down the costs. This will be a more stable approach.

Another way is to sell puts instead of buying stocks, as during plunges usually volatility will be elevated which allows for capturing of Additional option premiums. In addition, strike prices can be set even lower than current stock prices too allow for further cushion. 

I do believe that everyone will have their own way to make money in the markets. What's important is to make money, as long as the method makes money, who cares if it's left or right. [Cool]