We all know those people. The ones who balked at your advice, in spite of your urgent pleading and maybe in some cases actual begging. Of course these people mean well, the cautious personality type is incredibly important in balancing our world. But I’m not referring to the self-aware overly cautious individual. (No, this person well knows they have deep troubles with change and decision-making and have come to terms with the consequences for following their instincts.) These self-aware people have a long history of successes to be able to point to in the past where their calm, rational, methodical non-action ended up being the smartest action. No, I’m referencing instead those individuals who hear your entreaties and respond with a balking reticence like a child to their vegetables - while lamenting they didn’t enter sooner and now is “too late” to take action.

I call this attitude the Woulda Coulda Shoulda mindset. (I had to look up the order for this phrase and have determined this to be the most trusted.) I found this word order to also be the most fitting. These people hate change and yet bemoan (dare I say acrimoniously) those who did take action (or follow advice).

Now of course this is most evident to see in the world of FinTech, and in the fluctuating markets of stocks and cryptocurrencies. There are often common sentiments in these markets across assets and this correlation would be considered overall market sentiment, sometimes this market sentiment is described as bearish, often times bullish in nature. But for the Woulda Coulda Shoulda’s (going to call them WCS) the market is always negative.

The WCS’s of the world maintain a persistently negative outlook regardless of the market direction. If the market sentiment is bullish, the WCS will talk of not getting in early, of not being “already in position”, or perhaps you’ll hear them whispering, “I wish I’d been able to get in earlier, but now…” If however, the market is bearish and the market is lower than the anticipated value of the underlying asset, the WCS will persist in their mental block only this time they reject the advice to “enter a position” or do the very thing they claimed they wished they had done!

Be careful to not be a WCS. Don’t maintain a persistent negative outlook, don’t begrudge those who find success, and be neither quick nor slow in following trusted advice. Above all else, be positive minded. Acknowledge losses and lows, celebrate the highs (be they yours or another).

#bullish