Lose small, win big

In many situations, you'll noticed that all you need is one big break that pulls you out of a string of failures. The huge win that wipes out all your losses. You see this in investments, businesses and games. But of course, it also works the other way round more often than it should. You probably know someone who lost everything in a bad bet. After all, losing is part of the game so someone got to take the hit.

It is best to expect losses and aim to reduce its damage but Nassim Nicholas Taleb took it a step further and used the inevitability of losing as his strategy to win big. He planned his investment strategy around the fact that sooner or later a financial disaster would occur and aims to cash in on that.

He used a financial instrument known as options where you can make bets against the future of the stock price. You can obtain options to buy or sell stocks at a certain price. He systematically purchase options to buy stocks at a price which is most likely higher than it will be during a market crash.

Obviously the market doesn't crash that often, so most of the time he is slowly losing money. (due to the transaction cost of trading options) But when the day comes, he will exercise his options to recoup his losses and more. He limits the money he can lose while leaving the opportunity to make a much larger amount.

I think this is probably the best strategy you can ever adopt. You should try apply it not only to your investment portfolio but to everything in your life. We can't prevent failures and losses. So losing is fine as long as it's small but remember to leave the door open for yourself to win big.