Know the downside.
It is more important than focusing on the upside.
Know how much you are willing to lose.
And how will you bounce back if you lose?
With this in mind, there are only a few games that one can’t play.
Games that involve people and health should be avoided.
For business, it is mostly how much you are willing to lose for potential upside. If you build a 12-months runway, you should be fine. And know that a business almost always takes more money and time before it launches and breaks even, so account for that to avoid being stressed when it stretches and eats into your cash cushion.
When choosing not to take a risk ask yourself what do you lose by not taking a risk. It makes sure that you are not too conservative, and don’t miss out on a good opportunity.
If you are beginning, try things that are almost harmless and have some upside. This will give confidence and a buffer to go after opportunities and bigger risks. When doing that don’t spend too much time between opportunities. Move from one to another rather quickly so that you are making bigger bets soon.