I used to be super risk averse. One thing that helped me is to play games that punish being too risk averse. For me, that game was Poker. In Poker if you are to

I used to be super risk averse. One thing that helped me is to play games that punish being too risk averse. For me, that game was Poker. In Poker if you are too risk averse, since the game is naturally adversarial, you get crushed. I would play online on PokerStars with free fake chips and over time I could actively feel myself becoming more risk seeking. I no longer always thought my opponent was better than me. I would bluff in crazy positions just to see what happens. Occasionally I would overstep my boundaries and become too risk seeking. Overall the game forces you to become more rational with how you perceive and act on risk. Would highly recommend!