[r_hoods_ghost]

Racing games like Asseto Corsa or Automobilista paired with a VR headset and a decent wheel and set of pedals. Learning to race in VR will give you very immediate and visceral feedback about what risks are worth taking. Realistically though, if you want to train yourself to be more risk tolerant you need to take some actual risks in the real world. Try bouldering, abseiling, boxing, anything that makes you uncomfortable like talking to strangers, going to social events on your own if you're shy etc.