1. you take a risk but it ends in a loss or;
2. you play safe but after time you see that you could have made profit if you took that leap
the first one could be more painful because you lose some money after believing that you could have find success in engaging in a specific project but the second one could also be more painful because you will be plagued with what if's but at least you would not have lost some money you just simply did not gain anything
what decision would be harder to live with?
Always the decision that makes you lose in the end is more painful. It’s just a matter of self satisfaction to determine what’s most painful on this scenario. This is same to those guy that sell their holdings in good profit but the asset price they sold is just keep increasing after they sell that’s why they keep thinking about what if which is dumb thing to do.
So in this scenario, the 2nd option is just dealing with personal shit which is not really painful in reality while the first option is a straight up loss.