humans make mistakes and it is almost impossible to completely eliminate them from life but for you what would be more painful
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?
I believe the harder outcome to live with will depend on each one's personality. Those who are more aversive to risks will prefer to live with the fact their investments weren't very profitable, but at same time, they also didn't face losses. On the other hand, greedy people who don't get satisfied with small achievements, will prefer to risk everything for a huge reward, even though they don't accomplish this conquest in the end.
Also, traits like resilience are also worthy to be mentioned in this case. More resilient people won't face a loss as the end of the world, as they can always start from zero once again, while a more methodical individual won't bear the possibility of losing money, as it will be heavily disturbing over his mood.