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?
If I had to choose between first or second option, I would choose first because I know that if I take a risk and sadly lose, at least I'll gain some experience and life only gets better with experiences. I would love to quote Thomas Edison: I have not failed. I've just found 10,000 ways that won't work.