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 least painful is taking a risk which you know that the chances of failure is almost 99%, and still failed. I can live with this.
In the second one, it is playing it safe. But the profit is small and there will hardly be any lesson learnt here. Failure is a bigger teacher than wins. Great inventions and businesses have been borne out of losses. Many innovations and great products have been borne out of losses. But your risk must be calculated. They must not be one made on impulse. Risks that are not calculated are just nothing of effect.
You should shoot for the moon and if you don't hit it, you will land among the stars, so says a great proverb.