Being fearless means not feeling any fear, even when this emotion is called for. This can be a good thing or a positive thing, depending on the situation. Some of the most well known heroes through history were known for being fearless, but this is also true of some of the most despicable or criminal individuals as well. Many who are fearless enjoy taking risks or participating in extreme sports.
Fear is our worst enemy and it stops us from achieving our goals and dreams. Fear of failure, fear of loosing it all, fear of loosing the people that you love, fear of being laughed at, fear of even success. God wants you to achieve your dreams, He planted them in you, and so He wants you to get there. But in order to do so, you need to conquer your fears, not one or two but all of them. Only with God you can conquer your fear, He will help you if you ask Him, and when you conquer them, you will set yourself free.