You need room to fail. You need to know how to fail. You need to know how to get back up and you need to know how to stay in a humbled position.
To be in a place where you always see yourself as a student or the 'dumbest person in the room' is a great place to live. It's good to always be a student so that you're always learning. You can't learn if you think you know everything regardless of what you think you know about it.
You know what hinders you from being able to 'fail successfully'? Pride. Pride and ego will make you fight yourself about failing even if it could get you to where you need to be. Pride and ego don't believe in failure but if you believe in doing whatever it takes to reach your dreams then you must be willing to let go of your ego.
You must be willing to let go of your pride, what you think you know, how great of a guess you can make about anything and assumptions. You must allow yourself to be completely present in moments as a sponge trying to soak up new information.
Be a student.
When you fail, it's going to be hurtful and confusing. There can be pain in failure but success is just the result of getting back up after every fall. Is this not how you learned how to walk? Do you see babies quitting on learning how to walk after they fall and just watching all the other older people around them walk? No. They fall but they succeed because they never stop getting back up.
This is the discipline you want to have in every area of your life. No matter what happens, get back up. Honestly, this makes you so dangerous once it gets down inside of you because that means that you'll be back up on your feet or crawling if you have to at ANYTHING life throws at you. The liberty and freedom you have in your success come from your discipline to always get back up again.