It has become trendy today to talk about moving fast, breaking things, and failing. It is almost to the point of glamorizing failure with some suggesting entrepreneurs seek it out. It may just be a matter of perspective, but I think it's healthy to have some fear of failure. A healthy dose of fear can push you to make sure you are prepared for what lies ahead, and ensure that you actually don't fail.
At ICE, we had this saying that "only the paranoid survive." Inherent in this sentiment is that you should be afraid of failing and losing to others. Fear of failure can be a healthy response. This does not mean that you let the fear of failure paralyze you and prevent you from moving forward - quite the opposite. Rather, fear can be a powerful motivator.
If you are about to jump out of a plane with a parachute, you should absolutely be afraid to fail because that fear will make sure you prepare correctly. You will practice, learn from prior mistakes, and check all of your safety equipment. The fear of failure drives you to do things to make sure you are successful. You may still feel scared, but you will jump out of that plane, knowing that you have done everything possible to prepare for success, and that your chances of failure have been significantly reduced.
I think it also matters what you are doing. I can see in the early days of Facebook when Mark Zuckerberg famously coined 'move fast and break things', that the downside of this mantra was not all that risky. If Facebook is down, you might have some angry users that are unable to access their latest social media posts. However at ICE, if we were about to release a new version of our trading platform, handling trillions of dollars of energy commerce a day, its failure would end up on the front page of the Wall Street Journal. If the stakes are really high, then you should be a little afraid to fail. That way you do everything possible to make sure that you are successful.
Taking risks and failing is part of the natural course of entrepreneurship and life. There will always be mistakes, setbacks, and disappointments. You should take chances and learn from mistakes. Being afraid to fail however is natural and healthy. The fear will help you prepare and do everything possible to be successful. You should be afraid to fail. It doesn't mean you don't do it anyway. It just means you work that much harder to make sure you don't. And if you do fail, you move on and don't dwell on it. Just learn from it, and succeed next time.