Fear of failure is deeply ingrained in society and impacts entrepreneurship. The author recounts building a popular blogging platform as a teenager in the early 2000s that had hundreds of thousands of users but he was unable to pursue it further due to societal expectations to attend college. While regulations need reform, a fundamental shift is also needed in how society views success and failure to reduce the dampening effect on innovative ideas. Entrepreneurship requires taking risks but the fear of failing holds many back from pushing their ideas to completion.