This document discusses challenges facing Generation Y entrepreneurs in Africa. It notes that while Generation Y is often perceived as bold, innovative, and entrepreneurial, entrepreneurship is actually relatively uncommon among young people. Few young people own stock in private companies or are business owners themselves. The document outlines three pillars of entrepreneurship - being bold, planning carefully, and taking calculated risks. However, Generation Y entrepreneurs may struggle with overconfidence, impatience, miscalculated risks, and risk aversion. The document emphasizes that success is about thinking, learning from failures, exploration, and perseverance rather than never failing, brilliant strategies, or large social media followings. It promotes staying dedicated to outcomes through challenges.