Is school still relevant in the 21st century? The rise of the gig economy, the start-up business boom and the evolution of technology has created new employment and business opportunities. The Australian school system is struggling to adapt and equip students with the necessary skills to thrive. At school, content can no longer be king. Let’s value educators and those of us driven to help nurture the will and confidence in students to learn. Let’s also consider how our own success and failure stories can educate and keep it real. As a high performing student and perfectionist, Samantha started her law degree and entered the workplace believing she was on a straight career path to success. She soon found out that being able to write without grammatical errors and strictly follow processes would not grant her an A+ from employers and fellow colleagues. Instead, learning to fail fast, adapt to circumstances and build relationships enabled Samantha to thrive. She has since taken advantage of opportunities to work overseas, learn new skills through various gigs and is now at the frontline of innovation leading start-ups and corporate enterprises in projects involving digital transformation.