Though I originally enrolled in CCT as a means to prevent me from working too much, I ended up discovering I actually needed to do much more work –toward my creative development, instead of my professional development. While my “head-on” approach had proven effective and successful in my professional development when faced with challenges, it turned out that the same approach would be ineffective toward my attempts at personal change. Fears quickly emerged in my creativity that required my consideration - before I could enjoy any level of success. This synthesis considers the development and manifestation of my fears in creativity, and shares my experience, actions, and reflection in overcoming these fears in my personal creativity. Through the trial of seven actions focused on overcoming fear, I share how my thinking changed – which resulted in me finding comfort in creativity, and not discomfort with uncertainty.