When Olga Chaikouskaya arrived in the United States at the beginning of her career, there were several obstacles standing in her way. She spoke no English, had no money, and faced perhaps her biggest career barrier: she didn’t know how much she didn’t know. Now, after twenty years of financial experience across an array of industries, Olga reflects on that transition as a lesson in becoming comfortable with the uncomfortable. Two of the most powerful lessons she learned along the way were:  breaking free from the boundaries we place on ourselves and recognizing that mistakes are a necessary part of growth and learning.