Oral history interviews with Estonians whose lives have been changed by the intersection of the country’s digital revolution and its rejoining of the free world; ranging from key people involved with initiating and shaping the policies that made the digital revolution possible, to those who grew up with, and were able to make full use of, the new possibilities to learn, create and live in the new, interconnected world, focusing on Estonians who have migrated to California’s Silicon Valley. The interviews focus on the time just prior to Estonia’s regained liberty and up until the present, exploring different viewpoints on how the country was changed by the openness and opportunities made possible by the these events coinciding so fortuitously with the digital revolution, and how this has impacted Estonian culture, identity and outlook. Interviewees reflect on how the openness and new global opportunities have affected Estonia and their personal lives, their hopes and fears for the future, what being an Estonian means to them, their ties with Estonia, national identity, and Estonian cultural traits. Subjects covered include Estonia, Estonian history, interwar Estonia, World War II (1939-1945), Soviet occupation, Nazi occupation, the Estonian diaspora, the digital revolution, entrepreneurship, creativity and resiliency, and Estonian identity in the future.