Autonomy is a primary motive, as well as source of satisfaction, for those who start and run their own business. Autonomy is not inherent to business ownership – owner/founders must make concentrated efforts to achieve and maintain autonomy. This study aims to increase our understanding of autonomy by investigating how it is experienced, the factors that affect it, and the actions that business owners take to attain and retain it. We study these topics in the setting of an emerging market – Russia – and compare the outcomes with a similar study conducted in the Netherlands. Our cross-cultural comparison reveals that the way autonomy is experienced and attained can be viewed as an expression of survival values in Russia and of self-expression values in the Netherlands. We posit an underlying structural similarity by theorizing the level of experienced entrepreneurial autonomy to be the outcome of the balance of power and dependencies.