Book excerpt: To benefit the economy, Canada accepts thousands of professional immigrants each year. However, they often encounter unforeseen hardships in acculturation and employment pursuits which negatively impact self-esteem: a predictor of career success and life satisfaction. Since existing supports for professional immigrants have proven unsatisfactory, the current study aimed to identify and understand impacts of adjustment barriers on self-esteem to inform development of resources including career counselling protocols. Methodologies included analysis of qualitative interviews with professional immigrants who underwent retraining in Canada. Results revealed fluctuations in self-esteem throughout adjustment periods. Self-esteem was highest prior to immigration and upon initial arrival in Canada but significantly decreased during primary attempts at job searching and acculturation. During retraining and post-retraining employment, self-esteem increased but was threatened by remaining adjustment barriers. Eleven key impactors on self-esteem were revealed. By identifying challenges for professional immigrants, results can inform development of resources to encourage health and success.