To help support the family, Wright worked for Allan Conover, a Dean of the University of Wisconsin's Department of Engineering. He attended the University of Wisconsin briefly but rejected formal education in favor of life experience, which became a basic principal for his future education. In 1887, he left Wisconsin for Chicago to work in the office of Joseph Lyman Silsbee. But his real interest was in the work of another American Master named Louis Sullivan. Within a year, Wright transferred to the firm of Adler & Sullivan.

The young architect’s talent and skills were soon recognized at the firm and he became an important contributor to landmark projects including the Auditorium Building.

Despite conflict resulting in Wright’s departure from the firm, he always referred to Louis Sullivan as his "Lieber Meister" - his adored master.