In 1905, Ryan received the Rotch Prize of two hundred dollars for the regular student making the best record during their four years of studies.

Thereafter, she was invited to compete with only senior and fifth class men in the Junior Beaux Arts contest, in which she won second prize for a grand plan, elevation, and section of a public market.

[9] While at MIT Ryan was a member of Cleophan a club for women students that also included Matilda A. Fraser and Harriet F. Locke (see below).

[10] Ryan launched the first women's architectural practice in the United States in Waltham, showing a particular concern for the design of modest housing.

[13] Typical of her work during this time is the house that Ryan designed for her nephew as a wedding present in 1914, located at 19 Boynton Street, Waltham.

A small, 1-storey covered porch at the entrance is distinguished by an arched roof reminiscent of the work of George Washington Maher in the Chicago suburbs.

[20] When the United States entered World War I, Ryan gave her services without charge in designing and decorating the Army and Navy Canteen on Boston Common.

[21] Ryan offered her services to the government in Washington, D.C., and was the first woman employed in the War Department (in the gun carriage section).

Throughout this time, Ryan's many attempts to join the Massachusetts chapter of the American Institute of Architects were rebuffed solely because she was a woman.

Their business is listed under the heading "Architects" as "Ryan and Roberts" in the 1926 and in the 1927 Orlando City Directories, at 240 S. Orange St. and the Kenilworth Terrace address.

One of only 10 architectural firms listed in 1926, the others include Frank L. Bodine, Fred E. Field, David Hyer, Murry S. King, George E. Krug, Howard M. Reynolds, Frederick H. Trimble and Percy P. Turner.

[24] Each of these architects is notable and together these firms were supportive colleagues in promoting excellence in the built environment, as one can learn by reading the links to each.