Olaya Herrera studied law at the Universidad Republicana (later to become the Free University of Colombia), and founded a weekly magazine called El Estudiante (The Student) in a newspaper format, which was written by hand.

[4] Olaya Herrera is considered a member of the "Centennial Generation," corresponding to the cohort of political and intellectual leaders prominent at the time of the first century after the war of independence, roughly corresponding to the years from 1925 to 1940.

As a journalist for the newspaper El Autonomista (The Autonomist) which was owned by Rafael Uribe Uribe and Ricardo Tirado Macias, Olaya Herrera made a name by criticizing the "Regeneration," which was the name of the numerous policies that marked the return of the country to a unitary state government system, as well as the rise of conservative, authoritarian, and clerical power following the Colombian Constitution of 1886.

Back in his hometown of Guateque, Olaya Herrera maintained a newspaper called El Soldado Cubano (The Cuban Soldier) in which he showed his admiration for José Martí.

After the war Olaya Herrera continued studying law and finally graduated with a thesis entitled La Liberacion Condicional (The Conditional Liberation), which was then published by the university.

Upon his return from Belgium, Olaya Herrera joined the cause against the government of General Rafael Reyes criticizing the treaties between the United States and Colombia, and the loss of Panama.

Once President Reyes had to resign as a result of their action, on 16 March 1909, Olaya Herrera put himself forward for the Constituent Assembly and was later elected.

After the Wall Street crash of 1929 Olaya Herrera was given special powers and dictated some economic reforms that developed at some level the industry and attempted to manage the debt generated by the war with Peru which originated in 1932 when the Amazonian port of Leticia was taken over by invading Peruvian soldiers.

During his government Olaya Herrera tried to develop the Colombian national industry and for this he supported many infrastructure projects mainly highways, maritime and fluvial ports (Barranquilla and Buenaventura) and railroads.

He also supported public education and the exploration and exploitation of energy natural resources such as oil, mainly in the northern region of Catatumbo.

Olaya Herrera also tried to improve the association between guilds, for which he created a Bank of Agrarian Credit (Spanish: Caja de Crédito Agrario), the Mortgage Central Bank (Spanish: Banco Central Hipotecario) to finance low income housing and for the improvement of production and exporting of coffee products; the government of Olaya Herrera also created the National Federation of Coffee Growers of Colombia.