[4] Wolf's career in urbanism began at Wilbur Smith Associates, where he engaged in land planning focused on transportation.

He began teaching urbanism as an adjunct professor at the School of Architecture at the Cooper Union for the Advancement of Science and Art in 1971, and continued in that role through 1987.

Wolf also began working for the Institute for Architecture and Urban Studies in 1971, participating in a number of research initiatives, including: "The Street as a Component of the Urban Environment" (co-director with architect Peter Eisenman, 1971–1973); "Low-Rise High-Density Prototype" (co-director with professor Kenneth Frampton, 1971–1973);[5] and Union Square Redevelopment Program (director, 1972–1973).

In 2012, he was appointed to the Advisory Committee of the Quiet Skies Coalition, a group that seeks to preserve the well-being of communities on the easternmost reaches of Long Island suffering from noise pollution created by increasing air traffic.

Wolf’s biography The Sugar King: Leon Godchaux, published in 2022, attracted advance praise from distinguished authors and journalists such as Walter Isaacson, Henry Louis Gates Jr., Nicholas B. Lemann, Richard Campanella and Lawrence N. Powell.

[9] The book, which reached the New York Times e-book best seller list in 2016, celebrates New Orleans and explores the issue of growing up as a Jew in the South.