[1] From October 1987 to January 1994, Calloway was a reporter for the Boston Herald, where he co-wrote a daily financial column on the Financial District, Boston.
[1] From January 1994 to March 1999, Callaway was a reporter at Bloomberg News and led a team of financial reporters throughout Europe covering investing as well as the Northern Ireland peace process and the introduction of the Euro.
He won two Society of American Business Editors and Writers awards for a weekly commentary column he wrote for 12 years.
In March 2020, Callaway founded Callaway Climate Insights,[3] a digital newsletter tied to the intersection of climate change and finance.
He is married to Nanci Tolan Callaway, and they have a daughter, Alexandra, born in 1993.