In 1999-2001, Dakin was a Corps member at CityYear Boston. In 2006, he served as a Investigative reporting fellow at News21. In 2007-2008, Dakin worked as a Reporter at The Bond Buyer. From 2007 to 2009, he was an Alumni Board Co-chair at CityYear, leading a group of roughly 25 alumni in fundraising events, service days and mentoring. Currently, Dakin is a Reporter for Bloomberg News and Senior Finance Correspondent at Business Insider.