Woods was commissioned in the United States Army as a second lieutenant in the Armor branch and began the Armor Officer Basic Course at Fort Knox, Kentucky, in July 2003. While there, he volunteered for his first deployment to Iraq to lead a platoon of National Guard soldiers. Woods deployed to the Diyala province of Iraq, where he served for eleven months.[8]
Woods returned from this deployment to the U.S. in January 2005 and was transferred from Fort Bragg to Fort Carson, Colorado. Later that year, in June 2005, he made his second deployment to Iraq with the 3rd Armored Cavalry Regiment.[9]
Woods on active service in Iraq
Upon return from his second deployment, the Army selected Woods to teach at West Point, an unusual appointment for so junior an officer and one which would require him to earn a graduate degree first.[10] That year, he enrolled at the John F. Kennedy School of Government at Harvard University, where he studied for a master's degree in public policy.[9]
While at Harvard, Woods volunteered to mentor low-income minorities applying to college and numerous other community leadership activities, including co-founding the first student chapter of The Fuller Center for Housing and making three trips to New Orleans to assist families struggling to rebuild following Hurricane Katrina.[6] He was among a group of students awarded the Robert F. Kennedy Public Service Award for this work.[9]
Woods helping in the recovery after Hurricane Katrina in New Orleans
During the summer of 2007, Woods co-led a group of thirty cyclists across the U.S. to raise money for Habitat for Humanity through a non-profit group known as Bike & Build. The trip took them across the United States from the Outer Banks of North Carolina to San Diego, California. The group raised over $130,000 and built homes in five states during their trip.[9]
Before graduating in 2008, Woods competed for the opportunity to speak at Harvard's annual commencement and was selected as one of three students to deliver a commencement speech.[11][12]
Shortly after graduation, Woods reported to Fort Knox, Kentucky, for the Armor Captain's Career Course. Shortly thereafter, Woods outed himself as gay and was subsequently discharged under the government's now-repealed “Don't ask, don't tell” policy.[11] For this decision, Woods was ordered to reimburse the Army for the $35,000 tuition paid on his behalf to attend Harvard.[13] In December 2008, the U.S. Army completed the discharge process for Woods.[14]
After his honorable discharge from the Army in 2008, Woods worked as an aide for Governor David Paterson of New York.[4] On March 18, 2009, Woods declared his intention to run in the 2009 California's 10th congressional district special election to replace representative Ellen Tauscher, who was nominated by President Barack Obama to serve as Undersecretary of State for Arms Control and International Security. His campaign made it a high-profile affair receiving national attention.[11] However, his bid to become the first openly gay African-American elected to Congress ended when he lost a special election held on September 1, 2009, receiving under 9 percent of the vote.[15][16]
Following the campaign in California, Woods returned to Washington, D.C., where he worked for the nonprofit Be the Change, Inc. Woods helped run the organization's ServiceNation campaign devoted to increasing support for expanding national service programs like the Peace Corps and AmeriCorps. He served as the Director of the "Service as a Strategy" initiative, aiding in developing volunteer-driven solutions for American cities.[9] In 2011, Woods joined the 2011–2012 Class of White House Fellows.[17] Woods worked at the United States Office of Personnel Management under John Berry during this time.[9]