Totten is of English descent and was born in Salem, Oregon on September 16, 1970. His father was a Republican and a military veteran. Totten's grandfather was a World War II veteran.
Totten studied English literature at the University of Oregon in the early 1990s, after attending South Salem High School in the 1980s. He has stated that he did not like his time living in Salem and that he was glad to leave it.
In the 1990s, Totten wrote an opinion column for The Daily Iowan.
Totten's work has appeared in The Wall Street Journal, The New York Times, City Journal, the New York Daily News, The Jerusalem Post, the Daily Star of Lebanon, Reason magazine, Commentary, LA Weekly, Front Page, Tech Central Station, and the Australian edition of Newsweek.
In July 2007, Totten traveled to Baghdad to embed with several U.S. Army units before transitioning to Anbar province and embedding with U.S. Marines. In late 2007 he embedded with U.S. Marines in Fallujah, and he embedded again with the U.S. Army in Baghdad in late 2008.
Totten won the 2007 Weblog Award for Best Middle East or Africa Blog, he won it again in 2008, and was named Blogger of the Year in 2006 by The Week magazine for his dispatches from the Middle East.
His most recent book is Tower of the Sun: Stories from the Middle East and North Africa.
In the past Totten has described himself as a "weird combination of liberal, libertarian, and neocon" and later he described himself as politically centrist. He initially supported the Iraq War, stating during the run-up, "If you don’t join us now, when Saddam’s regime falls and Iraqis cheer the US Marines, you are really going to feel like a jackass. And your jackassery will be exposed beneath klieg lights for all to see." However, he believed that the critics of the war who noted the lack of progress from 2004 to 2006 were correct while the Bush administration was wrong. He supported the 2007 'surge' strategy.
On June 23, 2010, Totten applauded Barack Obama's decision to accept General Stanley McChrystal's resignation, and Totten labeled it "one of the best decisions the president has made since he took office."
Totten describes himself as an "independent journalist." Most of his trips—to Iraq, Lebanon, Turkey, Israel, Egypt, Libya, Bosnia, Kosovo, Georgia, and several other places—are paid for out of his own pocket, although he has also accepted funding from the Government of Azerbaijan, the American Jewish Committee and the Lebanese pro-western March 14 alliance for trips to Azerbaijan, Israel, and Lebanon, respectively.
In the early 2000s, Totten married Shelly Lynn Stephenson in Oregon's Multnomah County, and they spent their honeymoon in Spain in April 2002. He describes his wife as "conventionally" liberal. They are both registered Democrats and atheists, although Totten is a former Christian. They both live together in the Sunnyside neighborhood of Portland, Oregon.
Totten was briefly a Libertarian during the 1990s, but became a Democrat afterwards, though he has stated in the past that he was never fully content with being a Democrat and has considered going back to the Libertarians.
Totten's first book, The Road to Fatima Gate: The Beirut Spring, the Rise of Hezbollah, and the Iranian War Against Israel (Encounter Books, April 2011, ISBN 978-1-59403-521-0), reports his experiences in the Middle East, primarily Lebanon.
Other books include:Tower of the Sun: Stories From the Middle East and North Africa (2014)
Where the West Ends (2012)
Resurrection: A Zombie Novel (2014)
Taken – A Novel (2013)
In the Wake of the Surge (2011)
On the Hunt in Baghdad (2011)
In the Land of the Brother Leader (2011)
Raid Night (2011)