During Operation Iraqi Freedom he deployed to the Iraqi town of Ramadi in 2006 with SEAL Team THREE as commander of Task Unit Bruiser, which included Marc Alan Lee, Michael Monsoor, Jonny Kim, Kevin Lacz, and Chris Kyle. Willink also served as a Navy SEAL instructor during his career. He retired in October 2010 after 20 years of service.
Together with fellow former SEAL Leif Babin, Willink wrote the book Extreme Ownership and founded the consulting firm Echelon Front.
Willink hosts a weekly podcast with friend and Brazilian jiu jitsu practitioner Echo Charles, called Jocko Podcast.