In 2003, Holland departed ECM and formed his own label, Dare2 Records, on which he has issued almost all of his recent recordings. In 2005, Dare2 premiered with Overtime, a big band project including music commissioned by the Monterey Jazz Festival. A year later, Critical Mass featured his Quintet (the first with Nate Smith), and Pass It On in 2008, a sextet performing arrangements in a mini-big band style (with, among others, Robin Eubanks, pianist Mulgrew Miller, drummer Eric Harland.)
In 2010, Holland released two recordings: the live octet album Pathways, and Hands, a duet with flamenco guitarist Pepe Habichuela. In 2013, Holland dug deeper into his Fusion roots, unveiling his quartet Prism with Harland, Kevin Eubanks, and keyboardist Craig Taborn; and a year later, Holland teamed up with pianist and longtime friend Kenny Barron to record The Art Of Conversation for the Blue Note label.
The remarkable rate at which Holland leads or collaborates his way into fresh and exciting projects proves he has no plans to diminish the range nor frequency of his creative drive. His band lineups reveal that his ear is still to the ground, listening for and recognizing fresh and deserving talent, and that many are the musicians who are happy to perform or record with him. As Holland prepares to celebrate his 70th year, he is currently playing with a new group, the Aziza quartet, co-founded with Harland, saxophonist Chris Potter, and guitarist Lionel Loueke.