By the beginning of his high school tenure, Bailey began his teaching career as a private instructor and mentor in his high school music programs where he played the drum set, concert percussion, electric bass, upright bass, and other musical instruments.
By the summer of 2006, Bailey went on to receive the Steve Gadd Scholarship, awarded by Berklee College of Music and presented by Craig Zildjian.
[2] In 2011, right before Bailey graduated from Berklee College of Music, during his final semester, he broke and dislocated his right ankle leaving him to get multiple metal plates and screws surgically placed to repair the damage.
Bailey when on back to touring and recorded with Guggenheim Grant winner David Fiuczynski and Mononeon from 2009 to 2013.
Instrument(s): Drums•Bass•Fender Rhodes• Keys•Vocals•Guitar• Piano, Percussion•Upright Bass•Synthesizer Genres: Jazz•Fusion•R&B•Pop•Funk•Rock•Country•Soul•Microtonal Marcus Miller, David Fiuczynski, Judith Hill, Mononeon, Elan Trotman Marcus Miller,[6][7] Judith Hill, Jack DeJohnette, Phil Perry, JoAnn Condury,Chick Corea, Euge Groove, Tim Bowman, David Sanborn, Elan Trontman, Gerald Albright, Kirk Whalum, George Benson, Kevin Whalum, Keiko Matsui, Jeff Lorber, Jonathan Butler, Peter White, Allen Toussaint, Tosha Cobbs, Paul Jackson Jr., Rudresh Mahanthappa, Julian Vaughn, Jon Barnes, Darryl Williams, Lalah Hathaway, Adam Hawley, Joey DeFrancesco, Patrice Rushen, Tawanda, Matt Garrison, David Fiuczynski, Selah Sue, Alex Han, Vincent Reid, Jeffrey Osborne, Janelle Monae, Marcus Anderson, BK Jackson, Take 6, Tom Kennedy, Mike Stern, Gerald Veasley, Andre Ward, Richard Smallwood, Christian Sands, WAR, Bebe Winans, Ashmont Hill, Tony Ferrari, Brent Jones, Clint Holmes, MonoNeon, Lin Roundtree, Grace Kelly, James Carter, Eric Darius, Candy Dulfer, Phil Perry, Chiddy Bang, Wayne Lindsay, Aubrey Logan, Robert Glasper, Ravi Coltrane, Cory Henry, Russell Gunn, Chris Mann, Eric Marienthal, Gregory Porter, Oscar Peterson, Gabriela Martina,[8] and many more.