Simple enough, I was creating a timer job that got "stuck" initializing. After a few resets and reinstalls the custom timer job just would not exit from the initializing state. After a few IISResets and redeploys there was no change. The job would initialize but not complete. A check of the ULS showed errors associated with the new timer job:
"The previous instance of the timer job 'xyz', id '{Cf27333E-482D-47CC-B098-38B86167DBCF}' for service '{3eeee14-CEB0-450B-A6B8-AAB48549E6F8}' is still running, so the current instance will be skipped. Consider increasing the interval between jobs"
Strange error since the timer job had no actual executing code, basically it was a simple shell of a timer job. Ultimately the ULS gave it up… The SharePoint Timer service was getting Login Errors for Timer jobs trying to execute. Stopping the SharePoint Timer Service, re-entering the User Id and password and a start up allowed the custom timer service to fire without issue.