The California-born singer/songwriter Gregory Ackerman’s marvelous new album Still Waiting Still is shimmering with delicacy and strength. Buoyed by shadowy backbeats, sneaky melodies and Ackerman’s inimitable and unforgettable delivery, sonically Still Waiting Still falls somewhere between the work of Nick Drake and Elliott Smith. The album is as breezy as it is riveting–it’s a brilliant meditation on the quotidian life and its daily comforts and disruptions. Ackerman’s work is intimate and confiding and played with the kind of commanding interior strength that gives it an instantly timeless quality. It's a rich and seamless collection of woebegone West Coast loneliness that perfectly contrasts the sunrises and sunsets of Southern California with the corresponding highs and lows of the human heart. Woven through the waves of subtlety, the quietly rushing choruses and harmonic intricacy is a true sense of optimism—that things will get dark, sure, but that darkness will lift and let’s face it: we live for that lifting. In this conversation Gregory talks to Alex about handling self-doubt, transcending the fear of being judged and the never-ending pursuit of making art.