Musician, vocalist, and guitar-slayer Derek Day joins Kate for an electrifying and emotional conversation about what it really means to be an artist in today’s world.

Derek is the frontman for the LA-based group Classless Act, and has opened for–and toured with–rock legends like Motley Crüe, Def Leppard, and Joan Jett. He takes us backstage into his journey, from street busking at age 13 to headlining with icons. But this isn’t just about music. It’s about discipline, authenticity, and staying grounded in a business that often tries to strip artists of their truth.

In this episode, Kate and Derek explore:

• Why presence—not perfection—is the mark of a true performer

• How sobriety and journaling helped Derek fine-tune his creative self

• What icons like Nikki Sixx and Tommy Lee taught him about professionalism

• How he overcame the pressure to people-please and started playing for himself

• Why flaws, imperfections, and subtlety are where the soul lives in music

They also talk candidly about the music industry’s darker truths, the weight of public projection, and how to reclaim your art (and your peace) in a culture that wants everything curated.

This episode is a love letter to creative misfits, musicians, and anyone bold enough to live—and play—their truth.

MORE ABOUT THIS EPISODE:

(00:00:00) Welcome & Meet Derek Day

(00:03:00) From Promenade to Stadiums

(00:05:00) Performing as Spiritual Practice

(00:08:00) Energy Exchange: Audience & Band Chemistry

(00:13:00) Wisdom from the Legends

(00:17:00) Sobriety, Self-Work & Being Your Own Instrument

(00:24:00) Authenticity Over Algorithms

(00:33:00) Making the Album: I Can’t Imagine

(00:41:00) Risk, Rejection & the Power of Response

(00:46:00) Artist as Healer, Mirror & Messenger

(00:53:00) Final Reflections on Presence, Process & Purpose

If this episode speaks to you, please share with a friend, leave a comment, and drop a review—I’d love to hear your biggest takeaway!

Resources:

• Derek’s Website

• @derekdaymusic on Instagram

• Classless Act

• Think: X

Related Episodes:

• 009. Unleash Your Hidden Power & Boost Your Confidence With Bryan Ruby

• 014. Lessons From The Greats: Pink Floyd’s Scott Page On The Masters Of Creativity

Connect with Kate:

• Watch the episode on YouTube

• Instagram

• Website

• Book

Rawish is produced by Crate Media.