The Road to Recovery Tour: Skyler Ray’s Journey Through Music and Sobriety

There’s something about music that cuts deeper than words alone. A single lyric, a familiar melody, or even the rhythm of a beat can stir memories we thought were long forgotten and awaken parts of ourselves we may have buried. It reminds us of who we were before the chaos, before the pain, before substances clouded our vision. 

Pursuing our favorite hobbies before substance use can be a lifeline back to our core, a way of reclaiming the truest version of ourselves. Listen in as our guest this week shares how he turned his lifelong passion into purpose and found a way back home to himself.

Skyler Ray was born on November 28, 1990, in San Jose, California. He grew up in foster homes and spent multiple years homeless—going from being locked up to sleeping on the sidewalks of downtown Portland.

His music is deeply rooted in his life experiences, including addiction, incarceration, and homelessness. He is a firm believer in spreading hope and giving back to the community he once helped destroy.

Since being released from prison on November 30, 2018, Skyler has refocused on his music and is determined to share his message with the world. He continues to live in Portland, Oregon, and remains clean and sober.

In this conversation, Jamie Demeris and Skyler Ray discuss what it really takes to rebuild a life after addiction. Together, they explore the mindset shifts that turn relapse into resilience, why consistency and small steps matter more than giant leaps, and how reconnecting with your passions can anchor you in sobriety. 

Skyler shares how music became both his therapy and his message, and why vulnerability and self-respect are the foundation of lasting recovery. Whether you’re in recovery, supporting a loved one, or just searching for hope, this conversation will remind you that transformation is always possible.

Topics Discussed:

• The importance of continuously working on yourself 

• Why relapse isn’t a step back and how you can stand up stronger 

• Pursuing your passions and who you are at your core in sobriety

• Why small, consistent steps make the most impact

• Reconnecting with your why & remembering who you were before substances

• Learning to love and respect yourself

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CHAPTERS: 

​​0:00 Introduction to Positive Recovery MD

01:10 Meet Skylar Ray: From Addiction to Recovery

02:16 Skylar's Battle with Addiction

03:56 Turning Point: Embracing Music and Sobriety

12:50 The Road to Recovery Tour

19:35 Overcoming Disbelief and Embracing Change

22:54 Climbing the Corporate Ladder

23:43 A Humbling Demotion

24:17 Prison Reflections and Personal Growth

26:22 Musical Journey and Personal Transformation

29:14 The Power of Sound and Recovery

33:23 Chasing Dreams and Overcoming Challenges

40:33 Tour Dates and Final Thoughts

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Connect with Skyler Ray: 

• Road to Recovery Tour: https://www.officialskylerray.com/road-to-recovery-tour 

• Website: www.officialskylerray.com 

• Facebook: https://www.facebook.com/therealSkylerRay 

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Connect with PRC on Social:

• IG: https://www.instagram.com/positiverecoverycenters 

• FB: https://www.facebook.com/PositiveRecoveryCenters 

• TT: https://www.tiktok.com/@positiverecoverycenter 

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