From Stage Dreams to Silent Battles: Lindsey Ray on Letting Go of the “Perfect Career” for a True Life

On this episode of The Big Silence, Karena Dawn sits down with singer-songwriter Lindsey Ray — a powerhouse behind the scenes of the music industry with credits including Mariah Carey, Demi Lovato, and Tiësto. But beyond the accolades lies a story of self-reinvention, mental health awakening, and the hard decision to walk away from “success” in search of authenticity. From her childhood anxiety and people-pleasing tendencies to leaving a thriving music licensing career, Lindsey shares what it means to choose yourself — again and again.

Whether you're a fellow artist, a sensitive soul, or someone standing at the edge of a life change, Lindsey’s story offers hope that the biggest wins come when we stop performing for approval and start living for ourselves.

What Happens When Success Doesn’t Make You Happy Anymore?

Lindsey reflects on the emotional toll of chasing external validation — and what it took to finally start writing a new story for herself.

(00:02:10) The Silent Battle of Mental Health: From Anxious Childhood to Empowered Voice

• Lindsey opens up about suffering silently for years — and the weight that lifted once she could name and share her mental health struggles.
• Why childhood wounds often resurface in adulthood — and how Lindsey finds beauty in understanding that connection.
• How Tone It Up, The Big Silence, and building community around mental health gave her a new mission.
• Her journey from hiding anxiety to embracing it as part of her truth.

(00:08:30) From MySpace to Mariah Carey: The Wild Ride of an Indie Artist

• How a MySpace video and an open mic night changed everything.
• The unconventional way she ended up featured on a Tiësto track using an iPhone mic — while sick with strep throat.
• Why she created alter egos like Raelle and Aliana to explore different music styles.
• Learning the industry “rules” and why she ultimately rejected them to stay true to herself.

(00:21:00) When the Dream Isn’t Enough: Walking Away at the Peak of Success

• Despite success in sync licensing, Lindsey realized she wasn’t fulfilled — and decided to walk away from a decade-long partnership.
• The emotional, financial, and identity crisis that followed.
• Discovering that people-pleasing was driving her choices, not passion.
• Learning to let go of needing external approval and define her worth on her own terms.

(00:26:00) Rituals for Healing: How Lindsey Stays Grounded Today

• Her go-to grounding practices: walks in the woods, bath rituals, lifting heavy weights, and alone time.
• The importance of solitude as a sensitive person and empath.
• Setting boundaries around emotional energy and people-pleasing.
• The ongoing lesson: healing is not a finish line — it’s a lifelong practice.

(00:30:00) Redefining Success: Full Belly Breaths, Saying No, and Living Truthfully

• Lindsey redefines success as peace, alignment, and the courage to say no.
• How she’s learned to trust her body, her voice, and her path — even when it’s uncertain.
• The power of living authentically and inspiring others to do the same.
• Why letting go of what no longer serves you is sometimes the bravest thing you can do.

This episode was Filmed at the Thompson Nashville. 

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