#2504 - Skylar Grey

Joe Rogan and Skylar Grey discuss how artificial intelligence (AI) and other technologies intersect with the authenticity, creativity, and emotion found in music.

Artificial Intelligence CanNot yet Replicate Genuine Human Emotion

Ai-generated Music Lacks the Human Spiritual Connection and Experience, Differing From Authentic Composition

Joe Rogan asserts that real music carries emotion that AI cannot yet replicate. He notes that while AI music can sound cool, there is always a recognition that it is created by a robot and not a person. This lack of human origin means AI-generated songs do not possess the spirit, creativity, or genuine connection found in compositions made by people.

Emotional Depth in Music Arises From Real People Channeling True Feelings, Beyond Ai's Capability

Skylar Grey echoes this, describing her songwriting as therapeutic and always rooted in real emotion. She believes that the emotional depth and nuance in her work—and in music created by artists who channel authentic feelings—is beyond what AI can achieve. Rogan emphasizes that people are drawn to music because they know a human sat down to write it, expressing their own spirit and creativity, an essence AI lacks.

Technological Tools Faced Initial Resistance Before Acceptance

Innovations Like Auto-Tune Faced Backlash as Not "Real Music," yet Became Aids to Creativity

Skylar Grey acknowledges that every technological innovation in music faced criticism. She recalls the backlash when Auto-Tune was introduced, with detractors arguing it was not “real music.” Earlier, even the introduction of computers into recording was contested, while her earliest recordings with her mother were made on two-inch tape, without computers. As technology advanced, skeptics always raised concerns about authenticity.

New Technology Expands Artists' Vision, Not Replacing Artistry, Like Painting's Evolution With New Tools

Grey frames such innovations as creative tools, enabling artists to achieve their visions more effectively. Joe Rogan agrees, comparing it to the evolution in painting, where new materials or techniques expand what artists can express, but do not replace the fundamental value of human artistry and the imperfections that make art relatable.

Ai As a Creative Tool: Applications and Limitations

Ai Music Serves Practical Uses but Lacks the Unique Essence and Narrative of Human-Made Art

Skylar Grey notes that AI-generated music may have ...

Musical Foundation Built Through Family and Childhood Performances

Skylar Grey grows up in a deeply musical Wisconsin family, immersed in music from her earliest years. Her mother plays Celtic harp in folk bands and her father sings in a barbershop quartet. Her great-grandmother is an opera singer. Music is part of daily life; even as a toddler, Skylar harmonizes at family gatherings, astonishing her mother by singing harmony lines before she can fully speak.

By the age of six, Skylar performs a full hour-long show with her mother at a local library in Madison, Wisconsin, marking the beginning of a rigorous schedule touring the Midwest. Performing at venues like elementary schools, libraries, women’s health conventions, and even a Boy Scouts gathering, she misses school regularly, sometimes playing as many as six shows a week. Through these experiences, Skylar develops resilience and a belief in her musical path, even as she faces ridicule from peers for singing lighthearted songs such as “We Are the Colors of the Rainbow” and “Never Smoked Tobacco.”

Dropping Out and Pursuing Music Despite Resistance

Despite the challenging tour schedule and social pressures, Skylar’s conviction in her music never falters. At age twelve, she demonstrates remarkable entrepreneurial spirit by buying her first grand piano with money earned from performances. When she turns sixteen, a critical moment comes in the form of an algebra teacher who insists that music isn’t a real career. This comment serves as motivation for Skylar to leave school and pursue music full-time. Her high GPA reflects not academic inability, but a singular passion for her art.

Transition From Family Collaboration to Solo Career

At twelve, Skylar decides to perform pop music as a solo artist, disrupting the successful collaboration she has established with her mother. The move is difficult—her mother’s own career has become intertwined with their family act—but despite initial disappointment, Skylar’s mother ultimately supports her transition. Skylar’s decision is driven by an unwavering desire to follow her own creative path, even at the expense of letting down a loved one.

Early Professional Attempts and Initial Failure in LA

Driven by ambition, Skylar moves alone to Los Angeles at seventeen after securing a recording contract with Linkin Park’s label, performing under her birth names Holly Brook. Her debut album, however, flops, and the financial repercussions are severe. She spends her college savings on demos and living expenses, quickly going broke in the expensive city. To survive, she works a series of odd jobs—at Barnes & Noble, teaching gymnastics, and even editing pornography, a job she finds through a Craigslist ad. The porn editing job, which pays $30 an hour, is unsustainable; after two weeks of enduring the psychological toll and experiencing “Tetris Effect” hallucinations, she quits.

Breakthrough Success With Songwriting and "Love the Way You Lie"

With limited options and no team left in the ...

Solitude and Authenticity Essential for Skylar's Songwriting

Skylar Grey describes her creative process as fundamentally tied to solitude and authenticity. Preferring to work alone and outside the pressures of Los Angeles, she finds inspiration when she is by herself, allowing for honest emotional reflection. Even when collaborating with others' beats, she needs to be alone to channel her feelings, focusing on how the music emotionally resonates rather than what others might want to hear. Grey notes that her strongest songs are typically those that require the least effort; when songs flow naturally, almost as if she is merely channeling them, the result is more impactful. In contrast, songs that she overthinks or labors over seldom succeed or resonate. She emphasizes that spontaneous moments—such as thoughts occurring in the shower, while cooking, or even during moments of personal stress, like waiting outside the vet during her dog’s surgery—inspire her best songwriting. Scheduled studio sessions hardly ever yield the same magic.

Environmental and Psychological Factors That Support Creative Expression

Skylar reflects on how the environment of the Los Angeles music industry, dominated by so-called experts who were often frustrated artists themselves, overpowered her creative instincts, especially when she was younger. These influences led her to doubt her own intuition and temporarily stifled her creativity. Leaving that environment enabled her to reconnect with music on her own terms. After experiencing a breakup and setbacks in her career, taking time away from the industry allowed her to overcome a period of writer’s block and rediscover genuine inspiration. In discussing how she captures song inspiration, Grey notes the importance of being open to ideas whenever they arise, valuing moments of emotional clarity over forced creativity.

The Paradox of Perfectionism in Creative Work

Skylar Grey identifies perfectionism as a central struggle in her career. The pressure to deliver work as successful as her first number-one hit instilled a belief that every release must be exceptional. This mentality has led to long gaps—sometimes up to five years—between albums, as she repeatedly restarts and second-guesses her work, believing it is never good enough. As a result, she hoards a vast catalog of unreleased songs on hard drives and cloud folders, unable to release anything she deems imperfect. This self-imposed standard not only deprives the world of valuable music but also stifles her creative output. ...

Skylar Grey’s story highlights how the settings in which we live profoundly affect creativity, well-being, and personal growth. Her journey from Los Angeles to remote natural environments underscores the vital interplay between surroundings and the human drive to create.

Escape LA to Reclaim Creative Sovereignty and Health

At 23, Skylar Grey left Los Angeles for a remote cabin on the Oregon coast. She had been touring as a backup musician for Duncan Sheik but found that being in the music industry hub hampered her artistic instincts: "It started really eating at me, being like the backup musician. I was journaling a lot… I wrote, I just want a cabin in the woods where I can set up my studio and be away from all these people." This written desire soon materialized when her mother’s friend offered a rent-free cabin in Oregon if Skylar worked in her art gallery a few times each week—an opportunity she eagerly embraced.

Oregon Cabin: Isolation, Fear, and Creative Rediscovery

Skylar’s refuge was a small, one-room cabin with a single light bulb, lacking an internal bathroom. The bathroom, while having a flushing toilet and shower, was separate from the cabin, down a dark path—an unnerving prospect, especially at night when she worried about mountain lions. To ease her fear, she even wore a mask on the back of her head, following advice that eye contact could deter attacks. For six months, she lived in this isolated space without internet, facing the wilderness and her own anxieties.

Despite the fear and solitude, this period marked a turning point. Cut off from digital distractions, Skylar used the time to confront depression and writer’s block after a painful breakup. In this solitude, she slowly rekindled her passion for music, setting up her studio and rediscovering her drive. Her efforts paid off spectacularly—while collaborating with a producer from a local café that provided internet, she created the hook for "Love the Way You Lie," which soon topped charts worldwide. The transition from being broke and isolated to experiencing global musical success illustrates how seclusion and immersion in nature can rejuvenate creativity and career.

Natural Spaces Enhance Creativity With Unique Psychological and Physiological Benefits

Skylar and Rogan reflect on the special qualities of natural environments. They reference "forest bathing," a Japanese practice demonstrating nature’s ability to boost creativity and wellness. Rogan remarks that areas devoid of cell service or Wi-Fi not only eliminate distractions but fundamentally change how people feel: the world and even the air seem cleaner, undisturbed by human-made electromagnetic frequencies. This lack of digital interference is thought to benefit consciousness and physiology, with some evidence suggesting it affects all life, from bees to humans.

Skylar attributes her musical achievements to staying connected with rural settings, noting that her Wisconsin woods childhood and ongoing immersion in wild areas sustain ...

Turning Forty Prompted Reassessment of Life Direction

Skylar Grey shares that turning forty led her into a period of depression, rooted in reflections on her childhood and a sense that she was not truly present during those years because of constant work. She feels she missed out on appreciating her childhood, prompting a reassessment of her achievements and direction. Reaching this milestone also made her consider her musical career and the opportunities she let pass by the age of forty. Skylar admits to believing she has wasted potential, attributing it in part to not grinding hard enough in her early years, missing out on major opportunities, and a tendency toward perfectionism that stopped her from releasing more music.

Generational Differences in Attitudes Toward Work and Ambition

Skylar recognizes a generational divide in values regarding work and ambition. As a millennial, she places substantial importance on career achievement, describing her generation as driven to work incessantly. In contrast, she observes that Gen Z prioritizes work-life balance and rejects hustle culture, a stance that sometimes makes her wish she had their perspective. However, she admits that her reluctance to embrace non-stop grinding contributed to missed opportunities. Still, she acknowledges the merit in Gen Z’s approach: balancing work and life helps prevent burnout and supports mental health.

The Paradox of Self-Criticism in Creative Achievement

Skylar's creative output is deeply influenced by her perfectionism. While her high standards and self-critical mindset ensure that her music is emotionally authentic, thoughtful, and resonates with listeners, they often prevent her from releasing work as frequently as she’d like. Joe Rogan suggests, and Skylar agrees, that some degree of self-criticism is inherent to artists and even necessary for great work. However, finding a balance is crucial—allowing some self-doubt and critical thinking into the process without letting it escalate into paralyzing perfectionism.

Embracing Aging and Releasing Pressure for Creative Freedom

Approaching forty has allowed Skylar to question societal expectations about achieving certain milestones by a certain age and to reject the narrative that not meeting them means failure. She now focuses on prioritizing fun and spontaneity in her music, wanting to enjoy the creative process instead of being tortured by self-imposed pressure. This shift enables her to embrace the value of presence and creativity itself, rather than being obsessed solely with accomplishment or legacy.

Mapping Territory Through Experience for Better Decisions

Skylar, with ...