Jay Shetty & Jelly Roll ON 5 Ways to Overcome Guilt and Shame

Ever feel trapped by guilt or weighed down by the past? Many of us go through times like these, and you’re not alone in this struggle.

In this On Purpose episode, Jay Shetty welcomes Grammy-nominated artist Jelly Roll, a Nashville native who shares his journey from addiction and incarceration to stardom. Known for his raw lyrics, Jelly Roll has turned his struggles into songs of hope, healing, and redemption that resonate deeply with fans worldwide.

The artist opens up to Jay about how he found purpose through music, forged a path to self-forgiveness, and inspired others to rise from darkness.

Motivation to Become Better

Jelly Roll tells Jay Shetty about his father’s passing in 2019. It took an emotional toll on the artist, and it was the trigger for the changes that he made in his life after this event, including his weight loss journey. Roll discovered Jay's podcast during the pandemic, and he found it a source of guidance during these trying times.

Growing up, the artist's mother struggled with drugs and mental health, often staying secluded. However, he told Jay Shetty how she filled the home with her vibrant energy and music whenever she felt better. Friends and neighbors would gladly gather around her as she shared stories, music filling the space and creating a magical atmosphere.

Moments like these fueled Jelly Roll's early love for music - he saw its power to uplift and unite people, and it was something he was interested in. The artist began his career by writing poems and proudly performing them for his mother's friends. When he received encouragement from them and his mother, Roll's confidence grew. Over time, it solidified his passion for music and storytelling.

The Redemption Journey

Jelly Roll shares with Jay Shetty his evolution from being an early delinquent to the artist he is today. He used to be a jolly child, yet everything changed when he first got incarcerated at thirteen. The artist believes this behavioral change stemmed from his deep-rooted insecurities, eating disorders, and unresolved anger caused by his environment.

Seeking acceptance, Roll was drawn to the streets - there, he felt like belonging. Today, he sees his past self as someone lacking a moral compass, making desperate decisions that he now regrets. He used to see money as an escape and tried to get his hands on as much as he could, regardless of the consequences.

In the past years, Jelly Roll embarked on a journey of self-forgiveness and transformation. He admitted to Jay Shetty that his past self was filled with anger and manipulation, traits that he is now leaving behind. Today, the artist focuses on feeling positive emotions, such as love and empathy.

Jelly Roll explains that forgiving himself requires accepting responsibility for his past actions. It took him a long time to understand that genuine forgiveness begins with himself, and he doesn't need to shift the blame onto others. He started a journey of accountability, reflecting on his choices and their reasons.

The Guy in the Glass¹

Being incarcerated as a teenager disrupted Jelly Roll's social development and education. He described to Jay Shetty the juvenile justice system as a place that made him a "smarter criminal" rather than reforming him. In his opinion, there is a lack of educational programs and mentorship, which leaves young inmates disconnected from personal growth. Only later did the artist find resources like GED programs and AA, which finally provided a path for transformation.

Jelly Roll believes personal growth starts with taking accountability for your actions rather than drowning in self-blame. He shared with Jay Shetty how the poem The Guy in the Glass helped him become a better person; he now practices honest self-assessment, knowing he can't fool himself.

Shame Is Addictive

To forgive yourself, you need to overcome shame. Jay Shetty suggests regarding the mind's missteps as something that can happen rather than a deeply flawed character. This way, you can ease the guilt and shame that hinder your evolution. Jelly Roll shared that he struggles with a lifelong "shame spiral," especially regarding his weight. What helped him shift from seeing failures as valuable lessons rather than losses was his embracing accountability for his actions.

Moreover, Jelly Roll shared with Jay Shetty his struggle with food addiction, similar to his past battles with substances. He redefined his relationship with food when he changed his perspective on himself. He now believes that his physical health holds him back from his full potential, and he feels a spiritual calling to shed these limitations. Today, the artist prioritizes purpose over happiness.

Beautiful Marriage

Jelly Roll shares with Jay Shetty how his wife, Bunny, transformed his life; she gave him purpose and stability when he felt like the world was crumbling onto him. They impulsively married one night in Las Vegas - back then, he was battling addiction, financial instability, and a custody fight. Bunny supported him by securing custody of his daughter and helped build their life together.

Bunny's attitude toward the artist motivated Jelly Roll to prioritize their relationship and move away from his former destructive behaviors. Bunny's patience and insight allowed him to embrace self-acceptance, while her grounded presence balanced his restless lifestyle, supporting his career and mental health journey.

Growing in the Relationship

To maintain a relationship, you need to understand each other. Jay Shetty gave an example of his and his wife's Radhi opposite "fight styles": Jay vents while his wife needs space. They learned that their different responses didn't mean disrespect for each other but rather a personal way of handling conflict.

Jelly Roll opens up to Jay Shetty about embracing vulnerability alongside his wife. He now sees asking for help as a source of strength rather than weakness, and he and his wife can now see each other as partners in growth, helping and supporting each other every day.

Standing up for Addiction Victims

Jelly Roll's song Save Me has become popular in recovery centers and even requested at funerals. The artist is grateful for how his music helps people through challenging times, especially those in detox and early recovery. Jelly Roll also plays for inmates, including those with life sentences who may feel little hope. He sees it as an opportunity to spread positivity and create moments of joy even in dark circumstances.

Jay Shetty admires the artist's commitment to making a difference for those needing representation. Jelly Roll recalls meeting inmates during his performance at Oregon State Penitentiary, where prisoners, many of whom were lifers, formed a line for autographs. He had the opportunity to learn about their lives and dreams, discovering their human side.

Jelly Roll held a congressional speech addressing the drug addiction crisis. He uncovered the fentanyl epidemic that claims approximately 190 lives every single day. He questions why society remains complacent in the face of such calamity when it kills as many people as if a plane crashed every day. The artist told Jay Shetty that society needs to humanize people struggling with addiction and try to come up with legislation meant to support those who can't escape the habit by themselves.

Rewriting Family History

Following Jelly Roll's congressional speech, a bill was passed to address the opioid crisis. Many approached him with their stories of family members in recovery, including celebrities and law enforcement personnel. The artist explained to Jay Shetty that his message had a great emotional impact on others, yet the conversations also uncovered the deep-rootedness of the problem in society.

The artist opened up to Jay Shetty about his past as a drug dealer and about his daughter's struggles. His perspective on drugs drastically changed over the years, and he now understands the devastating consequences of addiction. Seeing his daughter fall into addiction, he committed to breaking the cycle of addiction and hardship within his family. Together with his wife, Jelly Roll is dedicated to breaking generational curses and showing that even those with troubled pasts can create positive change.

Connecting People

Jelly Roll describes to Jay Shetty how his concerts have evolved into a form of “church” for his audience. His wife encouraged him to embrace the role of a leader; she saw in him a natural gift for connecting people and helping them through music. So, he now aims to provide a space for emotional release, calling his concerts “church” to signify a place of comfort and community.

Similarly, Jay sees himself as an ambassador for spirituality,” helping initiate healing conversations. In his view, these gatherings are not just social occasions; they are opportunities to create meaningful dialogue and to help others find their paths to growth and understanding.

Jelly Roll's latest album, Beautifully Broken, contains the songs Heart of Stone and Unpretty - they reflect the artist's raw journey through pain and healing. He explains to Jay Shetty that his goal is to create music that resonates without needing a resolution. He wants each of his listeners to find meaning in each of his songs. To Roll, unresolved lyrics are powerful because they allow each person to relate to their own emotions deeply and continually.

Turning Tables

In a turn of events in Jelly Roll's life, he now works alongside his former prosecutor (Jim Todd), who once charged him. He told Jay Shetty how they now collaborate to help at-risk youth through the Dinkin Center for Juveniles, which teaches trade skills. He calls Todd a true hero because, after years of working for the system prosecuting young people, he saw the need to address systemic issues.

Another emotional moment in Jelly Roll's humanitarian work was being joined by Judge Calloway, who entered a songwriting program at the juvenile facility where he was once held. Watching her interact with young inmates outside the courtroom, Jelly Roll was moved to witness the genuine human connection they formed. The artist explained to Jay Shetty that he sees these full-circle moments as “redemption,” healing his past wounds while helping today’s youth.

More From Jay Shetty

Listen to the entire On Purpose with Jay Shetty podcast episode “Jelly Roll ON 5 Powerful Ways to Overcome Guilt and Shame & How to Finally Forgive Yourself” now in the iTunes store or on Spotify. For more inspirational stories and messages like this, check out Jay’s website at jayshetty.me.

‍¹Emma Baldwin, "The Guy in the Glass by Peter Dale Wimbrow Sr.", Poem Analysis, 7 December 2022, https://poemanalysis.com/peter-dale-wimbrow/the-guy-in-the-glass/.