Jay Shetty & Khloé Kardashian ON The Side that Nobody Knows

What if your greatest heartbreaks shaped your strength?

In this On Purpose episode, Jay Shetty sits down with Khloé Kardashian, entrepreneur, media personality, mother, and advocate for healing. They dive into the messy process of healing—relearning trust, rebuilding love, and figuring out what forgiveness really looks like.

Khloé Kardashian opens up about what it means to enter her 40s with clarity. She reflects on the painful lessons heartbreak has taught her, and how intentional healing, motherhood, and faith have transformed her life externally and deep within.

40s as the Most Empowered Milestone

Khloé Kardashian admitted to Jay Shetty that she was thrilled to turn 40. Unlike the fear or dread many associate with aging, she embraced this new chapter of her life with open arms. Her 30s were anything but easy. Between public breakups and hurdles in her career, the decade tested her deeply. For her, reaching 40 wasn’t just a birthday, but a reset button. She now has a moment to breathe, feel secure in her identity, and move past the emotional turbulence of her past.

Kardashian looks up to powerful women in their 40s and 50s—like Gabrielle Union and Jennifer Lopez—who are rewriting the narrative around aging. For her, getting older means stepping into wisdom, not decline. This new decade is no longer about meeting expectations set by others, but about living in alignment with what matters most. The shift, she notes, isn’t just something you see in the mirror; it’s emotional, even spiritual.

Challenging Expectations

Kardashian and Jay Shetty dove into the heavy expectations placed on women when it comes to life milestones—getting married, having kids, and hitting career goals. She says these timelines usually aren’t even ours. They generally come from outdated traditions, media buzz, or even loving but misguided family expectations. And when women don’t “tick the boxes” by a certain age, it can leave them questioning their worth.

Khloé Kardashian explains to Jay Shetty that growth doesn’t follow a one-size-fits-all route. Her 30s, though rocky, became a period of deep discovery. Moreover, she believes women should pause and ask, “What do I truly want?” Not, “What am I supposed to want?” Whether it’s choosing a nontraditional career path, starting a family later in life, or simply picking rest over hustle, all of those personal choices deserve to be honored.

She told Jay Shetty that the illusion of control often leads to heartbreak. But by the time you reach 40, you start to see what really matters: you know who you are, and more importantly, you give yourself full permission to live your way.

From Shame and Comparison to Self-Worth

Khloé Kardashian told Jay Shetty that comparison is the thief of joy. She lived many years under the shadow of constant comparison to her sisters, social media standards, and an unattainable image of perfection. Yet all it did was to wear her down instead of serving as motivation.

Over time, the media personality began changing her perspective on others, not with jealousy, but with curiosity and inspiration. This change came after she started to become more self-aware, mindful, and did a lot of internal work. She started noticing her thoughts, adjusted her inner dialogue, and became intentional about the messages she passes on to her children. She realized that maybe we’re not all meant to have everything, and that’s okay too. She now teaches this philosophy at home, with boundaries, gratitude, and honest self-reflection.

Kardashian shares with Jay Shetty the moment her healing began: when she stopped asking, “Why don’t I have that?” and started wondering, “Do I even want that?” For her, true empowerment came not through resentment, but introspection. She came to terms with the fact that growing sometimes means leaving people—or parts of yourself—behind.

Breaking Free from the Past

Khloé Kardashian revealed to Jay Shetty that one of the most powerful transformations came from letting go of shame, especially the kind tied to betrayal. Because her heartbreaks played out in public, she says it felt like reliving them every time they made headlines. This amplified the guilt and stalled her healing process. She admits that sometimes the weight of judgment made her feel like her mistakes defined her.

Time heals all wounds; through deep inner work, Kardashian began separating her identity from the pain. What once felt heavy and all-consuming started to look like resilience. Letting go, she told Jay Shetty, isn’t just about who hurt us. It’s about the stories we keep telling ourselves that hold us back.

Healing doesn’t mean forgetting the past. It means loosening shame’s grip on your present. That’s when she began to reclaim her happiness. She was no longer someone suffering through the story, but the one in control of writing it.

Self-Forgiveness and Accountability

Khloé Kardashian opened up about the fine line between owning up to your responsibilities and taking on blame. After experiencing repeated heartbreaks, she internalized the hurt, accepting maybe it was somehow her fault. But in time, she realized she couldn’t take responsibility for other people’s actions—only for her healing.

She confessed to Jay Shetty, “I’m my biggest bully.” While she extended compassion to others without hesitation, it took her years to show herself the same level of compassion. She kept reminding herself: “I made the best choice I could at the time.” Eventually, that helped quiet the doubts.

Kardashian noted that many people fall into extremes, either blaming others completely or carrying the whole burden alone. The media personality learned to stand in the middle. She’s learned to see her part in repeating some patterns without taking on the blame that doesn’t belong to her.

Therapy and the Power of Safe Spaces

Khloé Kardashian shared with Jay Shetty how therapy became a cornerstone of her healing. But it didn’t happen right away. For years, she avoided therapy. It was only when her sister Kim connected her with a therapist who felt like a friend, rather than just a professional, that she gave it a real try.

During those sessions, she realized how emotionally numb she’d become. She found herself speaking about trauma like it was someone else’s story—distant, almost clinical. Gradually, with her therapist’s help and tools like journaling, she began peeling back those emotional layers.

Jay Shetty emphasized the importance of normalizing therapy. For Kardashian, the key was feeling safe enough to open up. She also found that healing can come in many forms—not just talk therapy, but also prayer, writing, movement, and even quiet reflection.

Redefining Relationships

Khloé Kardashian admitted that her view of love has shifted dramatically. In the past, she committed to relationships fast. Now, she moves with more intention, especially as a mother. She’s drawn clear lines to protect her peace and to give her kids a sense of safety.

She told Jay Shetty about one of her most difficult decisions, like welcoming her ex, Tristan Thompson, and his brother into her home, even with all the past pain. While some people labelled it as weakness, she saw it as a conscious choice to show kindness without letting go of her boundaries.

Kloé Kardashian still values love, marriage, and connection, but she now approaches them with clarity. She allowed herself to mourn what didn’t work out. But she guards her joy now, no longer compromising peace just to keep a relationship.

Motherhood, Presence, and Building a Legacy of Love

Motherhood, she told Jay Shetty, turned her world upside down in the best way. What matters most now is being present, because her kids won’t remember designer clothes or big gifts. To her, it’s those simple, quiet moments—floor play, late-night chats—that her kids will carry with them forever. Even five minutes of genuine interaction can make a lasting imprint.

Kardashian also shared the reality of raising children in the spotlight. The fame, the constant scrutiny, and the online noise can become overwhelming. She’s doing her best to keep her kids grounded and safe from the chaos of fame. She wants her home to be stable and loving, built on routine, care, and faith.

Faith in Herself and a Higher Power

Khloé Kardashian and Jay Shetty talked about the difference between being lonely and choosing solitude. For the last three years, she has deliberately chosen to be alone, and she did it not because she wanted to avoid love, but to heal. The media personality wakes up early, meditates, and prays. These quiet routines provide her with a sense of stability. After years of jumping into relationships to avoid being alone, Kardashian chose to stay and sit with herself. And in doing so, she discovered a strength she didn’t know she had.

Raised in a home where prayer was second nature, Khloé Kardashian still leans on her faith daily. She told Jay Shetty that she communicates with God not only during times of struggle but also in moments of happiness. Faith is what keeps her grounded. It helps her forgive, trust again, and stay anchored through uncertain times. For her, faith isn’t tied to rules or tradition. Rather, it’s a personal relationship—something constant and real. It's a connection that helps her release the past, live fully in the present, and look to the future with hope, love, and quiet confidence.

More From Jay Shetty

Listen to the entire On Purpose with Jay Shetty podcast episode “Khloé Kardashian: My Side that Nobody Knows (Truth Behind Headlines, Divorce, Co-Parenting)” now in the iTunes store or on Spotify. For more inspirational stories and messages like this, check out Jay’s website at jayshetty.me.