Jay Shetty & Meggan Roxanne ON Stop Being a People Pleaser

What happens when you stop pleasing everyone but yourself? When does selflessness cross the line into self-neglect?

In this On Purpose episode, Jay Shetty welcomes Megan Roxanne, author and founder of The Good Quote. Roxanne is known for creating one of the most influential platforms dedicated to mental health and inspirational quotes. Today, she opens up and reveals how childhood trauma, generational challenges, and significant loss have shaped her emotional strength and personal philosophy.

The Oldest Wound

When Meggan Roxanne was only four years old, her grandma told her she didn't love her. The author told Jay Shetty that it was her first time experiencing physical pain as a result of someone's words. She recalls feeling a searing pain in her chest, unable to understand that these words would remain ingrained in her memory and shape the course of her life. Despite being raised in a loving home and showered with affection from her mother, that experience shattered Roxanne's sense of innocence.

The author opened up to Jay Shetty about her upbringing in a Caribbean family, where emotional intelligence and apologies were rare occurrences. She explains that her family navigated through generational patterns of emotional detachment, and her mother tried hard to keep her as far as possible from it.

Moreover, Roxanne described her grandfather as strict and emotionally distant, although others perceived him as charismatic. Because of this discrepancy between what her experience inside the family was and how others would interpret it, the author soon learned the difference between perception and reality.

Forgiveness in the Face of Pain

Despite never being close to her grandfather, Roxanne promised her dying mother that she would care for him in old age. She initially didn't want to, but because her mother insisted, she accepted. Now, the author told Jay Shetty that is was one of the most impactful choices in her life. Spending time with him and listening to his side of the stories made her more empathetic to his own struggles.

While Roxanne nursed her grandfather back to health, helped him walk again, he began to share emotional wounds that he had carried and passed on. The author's decision to choose forgiveness over comfort is rare. Yet she told Jay Shetty that learning to forgive her grandfather was one last gift from her mother. It taught her empathy and healing, aiming to break generational cycles.

Creating Boundaries with Compassion

Jay Shetty and Megan Roxanne discuss the subtle distinction between forgiveness and enabling. She believes that true forgiveness involves setting clear boundaries, too. She explained how her mother struggled to stand her ground with her family, but the author was determined not to repeat that pattern.

Roxanne told Jay how she taught her grandfather boundaries when it came to her. Once, while she was looking after him, he disrespected her, and so she left. The author chose to physically distance herself from him until he learned not to cross that boundary anymore. Because she did that, she could also notice improvements in her grandfather's behavior towards her. Her walking away gave her grandfather a clear choice: honor her emotional space or lose her support.

People-Pleasing vs. Genuine Kindness

Meggan Roxanne explains to Jay Shetty that chronic people-pleasing often stems from the belief that you can control another person’s happiness. This is a distorted mindset that often results in emotional burnout and one-sided relationships. The author recognized that although she sincerely wanted to create a safe, happy space for people, she was compromising her own mental and emotional health in the process.

Yet you can never 100% truly please someone else. The only thing you can do is offer a supportive environment, but how people respond to that setting is entirely their responsibility. Meggan Roxanne told Jay Shetty that kindness without reciprocity can easily turn into resentment. So, in her quest for kindness and firm boundaries, he had to answer difficult questions, such as "Why did others seem more comfortable establishing their boundaries than I am?"

From Tumblr to The Good Quote

Meggan Roxanne takes Jay Shetty through the origin story of The Good Quote. It started out on Tumblr during a dark period of her life, when her deepest desire was to heal. After listening to a Wiz Khalifa mixtape, there was one lyric that truly inspired her, and she wrote it over a picture. She then began overlaying quotes on images in an attempt to share how she felt with the world, and soon gained twenty thousand followers overnight.

Roxanne quickly realized that others were just as inspired by these quotes as she was. Her success in building community led to a short-lived clothing line and, ultimately, to Instagram, where The Good Quote exploded in popularity. Despite its success, Roxanne wasn't ready to show her face publicly. She hid behind her work for a decade, for fear of racism and self-doubt. The impact of digital storytelling and emotional expression made The Good Quote a beacon for those navigating their hardest times. She did not create it for fame—it was born from a need to survive.

Reclaiming Her Voice

Megan Roxanne admits it took her years of encouragement from the very readers she was promoting. She struggled with impostor syndrome, comparing her engagement, questioning her skills, and only gradually began posting her own words. Yet the turning point came when she realized that her quotes—based on her personal experiences—had power.

Roxanne understood that she was no longer a content curator but a creator. Moreover, influence shouldn't be measured in likes but in the true impact your work has on other people's lives. The author told Jay Shetty it felt empowering to regain her own voice, as it enabled her to turn her vulnerability into strength and to use her words as a form of activism, especially for Black women facing trauma and seeking healing.

Listening to the Inner Voice

Megan Roxanne discovered her inner voice from an early age, nurtured by her mother and spiritual elders. She shared with Jay Shetty that she was able to create an internal dialogue that guided her important decisions. She did that through affirmations, storytelling, and spending time alone. Now, she communicates with her intuition, even when it slightly misleads her.

The author emphasizes the importance of consistently listening to inner guidance to avoid creative and emotional burnout. She believes that intuition is like a relationship—it needs to be cultivated, honored, and you need to actively engage with it daily. Additionally, Roxanne told Jay Shetty that disregarding intuition weakens it.

When going through times of uncertainty or change, the author turns to her intuition. 

She explained that fasting is one of her go-tos when she needs to clear her head; it feels like stripping away external substances to make room for genuine reflection. For Roxanne, fasting silences the negative inner chatter and gives her space to hear what her body and soul truly need. It's not just about abstaining from food but a practice of creating space for clarity and connectivity.

Grieving Her Mother

Megan Roxanne opened up to Jay Shetty about her mother’s death. Between the years 2020 and 2021, the author lost over 20 loved ones, including both parents. Her mother was diagnosed with stage four cancer, and Roxanne became her full-time caregiver, a task that significantly impacted and altered her life and worldview.

After her mother’s death, the author struggled with depression, substance abuse, and suicidal thoughts, feeling her identity collapse. The emotional weight of grief ultimately led Roxanne to a spiritual and emotional reset and it encouraged her to reparent herself and find strength within.

Meggan Roxanne is happy she caught her mother on camera multiple times before her death. Now, whenever she misses her, she has footage and voice recordings to remind her of her mother's voice. These memories became a vital source of comfort for her and aided in her healing journey.

Moreover, she emphasizes to Jay Shetty the role of community and support for people navigating grief. Although her healing journey had its ups and downs, she gradually rebuilt herself with the help of therapy, writing, and creative expression. She transformed the love she once defined externally into an internal guiding force.

From Darkness to Light

Megan Roxanne turned her pain into a platform for healing. With her newest book release, How to Stop Breaking Your Own Heart, the author feels a strong desire to convey her message and honor her mother’s legacy: her mother’s warmth, generosity, and continuous support live on in the lessons she shares.

Megan Roxanne’s intention is to be a source of light for others, just as her mother was for her. She now approaches The Good Quote with renewed purpose: to foster true connection, healing, and emotional literacy. She urges listeners to remember that in healing ourselves, we create spaces for others to heal too.

More From Jay Shetty

Listen to the entire On Purpose with Jay Shetty podcast episode “If You’re a People Pleaser Listen to This! (Why Putting Yourself First Isn’t Selfish, It’s Necessary For Real Connection)” now in the iTunes store or on Spotify. For more inspirational stories and messages like this, check out Jay’s website at jayshetty.me.