Jay Shetty & Simon Sinek ON Not all Friendships Are Meant to Last

In this On Purpose episode, Jay Shetty sits down with Simon Sinek, a leadership authority, author of Start With Why, and a distinguished motivational speaker. Sinek is the host of the podcast A Bit of Optimism.

If you met them today, would you still choose them as a friend?

In this On Purpose episode, Jay Shetty sits down with Simon Sinek, a leadership authority, author of Start With Why, and a distinguished motivational speaker. Sinek is the host of the podcast A Bit of Optimism.

They discuss the ties that bind us together as humans but also sometimes hold us back. Sinek and Jay Shetty touch on the fragile nature of adult friendships, the quiet link between burnout and loneliness, and the courage it takes to let go when a relationship no longer aligns with who we are.

The Universality of Human Struggles

Simon Sinek explained to Jay Shetty that human behavior tends to be universal and remain fundamentally consistent across cultures and various contexts. We all face the same challenges in relationships, whether romantic, in the workplace or in friendships, such as miscommunications, the need for validation, and confrontation. Sinek also emphasized that, while surface-level differences (like culture or language) exist, our emotional needs and pain points remain universal.

Moreover, Sinek explains that we are tribal animals and that we feel safe from the feeling of belonging to a tribe. Evolutionarily, we are wired to seek affiliation with a group, be it a football team, a book club, or a professional organization. Sinek told Jay Shetty that people develop genuine bonds over shared values, rather than superficial similarities. When people are unsure of their values, they often define themselves by what they stand against.

Sinek notes that it's easier to create artificial enemies just to feel a sense of belonging, mainly because they lack clear motivation and the ability to articulate a personal purpose, so they transform the conflict into their objective.

Loneliness and Burnout

Research shows a majority of adults report disconnection; one study found that 65% of adults felt lonely during the pandemic.¹ Yet, instead of recognizing loneliness as the root cause of their emotional state, many tend to mislabel their symptoms, often using terms such as burnout, exhaustion, and stress. However, there is a deeper layer.

Simon Sinek gave an example from the military realm: when a leader noticed their team showing signs of burnout, they asked how many were actually feeling lonely and were surprised by the staggering number of raised hands.

Sinek told Jay Shetty that burnout isn’t always about workload; it sometimes stems from isolation. It is important to understand that you can help reduce others’ emotional fatigue by making them feel seen and heard, whether from a friend's or a leader's perspective.

In the past, we used to have larger communities (faith communities, close-knit families, and stable work environments) that gave us a sense of belonging. However, these support networks have become fractured today, leaving many of us longing for connection. In the absence of traditional institutions, friendships become a critical pillar in our lives.

The Fragility and Power of Modern Friendships

Simon Sinek raises the question: why do we invest in romantic relationships with therapy and counseling, yet view friendships as disposable? Jay Shetty also notices this phenomenon, pointing out how easily we abandon friendships after one disagreement. Sinek witnessed a decades-long friendship end over a single conflict. He highlights that we need to learn the skills required for healthy friendships: listening, holding space, and managing conflict. According to him, they are the same we need in romantic or professional relationships.

Simon Sinek shared with Jay Shetty that, despite being a professional communicator, he was accused by his closest friends of being a poor listener. It wasn’t until he took a listening course that he realized he was applying his skills selectively; he was listening well to strangers but not to those closest to him. Sinek shared this anecdote to show that even leading figures who teach emotional intelligence may struggle to apply it consistently in personal contexts.

Friendship, Health, and Longevity

Simon Sinek explains to Jay Shetty that friendship is the ultimate biohack. In addition to being a simple emotional support, strong and supportive friendships have the power to reduce depression, alleviate anxiety, and even promote physical health.

The so-called Blue Zones are areas where people live longer, healthier lives. While diet, movement and purpose play a crucial part in these regions, their social networks and sense of belonging play an equally important role in longevity. People there dine together regularly, maintain multi-generational friendships, and deeply connect with their communities.

Jay Shetty brought up the Disney hugs, where Disney characters are trained to hold a child’s hug until the child lets go first. If we applied the same standard to friendships - holding on emotionally or physically until the other person is ready to let go - it could deeply impact relationships. Simon Sinek argues that connection is felt, not measured. Today, we’ve become too reliant on metrics: we count steps, sleep cycles, protein intake, often at the expense of trusting our own feelings.

Friendship vs. Family

Jay Shetty and Simon Sinek discuss how family and friendship can sometimes feel like conflicting circles. Evolutionarily, humans used to live in communities of up to 150 people. While some people without strong family bonds fill those gaps with many friendships, others who are close to their families may avoid having too many friends. Sinek explains that it shouldn’t be an either/or choice; we are designed to live in existing communities and rely on both family and neighbors for emotional support.

Simon Sinek describes his visit to Dharavi, one of the world’s most densely populated slums. People there developed a strong sense of community, in spite of their financial hardships. Neighbors watch over children and, generally, the community members look out for each other.

In contrast, wealthier communities often build walls instead of bridges, both literally and figuratively. Sinek told Jay Shetty that he learned that strong community ties give us a sense of belonging that money alone can’t buy.

Rediscovering Identity Through Shared Values

Jay Shetty noted how we often tend to bond with others over superficial similarities such as accent, hometowns, or cultural quirks. However, Sinek explains that it is also important to understand others’ core beliefs. These help a strong friendship bloom.

Simon Sinek told Jay Shetty that he now introduces himself not by job title but by what he believes in. He leads with “I teach leaders and organizations how to inspire people.” He confessed that, after making this switch, he attracted more genuine connections from people who resonated with his mission rather than being impressed by his job title alone.

Simon Sinek and Jay Shetty agree that authentic relationships form more easily when people are willing to be vulnerable about their values. Leading with belief rather than profession helps purposefully build durable, meaningful friendships beyond surface-level networking.

Letting Go and Growing Together

When is it time to outgrow a friendship? Simon Sinek explains to Jay Shetty that a friendship should be “additive”; it should contribute to your growth, joy, or support in some way. Sometimes people naturally drift apart or stop contributing to each other’s well-being. In such cases, a formal breakup may not be necessary, since it’s a graduation, not an abandonment.

Jay Shetty and Simon Sinek also explore the idea of personal evolution. Many people confuse purpose with the method of delivery. For instance, being a podcaster, writer, or speaker is not an identity, but merely a vehicle. Simon Sinek underscores that he is not afraid to abandon these media if they no longer serve his message. The root, the “why,” remains unchanged: to inspire people to feel fulfilled and safe in their lives. If friendships or careers become obstacles to that purpose, it’s okay to take another path.

Navigating Envy, Growth, and Imperfect Support

Simon Sinek shared with Jay Shetty how he navigated the emotional difficulty of watching a friend achieve financial and professional success while he was struggling. Often, it's harder to celebrate a friend's success when you feel like your life is currently on hold. Sinek recounts the pain, jealousy, and self-doubt that he experienced. Yet in spite of the discomfort, he chose to sit with his feelings, examine them, and remain committed to the friendship.

Simon Sinek explained that friendship requires emotional maturity on both sides. You need to be able to sit with envy without lashing out, and to support others without feeling diminished. He also spoke about earning “serotonin moments”, when you feel genuine pride in someone else’s achievements, not because it benefits your ego, but because you share an investment in each other’s growth.

Communication in Difficult Moments

Jay Shetty asked Simon Sinek for advice on a scenario that many people might relate to: one friend is experiencing joy, while another is dealing with sorrow. It may feel daunting having to navigate such disparate emotional experiences, yet Simon Sinek highlights the importance of open communication. Instead of completely withdrawing for fear of saying the wrong thing, Sinek suggests being honest, even if clumsy.

Simon Sinek recommends saying, “I don’t know what to say, but I want you to know I love you.” Even if it may feel awkward, openness is often followed by understanding. Conversely, not saying anything for fear of coming across as inappropriate may hurt more than communicating an imperfect message. Sinek believes that the intention behind your message is paramount. You need to be able to reset the conversation midstream, gently guiding someone when they are offering the wrong kind of support or clarifying what you need in the moment.

The Metrics Trap

In today’s data-obsessed culture, many outsource their feelings to numbers, measuring sleep quality, hug duration, and even emotional states. Sinek laughs about the absurdity of calculating oxytocin release during a hug. He believes that by relying on external metrics, humans risk losing touch with their inner guidance.

Simon Sinek also told Jay Shetty that the best moments in life (connection, healing, love) are earned, not measured. You shouldn't judge friends by how often they text or whether they meet emotional standards. Instead, focus on how meaningful the relationship feels to you. Sinek explains that serial-produced pottery items may look flawless, but, in the end, it's the small imperfections that render an object more beautiful. In his opinion, the same principle applies to friendships.

Simon Sinek urges listeners to treat friendships as ongoing practice: communicate openly, forgive often, and acknowledge what the friendship adds to your life. Silence breeds assumptions, but when expectations are clear, friends feel safe even during disagreements.

More From Jay Shetty

Listen to the entire On Purpose with Jay Shetty podcast episode “Simon Sinek: Not Every Friendship Is Meant to Last—And That’s Okay! (THIS is How to Know If It’s Time To Walk Away From Adult Friendships That No Longer Fit)” now in the iTunes store or on Spotify. For more inspirational stories and messages like this, check out Jay’s website at jayshetty.me.