Do you struggle with self-doubt sometimes?

What helped you get through a tough emotional season?

Today, Jay sits down with award-winning rapper, actor, and activist Common for a deeply moving live conversation recorded at the legendary Chicago Theater. Known for his poetic lyrics and conscious artistry, Common opens up about his journey from a young boy on the South Side of Chicago to becoming an Academy Award, Emmy, and three-time Grammy winner. In this intimate conversation they explore the emotional and spiritual work behind his success. From heartbreak and rejection to healing and purpose, Common shares what it really took to become the man he is today.

Common shares personal stories of growth and transformation, starting with his childhood dream of becoming a professional basketball player and how he eventually found his voice through writing and music. He reflects on the moments that shaped his purpose, including the story of Emmett Till, which moved him to live with more intention. Common also opens up about the heartbreak that forced him to confront the ways he was dimming his light, and the daily spiritual practices that help him stay grounded today, like reading scripture, praying, practicing gratitude, and staying active.

Jay and Common also dive into what it means to be vulnerable in hip-hop, why self-love is the foundation for every other kind of love, and how trusting the divine plan can turn disappointment into direction. They explore how trusting a bigger plan can help turn setbacks into clarity, and share personal insights on setting boundaries, building real friendships, and staying connected to your highest energy.

In this interview, you’ll learn:

How to Transform Pain into Purpose

How to Stop Dimming Your Light in Relationships

Why Vulnerability is a Superpower in Creativity

How to Build Daily Practices for Spiritual Alignment

How to Trust God’s Plan, Even When It’s Painful

How to Attract Friendships that Match Your Frequency

Whether you're moving through heartbreak, looking for direction, or trying to reconnect with your purpose, this conversation is a powerful reminder that your story matters and you're right where you need to be.

With love and gratitude,

Jay Shetty

What We Discuss:

00:00 Introduction

01:13 Live In Chicago

02:15 Common Before the Fame

06:11 Jay On His Childhood & Upbringing

06:44 Pain As A Catalyst for Creativity

09:01 Proximity To Greatness Is A Motivation

10:11 Living Our Dreams To The Fullest

13:49 How to Trust God's Plan

16:46 Trust That There’s a Bigger Plan

22:19 Transitioning Between Careers

30:15 Attracting & Building New Friendships

36:18 Everyday Routine For Body & Mind Care

40:40 A Poem From the Audience

43:21 My New Favourite Colour

48:49 Pushing Through Fear As A Motivator

53:33 Letting Go and Letting God

55:26 Common On Final Five

Episode Resources:

Common | Website

Common | YouTube

Common | Instagram

Common | X

Common | Facebook

See omnystudio.com/listener for privacy information.

Today, Jay reframes how relationships are built—not through surface-level attraction or blind chemistry, but through clarity, communication, and intentionality. He presents nine transformative questions that often go unasked in modern dating, not because they’re unimportant, but because they’re uncomfortable. Jay explains that avoiding these conversations leads to assumptions, unmet expectations, and unnecessary heartache. He underscores that a healthy relationship isn't defined by constant harmony, but by the courage to ask, listen, and grow together.

Blending personal stories, practical wisdom, and psychological insight, Jay highlights how asking the right questions early can reveal compatibility, values, and emotional readiness. He breaks down how these conversations create a shared language, prevent miscommunication, and ultimately strengthen the foundation of any relationship. Rather than using questions as ultimatums or pressure points, he encourages approaching them with curiosity and empathy.

In this episode, you'll learn:

How to Ask What a Healthy Relationship Means to Your Partner

How to Talk About Fears Around Commitment Without Pressure

How to Discuss Conflict Styles Before an Argument Happens

How to Know If Someone Is Truly Ready for a Relationship

How to Align on Boundaries and Independence in Love

Love doesn’t have to be a guessing game. The more willing we are to ask real questions and embrace honest conversations, the more aligned, peaceful, and fulfilling our relationships can become.

With Love and Gratitude,

Jay Shetty

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What We Discuss:

00:00 Intro

02:03 The Conversations We Avoid in Modern Dating

03:36 #1: What Defines a Healthy Relationship?

08:17 #2: What are You Afraid of When It Comes to Commitment?

12:30 #3: How Do You Handle Conflicts?

19:44 #4: What are Your Long-Term Intentions?

22:02 #5: What Does Emotional Availability Mean to You?

25:10 #6: Do You Prefer to Recharge Alone?

27:49 #7: What Does Being Ready Mean to You?

31:30 #8: What Does Independence Look Like to You?

32:52 #9: What Are You Still Healing From?

See omnystudio.com/listener for privacy information.