Club Shay Shay – Miguel (Part 1)

Host: Shannon Sharpe
Guest: Miguel (Grammy-winning singer, songwriter, producer)
Date: November 5, 2025

Overview

This episode of Club Shay Shay features an in-depth, emotionally rich conversation between Shannon Sharpe and R&B superstar Miguel. They discuss Miguel's new album "Chaos," the journey of personal and artistic growth, love, sacrifice, career milestones, and the hard lessons learned along the way. The episode weaves together live music, candid vulnerability, and reflections on music industry realities, relationships, and the power of self-awareness.

Key Discussion Points

1. Performing “Always Time”: Pain, Growth, and Letting Go

[03:33–07:42]

• Miguel opens the episode by performing “Always Time” live, a ballad from his new album “Chaos.”
• Shannon Sharpe is visibly moved and remarks on how the song’s emotional depth speaks to heartbreak and letting go, noting, “I can tell when someone sings a song and it’s coming from a place of hurt...” [07:42]
• Miguel explains the song’s genesis:

  “It started out as… there’s always time, and because of love, there’s always time. Over time, I’ve learned that sometimes love means letting go… The song encapsulates a whole relationship.” [09:56–11:40]

2. The Paradox of Love: Holding On vs. Letting Go

[11:40–15:24]

• Shannon and Miguel discuss the counterintuitive challenge of loving deeply but recognizing when to let go for both people’s sake.
• Miguel:

  “As a human being… I learned over… a long span of my life where there’s a lot of growing and learning in real time. The song reflects that.” [12:16]

• The conversation explores how ending a relationship can be harder for the one who doesn’t want to end it, and how the pain is often an indicator of the depth of the investment and personal growth needed.

3. Communication and Apology Styles

[15:24–16:51]

• Miguel shares new personal insights on how people have different apology “styles,” not just love languages.
• Miguel:

  “I just learned about apology styles… For me, it’s by action, planned action... I receive it that way.” [15:46]

• Both agree on the challenge of making oneself understood and the lifelong process of honing interpersonal skills.

4. On Long-Term Relationships and Personal Accountability

[16:51–21:42]

• Shannon highlights the unique pain of ending a long relationship—Miguel was with his ex-wife from age 19 to 36.
• Miguel:

  “I know where I went wrong though—I wasn’t whole… Even being able to say and admit that I’m not whole… changes my approach. I didn’t communicate… I didn’t build…the trust as a friendship to protect that later on… It’s all clear in hindsight.” [17:57–19:55]

• He reflects on the danger of entering relationships before knowing oneself and the importance of honesty from the outset.

5. Healing, Reflection, and Moving Forward

[26:24–29:17]

• Miguel embraces his learning process:

  “I’m a much more aware person now, and I hate that I had to learn it the hard way, but we must continue, you know… this song 'Always Time' represents… honoring the time, effort, and sacrifice we both put in.” [26:24]

• Shannon emphasizes moving forward as a universal necessity; both men agree on the value of learning from mistakes and the difficulty and necessity of letting go to grow.

6. The Journey of Self-Work and the “Chaos” Album

[31:35–36:57]

• Miguel released his album “Chaos” on his 40th birthday, marking a decade of intense personal work (“the last 8 years have been me work”).
• Miguel:

  “The album isn’t about love or sex, it’s about how painful it is to be human... I did a lot of avoiding of my own work that I needed to do, to lock in with me in the journey of being a musician…” [34:06–35:45]

• His next decade is dedicated to supporting Black, Brown, and Latino creators from underserved communities.

7. Sacrifice, Ambition, and the Cost of Excellence

[36:57–43:18]

• The sacrifices demanded by excellence are confronted head-on.
• Shannon admits:

  “I can’t love you like I love football, I can’t love you like I love the pursuit of greatness. And so I sacrifice—kids’ events, family events, relationships. That’s what killed my relationships… Freedom is the goal.” [39:10–41:00]

• Miguel recognizes the need for better communication about sacrifice and hopes to remain more present in his next decade.

8. Relationships, Presence, and Learning to Communicate

[49:01–53:17]

• Miguel expresses a desire to be more present in his relationships and discusses how Scorpios (his sign) are communicative—but often in a way only they understand.
• Shannon and Miguel share stories of failing to communicate effectively with partners and the necessity of “learning a second language” to make oneself understood by a loved one.

9. Artistic Pride, Legacy, and Creative Process

[53:17–66:07]

• Miguel names “El Plato" as his favorite song on “Chaos” because it celebrates the legacy of sacrifice across generations:

  “That song is about how proud I am to have gone through what I’ve gone through… My soul is still standing.” [53:21–54:49]

• He details the creation of “Sure Thing,” revealing it was almost given to Usher and perhaps even heard by Michael Jackson.
• Miguel recalls writing “Sure Thing” at age 19, reflecting, “I was aspiring to have love like that… What you know about love at 19?” [58:38]

10. Music Industry Realities, Streaming, and Artist Ownership

[81:34–85:32]

• Miguel breaks down what streaming means financially:

  “27 million [streams] a month… every million translates to about $4,000 currently. So do the math.” [81:50]

• He critiques the streaming paradigm for devaluing musicians’ work and argues that artist-owned platforms should be the future.
• He’s passionate about the need to “reaffirm the value of music,” seeing current systems as unsustainable for most artists.

11. Advice for Young Artists

[91:20–91:53]

• Miguel’s key advice:

  “Be your own hero. Operate by your values. If you don’t know the answer, go with the best option and adjust... Overthinking will stunt the growth. Live by your values.” [91:20]

Notable Quotes & Memorable Moments

• On Love and Letting Go
  “Maybe this time, love means letting go… I think the song kind of encapsulates like a whole relationship.” – Miguel [11:40]

• On Communication and Apology
  “I’ve learned that I’m by action, planned action… That’s the most impactful way of me saying I’m sorry.” – Miguel [15:46]

• On Personal Growth
  “I wasn’t whole…even being able to say and admit that I’m not whole...changes the way that I approach things.” – Miguel [17:57]

• On Sacrifice for Greatness
  “I can’t love you like I love football... had I poured into a relationship what I poured into football, but when I laid in my bed as a kid…that wasn’t in my dream.” – Shannon [39:10–40:08]

• On Presence in Relationships
  “I want to maximize on the time that I have when I have it, make it really count so that when you’re present, you’re really present…” – Miguel [49:33]

• On Generational Sacrifice
  “We are the summation of all the sacrifices made by those before us… I’m really actually proud of myself… my soul is still standing.” – Miguel [53:21–54:49]

• On Creating “Sure Thing”
  “I was a starving artist… I was willing to give it up if it was gonna mean getting to the next level.” – Miguel [65:29–65:32]

• On Streaming Economics
  “Every million translates to about $4,000 currently. So do the math... Streaming as it is devalues the art and sacrifice of a lot of people.” – Miguel [81:50–82:10]

• Advice to Aspiring Artists
  “Be your own hero. Operate by your values... Overthinking will stunt the growth.” – Miguel [91:20]

Timestamps of Key Segments

| Time | Segment | |------------|--------------------------------------------------------------------------------| | 03:33–07:42| Miguel performs “Always Time” | | 09:42–11:40| Song origins and emotional backstory | | 16:51–19:55| Reflections on young love and personal accountability | | 26:24–29:17| Honoring the relationship, learning and moving forward | | 31:35–36:57| The journey to “Chaos,” self-work, supporting underserved creators | | 36:57–43:18| Sacrifice, ambition, the cost of greatness, struggles with balance | | 53:17–54:49| Miguel's favorite song: "El Plato" and generational sacrifice | | 62:14–66:07| The making of “Sure Thing,” pitching it to Usher | | 81:34–85:32| Streaming realities, artist ownership, economics of modern music industry | | 91:20–91:53| Miguel’s advice to the next generation of artists |

Final Thoughts

This episode is a masterclass in introspective conversation. Miguel and Shannon Sharpe, both high achievers in their respective fields, communicate honestly about the joys, losses, and lessons that come with greatness. Their discussion transcends music and sports to touch on what it means to live intentionally, love deeply, own one’s journey, and keep growing—even when it hurts.

For those interested in the creative process, personal transformation, and the hidden challenges behind success, this episode is essential listening.