Ear Hustle: The Loop Ep. 5 – "Yes, And..."

Release Date: December 3, 2025
Hosts: Nigel Poor and Earlonne Woods
Podcast: Ear Hustle, Radiotopia

Main Theme

This episode of Ear Hustle centers on the life of Kaysha, a young woman from Southside Jamaica, Queens, whose journey embodies the cycle (the “loop”) of struggle, resilience, and fleeting stability that defines the lives of so many young people entangled in poverty, foster care, and the criminal justice system. Through Kaysha’s honest storytelling, listeners experience her challenges with family instability, foster care, cycles of housing insecurity, brushes with the law, creative ambition, and complex relationships—with herself, her siblings, and the adults trying to support her. The episode also explores the impact of New York’s Drama Club, a theater program for youth impacted by incarceration, and discusses the bittersweet realities of programs that cannot solve everything.

Key Discussion Points & Insights

1. Meeting Kaysha: Identity and Guardedness

• Kaysha’s Duality & Defense Mechanisms (03:14–04:12):
  • Kaysha describes being guarded around new people to protect herself:

    "I just don't have trust for people. So I just want to know like what y' all about... When you're quiet, you get to just listen and take everything in and see—who do I have to be to protect myself in this moment?" (03:23, Kaysha)

  • But says her true self is “goofy” and positive:

    "The real me? She's goofy. She's honestly just goofy. Always laughing, always helping…I just never had nobody be nice to me." (04:12, Kaysha)

2. The Cycle: Kaysha’s Life Story

• Neighborhood and Early Exposure (08:43–09:29):

  • Kaysha details growing up in gang-heavy Southside Jamaica, being involved from middle school (12–17), initially handling drugs but later “carrying a mask and a gun.”
  • Her involvement stemmed from seeking money and community—she didn’t want to be alone, as her family life was unstable.

• Family Instability and Foster Care (09:29–10:52):

  • Her mom struggled with addiction, her father was in and out of prison; Kaysha became responsible for siblings, with all placed in foster care at infancy.
  • Kaysha became next of kin, feeling pressured to care for siblings:

    "So when I became legal, next of kin is me. So I'm now getting the call like, you have a child? And it's like people are calling me, acting for the stuff for them, and it's like, I don't have it." (10:18, Kaysha)

• Being Pulled Back In (11:04–11:46):

  • Despite periods of promise—college and track—injury, depression and financial necessity pulled her back to “the hood,” leading to arrests and stints in juvenile detention.

• Turning Point: Responsibility for Sister (11:46–12:02):

  • Kaysha attributes maturing and shifting attitudes to her relationship with younger sister Eldora:

    "I couldn't let that baby go through what I went through. So I tried to, like, step up and do more." (11:58, Kaysha)

3. The Importance—and Limits—of Support Systems

• Drama Club’s Role (12:42–14:18, 21:31–21:49, 39:36–40:14):
  • Drama Club, a community-based theater program, became one of the rare dependable supports—offering work, purpose, and adults who cared.
  • Kaysha credits them:

    "They help you mentally, physically, emotionally. Like, they're always there for you. They're gonna make sure you good." (13:50, Kaysha)

  • Even when housing instability returned and she had to crash at a dangerous squat, Drama Club connections later helped her access stable housing:

    "It happened as soon as I thought I had to go back to my old life. And it's like, it showed me that, like, nah, you don't gotta do that. We got you." (21:42, Kaysha)

4. Falling Through the Cracks: Instability and the Loop

• Losing Support and Risking Homelessness (16:11–16:53):

  • When aged out—and even before—foster care support evaporates:

    "Kaysha was in danger of becoming homeless. So she turned to some of those guys she knew from her neighborhood, and they took her in." (16:23, Nigel)

  • Living at a squat with gang members—“not people I want to necessarily be around… they bringing me back.”

• Temptation and Survival (17:56–18:41):

  • She recounts the ease and allure of “fast money” and the struggle between personal values and immediate needs:

    "There's a risk to it. But you get that money once that money in your hand, you're not thinking about no risk. You're not thinking about no getting caught, no trouble, no police, no nothing like that." (18:40, Kaysha)

5. Hope, Creativity & Setbacks

• Music as Expression and Survival (23:13–23:44, 46:22):
  • Kaysha strives to make it as a rapper and model, sharing original lyrics on the show.
  • Hosts discuss the daunting odds and practicality:

    "And so it worries me when that's someone's game plan, because it is a huge long shot." (23:19, Nigel)

  • Kaysha is undeterred, finding hope in her creative outlet—even if the income is minor:

    "I make some money. Is it enough to live on?… When you don't gotta pay rent, life is good." (46:08, 46:22, Kaysha)

6. Disappearance and Depression

• Dropping Out and Disappearing (29:54–38:32):
  • After doing well for a period, Kaysha falls off the grid—calls unanswered, social media wiped, Drama Club no longer attended.
  • Later, Kaysha reveals she was at a low point—depressed, nearly homeless, isolated after an incident with her sister:

    "I deleted the social media, like, literally an hour or two before I did what I did. So it was me literally disappearing… I felt like I had nobody or nothing. My bank account was empty. I had nobody I could call. I had no more places to go. I had no more options." (37:59–38:32, Kaysha)

7. Recurring Connections, Small Victories

• Drama Club as a Lifeline (39:36–40:14):

  • Despite absences, Kaysha is always welcomed back, reinforcing the power—and limits—of unconditional support:

    "Every time I do disappear and I come back, it's a lot of love... Just to see me grow, see me mature... So it's like knowing that I'm making somebody proud because I don't have nobody to tell me I'm proud." (39:40, Kaysha)

• Rebuilding Familial Ties (42:43–43:36):

  • Now living with her estranged father, Kaysha finds a new, however imperfect, sense of “home”:

    "I only got to know him after I found him on Facebook when I was a teenager... Once we put both our trauma aside and we just bond with each other. I'm really my father's kid." (43:03–43:36, Kaysha)

8. Facing the Cycle Honestly

• On the ‘Loop’ and Limitations (40:14–40:36, 54:59–55:45):

  • The cycle of poverty, crime, foster care, and adult incarceration is persistent. Even programs like Drama Club can’t ‘break’ it alone.

  • Drama Club’s outgoing founder, Josie Whittlesey, reflects:

    "My mission was to slow the flow into prison, into adult prison, interrupt that school to prison pipeline... But there's so many factors that I'm not sure as wonderful as a drama club is, it's going to be able to interrupt." (53:27–53:56, Josie)

  • Success, Josie learns, is redefined in small moments:

    “Success looks like engagement, laughter, surprising yourself, connecting with others, forgetting where you are.” (54:03, Josie)

9. Self-Reflection and Storytelling Ethics

• Who Holds the Story? (48:02–49:10):

  • The team and Kaysha openly discuss consent, ethical storytelling, and checking on participant well-being:

    "Would you be upset if you heard in this story that I say, I'm worried about you?" (49:12, Nigel)
    "No, I'm worried about me. I don't even trust myself sometimes." (49:16, Kaysha)

  • Kaysha’s summary of her own arc:

    "I had nothing, and I never gave up. No matter how much I wanted to, no matter how much I felt like, fuck this shit, I stayed and I'll make it to the next time." (49:41, Kaysha)

Notable Quotes & Memorable Moments

• On Survival and Despair:

  "I had no more places to go. I had no more options... I felt like I failed." (38:04, Kaysha)

• On the Pull of Old Habits:

  "I'm back in the life. Have I been more involved in both [gang/drug worlds]? Yes. But am I doing any of those? No. Like, I myself am not, but have I surrounded myself with people like that again? Yes." (44:45, 45:02, Kaysha)

  "We ain't doing nothing but literally dying and get it and getting locked up. I can't live that life." (45:21, Kaysha)

• On Support Networks:

  "Every time I do disappear and I come back, it's a lot of love... So it's like knowing that I'm making somebody proud because I don't have nobody to tell me I'm proud." (39:40–40:14, Kaysha)

• On Small Successes Amidst Systemic Barriers:

  "Success looks like engagement, laughter, surprising yourself, connecting with others, forgetting where you are." (54:03, Josie Whittlesey)

Significant Segment Timestamps

• Intro to Kaysha & Her Guardedness: 03:14–04:12
• Life in the Neighborhood: 08:43–10:52
• Responsibility for Her Sister & Foster Care: 11:51–12:10
• Losing Housing & Return to ‘The Life’: 16:11–17:49
• Depression & Disappearing from Support Systems: 29:54–38:32
• Climbing Back Out & Drama Club’s Impact: 39:36–41:08
• Living with Dad, Facing the Future: 42:43–43:36, 44:45–46:22
• Music as Hope & Survival: 23:13–23:44, 46:22
• Ethical Storytelling and Reflection: 48:02–49:41
• Closing Reflections on Systemic Change (Josie): 53:27–55:45

Conclusion: Themes & Emotional Impacts

• The episode gives rare, unvarnished insight into the lives of vulnerable youth—their potential, pain, and the cycles beyond their control.
• The hosts address the power and the limitations of care, community, art, and mentorship as well as the emotional cost borne by those “in the loop.”
• Final words underscore both the gratitude for Kaysha’s openness and the bittersweet truth of loops: some end, but new ones begin.

Notable Final Moments

Kaysha, on her own story:

"I never gave up. No matter how much I wanted to, no matter how much I felt like, fuck this shit, I stayed and I'll make it to the next time." (49:41, Kaysha)

Josie Whittlesey, Drama Club founder, on ‘making your scene partner look good’:

"It's the hardest one, I think, because it's about bailing someone out when you see that they're lost at sea. I find it hard. So I'm always surprised. That's their favorite rule. It's a sophisticated rule." (56:03, Josie)

Summary Takeaway

"Yes, And..." follows Kaysha through loops of hardship and hope, showing that love and solidarity—while not always enough to “break the cycle”—can offer moments of recognition and bravery that matter. The recurring presence of caring adults, supportive programs, creative outlets, and self-reflection ultimately help Kaysha (and listeners) hold onto hope for another try, another chapter, another “yes, and…”