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Living across borders means more than booking flights home. It often means caring for aging parents, managing family property, navigating two legal systems, and preparing for the unexpected.

In this episode, Kerry-Ann is joined by attorney Renee Kendall of Caribbean Legal Solutions to explore the realities Caribbean families face when life spans multiple countries. Their conversation goes beyond wills to discuss elder care planning, powers of attorney, healthcare proxies, land ownership, estate administration, protecting yourself from fraud, and why organizing your affairs today is one of the greatest gifts you can leave your family.

Whether you're helping parents back home, own property in the Caribbean, or simply want to spare your loved ones unnecessary stress one day, this episode offers practical guidance for anyone whose life and family exist across borders.

In this episode you'll learn:

• Why planning before a crisis matters
• How wills fit into a broader estate plan
• The importance of powers of attorney and healthcare proxies
• Common challenges of managing land and legal affairs across countries
• Practical steps you can take now to organize your documents, digital accounts, and family information
• How to avoid common pitfalls when buying or inheriting Caribbean property

Planning for the future isn't about expecting the worst. It's about making life easier for the people you love.

Renee Kendall is a New York attorney and founder of Caribbean Legal Solutions. Her practice focuses on estate planning, real estate, and helping Caribbean diaspora families navigate legal matters that span multiple countries. Through Caribbean Legal Solutions, she connects clients with trusted legal professionals across the Caribbean while providing guidance on cross-border estate and property matters.

Contact Caribbean Legal Solutions - https://caribbeanlegalsolutions.com/

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1. Donate: If you believe in our mission and want to help amplify Caribbean voices, consider making a donation.
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A Breadfruit Media Production

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Is Jamaican Patois really "broken English"? How did Caribbean languages develop, and why do debates about language continue to spark strong reactions throughout the region and the diaspora?

In this crossover episode from Breadfruit Media sister show, Strictly Facts, Dr. Alexandria Miller speaks with linguist Dr. Joseph T. Farquharson about the history, structure, and future of Caribbean languages. Together they unpack common misconceptions, explore African linguistic influences, and discuss what language recognition means for cultural identity and belonging.

Key Takeaways

• Caribbean languages are complete linguistic systems, not failed versions of European languages.
• African languages played a significant role in shaping Caribbean grammar and speech patterns.
• Migration and music helped preserve and globalize Caribbean languages.
• The Cassidy-JLU writing system provides a standardized approach to writing Jamaican.
• Language recognition is connected to identity, education, cultural preservation, and access.

Mentioned in This Episode

• Carry On Friends episode with Dr. Kari-Lee Grant
• Carry On Friends episode with O'Neil Madden
• COFMG Insights Paper - Jamaican New Testament
• Strictly Facts Podcast

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1. Donate: If you believe in our mission and want to help amplify Caribbean voices, consider making a donation.
2. Get Merch: Support Carry On Friends by purchasing merchandise from our store.

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A Breadfruit Media Production

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What happens when a first generation is told “you’re not Jamaican” in one but never fully seen as American either?

In this episode, I explore Lens 6 of the Caribbean Diaspora Experience Model (CDEM): "You're Not Either Or, You're Both And". Through stories from podcast guests, family experiences, and observations over more than a decade of podcasting, I unpack the emotional complexity of Caribbean identity in the diaspora for first generation Caribbean Americans.

This conversation explores what it means to navigate layered identities when your heritage, upbringing, geography, and community experiences don’t always align neatly. From being called a “Yankee” by family members to reconnecting with culture later in adulthood, this episode validates the experiences of people who have spent years trying to prove they are “Caribbean enough.”

The episode also explores:

• Why some immigrant parents distanced their children from culture
• The role of fear, assimilation, and survival in shaping identity
• Why accents and language don’t determine belonging
• The emotional impact of cultural gatekeeping
• How Caribbean identity evolves across generations

At the heart of this episode is a reminder: you do not have to choose between identities. You can be Caribbean and American. Jamaican and Canadian. Guyanese and Brooklyn-born. Identity is layered, lived, and evolving.

Resources Mentioned

• Caribbean Diaspora Experience Model (CDEM)
• Previous Lens Episodes:
  • Lens 1: Where You Start Shapes the Journey
  • Lens 2: Where You Live + What You Seek = How You Connect
  • Lens 3: Cultural Anchors Keep Us Rooted
  • Lens 4: Your Identity Will Shift
  • Lens 5: Culture Influences How We Show Up At Work

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Support How to Support Carry On Friends

1. Donate: If you believe in our mission and want to help amplify Caribbean voices, consider making a donation.
2. Get Merch: Support Carry On Friends by purchasing merchandise from our store.

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A Breadfruit Media Production

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A school party should be simple: put on your outfit, meet your friends, dance for a few hours, go home. If you grew up Caribbean American, you already know it’s never that simple. Permission is a process, timing is everything, and one wrong tone can turn a “maybe” into an automatic no.

This is a special crossover episode from my audio storytelling series Voice Note Stories which is built around a true story from my senior year of high school. What follows is peak Caribbean parenting and lifelong lessons about respect and consequences. Sometimes the most memorable moments aren't the parties themselves, but the dramatic exits.

Voice Note Stories captures Caribbean cultural experiences through brief, authentic storytelling. If this brought back memories, follow, share with a friend who gets it, and leave a review so more listeners can find Carry On Friends and Voice Note Stories.

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Support How to Support Carry On Friends

1. Donate: If you believe in our mission and want to help amplify Caribbean voices, consider making a donation.
2. Get Merch: Support Carry On Friends by purchasing merchandise from our store.

Connect with @carryonfriends - Instagram | Facebook | YouTube
A Breadfruit Media Production

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A Jamaican patty can take you back in one bite, to lunch money days or some other memory. Franklyn is a Jamaican entrepreneur helping grow to Juici Patties franchises in the United States. We talk about why that nostalgia comes with real responsibility when you’re carrying a beloved Jamaican brand into cities like New York and markets across the country.

Franklyn shares his journey from Jamaica to school in Tennessee, finishing his degree in Florida, working in software engineering, and then stepping fully into franchise ownership. From there, we dig into the business side of Caribbean food. He explains why consistency is everything, why one average patty can hurt the whole brand, and how a viral moment only matters if the product can back it up.

Is it possible to normalize the Caribbean Food category the way Italian and Mexican food have been normalized without losing culture or ownership? Franklin addresses that concern head-on, then closes with what he hopes successful Jamaican brands can do for Jamaica itself through investment, development, and long-term economic lift.

If you care about Jamaican patties, Caribbean American identity, or how to scale a food brand without selling out, press play, follow, and share this with a friend then leave a review and tell us your go-to patty and drink pairing.

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Support How to Support Carry On Friends

1. Donate: If you believe in our mission and want to help amplify Caribbean voices, consider making a donation.
2. Get Merch: Support Carry On Friends by purchasing merchandise from our store.

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Aria Collins is Grenadian-born, Brooklyn-raised, and now based in Charlotte, North Carolina. After moving south and losing easy access to Caribbean food, she started rethinking her relationship with food, health, and culture. She turned that journey into Prep and Ting, a Caribbean-centered approach to meal prep and intentional eating.

In this episode, we talk about what it’s like to crave the food you grew up on when you can’t just run to the Jamaican spot or grab a roti. We dig into the cultural habits around food that Caribbean people carry like cleaning your plate, Sunday cooking rituals, how we prepare meals and how being intentional about those habits can change how you feel in your body without giving up the food you love.

We also get Aria's personal experience with Lens 1 and Lens 2 of the Caribbean Diaspora Experience Model.

Connect with Aria:

Instagram: @prepandting

Website: www.prepandting.com

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Support How to Support Carry On Friends

1. Donate: If you believe in our mission and want to help amplify Caribbean voices, consider making a donation.
2. Get Merch: Support Carry On Friends by purchasing merchandise from our store.

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A Breadfruit Media Production

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In Part 2 of this conversation, Kerry-Ann Reid-Brown continues her discussion with organizational psychologist Dr. Kerriann Peart about what Caribbean women experience in professional spaces.

This episode explores topics we rarely talk about openly, including how perimenopause, burnout, and ambition culture intersect with work and identity.

Together they discuss:

• Why Caribbean women often push themselves to the point of burnout
• The hidden impact of perimenopause on professional life
• Cultural expectations around ambition and hard work
• How to recalibrate ambition at different stages of life
• Why learning to regulate yourself is essential for longevity in your career

This conversation continues the discussion started in Part 1, where they explored Caribbean identity in corporate spaces and the challenges of navigating workplace culture.

• If you haven’t listened to Part 1 yet, start there.
• Also listen to episode covering Lens 5 of the Caribbean Diaspora Experience Model on How Culture Impacts how we show up at work. Audio | Video | Blog

Connect with Dr. Kerriann Peart: Website | LinkedIn

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Support How to Support Carry On Friends

1. Donate: If you believe in our mission and want to help amplify Caribbean voices, consider making a donation.
2. Get Merch: Support Carry On Friends by purchasing merchandise from our store.

Connect with @carryonfriends - Instagram | Facebook | YouTube
A Breadfruit Media Production

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What happens when Caribbean cultural identity meets corporate expectations?

In this powerful conversation, Kerry-Ann Reid-Brown sits down with organizational psychologist Dr. Kerriann Peart to unpack the challenges Caribbean people - women especially, face in professional spaces. From cultural misunderstandings and workplace microaggressions to burnout, “boreout,” and the pressure to fit into corporate norms, this discussion explores how identity, authenticity, and professional well-being intersect.

They also discuss how Caribbean cultural values such as integrity, excellence, and community shape how we show up at work, sometimes in ways that clash with corporate culture.

This is Part 1 of a two-part conversation that dives deep into navigating professional life without losing yourself. Mek sure you come back for Part 2. In the mean time check out:

Resources Mentioned

Lens 5: Culture Influences How We Show Up at Work: Audio | Video | Blog

Connect with Dr. Kerriann Peart: Website | LinkedIn

Subscribe to the Newsletter

Support How to Support Carry On Friends

1. Donate: If you believe in our mission and want to help amplify Caribbean voices, consider making a donation.
2. Get Merch: Support Carry On Friends by purchasing merchandise from our store.

Connect with @carryonfriends - Instagram | Facebook | YouTube
A Breadfruit Media Production