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KareemJacksonLIVE!

Explore Global Opportunities for Entrepreneurs and Expats

Exit. Evolve. Succeed. 🌍 Why Stay Stuck? Time to Re-invent Yourself! 🚀 Ask Kareem Q&A

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On this episode of Kareem Jackson Live! On The Set, we’re diving into real talk about divesting from the “New Plantation America Experiment” and exploring life beyond the US. In a world where people are working longer and life expectancy is dropping, it’s time to seek new opportunities. Entrepreneurs and home-based professionals are rebranding themselves by moving abroad, investing, and thriving in countries like the Philippines.

With rising stress, violence, and economic instability in the United States, why stay trapped in a cycle that’s no longer working for you? Re-invent yourself—and your business—on your own terms. Escape the grind and explore what freedom truly feels like outside of the borders of the U.S.

Join us for this conversation on how you can make your great escape! ✈️

#LifeAbroad #EntrepreneurLife #ReinventYourself #NewBeginnings


Welcome back to Kareem Jackson Live! On The Set, where we get real about life beyond the borders of the United States. Today, we’re diving deep into what it means to stop participating in this “New Plantation America Experiment.” It’s time to take control of your own narrative, your own destiny.

Imagine if we just left—divested from this system that’s got us locked in as consumers, never fully owning our lives. The future’s looking grim for so many. Retired folks who did everything ‘right’ are still clocking in to make ends meet, despite having homes, 401(k)s, and the so-called American Dream. And yet, the system continues to fail them as life expectancy drops and stress takes its toll.

That’s why so many, especially entrepreneurs and home-based professionals, are opting out. They’re realizing it’s possible to re-invent, re-brand, and live a better life—whether that’s in the Philippines, Ghana, Mexico, or somewhere else. And it’s not just individuals; even big companies start one way and evolve. So why not us? Let’s talk about the power of rebranding yourself, even if it’s not in the U.S.


ASK KAREEM:

Here are 15 questions from our guests on the “Ask Kareem” episode, covering hot topics like dating abroad, leaving the U.S. or U.K., outsourcing, and advertising on the show:

  1. David Carter, 38, Los Angeles, USA (Democrat): “What’s the first step to leaving the U.S. and starting life in the Philippines? I have a good job here, but I feel like I could have a better life abroad. How do I prepare financially?”
  2. Melinda Lewis, 42, Manchester, U.K.: “I’ve heard a lot about how affordable it is to live in the Philippines compared to the U.K. Can you break down the monthly cost of living for a single woman like me looking to move?”
  3. Sarah Gomez, 29, Houston, USA (Republican): “Is it really possible to find love abroad, and how do you navigate cultural differences when dating someone from another country like the Philippines?”
  4. Jason Blackwell, 35, London, U.K.: “I run a small business here in London, and I’m curious how I can outsource more tasks to the Philippines to cut costs. What’s the best way to get started?”
  5. Jessica King, 47, Chicago, USA (Declined to say): “I’ve been hearing a lot about the mental health benefits of leaving high-stress environments like the U.S. How has living in the Philippines improved your quality of life and mental well-being?”
  6. Michael Andrews, 55, Dallas, USA (Republican): “How do you find a serious, long-term partner in the Philippines? I’m not looking for something casual, and I want to be sure I’m going about it the right way.”
  7. Rebecca Cruz, 31, Cebu, Philippines: “For someone thinking about leaving the Philippines for a career abroad, like in the U.S. or U.K., what are some things to consider? Is it worth it financially?”
  8. Tom Richardson, 60, Glasgow, U.K.: “I’m close to retiring and thinking of moving to the Philippines for a slower pace of life. What should I know about healthcare and retirement benefits for expats there?”
  9. Cynthia O’Hara, 50, New York, USA (Democrat): “How can I advertise my small business on your show? I’m looking to reach an international audience, especially those interested in relocating abroad.”
  10. Kenneth Ortiz, 40, Quezon City, Philippines: “Is it easier to start a business in the Philippines compared to the U.S. or U.K.? What are the main challenges for expats when trying to launch a venture here?”
  11. Michelle Hampton, 34, Birmingham, U.K.: “I’ve heard of people outsourcing everything, from personal assistants to social media managers, to the Philippines. How reliable are the workers, and what’s the best way to find trustworthy help?”
  12. Brian Taylor, 28, Miami, USA (Republican): “What are some of the biggest misconceptions Americans have about the Philippines? I’m considering moving but don’t know what to expect in terms of lifestyle and culture.”
  13. Hannah Stewart, 45, London, U.K.: “As a woman in my 40s, I worry about dating in a new country. How is the dating scene in the Philippines for older expats?”
  14. Eric Lee, 36, Manila, Philippines: “What are your tips for expats like me who are married to a Filipino and want to make sure we’re staying connected to the local culture while also balancing my Western background?”
  15. Tiffany Wilson, 30, San Francisco, USA (Democrat): “How can I take my digital business global by outsourcing most of the work to the Philippines? What are the costs and potential issues I should be aware of?”

Thanks for tuning in! We appreciate your questions and perspectives from all over the world. Whether it’s relocating, outsourcing, dating, entrepreneurship, or advertising, the journey toward success is for everyone!

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