Expat Challenges: Pricing, 'Island Time', and Assimilation

Shakeemah Smith, aka The Passport Abuser, is a solo traveler who has visited 92 countries and helped more than 12,000 people ace their first solo trip. A former social worker from East Orange, New Jersey, she built her platform, Travel Like a Bawse, to teach practical strategies for traveling more affordably and flipping everyday bills into airline miles. She later relocated to Antigua and Barbuda, where she now lives as an expat. 

In this episode, we talk about the personal shift that makes solo travel possible, how to travel for free without credit cards, and what it’s really like to move abroad and build a life in the Caribbean. 

Shakeemah opens up about calling off her wedding three months before the big day, boarding her first solo flight to Paris in the middle of heartbreak, and realizing she didn’t know how to be alone. What follows is a conversation about self-trust, identity, and deciding to meet the “2.0 version” of yourself instead of waiting for permission. 

We also get tactical. Shakeemah shares the exact systems she used to earn airline miles through everyday expenses like gas, groceries, utilities, and dining. And we talk honestly about leaving the U.S., adjusting to island life, and what it means to create safety and belonging on your own terms. 

If you’ve been waiting for the right time, the right money, or the right person to travel with, this one might challenge that story. 

Who would you become if you stopped waiting and just went? I'd love to hear your thoughts, and I hope you’ll share by sending me an audio message. 

Tune In To Learn: 

• How growing up near New York City shaped her worldview and early curiosity about the world 

• Why ending her engagement forced her to confront her fear of being alone 

• The insights and exercises that helped Shakeemah move from emotional dependence to independence and from fear to self-trust 

• Why she believes solo travel is a fast track to trusting your instincts and enjoying your own company 

• The moment she decided to build a framework to help others take their first solo trip 

• How she turned 34 countries’ worth of lessons into a structured framework for new travelers 

• The overlooked airline shopping portals that generate miles without opening new credit cards 

• How to earn flights from gas, electricity, and everyday bills you’re already paying 

• The mindset behind “bills to boarding passes” and why it works long term 

• Why she moved to Antigua and Barbuda during 2020 and what that decision taught her about safety and lifestyle design 

• The cultural adjustments of living on island time and navigating life as an American expat 

• And so much more 

Resources: 

• Sign up for our FREE newsletter 

• Travel Like a Bawse 

• Bills to Boarding Passes FREE masterclass 

• Instagram 

Want More? 

• How to Win at Travel with “The Points Guy” Brian Kelly 

• Seizing Your Opportunity to Travel, Saving Money as a Solo Traveler, Lessons from a Career Break, and How to Figure Out What You Want (In 60 Seconds) with Leslie McKellar 

• 7 Mistakes to Avoid When Moving Abroad (Or Traveling Long-Term) with Chrishan Wright 

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