Teaching Abroad and Building a Side Hustle as a Financial Strategist — with Kennedi Crosby

Kennedi Crosby is a secondary math teacher with six years in the classroom, and a journey most teachers don't get to live. She has taught in New Orleans, Washington D.C., Kuwait, and now China. Somewhere along the way, she also became a financial strategist working specifically with teachers: walking them through the kind of financial education most of us never got.This episode moves through her winding path. From biochemistry pre-med at an HBCU, to teaching algebra in New Orleans. To the international classroom in Kuwait. Through the brutal reverse culture shock of coming home to the U.S. job market — over two hundred applications, less than ten interviews, a year and a half of stringing together seven jobs at once. And into her current dual life: math teacher in China + financial strategist for teachers stateside. Part travel story, part U.S. system reality check, part very practical money advice from someone who learned it the hard way.This episode covers:• Kennedi's path from biochemistry pre-med to math teacher • What teaching internationally actually looks like — IB curriculum, 48-hour offer letter decisions, schools that start their hiring cycle in September, and the contract realities most U.S. teachers don't know about• The reverse culture shock of coming home: why returning to the U.S. job market after teaching abroad was harder than the original move• Seven jobs at once: tutoring, bartending, nannying, online teaching platforms, what a year and a half of stringing it all together actually looks like with no salary, no benefits, no safety net• How Kennedi became a financial strategist — a LinkedIn outreach from another educator that opened a new chapter of her teaching life• What a financial strategist actually does (a "thought partner" for your money) and what a first conversation with one looks like in practice• The generational money advice gap — why what worked for our parents and grandparents won't get you to retirement on a teacher's salary in 2026• Pay yourself first: the one shift Kennedi most wants teachers to make next, and why it has to come before everything else🍏 Heads up: this episode contains (very!) brief adult language. Tagged E for explicit.Connect with Kennedi:linkedin.com/in/kennedi-crosbyKennedi Crosby works as a financial strategist with the Miliare Group. Always consult a licensed financial professional before making significant financial decisions.🎧 Subscribe now for new episodes every Tuesday.Come hang:Instagram → @teacherswithmoneyInstagram (Christa) → @christajeanjonesLinkedIn → Christa JonesLet's finally start your Teachers Pay Teachers store, together! → TPT Launch LabThis podcast is for educational and entertainment purposes only and does not constitute financial advice.