An American Millennial Chasing Dreams in New Delhi, India
I booked my ticket to India a week before Charlie Kirk was murdered. I’ve been living in Saket, New Delhi, India since October 4th.
As a millennial raised on the American Dream, I feel baby boomers struggle to grasp today’s challenges. It’s hard telling an older generation that the Dream has become uncertain. Artificial intelligence will replace jobs—slowly or quickly—and the old “grin and bear it” and “work hard” mottos no longer apply. After the 2008 financial crisis, COVID-19, and the rise of AI, my generation and I are exhausted from constantly starting over.
The American Dream
What was once uniquely American has become a universal hope: a good life for everyone. In 1931, James Truslow Adams defined it as:
“a dream of a social order in which each man and each woman shall be able to attain to the fullest stature of which they are innately capable, and be recognized by others for what they are, regardless of the fortuitous circumstances of birth or position.”
That ethos belongs to any human, anywhere (as explored in this insightful JSTOR article on Adams and the origins of the Dream).
Today, I’m an American living an Indian dream—with far more hope than I had in the United States.
Travel Background
My dad and uncle founded InsureMyTrip in 2001, creating the first major U.S. travel insurance comparison site. Strict regulation keeps prices identical across providers, but InsureMyTrip lets travelers compare every top policy in one place—a huge advantage.
Our reps knew the full landscape, not just one product. I worked there five years and rebuilt the affiliate program, growing it from $80,000 to $3.2 million annually by 2023. I partnered with leading travel bloggers and companies so their audiences could choose the best coverage. That experience taught me the realities of travel better than most influencers ever learn.
Moving East
After InsureMyTrip, I tried corporate jobs in Fort Lauderdale and burned out fast. Leadership felt disingenuous, upward mobility felt fake, and consumerism demanded endless salary chasing. I’m terrible at office politics—too blunt and funny for it.
Then everything accelerated: crypto highs, social media chaos, AI looming. I panicked: work for someone else’s dream, get exploited, or get replaced by tech? No thanks.
The answer was clear: use my family’s travel knowledge and connections to build my own thing—Chapter Charlie. Even though I hadn’t traveled much in my twenties, understanding travel insurance gave me deeper insight than most “seasoned” bloggers have.
It’s January 5th, and I’m in Saket, New Delhi, building my own dream. I want to show the good side of India, share the real ins and outs of long-term travel abroad, and document starting a business in uncertain times.
