Jennifer De Witt

Jennifer De Witt is a certified travel advisor, digital strategist, cat diplomat, and chaos whisperer who decided a long time ago that “normal” was the least interesting option. From pioneering social media before it had rules (or dignity), to house-sitting her way across multiple continents, Jennifer’s career reads less like a ladder and more like an abstract painting—bold, layered, and occasionally featuring a foreign country.

These days she builds bespoke luxury itineraries with the soul of a storyteller and the planning chops of a crisis-trained operator. Clients come to her when they want a trip that changes something and not just a hotel booking, but a perspective shift, a culture immersion, a plan with a backup plan that still leaves room for awe.

Her past lives include: ESL teacher in Japan and Poland, freelance writer, digital fixer for arts orgs and universities, board member of AIGA Orlando, head bagel chef, content ghost for brands trying not to be cringe, founder of a successful but now closed (RIP) marketing collective, and cat-sitter in like... so many places. She's a serial reinventionist who has lived everywhere and belonged nowhere, and that’s exactly how she likes it.

Catch Jennifer on August 29th as she dives into what “nomad” means when you burn the rulebook, live on instinct, and write your next chapter from a kitchen table in someone else’s house.