Why we built Healthy, Wealthy & Wise Workshops

After leading retreats and teaching personal finance for a decade between us, we kept hearing the same thing from past guests: 'I learned so much — but I wish you'd talked about money too.'

Money comes up on retreat whether we plan for it or not. Travelers are often at an inflection point — a new job, a career pivot, a recent windfall or loss — and the questions surface. What is enough? What am I optimizing for? How do I build a life that holds together?

After the third or fourth time we caught ourselves doing impromptu finance Q&A by the pool at 11pm, we realized: this was the trip we wanted to lead all along.

In 2024 we ran our first pilot — six guests, one teacher, one CFP — in Costa Rica. By the end of week one, every guest had drafted a 12-month plan that integrated their physical, emotional and financial lives. They became our advisors, and they became our friends. We are still in a group chat.

This is how every HWW retreat begins now: as a small experiment co-designed with a panel of past guests, then opened up to the rest of you. We are not a big-bus tour operator. We never want to be. Welcome.