Ep43 - Self Driven

Ep43 - Self Driven

We catch up with an old colleague who shows us how retirement, road trips, Teslas, and AI can all collide in the best way. From a 10,000-mile cross-country journey using full self-driving to discovering quirky roadside stops with ChatGPT and Grok, his story is about embracing technology, staying curious, and finding freedom in the unexpected. Self-driven is about moving ever forward and finding your way.

Ep42 - Budget Blues

In this episode, Kendra and Shawn recap their chaotic, funny, and sometimes sketchy journey through the Midwest, Canada, and back toward the Rockies. From visiting their daughter at a communal workaway farm to losing their truck Val near Mount Rushmore, meeting “Rusty,” surviving Midwest roadkill and construction, and enduring a bizarre late-night confrontation at a Budget Inn, the trip delivers plenty of road-warrior drama. The episode ends on a high note at Glacier National Park, where stunning scenery, a grizzly sighting, and dark humor about wilderness survival remind them why they keep choosing life on the road. Apologies from the staff: the microphone receiver disconnected midway through the recording, and we lost the best sound quality. Please be patient, and thanks so much for listening!

Ep41 - Floating Freedom

In this episode, we interview an adventurous retired couple who traded traditional life on land for full-time life aboard a sailboat. While they joined us from Greece and we recorded from Canada, we talked about what it really means to live on the ocean — from learning to sail, provisioning, weather, maintenance, close calls, medical concerns, and navigating around massive ships, to marriage, teamwork, fitness, and finding freedom after retirement. Their story is about more than sailing; it’s about reinvention, courage, and choosing a life of adventure with the ocean as home.

Ep40 - Slipping Gears and Secret Tunnels

Join us as we take listeners on a whimsical, nomadic trekacross the Midwest, navigating everything from a "catastrophic" water main break in historic Galena to a transmission-slipping scare in Chicago. Their journey blends deep dives into 19th-century architecture and dark legends of secret tunnels with humorous observations on "sarcastic" kitchenettes, "terrifying" river fish, and the vibrant tulip fields of Holland, Michigan. Between segments on "Big Hair Friday" experiments and the etiquette of baseball hats in steakhouses, they find beauty in the rolling "Driftless Area" and the idyllic, golf-centric lake communities of Stanwood, all while their dog, Django, expertly adapts to life on the road.

Ep39 - The Old Mississip!

Follow us as we continue north from Sioux Falls to beautiful La Crosse, Wisconsin. We wander the almost empty streets of this historic town while the temperature falls from 80 degrees to 20 degrees in an hour. And what is that loud siren? Small trigger warning for sexual abuse discussion.