Travel Tales Podcast
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A fair-skinned Chicagoan making his home in sunny Costa Rica? Why not?
In 2025, return guest Bob Gillespie followed through on a plan that had been in the works for years- to move to Costa Rica when his son finished high school and left for college.
Bob was a standup comedian in the 90’s but he always had a head for business and numbers. He eventually took the business route full-time and continues his career in finance to this day, only now, he can do nearly all of it remotely.
The “remote” part is a blessing, since he and his girlfriend can continue to work while being year-round residents in northwestern Costa Rica, where their American salaries can go a much longer way than in the Windy City.
And they never have to scrape ice of their windshields again.
We caught up with Bob at his new casa to see what life as an expat is like: how he’s dealing with the bureaucracy, the language, the housing and infrastructure, and the overall culture clash.
Bob also gives great advice for those who are thinking about moving abroad, not just to Costa Rica, but anywhere.
Thanks, Bob! Enjoy the sunshine!