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Workationing has a new Gringa! Ashley Osmond is introduced to the podcast audience as the new co-host. She comes in hot with stories of her appearance as “Kate” on The Celebrity Apprentice and her high-profile family (she’s related to Donny and Marie Osmond).


Kari met Ashley at a friend’s houseboat party in Amsterdam about a year ago, and the ladies became fast friends – and soon to be travel companions (The Workationing Podcast is going to Goa, India!). 


An experienced solo traveler, Ashley came into the digital nomad lifestyle by teaching English, and has since moved into remote recruiting work. Her company recently co-hosted an event with the Summit Institute in Utah, and she talks about the value of in-person networking at events.


While Ashley was in Utah, Kari was coordinating a Magical Mystery Birthday tour that took her through 7 countries in 3 days: Turkey, Germany, The Netherlands, Belgium, Luxembourg, France and Switzerland.


The birthday tour ended at a chalet nestled in the French Alps, overlooking Lake Annecy. Heads up: if you’re looking for a party theme that slays on Insta, “Stupid Formal” is where it’s at. 


Ashley had to figure out what to do with her dog while she’s in India, and the Workationing Facebook group came through for her in a big way: somebody recommended Trusted Housesitters, and the problem was solved.


Several people in the Workationing group are able to live the digital nomad lifestyle by getting free housing in exchange for watching other people’s pets while the homeowners are out of town. Ashley’s working it the other way


Links mentioned on the podcast:


Trusted Housesitters (for free lodging, or free house/pet sitting services) – 


BetterHelp Online Therapy: get a week for free via our affiliate link here –


Interested in teaching English abroad? Check out this link –

Want to learn about digital nomad life, network with other remote workers and keep up with the ladies in real time? Join the Workationing Facebook group here –

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