Episode Details

Jessica O’Reilly is a hilariously unconventional writer, digital nomad, YouTuber, and workout queen. Her YouTube channel, Comfort Is For Wimps dives deep into her life as a digital nomad—couch-surfing in Afghanistan, checking out Medellin’s love hotels, and babysitting rich people’s pets in lieu of rent. Along the way, she examines the disparities in the cost of living between countries, passes the mic to locals, and through it all, rocks a splendid sense of humour. Hit up her Instagram for zingers like, “I don’t fall in love. I audition for the role of ‘lesson I had to learn the hard way.’”

Jessica O’Reilly is the perfect complement to your Instagram relationship coach. Make sure to listen to the end for the stellar advice she gives to “Should I LTR or Should I Bounce.” A committed digital nomad falls in love in a city he does not fancy. It’s the deepest connection he’s ever had, but she can’t follow him around the world. What should he do? Jessica and Erica can’t fix it—but we have thoughts.

Subscribe to Jessica’s YouTube Channel @comfortisforwimps

Follow Jessica on Instagram @comfortisforwimps

Erica on Instagram: @erica.j.schmidt

Erica on Substack (new!): @ericajschmidt

Erica's website: ericajschmidt.com

Erica’s Interview with Jessica O’Reilly from Comfort Is For Wimps

00:00:00 This Is Your Strange and Beautiful Life Theme Song + Jessica O’Reilly’s bio

00:03:06 How Jessica and Erica met in Varanasi, India

00:06:12 Jessica’s Motto and YouTube channel, Comfort Is For Wimps

00:10:48 Is confidence fake it til you make it?

00:13:00 How to Solve the Problem of Paying Rent

00:20:44 What is a digital nomad? Are you a digital nomad? The challenge of the day job, monetizing your joy and art, etc.

00:28:23 Staying healthy and reasonably sane while travelling. Jetlag hacks, packing cubes, workout schedules and more.

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