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.

00:37:05 Losing your job and finding your niche

00:41:38 Friendship and Romance on the Road. Is it lonely? (Yes.)

00:48:05 Humour, self deprecation and self-help

00:51:25 Listener question: Do I LTR or do I bounce? A lovestruck digital nomad wonders if he should stick around in a city he doesn’t love for the first real connection he has felt in a while.

00:55:00 Freedom in commitment

01:03:14 Jessica O’Reilly’s Routines and A+ workout habits:

01:05:29 Jessica O’Reilly’s Spectacular TED talk

01:07:58 Wrap-up and final theme song

Listener Question from Do I LTR or Do I Bounce?

Dear Jessica and Erica,

I’ve been a digital nomad for almost a year now. I totally love it! In general, I’ve tried to stay away from serious relationships that could cost me my freedom.

However, I recently met a local during my travels, and suddenly I’m head over heels in love. I’ve never managed to connect with someone like this, and it feels awesome. We’ve been hanging out for four weeks now which is way longer than I’d tend to stay somewhere. Now the tricky part is that I want to continue my nomadic lifestyle whereas she wants to stay. She doesn’t have the kind of lifestyle that lets her travel for much longer than a couple weeks at a time, barely a couple of times per year, and never without tons of planning. She has a job that isn’t mobile, a house, and even a dog. I get that this is what a lot of people want in their lives. But it’s not what I want. At least not right now.

I’d consider staying a bit longer, but honestly, I don’t really like her city. It’s her I love. I don’t know how to navigate my love for her with my dream of living a location-independent lifestyle. I worry I’m just a selfish avoidant jerk with a closed heart. Do you have any experience with this? Should I extend my stay and see what happens? What do you think I should do?

Love, Do I LTR or Do I Bounce

If you enjoyed this episode, you might also like: How to Be a Writer with Kyle Stevenson, ChatGPT Is My Therapist, and Funemployment with Erica J. Schmidt.

To support this independent podcast, please consider purchasing a Lil and Bud dog greeting card at ericajschmidt.com/merch. You can also make a one-time donation here at The Donate Button.Feel free to get in touch for other sponsorship possibilities. My infinite thanks for all of this.

More infinite thanks, as always, to Taes Leavitt (darling big sister, Big Heart Journey), Sherwin Tjia (technical and creative advisor, Sherwin’s Quirky Events,Episode 22) and my dearly departed aunt Eileen Gun, whose generous gift helped to fund my new podcast equipment.

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