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The Jordan Harbinger Show

1191: Digital Nomads | Skeptical Sunday

The Jordan Harbinger Show

Jordan Harbinger

Social Sciences, Self-improvement, Entrepreneurship, Talk Radio, Business, Science, Education

4.8 • 12.1K Ratings

🗓️ 3 August 2025

⏱️ 61 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Working from the beach seems like a dream, but Jessica Wynn shows how being a digital nomad is mostly Wi-Fi nightmares and visa hell on Skeptical Sunday!

Welcome to Skeptical Sunday, a special edition of The Jordan Harbinger Show where Jordan and a guest break down a topic that you may have never thought about, open things up, and debunk common misconceptions. This time around, we’re joined by Jessica Wynn!

Full show notes and resources can be found here: jordanharbinger.com/1191

On This Week's Skeptical Sunday:

  • Digital nomads are remote workers, not vacationers — they need real skills and jobs to sustain constant travel while managing clients across time zones and unreliable Wi-Fi connections.
  • The digital nomad lifestyle costs more than advertised due to short-term housing, visa fees, coworking spaces, storage, and constant travel expenses. So-called "financial freedom" is often just financial reshuffling.
  • Beware the "digital nomad course industrial complex." Scammers sell empty promises to desperate people, creating pyramid schemes that prey on those seeking lifestyle change.
  • Digital nomads can harm local economies by driving up rents and displacing residents, turning neighborhoods into overpriced Instagram backdrops that locals can no longer afford.
  • If pursuing digital nomadism, start with solid remote work skills and reliable income. Go off the beaten path, support local businesses, learn basic language skills, and respect that locals aren't resort staff.
  • Connect with Jordan on Twitter, Instagram, and YouTube. If you have something you'd like us to tackle here on Skeptical Sunday, drop Jordan a line at [email protected] and let him know!
  • Connect with Jessica Wynn at Instagram and Threads, and subscribe to her newsletter: Between the Lines!

And if you're still game to support us, please leave a review here — even one sentence helps!

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Transcript

Click on a timestamp to play from that location

0:00.0

Welcome to Skeptical Sunday. I'm your host, Jordan Harbinger. Today I'm here with Skeptical

0:07.6

Sunday co-host writer and researcher Jessica Wynn. On the Jordan Harbinger show, we decode the

0:12.3

stories, secrets and skills of the world's most fascinating people and turn their wisdom into

0:16.5

practical advice that you can use to impact your own life and those around you. Our mission is to help

0:21.5

you become a better informed, more critical thinker, and during the week we have long-forms

0:25.3

conversations with a variety of amazing folks, from spies to CEOs, athletes, authors, thinkers,

0:30.5

performers. On Sundays, though, it's Skeptical Sunday. A rotating guest co-host and I are going to

0:35.0

break down a topic that you may have never thought about and debunk common misconceptions.

0:39.7

Topics such as why expiration dates on food and medication are kind of nonsense, acupuncture,

0:45.0

astrology, recycling, homeopathy, hypnosis, internet porn, diet pills, and more.

0:50.0

And if you're new to the show or you want to tell your friends about the show, I suggest our

0:53.1

episode starter packs.

1:13.9

These are collections of our favorite episodes on topics like persuasion, negotiation, psychology, disinformation, crime and cults, and more. It'll help new listeners get a taste of everything we do here on the show. Just visit jordanharbinger.com slash start, or search for us in your Spotify app to get started. Today on Skeptical Sunday, we drag the buzzphrased digital nomads out of its beach hammock and see if there's any substance under all the sand.

1:16.7

On the surface, digital nomads are the ultimate fantasy.

1:19.6

Remote workers, untethered from cubicles, jet-setting to sip, iced coffee in Bali,

1:23.7

and then they work from a rooftop bar in Lisbon, making passive income along the way.

1:28.0

But what is behind the Instagram posts and YouTube clips of perfect sunsets and exotic locations?

1:33.4

Is it freedom? Is it fraud? Is it a cultural shift? Or just a new way to burn out, but with

1:38.4

better weather. Joining me today is writer and researcher Jessica Wynn. So, Jess, first, what is a

1:43.4

digital nomad in the first place?

1:44.6

And more importantly, how's the weather in Bora Bora?

1:47.2

I wish I knew, but it's pretty nice here in Southern California, so no complaints.

...

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