Intro

How do you choose where to live, what to do, and when to go home when your life is fully remote?

Remote Roundup is a monthly series hosted by Zero To Travel’s associate producer, Caitlin Sunderland, and partnerships manager, Janessa Klatt. Explore what's new in remote work and travel, including helpful tools and resources, need‑to‑know trends, destinations, and insight into what it really means to live and work around the world.

In this episode, they’re reporting in from two wildly different corners of the world with stories, struggles, and insights about what it actually looks like to live and work abroad right now, plus a practical holiday wish list.

Caitlin and Janessa open up about the hard choices digital nomads face around holidays, family, and missing big life events. They talk about the growing trend of unexpected remote careers and explore how people are adapting traditional jobs to fit this lifestyle, a conversation about the myth of the laptop-on-the-beach image that won't die, and more. 

What has been your biggest struggle being away from home when you travel? We’d love to hear about it, and hope you’ll share them by sending me an audio message.

Tune In To Learn:

• Why Bangkok’s scale, café culture, and mall scene work so well for remote living

• How Oaxaca brings together community, creativity, and tradition, especially around Day of the Dead

• How Caitlin pulled off a cheap(ish) last-minute flight to Asia with an airport transfer hack

• What it’s really like to grieve major life moments from abroad, and insight into deciding when going home makes sense

• Thoughts on how to take traditional skills and repurpose them into location-independent careers

• An honest take on the “laptop on the beach” stereotype (and why it’s still everywhere)

• A holiday gift guide with digital nomads in mind

• Two travel fail stories that involve passports, bowel movements, and a nearly missed bus in the Italian countryside

• And so much more

Resources:

• Sign up for our FREE newsletter

• Caitlin on Instagram

• Janessa on Instagram

Want More?

• Remote Roundup: True Costs of Long-Term Travel, Taxes & Borderless Living, an Underrated Productivity Habit, + More (October 2025)

• Building a Travel Lifestyle: Digital Nomadism, Slow Travel, Exploring Latin America with Kyle Cohenour

• From Expat to Digital Nomad: Finding Your Travel Rhythm, Balancing Burnout, and the Digital Nomad Lifestyle with Kristin Wilson

Thanks To Our Sponsors

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