Self‑Employment Tips: Tax Set‑Asides & PTO Fund

Join Caitlin and Janessa in this Remote Roundup as they catch you up on where they’ve been lately, the travel mistakes they’re learning the hard way, and the systems that keep long-term travel from turning into financial and emotional whiplash. 

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, Caitlin and Janessa share what it’s like spending a season in a southern hemisphere coastal hub and time in a vibrant Latin American capital known for culture, markets, and museums. You’ll get Caitlin’s solo travel hot take and the #1 travel mistake she keeps repeating so you don’t have to, and hear from Janessa on her perfected expense tracking system with tips for self-employed travelers. 

What’s one “comfort” you’re keeping in your travel life right now, even if it costs a little more or takes up a little more space? I’d love to hear your thoughts, and I hope you’ll share by sending me an audio message. 

Tune In To Learn: 

• Considerations for making Cape Town a long-stay base, what to expect in the cultural capital of Mexico City, and a magic town you may want to add to your Mexico itinerary 

• Why it’s so easy to keep falling for the budget airline trap and more hidden fees you need to be aware of  

• Why you should always check your entry stamp and never assume you’ve been granted the maximum tourist stay 

• Janessa’s system for remote work and travel budgeting, including expense tracking apps, annual reviews, tax set-asides, and building a DIY PTO fund 

• Why Caitlin says she hates solo travel (yet still thinks everyone should do it), and why we need to redefine what “solo” means 

• A common travel mistake and what it can reveal about the expectations we carry into travel 

• And so much more 

Resources: 

• Sign up for our FREE newsletter 

• Caitlin on Instagram 

• Janessa on Instagram 

• TravelSpend 

• Trabee Pocket  

Want More? 

• Going Nomad with Jason Robinson 

• Joys of Solo Travel with Manjinder Kang 

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

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• Listen to the Planet Visionaries podcast on Apple and Spotify. 

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