In this episode, Jeff sits down with Sasha Farley, a remote work expert and consultant, to break down what most managers, teams, and companies get totally wrong about productivity, focus, collaboration, and remote work.

There is science and biology behind the traditional 9-5 doesn't make sense for your brain or body.

In this episode you’ll learn:

It’s neuroscience… and wildly relevant for anyone who works online.

You can find Sasha on her website: https://www.sashafarleyconsulting.com/

And LinkedIn: https://www.linkedin.com/in/sashafarley/

This week Jeff and Marisa answer your most-asked questions about life as a digital nomad. From healthcare abroad to giving up your home base, they're breaking down the logistics that keep people from taking the leap. No fluff, just honest answers from people who've lived it.

Here's what they covered:

🌍 Digital immigrants vs. digital nomads — Are remote workers settling down abroad for good? The shift is happening.

🏠 The home base dilemma — Keep paying rent back home or cut ties completely? There's no right answer, but there are patterns.

💰 Is the American Dream actually dead? — The numbers are brutal. We talk about what's replacing it and why people are looking elsewhere.

🏥 Healthcare abroad — The fear that stops most people. What it's really like, what it costs, and the stories you need to hear.

😨 "What if something goes wrong?" — Real talk about the risks, the unknowns, and how to think about them differently.

🛂 The post-national generation? — Tax residency, passport games, and whether digital nomads are creating a whole new identity.

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Your brain is designed to keep you safe, comfortable, and efficient. But what if "safe" is actually keeping you stuck?

In this episode, Jeff and Marisa dive into the neuroscience of why we get trapped in routines (even good ones), and how travel literally rewires your brain. Spoiler: it's not about escaping your problems, it's about building new neural pathways that make you more resilient, creative, and alive.

Here's what we cover:

🧠 Why your brain fights change: The biological reasons you stay in ruts, even when you want something different (hint: dopamine, efficiency, and survival mode).

⚡️ Neuroplasticity 101: How new experiences create new brain pathways, keep you young, and build emotional resilience.

🏃‍♂️ From running to rucking: Jeff's accidental discovery in Costa Rica that changed his entire exercise routine (and why he never would've tried it at home).

🌍 All travel is not created equal: Why an all-inclusive resort won't rewire anything, and what kind of travel actually creates transformation.

💃 Real examples from the road: How paddle, mezcal, zouk dancing, boxing, and pickleball became part of their identities simply because they were in the right place at the right time.

🪜 Start small: You don't have to sell everything and move abroad tomorrow. Even turning right instead of left on your daily walk can start the rewiring process.

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This week Jeff and Marisa talked about the five big regrets of the dying. Morbid sounding? It's not...

This is all about learning from people who had wished they had lived life another way. You can take these lessons and apply them to your life right now, before it's too late. Here are the things they talked about:

💫 “I wish I’d had the courage to live a life true to myself.”
Too many of us follow blueprints built by others. Here’s how to start listening to your own voice instead of the world’s.

💼 “I wish I hadn’t worked so hard.”
The grind feels like a flex, until it’s not. We dig into what “enough” really looks like and how to create a life where you don't need to feel like you have to distract yourself with work accomplishments.

💬 “I wish I’d had the courage to express my feelings.”
Unspoken feelings turn into resentment towards yourself and others. How honesty, even when it hurts you and others, leads to deeper connection and peace.

🤝 “I wish I had stayed in touch with my friends.”
Life gets busy, but relationships are what it's all about. Simple ways to rekindle old bonds and keep your people close no matter where you are.

😊 “I wish I had let myself be happier.”
We talk about permission to feel okay with yourself, being present, and the little choices that build a lighter life.

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Have you ever lived/traveled to a place where you got the feels that something wasn't quite right? Have you ever landed somewhere and felt "Oh my god, this feels like a home I've never lived in before!"

That's because your nervous system has a geography! It's not woo-woo, it's fact.

There's some science to this! And it's based on your personality traits. Literally, there are aspects to your personality that can/do determine where you should be traveling. In this episode we talk about:

🌎 Where you thrive vs. where you wilt: the Big Five traits, what they are and where they're mapped across the world.

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Legalese and logistics shouldn’t stop you from living and working anywhere. In this episode, we unpack the confusing stuff: work-from-anywhere policies vs. hire-from-anywhere roles, W-2 vs. 1099, employer-of-record (EOR), visas, and taxes.

So you know what job listings actually mean and how to navigate them. No promises, no legal advice, just clear explanations and what to consider next.

Highlights:

🧭 Why this feels overwhelming — The “legal stuff” that keeps people from even applying.
🏷️ WFA vs. HFA (the #1 confusion) — Policy (where employees may work) vs. hiring scope (who they can legally employ).
🌍 Time zones & trade-offs — Yes, Bali is dreamy… but 2 a.m. meetings are real, and a fair ask.
🧾 W-2 vs. 1099, explained — Security, benefits, flexibility, and real positives on both sides.
🧩 What is an Employer of Record (EOR)? — The third-party workaround that lets companies hire globally (and pay you locally).
📬 Where to find legit WFA jobs — The email list shout-out and why curated roles matter.
🛂 Visas, simplified — Tourist stays vs. digital-nomad visas (and why you shouldn’t solve visas before you have the job).
💰 Taxes, simplified — The high-level view, why it depends on you and the country, and when to speak to a pro.

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***Not legal/tax advice. Your situation is unique—consult a qualified professional for specifics.

Jeff and Marisa dive deep into hustle culture, the infamous “996” work schedule, and why overwork isn’t just toxic, it’s literally taking years off our lives.

From Silicon Valley badge-of-honor busyness to nomads redefining success, this episode is a reality check on what really matters: health, freedom, and time.

🔑 Episode Highlights:

🧳 Nomad Life as a Wake-Up Call — How travel revealed there’s another way to live.

🏆 Titles vs. Time — Why chasing job titles is an identity trap.

🧠 Overwork = Smoking? — The shocking stats showing how workaholism slashes your lifespan.

Perfect for anyone questioning hustle culture, corporate conditioning, or craving a healthier definition of success.

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Every few months, another article comes out declaring that “digital nomad life is over.” Usually written by someone who hated it, moved back home, and now insists everyone else should too.

In this episode, we’re calling B.S. and breaking down the 10 most common reasons people actually give up on nomad life—from loneliness to burnout to money stress. Some are valid. Some are myths. All of them are worth talking about.

🕒 Episode Highlights:

🏢 The Latest “Nomad Life is Dead” Article
Why the media keeps pushing people back to the office.

👯 Loneliness & Shallow Friendships
Why some nomads can’t find real connection, and how to avoid it.

📶 Internet & Work Challenges
The practical hurdles of trying to stay productive anywhere.

🧠 Mental Health & Burnout
Why nomad life won’t “fix” deeper issues, and what helps instead.

🌞 Heat & Humidity

Yeah, some places are hot, and some are humid...it's not a reason to give up on the digital nomad lifestyle

🤯 Distractions happen

You wouldn't believe the "reason" this person gave as a hardship of traveling as a digital nomad...

🎧 Tune in for laughs, honesty, and practical tips to avoid the pitfalls that send nomads packing.

If you want expert career coaching help getting hired for a fully-remote role, write "Get Hired" to [email protected]

Not all “remote jobs" mean the same thing. Some let you log in from anywhere in the world, others tie you to a city or region, and many have hidden expectations around hours, objectives, or even eligibility.

In this episode, we break down what remote really means, how to read between the lines in job postings, and which setups actually give you the freedom you’re looking for.

🔎 11 different kinds of remote jobs
What each model really implies for your day-to-day life.

📑 The fine print in job postings
Which details are negotiable—and which can lock you in.

🏢 Company examples we like
Real-world cases of remote done right.

🌍 Work from anywhere vs. Hire from anywhere
Why the difference matters more than you think.

🎧 Tune in to make sure your next “remote job” truly fits the lifestyle you want.

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We’re back with Part Two of the Digital Nomad Location Awards...and this time we’re giving shoutouts to the places that stood out for food, vibes, community, and more.

If you’ve ever wondered where nomads go for the best meals, the most inspiring environments, or the strongest sense of belonging, this episode has you covered.

Grab a drink (we did 🍻) and get ready to add a few new spots to your must-visit list.

🍜 Best Food Scene
Which country stole our hearts (and stomachs) with its eats.

🎨 Most Inspiring Vibes
The cities that make you feel creative the second you land.

🤝 Strongest Community Feel
Where nomads actually connect beyond surface-level.

💸 [00:35] Best Bang for Your Buck
Top picks for affordable living without cutting corners.

🌿 [00:44] Chillest Places to Recharge
The locations where slowing down just feels right.

🤣 [00:52] Funniest Stories Along the Way
Unexpected moments that could only happen as a nomad.

🎧 Tune in for laughs, surprises, and maybe your next destination.

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