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The Workationing Podcast

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Ep 40 – What Happens at FreedomFest in Vegas (Doesn’t Stay in Vegas)

Kari and Kelly are in Las Vegas for the FreedomFest conference, which apparently draws quite the male chauvinist crowd. The ladies detail their experiences at the conference – both Kari and Kelly were approached by different men at the conference, who asked the ladies to prostitute themselves. One man is the president of a libertarian think tank (he offered to fly Kelly to exotic locations in exchange for sex), the other is a fairly large donor (he asked Kari if she’d like to be his escort...

Duration: 02:27:07

Road Trip Through the Desert to Bury our Dear Friend Dom (Bucket list #8-9)

Kari and Kelly are back from hiatus and coming in hot from the Paris hotel and resort in Las Vegas. In this episode, the ladies talk about about two bucket list items they crossed off on the way there: road tripping from Los Angeles to Las Vegas, and burying their dear friend Dom in the desert. The ladies rent a fancy car, and inspired by the movie Fandango (starring THE Kevin Costner), they get a shovel and start digging a hole in the Mojave Desert to put Dom in. The plan is to come back...

Duration: 01:51:09

Ep 38 – We Lost 105 Pounds!

In a time and place when you can lose weight from anywhere, two ladies in their mid-to-late 27s have decided to – and so far, Kelly and Kari have lost over 100 pounds this year (combined). The ladies have received many emails about their weight loss journey, and in this episode they talk about how they managed to lose the weight equivalent of a chubby fifth grader. Kelly’s about to get a full feature in Women’s Health for her efforts! Traveling the world while working as digital nomads,...

Duration: 02:00:28

Ep 37 – Workationing’s 6-month Recap and Reflection

It’s been a year since Kari and Kelly decided to embark on the adventure that became Workationing, and six months since they’ve been on the road. It’s been quite a trip so far, and now that the ladies have been “out here” on the road for a while, they’re wondering why it took so long to make the jump. In the beginning, it seemed like all of the barriers to entry into this digital nomad travel lifestyle were insurmountable. However, as the ladies learned, once you take the first step and...

Duration: 02:15:24

Ep 36 – Where We Went Wrong: The Acapulco Edition

Kari and Kelly have successfully escaped from Acapulco, and are in San Diego, California breathing the sweet air of American freedom. They left a few days earlier than planned, but it wasn’t soon enough. Several mistakes were made in the planning process of this leg of the Workationing adventure – chiefly, the ladies never should’ve landed in Acapulco in the first place. Once again, decision fatigue set in and led the Gringas somewhere weird – and unfortunately, that wasn’t the only error...

Duration: 00:28:37

Ep 35 – Dear God, Get Us Out of Here!

The ladies HATE Acapulco, and can’t wait to get out. June was the deadliest month in Acapulco’s history, with 2,234 murders – it’s very murdery out here, and the Gringas are ready to leave. Aside from all the killing that goes on courtesy of the cartel activity in the area, there are other problems. Gabriela the Airbnb host has turned into a Code Red stalker, and has done everything from send a “real estate agent” in to take pics of the house (pre housekeeping service) to text message...

Duration: 00:56:58

Ep 34 – Cartel Country 2: Gringas in Acapulco

Santiago is back in town (check out the Medellín episodes to get the full story on this character), and he came just in time to see Kari and Kelly through some sort of crazy food poisoning flu situation. Kelly finally Googles Acapulco, which – turns out – is the most dangerous city in Mexico, and has been since 2012. The ladies talk about some of the cartel activity that occurs in the Pearl of the Pacific, including: assassinations via jet ski, multiple heads on pikes outside of...

Duration: 02:56:08

Ep 33 – Staying in John Wayne’s Sex Dojo (Bucket List #7: The Los Flamingos)

The ladies are having a hell of a time in Acapulco, and not in the good way. To escape from their Airbnb compound for a couple of days, they decided to hit up the local hotspot all of the cab drivers keep telling them about: The Los Flamingos Resort, which was once owned by John Wayne. The entire hotel is, pink, kitschy, and everything Kari’s ever dreamed of in a throwback resort. Formerly referred to as Hollywood Gang Hideaway (from 1950-1984), the resort – and in particular, Casa...

Duration: 01:51:12

Ep 32 – We Made it to Acapulco, Mexico!

The ladies have gone from Montreal to Boston to live tweet from the Pride parade (work is tough sometimes), and have now settled into their Airbnb in Acapulco. How’d they find this place? It starts with, the Flo Rida music video for Whistle and a $177 one-way flight – and ends with some killer views and regrets. Acapulco is hot AF, and the sweat situation is making it a real challenge to stay hydrated. Kari got sick almost immediately upon arrival, and a stranger broke into the...

Duration: 01:50:34

Ep 31 - Harsh Truths from Your Gringas

This one is mostly for the ladies, but guys, there’s lots for you to learn here, too. On this episode Kari and Kelly are talking about some of the harsh truths that they’ve come across while doing this whole intentional living thing. One of the harshest of these truths is that what you look like actually does matter — and not just in some abstract way. It actually affects every part of your life from how you are perceived by others (do they think you are likeable, trustworthy, and...

Duration: 03:09:24

Ep 30 – Bitcoin, Ethereum & Altcoins (oh, my!): Hodling on to Cryptocurrency and Regret

Kari and Kelly have known about Bitcoin since the early got in, the other is hodling on to some bithurt. In this episode, the ladies talk about their histories with cryptocurrencies and the insane amount of regret they – and other people they know – have about not buying in soon enough (or not hodling on long enough). Don’t know what hodl means? No prob, Kelly’s got you covered with a dramatic reading of the HODL forum post that went viral. There’s also an acapella rendition of...

Duration: 01:37:14

Ep 29 – Getting Unstuck: How to Escape a Shitty Situation

The most powerful force in the world is habit, and the ladies are creating some new ones for themselves. One of these habits is clocking 10,000 steps on their FitBits each day, which leaves a lot of time for talking. Specifically, talking about escaping. The Escape Room activity during Kelly’s birthday got the ladies thinking about ways in which they’ve been trapped, and ways they see their friends getting trapped in situations that prevent them from being happy, accomplishing goals and...

Duration: 01:17:32

Ep 28 – Escape Room and Poker Tournament (Bucket List #5-6), Plus Kelly’s BD

Operation: Make Kelly Cry was a smashing success, and Kelly had one of the best 27th birthdays she’s ever had. To celebrate another year of being 27, the ladies had a bucket list weekend: two items crossed off of their bucket lists in two days. The first bucket list item was escaping the zombie apocalypse at A/MAZE Montreal, a big warehouse that features several different escape room scenarios. After being infected with the zombie virus, Kelly and Kari must escape out of a locked room,...

Duration: 00:35:19

Ep 27 – We Made it to Montreal!

Kari has her car back for this leg of Workationing, and the ladies made it through Vermont, across the Canadian border and into their Airbnb in the Pointe St. Charles area of Montreal. Approximately a third of the way through the gentrification process, this neighborhood is about as diverse as they come. Plus, Jock is in town – the Gringas first met him in Medellin, and he randomly happens to be staying in Montreal for business. Fancy cars intermingle with crackie looking homeless people...

Duration: 00:45:50

Ep 26 – Gringas on a Diet: The Hangering

If there’s one thing Kelly and Kari love, it’s being on a diet – and in Montreal, Canada they’ve decided to get serious about it. Since Workationing started, Kelly is down 50 pounds and Kari’s knocked off 15 – but there’s still a little ways to go before they reach their goal weight. The Gringas are thoroughly enjoying dieting delicacies like raw cauliflower, vitamin gummies and all the eggs they can handle. Kelly can’t stop lunging everywhere, and Kari plans to ride her burpee...

Duration: 00:44:37

Ep 25: Kari’s Birthday & Favorite Place in the World

It’s Kari’s birthday, and the ladies are spending the time at the world famous Indian Head Resort in beautiful Lincoln, New Hampshire. Kari often says that it’s entirely possible that she’s going to travel the world looking for the perfect place to live, only to end up back in Lincoln. Kari is VERY excited to tell the listeners about Lincoln. Lincoln is like the land that time forgot and has a bit of everything: trained bears, dinners on trains, moose watching, skiing, rock climbing, an...

Duration: 00:29:39

Ep 24: Adventures in Coliving

Kari and Kelly are in Manchester, New Hampshire for the next week – and they’re sharing a large house with five other adults, like a grown-ass version of The Real World. What happens when seven people share a space on an ongoing basis? Is it amazing, or a recipe for disaster? The ladies talk about their experiences, how much coliving rentals cost in both the US and abroad, plus what’s included. Coliving has always been sort of a hippie thing, but millennials are taking it over – or at...

Duration: 00:41:20

Ep 23: Living Intentionally – What’s it Mean, and How Do You Do It?

Intentional living has been a primary focus for Kari and Kelly throughout the whole Workationing process – dating back to the very beginning, when they first decided to become digital nomads in the first place. In this episode, the ladies talk about the 5 Ws of living intentionally (which they stole from a journalism club in high school). Who is your life right now, and do they belong there? What are you doing, and are you happy about it? When is the right time, if not now (note: there...

Duration: 00:50:14

Ep 22: Floating in an Isolation Tank (Bucket List Item #3)

The Gringas have learned from their mistake in Medellín, and so they decided to front-load their bucket list item for this leg of Workationing: floating in an isolation tank. What’s it like to float in a black box filled with 93.5º water and 850 pounds of Epsom salt? They’ve always wanted to find out, and they tried it...for the full 90 minutes. Some people hallucinate while floating in isolation tanks, as if they’re on LSD or magic mushrooms. Other people take strokes off of their golf...

Duration: 00:38:33

Ep 21: The Matt Simon Interview

After Medellín, the ladies have questions about drug policy and its impact on Colombia – and they’ve found a man with answers. Matt Simon is the New England Political Director and Policy Analyst for the Marijuana Policy Project, and he came to visit the Gringas for a week in Medellín. In this interview, Kari and Kelly ask Matt about drug policy in the United States, and what the ramifications of the international War On Drugs are in places like Colombia. Is there a better way to approach...

Duration: 00:38:41

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