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Andrew Henderson wrote the #1 best-selling book that redefines life as a diversified,
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Kari DePhillips: Untether your life first #NomadWeek


Kari DePhillips for Nomad Week

This post is part of our second ever Nomad Week series, where we interview interesting Nomad Capitalists all across the globe, revealing their adventures, knowledge and travel tips. I had the pleasure to chat with Digital Nomad Freedom Summit guests of which Andrew was a speaker, as well as the pioneers of industry and their perspectives on living and doing business overseas. You can read the entire series here.  

Kari DePhillips is a California born digital nomad who is constantly on the move. I managed to take a couple of hours of her time in between her travels to talk about her beginnings and business. She is the founder of  The Content Factory– a digital PR agency that manages the social media, content, SEO and online PR for several national and international brands. As she travels the world with her best friend and colleague Kelly Chase, they are documenting their travels, adventures and technical hacks over at Workationing Podcast.

Where are you living now?

I have just arrived to Montreal, Canada 2 days ago.

What’s your favorite thing about the city (in detail)?

I just got here, so I’m still scoping things out. The city looks clean and vibrant, and the food here is amazing. I cannot eat enough poutine, and there are several different varieties. Montreal is also within driving distance of the US, which is convenient because I have a few client meetings in Boston and New York coming up.

What’s your LEAST favorite thing about the city?

The culture and people aren’t much different than in the US, which is a major selling point of travel for me.

Is there a little known fact about the city people might find interesting?

Montreal has a Bitcoin Embassy, and there seem to be many people in the city interested in digital currencies.

What is your favorite place you ever lived and why?

Lincoln, New Hampshire. It’s a tiny year-round resort town in the White Mountains of New Hampshire, about 2 hours north of Manchester (3 hours north of Boston). It’s the cutest town I’ve ever been in in the US, and reminds me a little bit of Tahoe but on a much smaller scale – and without the gambling. There are a ton of things to do, from hiking and tubing down the river to skiing and snow shoeing. The stores are mostly family owned, and there are very few chain stores.

What is your LEAST favorite place you ever lived and why?

Happy Valley, California. It’s extremely hot and dry up there, so everything is brown a solid 7-8 months of the year. There are a lot of outdoorsy things to do when it’s not 100 degrees and climbing.

What was the EASIEST country you ever visited (ie: easiest immigration, easiest to open a local bank account, etc)?

Canada. The border crossing (via car) both ways is faster than Mexico – last year I spent 4.5 hours, in the very hot sun, in a traffic jam waiting to get through the immigration checkpoint. We didn’t run out of gas during this traffic jam, but other cars did.

Have you ever had any problems in a country? (ie: immigration issues, getting robbed, etc.)

I was robbed at gunpoint (twice) when I lived in Pittsburgh within a span of two years. The biggest problem I’ve encountered outside of the country was in Medellin, Colombia – I paid in cash at a restaurant and the waiter seemed fairly convinced that it was counterfeit money, but eventually the restaurant manager accepted the cash and let us go. I also saw a lot of underage prostitutes in Medellin, which was unsettling.

Do you prefer one region of the world over another, and why? 

I like to stay within +6 hours of EST, so meetings with clients and employees are during my normal-ish working hours as well. I love the beaches of the Caribbean, and have spent quite a bit of time in Puerto Rico, the Virgin Islands and Playa del Carmen.

Is there anything that would make you settle down and stop traveling as much?

Not right now.

Who has been the most influential person on your travels (someone that encouraged you to start, or someone who has influenced you along the way)?

Tim Ferriss.

If were coaching a new nomad, what you recommend they do to get started?

I would recommend that they find a job that allows them to untether their life – and then keep it for a year before they start to travel, to make sure it’s actually a tenable arrangement for them. Start out with shorter and/or more local trips, and see how you work from the road. Does your productivity suffer? Do you actually like working remotely?

Many people think they want a remote job, but after they have it for a while they decide that ultimately they’d rather be in a more social office environment. Before you light your life on fire and go travel to some foreign land for an extended period of time, you should know for sure that you can (and will) work while traveling in a way that enables you to keep your job.

I also wrote a guide to untethering your life, which your readers might find helpful. In this guide, I walk the reader through the step-by-step process I used to source more freelance work than I could handle (mostly via Craigslist). It worked very well for me as a freelance writer, but the same process can be followed for website developers, graphic designers, social media managers and just about any other job in digital marketing

What country would you recommend a new nomad go to FIRST?


What is one country that you have not been to but is high on your list, and why?

The Maldives, because they’re sinking and won’t be around forever. I’d like to see them while the seeing is still good 🙂

What was the most unexpected surprise you ever encountered as a nomad?

I stayed in the penthouse suite of a very nice building in Medellin recently – I thought it was the safest and best choice. Turns out, the building was mostly filled with sex tourists enjoying long-term stays (incidentally, they were mostly American). Most of the time we went up to the rooftop pool, we saw much older men with what appeared to be teenaged girls – it was gross and wore on us over time.

What was the biggest mistake you made that other nomads can learn from?

Ladies: check the byline of the travel articles you read. If it was written by a male, take that into consideration – in many countries, men have a much different experience than women (this was certainly the case in Colombia).

How do you meet new people while living the nomad lifestyle? Do you ever get lonely?

I travel with my bestie/colleague, so life is less lonely for us than it is for single travelers (or it seems to be, based on the single travelers we’ve met so far). is great, as are digital nomad Facebook groups – the digital nomad FB group in Medellin had over 1k members in it, and there was tons of good advice re: things to do, places to go, where to eat, etc.

If you are interested in reading more about Kari and her business, find her at The Content Factory and Workationing Podcast.


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