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Lisbon, Portugal

Lisbon, Portugal

If you want to start living a different life, you have to do something differently.

I couldn’t believe it. After spending 22 years of my life in school, doing everything right and graduating at the top of my class with with healthy side of student loan debt, I was about to start my long-awaited career working in… (wait for it) -

..a basement cubicle of an Orlando office park.

I wanted to cry. 😭 Was this real life or the set of Office Space? Was this what I worked so hard for? To start my business career in a basement with a red stapler?! No. I couldn’t accept it.

So, I turned down the job, threw my resume in the trash, and got a one-way ticket to Costa Rica. Waaaaaaaay before The Four-Hour Work Week came out.

With only $200 in my pocket, I took a chance and never looked back.

Nearly 14 years later, I’m still living my dream life - working on my laptop from wherever I want in the world (60 countries and counting!). 🗺

We all want to experience freedom. We all want to explore.

No-one wants to feel tied down.

No-one wants to feel constricted to a desk and to see their days wasted away within 4 boring walls - (especially if those walls are in a basement!)

If you’re reading this, it probably means you’re ready for change. Ready to claim back your life and your time by experiencing the beauty of working from home with complete freedom and flexibility.

Believe you me - there’s more to life than just sitting in an office grinding away for endless hours. I have been there. I saw the writing on the wall. And I said, hell no.

But today, I have the ability to travel the world and to work from wherever I want, whenever I want. I am not tied down – I am free.

And I am here to help you achieve the very same thing!

You know you’d like to travel more, have more flexibility, or work less.

But how?

In 2019 and beyond, there’s no reason why you can’t live where you want, work where you want and how much you want, PLUS - have more free time for the things that matter most.

It’s time to stop thinking and start acting. There are plenty of ways to make a living online without having to commute to a job just for a paycheck. ❌🚘❌

The biggest problem is - where do you even start? It would take a lifetime to find everything you need to know on Google.

That’s exactly why I created the Digital Nomad Challenge –

a shortcut to attaining the laptop lifestyle.

For the first time ever, I’ve put together the 30 most important things I’ve learned in over a decade as a digital nomad. The same advice and guidance I share with my private relocation and consulting clients at upwards of $250 per hour.

Working on my laptop from Nicaragua in 2007

Working on my laptop from Nicaragua in 2007

There’s no need to spend years thinking and planning your future when there’s a simple short cut to leaving the 9-5 behind once and for all.  

On any given day, I could be in London, Paris, Rome, Bali, or Tokyo with a few digital nomad friends, living our best lives. Not just on Instagram, but in REAL LIFE.

And the nay-sayers?

Yep, they’re still commuting to jobs they hate 40+ hours per week. They might be higher on the corporate ladder than they were before, but they’re stuck in the rat race.

They did everything right – college, grad school, and a 9-to-5 job. So did I, until I decided to STOP following the status quo and START living life on my own terms.

Mark Twain said it best when he said: “The secret to getting ahead is getting started.” The Digital Nomad Challenge is here to help you do just that.

There’s never been a better time to be alive!

You don’t have to ask permission to live your best life -

you just have to start 🚀🚀🚀

👩‍💻 How will the Digital Nomad Challenge help you work & travel? 👨‍💻 

Athens, Greece, 2018

Athens, Greece, 2018

The 30-Day Digital Nomad Challenge is set of thirty actionable challenges - presented at a pace of one per day - designed to help you jump start your journey to location independence.  

Each day you’ll receive an e-mail and a video with instructions to help you:

✓ Start Your Digital Nomad Journey

✓ Figure Out What You Can Do to Make Money Online

✓ Find (Legitimate) Remote Jobs

✓ Present Yourself Online and Get Hired

✓ Learn to How to Become a Freelancer or Set Up an Online Business

✓ Get the Tools, Apps, and Insurance You Need for Your Remote Office

✓ Create a Budget for Work and Travel

✓ Find Housing in the Best Destinations for Digital Nomads

✓ Know What to Pack for Your First Trip Abroad

✓ Meet a Community of Like-Minded People

✓ And much, much more....  

Each day will help you get immediate answers to the questions that you’ve been searching for online, remove blocks that have been keeping you stuck in your day job, and start creating a plan to achieve ultimate freedom in your life.  

At the end of 30 days, you will have made more progress toward taking control of your future than ever before.  

The Remote Work Revolution is here. Stop waiting for permission - thousands of people have already made the leap from 9-to-5 to location independence and you can do it to. Don’t waste another year commuting to a job hate or living a life that doesn’t inspire you.  

You’ve seen digital nomads working from our laptops from Bali to Chiang Mai. But it doesn’t just happen on Instagram - it’s real and it’s within reach for anyone with an internet connection. Give yourself the next 30 days to bring you closer to living your best life. What do you have to lose? 

Figure out if you have what it takes to work from home:

  • Find out all the ways you can make a living while working remotely, INCLUDING where to find legitimate, high-paying remote jobs. 

  • Learn how to reclaim more than 2,000 hours of your time per year that’s otherwise wasted in meetings, commuting, and office distractions. 

  • Pinpoint and eliminate any blocks that have been holding you back. 

  • Learn the best ways to find LEGITIMATE remote jobs. 

  • Take steps to figure out how to create your own job. 

  • Learn how to structure your day to stay productive and motivated. 

  • Learn how to work while traveling. 

  • Get tips on how to stand out online.  

  • How to create a freelancing profile. 

  • Figure out which type of digital nomad job is for you. 

  • Stop procrastinating and take control of your life.  

  • Plus:

    • Make friends

    • Get inspired

    • Meet potential business partners

    • Get support from our community

    • Join live video Q&A’s  

    Take the first 30 steps to becoming a digital nomad (It’s not as hard as you think – you just need to know where to start!)  

Are you ready to take the Digital Nomad Challenge?

“A journey of a thousand miles must begin with a single step.
— Chinese Proverb


✓ 30 Custom Challenges Delivered Daily

  • Week 1: Mindset & Opportunities

  • Week 2: Remote Jobs

  • Week 3: Freelancing & Online Businesses

  • Week 4: Travel & Community  

✓ 30 Custom Video Messages From Veteran Digital Nomad Writer, Speaker, and Coach Kristin Wilson  

✓ Printable 1-Month Calendar With custom daily illustrations to track progress  

✓ Group Slack Channel For Accountability and Community  

✓ End of Challenge Wrap-Up Live Webinar With Kristin from Traveling with Kristin



Kristin Wilson of Traveling with Kristin

Kristin has lived and worked in 60 countries during the past 15 years. Since starting her first online business in 2011, she has helped over 1,000 remote workers relocate worldwide.

Today, she helps people go from 9-5 to location independent through talks, workshops, her Facebook Community for aspiring digital nomads, and free online content. Access over 200 videos on her YouTube channels: Traveling with Kristin and Digital Nomad TV. Or, tune in live to her weekly podcast for entrepreneurs, freelancers, and remote workers: Badass Digital Nomads.

Your video this morning made my day and gave me so much happiness that I had to share it with my friends. I can’t think of a better person to teach people to become digital nomads than you!
— Patrick Farrell

Kristin is a Top Writer on Medium and Quora in Travel, Remote Work, and Location Independence. Her work has been featured in Bloomberg Business, NY Times, ESPN, HGTV, Huffpost, Business Insider, and more. You can pre-order her first book, Digital Nomad 101 - The Ultimate Guide to Location Independence here.


No one understands the way we work [remotely] but when we see someone like you on the internet... we really relate and it’s so inspiring. Thank you.
— Kazi Noor  

“I just wanted to say that I'm one of your subscribers on YouTube, and I really enjoy your content. You are helping so many of us that are already nomads, or trying to become one. I really appreciate the knowledge and wisdom you give to us all. I look forward to seeing more of your videos in the future.” - Harden  

You are doing something very helpful for so many people. The knowledge and information you share with people has value and entertains at the same time. Thank you.
— Jihvko Starev  

“Thank you Kristin, keep up the good work, you are doing awesome things that will help many succeed and live a better life.” - Teklordz

I think, this is the best advice I’ve gotten in the last 17 days.
— Jhasketan Garud

“Very educative content from a super talented vlogger. You deserve to be known by more people. Thanks for uploading Kristin .” - Mended  

Your stream is more educational than a stream. Tens of thousands of people should be watching this. You’re probably the most intelligent girl streamer on twitch. I’m learning so much.

Hey Kristin, I know that there are a lot of travel vloggers, but I just wanted to tell you that you have a talent and you’re going about it the right way. You should definitely keep going and keep creating. You’re on the right path for sure. I’m rooting for you!” - Stephen Ulilis  

So much wisdom and realness. Thank you for being a great role model.
— Ben Keene
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