How to quit your job and become a digital nomad in 90 days

How to Quit Your Job and Become a Digital Nomad in 90 Days: Getting Started

By Rob | July 6th, 2016 | 70 Comments
THIS POST MAY CONTAIN AFFILIATE LINKS.

Right now I’m working from a hammock in Costa Rica, about 50 feet from the beach.

What a cliche!

But it’s true…

For the last 6 months I’ve been able to make a full-time living as business blogger on my $300 Dell laptop — with an hourly rate more than double what I was making as a healthcare analyst.

Upwork Profile with Hourly Rate
My Upwork Profile. One of the primary places I find new clients.

I’ve been able to match my corporate paycheck working about 4-6 hours a day. This has allowed my wife and I to pack up our possessions, move out of our apartment in the US, and spend the summer at Airbnbs in Costa Rica – for about half the cost of living back home.

It’s been an epic adventure – and I love knowing that I never need to worry about having a job again. Even if  I decide to work for a company in the future, I’ll never have to take a job simply because I need a paycheck. I’ll be able to work because I value the organization and love what I do, not because I’m dependent on the salary.

Although I still have to work incredibly hard, I love the freedom that comes with controlling my own schedule. I’ve traded my boss for clients, and my suit for board shorts – both of which are far easier and less stressful to replace.

So that’s me in a nutshell…and now, let’s talk about making YOU a digital nomad!

How to Quit Your Job and Become a Digital Nomad 35 Expert TipsAfter the awesome response I got with the article How to Quit Your Job and Become a Digital Nomad: 35 Experts Share, I discovered that a lot of people are eager to learn more about going out on their own. And, when I shared this article on the Reddit Digital Nomad sub, one area where people constantly wanted more information was regarding the “How?”.

Although the 35 experts article had shared ways that people worked as digital nomads, it didn’t provide a concrete, step-by-step guide to becoming a digital nomad.

So that’s what this blog post (or series of 14 blog posts) will be all about. Over the next 3 months I will provide you with a weekly step-by-step transition plan to go from employee (or unemployed) to self-employed digital nomad in 90 days. We’ll discuss setting up a freelance consulting business, making the most of travel deals and credit card rewards, and preparing for a 100% remote career.

For FREE!

Ready to learn more?

What is a digital nomad and do you qualify?

What is a digital nomad
This infographic is the exceptional artwork of NeoMam Studios

A digital nomad is simply someone whose job allows them to work remotely, on their own schedule — from anywhere in the world. 

Although the stereotypical digital nomad is someone sitting on the beach in Jamaica or working from a Bangkok coffee shop, that’s not a requirement. In fact, you can essentially be a digital nomad if you’re a work-from-home mom, a retiree making additional income online, or a college student selling gigs on Fiverr or posting YouTube videos between classes.  All that’s required is you have the ability to work on your own terms.

While a portion of the content I share will be focused on planning your life and work as a traveling digital nomad, the majority of my tips will benefit anyone looking to become self-employed.

Thus, these articles will help you transition from your current job to a fully remote and independent lifestyle – regardless of whether that means working from Cambodia, or your Minnesota living room.

Who will benefit from this course?

The three paths to becoming a digital nomadThere are three ways to become a digital nomad.

  1. Get a remote job as a traditional employee.
  2. Become a self-employed freelancer or consultant.
  3. Create your own startup, blog, or other business.

This course will help you with option #2: establishing yourself as a self-employed freelancer/consultant. While the other two groups will find some value in this content, it’s largely for those looking to provide a service independent of any business organization.

If you want a remote job, then you don’t need to spend 90 days preparing for the transition. Although you may appreciate the travel advice, you won’t need to hone your skill set, find clients, and manage the many business responsibilities that the other two groups have – because you’ll be an employee. To become a digital nomad by finding a remote job, simply visit WeWorkRemotely and Angel.co for great remote opportunities with established companies.

Meanwhile, if you’re trying to launch a “real” startup (or a blog, photography business, etc.), you should not become a digital nomad. Why? Because there’s a lot of risk and effort involved in developing and marketing an app, product, or software. Although you can become a digital nomad after launching a successful business, you really need to focus your initial energy on the business – not on traveling.

Which leaves us with freelancers and consultants! This is the perfect middle-ground. You have full flexibility of your schedule (unlike an employee) and you have a guaranteed source of income (unlike a startup). This perfect combination allows you to make a living doing something you enjoy, right now, from anywhere in the world.

So, if you’re ready to make a stable living on your own schedule – and see the world in the process – then you’ve come to the right place!

What can you expect from this 13 week FREE digital nomad course?

My goal is to help you replace your current paycheck using nothing more than your computer and an internet connection.

If you have a college education, you should be able to earn $25-100/hr by the time you’re done with this course. If you don’t have a degree, or want to develop a new skill set, it may take a bit longer. But earning this much is still possible!

The digital nomad course outline

How to become a digital nomad in 90 days course syllabus

For the next 13 weeks I will take you through the entire process of deciding on a freelance skill set, establishing a client base, managing the business elements of being self-employed, preparing for a nomadic/traveling lifestyle, and making sure that you are financially secure for the future.

Each week will consist of a day-by-day list of things to accomplish on your journey to digital nomad. Although the tasks will vary, each week will have a central focus, as follows (These items will become hyperlinks once that week’s post has been published):

By the end of this 13 week series, provided you put in the time and energy, you will be a digital nomad!

To ensure that you stay on top of this course, consider subscribing to the Money Nomad newsletter. I’ll send each article on Wednesday – giving you a few days to prepare for the next week’s activities.

What’s the time commitment to succeed in this course?

Thomas Edison Hard Work Quote

This course assumes that you can commit two hours a day, six days a week, to establishing yourself as a digital nomad. Totaling 12 hours a week.

When you’re working full-time this can seem like a lot. But the reality of it is, if you can’t juggle setting up your own business while working full-time, you probably won’t be able to manage your business while traveling.

Everyone wants to make a full-time living working 4 or less hours a day, but few people are serious about putting in the work. You’ll never succeed as a daydreamer – you have to take action.

I’m going to show you exactly how to succeed for free – but it’s going to require a substantial time investment from you. Reading these articles isn’t enough. You have to implement.

Consider this a test run to determine if you have what it takes to be a self-employed digital nomad. If you are able to maintain discipline and focus during the next 90 days, you can quit your job confident that you will be able to succeed as a digital nomad.

Why I decided against charging for this course

When I began preparing for my transition from employee to digital nomad I did a lot of reading. I wanted to know how to make money, where to make money, and exactly what I needed to do to succeed.

But here’s the bad news – the majority of the courses and programs I found cost anywhere from $200-$2,000! Some even required an ongoing membership fee of $25-50/month.

While I value education (and may sell my own course in the future), I was skeptical of most of these programs. After all, if you already know how to make money online, why do you need to sell that information?

To me, many of these individuals seemed to be mediocre at what they were doing, and simply trying to find an alternative way to make money by selling their how-to strategy. Of course, this isn’t the case with everyone – and for the right people, paying for a course, consultant, or some other structure can be smart.

But for me, I wanted a practical and free process to follow.

I never found it.

Which is why I decided to launch this blog series….

Now that I’ve had a bit of success as a consultant/freelancer myself, a lot of people ask me how to do it.

It was tempting to put this advice in a course and sell it for $500 like everyone else does. But I couldn’t bring myself to do it!

I know what it’s like to be in a position where you feel trapped by your job or circumstances. To feel like you’re missing out on your full-potential. To anxiously realize that you aren’t enjoying the life you’re living – afraid you’ll never achieve what 8 year old (or 18 year old) you dreamed of.

For me, one of the greatest discoveries was learning that I could become self-employed and fully replace my corporate income. I can make a living (and a good one) on my own terms, from anywhere in the world.

This is something that I want others to be able to experience and enjoy – which is why I decided against charging for this content.

So, I hope you enjoy this free course on how to make a living remotely. If I can help you establish your dream job (or simply an enjoyable transition job) as a freelancer or consultant, than I will consider this 13 week series a 100% success.

Recommendations

Side note: Instead of charging for this course, I periodically include affiliate links for products I use and value in my blog posts and on my Recommendations page. These brands provide me a commission when you subscribe through my links. Because I only recommend services/products that I support and usually use myself (such as AirBnB and Ebates), you can be assured that I will only mention products that I believe can benefit you in your digital nomad endeavors.

How to prepare for this course

My goal is to make becoming a self-employed digital nomad accessible to anyone who is willing to put in the time!

If you can commit to 12+ hours of work a week for the next 13 weeks, I will show you how to develop yourself into a freelance/consultant on virtually any area that interests you – whether that’s writing, graphic design, social media management, photo editing, etc.

To get started:

  • Subscribe to MoneyNomad.com so you can receive each week’s projects and tips.
  • Schedule two hours a day (or 12 a week) into your calendar to commit to becoming a digital nomad.
  • Begin exploring what freelance skill set you would like to develop by examining the jobs and opportunities available on sites like Fiverr and Upwork. This will help you discover what people are willing to pay for.
  • Ask me questions! Leave comments or contact me directly anytime you might need further clarification or advice. I’ll either answer directly or share an article that can help you resolve your questions.

That’s it for now! Next Wednesday I’ll send you week one’s activities that will help you determine your “why” and “how” of becoming a digital nomad. We’ll explore your motivation, financial needs, and skill sets. By the end of next week you should have a solid understanding of how you’ll grow your freelance business.

The price of success is hard work, dedication to the job at hand, and the determination that whether we win or lose, we have applied the best of ourselves to the task at hand. – Vince Lombardi

For the comments: What questions do you have about becoming a digital nomad or remote freelancer? Is there anything that you feel like is really holding you up? Share your thoughts on the DN lifestyle below and the rest of us can offer our insights, or be inspired by your success!

About Author Rob

Rob blogs at Money Nomad - where he shares strategies and tips for becoming a remote entrepreneur. When not working on his own projects, Rob writes articles for businesses and thought leaders. You can find him on Twitter @rlerich.

70 thoughts on “How to Quit Your Job and Become a Digital Nomad in 90 Days: Getting Started

  1. Looks like you have been busy and congrats on your success so far. If I remember correctly, Pat Flynn takes a similar approach with several of his eBooks. If people like what you have, you will still get rewarded and compensated.

    As you mentioned, sites like Upwork are a great way to get started. Their commission fees are a little high in my opinion, but, it’s very hard to find freelance work as a newbie without an online presence.
    Josh recently posted…Financing Family Vacation (Part 2)My Profile

    1. Thanks for stopping by Josh! And that’s my hope. Providing value is always compensated in some form or another, so I’ll just focus on maximizing the value contribute I’m able to provide.

      And yes, especially with Upwork’s increase in fees, it’s not the best way to grow a thriving freelance business. However, it’s still one of the easiest places to find great projects.

      As you mention, one you establish an online presence for yourself, it becomes much easier to find clients (and high paying ones) independently. The goal of this course is to help people get that first sale, and build up that portfolio — which is critical for the better paying jobs.

      Thanks for stopping by and hopefully I can deliver on all of my extraordinary promises above… 🙂 time will tell.

    1. Awesome Wendy! I hope you’re able to make the transition over the next several months. Good luck and stay committed!

  2. What a great article ! This what I was looking for long time ago. Digital nomad lifestyle is my sream and I will do anything I could to make it happens. Cant wait for your next chapter, Rob !

  3. Hi,

    How suitable is this course for somebody with zero skills. A non-professional. What sort of employment is available on upwork for example for that sort of person.

    1. Hi Derek! Great question. Although it’s far easier to make money freelancing by using a skill set you already have, I’ll definitely discuss ways to develop new ones as well – so it may take you a bit longer to make “serious” money, but you can start making a few bucks right away. I’ll share more about this next week – so stay posted!

  4. Hi Rob, great idea!
    I have only one issue. I don’t know what type of work should I do. I really want to be self-employed but my skill from previous job are not much applicable.
    I worked as SW tester (but I don’t know how to program).

    I quitted my job and moved to abroad. For now I’m traveling and searching for any backpacker job. I thought I will find out while traveling but that didn’t happen.
    How should I figure out what to do?

    1. Hi Mira! Next week we’ll definitely work on brainstorming new ideas. And hopefully you’ll find something that you can monetize while abroad. I’m sure you can — it may just require developing a new skill (and it doesn’t have to be a complex or confusing one).

  5. Thank you so much – really kind and open of you to share your wisdom.

    I’m currently working on figuring out remote work options as well: I have a PMP and opened up a start-up communications company that utilizes acting and improv based techniques to improve Public Speaking/Presentations and Teambuilding. But, I’m having a hard time figuring out how to make any of these skills remote/from computer workable. Everyone tells me I should have a technical skills (from programming to web design). Has any one been able to use soft-skill or service based companies and gone remote – perhaps automating through videos or over skype or something?

    Thank you!

    HD

    1. Thanks for stopping by Hamed. It might be a bit more difficult, but it’s definitely possible through consulting and/or creating a video series. I would start by documenting your entire process, objectives, and outcomes — then find a way to share that with others remotely!

      People pay for results, if you can help them achieve those results without being there in person, they will certainly pay you. Again, it’s not as easy and quick to create a “business” as opposed to offer a service, but it’s still possible.

    1. Thanks Kelsey! It’s definitely great to have a bit of flexibility — and I’m excited to see you progressing this direction as well. 🙂 I’m excited to share your story with my readers early next week!

      Keep it up.

  6. Hey Rob! As always love your content! Glad to hear that you are living the dream! I know that you have worked long and hard to have the lifestyle that you currently have. I cannot wait to take your course. I do have a question–I normally find writing gigs from job boards but heard that cold pitching is more effective. What has been the turning point for you gaining higher paying gigs? Do you recommend cold pitching?

    1. Thanks for stopping by Amanda! I’m still impressed with how fantastically your blog is growing.

      And great question. I’ve actually only cold pitched a handful of clients. It can work if you come across a business blog that doesn’t seem to receive regular content (or seems to have just had a writer leave). But actually, what has worked better for me is to partner up with designers or agencies. I simply offer to do content for their clients (or through the agency itself) and either give them a small cut or a one-time fee. As they already have the clients, it prevents you from needing to sell!

      Meanwhile, my own websites have received traffic and requests as well. But if you want to get clients from your website, don’t just create a blog, create a business site — which talks about concepts useful for your clients. Too many freelance writers blog about freelance writing — which attracts more freelance writers but doesn’t draw in clients. Instead, write about what your clients might be interested in and you can land quite a few more gigs.

      Additionally, I’ve discovered that it’s tremendously valuable to focus on a skill that provides recurring work. Because a lot of my work consists of blog posts, I don’t need to find additional clients that frequently. Right now I have around 10 that I write for on a regular basis (with a few larger book projects here and there) and keep myself completely occupied! Almost too busy sometimes. Because my turnover is low, I can keep my eyes open and only accept the best paying projects.

      So, as I will make the exclusive focus of one of these weeks – customer service is essential. Keeping clients is far easier than getting new ones — and referrals can make life far easier. In fact, I’ve only had to “apply” to maybe 2-3 projects over the last couple of months. The rest of been ongoing or come to me.

      And with your fast-growing reputation Amanda, I don’t think you will have much of a problem finding some great clients. But we can keep discussing that! And I’ll share some of these strategies over the coming weeks as well. Great comment and thanks for sharing!

  7. Hey Rob!

    Really looking forward to your course. Sounds really interesting!
    Glad you are willing to do it for free! Very kind of you!
    Would be great to get some advice and tips on how to start a life as a digital nomad. Been looking into doing a social media virtual assistant job and thinking about blogging as well. Just need to find most suitable area for myself and some help how to get there.

    Cheers 🙂

    1. Hi Pauline! Well we’ll definitely try to make that happen. Hopefully you’ll find a tremendous amount of value in the following weeks. Feel free to constantly ask questions as we continue to explore this process together.

      Enjoy your day,

      Rob

  8. It’s great that you put this together.

    Both Ms. Financial Slacker and I have been living the digital nomad life for a decade. Actually she has been working that way for almost 14 years and me for 9 years.

    Although we are digital nomads, we mostly work from home or from a family vacation house at the beach. Over the years, sometimes we travel for work, sometimes we are working remote jobs, sometimes we freelance.

    The benefits are extraordinary. We spend time with the kids. We don’t have to deal with traffic or daily commutes.

    There tends to be a little less predictability than having a regular paycheck, but the flexibilty is worth it. You just need to plan.

    Thanks again for launching this course. I hope folks take advantage.
    Financial Slacker recently posted…June Employment Increases, But Why?My Profile

    1. It sounds like you have really been enjoying the flexibility! Thanks for stopping by and sharing. And you are absolutely right — it does create a bit less stability. But, if done right, it can be about as secure as most people’s jobs.

      Maybe I’ll need to feature you on one of these future posts!

  9. What a great idea Rob! It is amazing how these new opportunities have opened up and you are able to share how you have benefited from the digital age. Travelling around the world to beautiful places while earning a great income seems like a dream to many but hopefully following your journey and course will allow many like myself the courage to join!
    Stefan – The Millennial Budget recently posted…June 2016 Income ReportMy Profile

    1. Thanks for the support Stefan! And I have no doubt that you could succeed with the remote lifestyle if that’s something you decided was right for you. Thanks for commenting!

  10. Looking forward to this! I just recently crystallized in my head the desire to do this. I hate the lack of freedom that traditional jobs provide and worse, the more successful you are at your traditional job, the less freedom you have. At least that how it looks to me.
    THanks for doing this!

    1. You’re absolutely right! That’s the irony of it, the higher up you go, the more work you have to put in. Meanwhile, if you find a way to start your own business (or even just freelance/consult) the more successful you get, the more flexibility you can choose to have (although may people keep working long hours because they enjoy what they do).

    1. Thanks for sharing Rudy! I really appreciate it. And I’ll definitely share that roundup post across my social media accounts. Hopefully this 14 week blog series can help a few people make that leap!

  11. Thank you for the info! Question, what do you do about health insurance? Concerned about cost of prescriptions/Drs visits without the health insurance I receive through my current full time job.
    Thanks again!

    1. Great question Amanda. And it’s true, insurance quickly becomes a big cost once you’re self employed. The best prices I’ve currently found for insurance are through the Freelancers Union — where minimum coverage for someone relatively healthy starts at about $200/month. To get the coverage that many employees offer, it will probably cost closer to $400-500/month. So this is definitely something that needs to be pondered and a subject I will discuss later.

      However, if you’re outside of the US for more than 6 months, you aren’t required to have US insurance. And, in many countries healthcare costs are far lower than at home in the US — meaning that you can buy insurance (or even pay for full procedures) for a very reasonable rate. We’ll definitely discuss this further in the future!

  12. What a great piece of inspiration I’ve found here in this post, Rob. Please accept my gratitude! I am really feeling like going into it, the DM lifestyle I mean. Though it seems to me that you are running slightly out of schedule and the new posts didn’t appear yet, but anyhow, I am up to scan all the info you have shared so far.

    And now I will proceed to my question > Have you got any suggestions on the matter of the tax payments? What are the primal concerns for a self-employed individual? Traveling to various countries might change your status as a self-employed and by this means, the terms of tax payment should vary too.

    I am a EU native, which implies certain distinctions in legal matters, but I suppose that it should be quite similar to the US.

    Thanks

    1. Hi German,

      Thanks for stopping by! I’m scheduling the posts to go live every Wednesday — so week two should be up tomorrow!

      Regarding taxes, that’s a great question. And, unfortunately, it’s one that you probably need to get lined up with a lawyer or tax professional in your own country.

      Because you are doing business online, I know that it’s often acceptable to travel on tourist visas and take care of taxes based on your home country – in the same way you would if you worked as a local freelancer/consultant. So, that’s not the most detailed answer, but hopefully it gives you some food for thought!

    1. Thanks for the heads up Eric — I’ll link this one right away. And I’m glad you’ve fund and are hopefully enjoying this massive series. Hopefully this series (along with great guest posts from other bloggers) will make Money Nomad a go-to source for people wanting to transition into the digital nomad lifestyle. Thanks for reading and for all of your great content.

  13. Hi Rob,

    It’s great to be able to see your website. I really like this article. I can relate to most of the experience and ideas you have mentioned. Thank you for coming up with this blog.

    I currently quit my job and have 90 days to prepare for this digital nomad journey. It’s nice to know that people like you are helping and sharing the experience. I’m more inspired than ever.

    More power to you and this site.

  14. Rob,
    Love, love, love your articles! Well rounded & articulate, I must say. They’re addressing many of my career questions and concerns. Thank you for using your God-given talents to provide quality content at a reasonable rate which everyone can afford 😉 Your efforts are already being rewarded. Best regards to you & Mrs. Nomad!
    ~An Andrews fellow

    1. Hi Ashley! I’m so glad you’re enjoying the articles and I definitely hope that they add a bit more inspiration to your own journey as well. 🙂 Have an amazing day… AU!

  15. Hi Rob,

    Thanks for a great article. I have joined Freelancer and Upwork looking for mostly academic writing jobs but after about four months nothings has come through yet. After reading this article I realise that I need to start afresh and go through your course.
    Thank you this article has revived my desire to be a freelancer with the long terms view of quiting my day job.

    Regards,
    Thembela.

    1. It’s certainly not easy — especially at first. But keep with it! The jobs grow exponentially. Each project leads to another. Good luck!

    1. Hi Paloma,

      I returned to the US a few months back, but Costa Rica is INCREDIBLY safe. Of course, you want to be smart when in the cities (just like any city), and it definitely helps to speak some Spanish, but my wife and I felt very comfortable the entire time we were there.

      Not only are the people friendly, but the Police force is very positive and ethical, and you really have little to worry about.

      That being said, if you are loud, carry an expensive camera in the open, and jump in cars with strangers, you might get yourself into trouble. But we didn’t have any problems. And you shouldn’t either, especially if you stay out of the big cities and enjoy the beautiful countryside.

      Any time you travel I recommend that you email a copy of your passport, license, and maybe credit cards to yourself. Also, have a backup credit card/cash hidden in a separate place. But if you feel comfortable in New York, Paris, or London, you’ll be fine in Costa Rica (it’s WAY safer).

  16. Hey, we recently published a post on how to get ready before setting off to become a digital nomad. It hits on a few points mentioned here, but a few others too – hope it’s of help to anyone else looking into the lifestyle!

  17. Hello Rob!
    First of all, I want to say that I read your ebook, “The 7 Step Guide to Making Money as a Freelancer this Weekend” and I learned so much. I’m very interested in becoming a freelancer. I’m excited that I came across this article too, and I definitely want to do the steps in this course! Thank you for the inspiration. However, I noticed that there are no hyperlinks from Week 6 to Week 13. Is that because this course is still on-going? Regards, Erin C.

    1. Hi Erin! Glad the book was helpful. And yes! I need to complete this series. Perhaps I’ll strive to complete one more article a month until I have it wrapped up. Thanks for the reminder and feel free to reach out if I can help answer any questions in particular.

      1. Hello again and thank you for your response! That’s good to know; I look forward to reading the articles, as well as reading more of your other articles on your blog. I do actually have a question on that note–if a client wants you to do a job for them (as a freelancer), but they’re out of state, if you were to accept the job: would you pay for the expenses to go out there, or would they do this? Does it depend on the client? This is unrelated, but also I want to let you know that you inspired me to start a blog; which I did a couple days ago. I’m still at the beginning stages, so I just have 1 post for now, but if you’re interested in checking it out sometime, the url is: insideabusinessgirlsworld.wordpress.com. Best, Erin

        1. Great job getting your on blog started! You’re off to a great beginning. And good question regarding travel. If the work can be done remotely, then travel isn’t an issue. However, if they do want you to travel, you will need to discuss that when agreeing to take on the project and incorporate that into your contract/rate. You definitely want to make sure that your travel time and expenses are compensated!

          1. Hello Rob,
            Thank you for the encouragement and for explaining that! That’s definitely good to know. I hope you have a wonderful rest of the day. Sincerely, Erin

          2. Thanks Erin! You as well. And again, I appreciate the push to wrap up this series. I’ll have to get on that!

  18. Hi Rob

    Great series so far! Refreshing to see someone put the time an effort into making this information available without looking to charge/make a profit for it! Have learned heaps already, look forward to the next segments whenever you get around to them!

    Great work!

    Danny

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