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How to Quit Your Job and Become a Digital Nomad in 90 Days: Week 2

Preparing your finances for self-employment and the digital nomad lifestyle

Welcome to Week 2 of the series How to Quit Your Job and Become a Digital Nomad in 90 Days!

This week focuses on how to prepare your personal finances for the transition from employee to self-employed traveler. To explore ways to make money as a digital nomad, and to determine if the digital nomad lifestyle is right for you in the first place, start at week one.

Why money matters before you quit

If you’re eager to become a self-employed digital nomad, able to make money while you travel, then being employed is one of the best situations you can be in!

Don’t get me wrong, if you’re unemployed right now, becoming a freelancer/consultant is certainly a good option. However, when you already have a job, you are able to worry less about your current finances and focus more on preparing for your future transition.

Although it’s very likely that you can match, and eventually surpass, your current salary once you’re self-employed, it won’t happen overnight. By growing your business while still employed, and saving up for an effective transition, you’ll be able to become a digital nomad relatively free from financial stress..

Week 2 schedule: Preparing your finances for self-employment and the digital nomad lifestyle

As you go through this week’s lessons, remember to do the activities for each day! This week they will include a combination of preparing your finances and growing your business – so don’t skip over them.

Remember, the key to success in this transition is putting in the time. If you can commit two hours a day to your transition, you’ll be well on your way to success!

Here’s what week two looks like:

Day 1: Decide on your digital nomad starting location

Day 2: Determine your needed income level

Day 3: Take a hatchet to your expenses

Day 4: Begin saving for the transition

Day 5: Discover how to travel inexpensively

Day 6: Maintain focus on your day job

By the end of this week you should have a solid understanding of how much money you’ll need to make an effective transition from employee to digital nomad, along with how you can prepare your finances for a smoother escape. Let’s get started!

You need nothing to be free

Day 1: Decide on your digital nomad starting location

“For my part, I travel not to go anywhere, but to go. I travel for travel’s sake. The great affair is to move.” – Robert Louis Stevenson


As a digital nomad your work is at your fingertips – from literally anywhere in the world. With the internet available in nearly every corner of the earth, there are very few places unavailable to the wanderlust solopreneuer.

But when you begin your journey as a self-employed digital nomad, there’s one thing that’s very important to remember – you’re not on a year long vacation, you’re working. It’s easy to envision “working” from a laptop on the beach for two hours, and then seeing yourself traveling, trying new foods, and hanging out with locals.

The reality is, if you want to succeed, don’t think of it as a vacation, think of it as a full-time job, but in a different country. You still work for 6 to 8 hours a day, and then you spend your evenings, weekends, and occasional holidays experiencing your new backyard. As your business grows and you realize the time commitment necessary to maintain your lifestyle, you can be more flexible with how much time you spend exploring/traveling vs. working.

However, there are parts of the world that make it much easier to live on little – such as Southeast Asia. Therefore, as you decide on a place to live, keep in mind the cost of living as well. If you want to remain in the US or Europe, you’ll need to work much longer hours to cover your basic expenses. Meanwhile, if you’re willing to explore some cheaper locations, you may be able to cover your expenses with just 1-2 hours of work a day. The choice is yours!

Considering the initial time commitment and ongoing costs of travel, I suggest staying in your first place for at least one month – possibly two or three. This will allow you to fully explore the location while still spending your days on full-time work. If you jump around too much you won’t have the time to work or experience what each location has to offer.

Daily tasks

  1. Brainstorm where you want to begin your digital nomad journey. If you don’t have an idea already, spend 30 minutes thinking about where you’ll start your life outside the office. Where would you be happy to work from for a few months while building up your business and skills? If that’s your current hometown, that’s fine too. Consider the cost of living, infrastructure, language, and safety of the countries you’re looking into. But remember, there are always horror stories – so don’t let yourself be scared by a few blog posts. However, if you see a consistent theme, be cautious.  
  2. Spend the next 90 minutes applying to, or working on, projects. If you’ve already landed your first freelance project, the congratulations! Spend the next hour and a half working on it. If you haven’t landed a project yet, then I recommend that you get back on your Upwork profile and start applying! Read this post for further tips on how to apply for jobs on Upwork (or any other freelance platform for that matter).

Success story

Sometimes you can discover your digital nomad niche while on the road. Stephen Palmer was an Irishman living in Australia when he came up with the concept for – where he shares advice for Irish who are traveling and moving to Australia. Although it’s a site with a very small and specific niche, Stephen is now making over $15,000 a month from the site! You can listen to his full story on the Lifestyle Income podcast.

As we can see from Stephen’s success story, finding a very specific niche can expedite your business’s growth. Whether you’re starting a blog or running your freelance business, don’t try to be something to everyone – figure out who your primary customer/reader should be, and focus on them.


  • BaseTrip is a great free site that helps you discover what you need to travel to any given country.
  • Andrew over at Nomad Capitalist share a great post on the four ways to live a digital nomad lifestyle — it’s a great read, especially as you try to figure out how to balance your business and passion for travel.
  • The free app Duolingo can help you learn a variety of languages – definitely worthwhile if you’re heading somewhere that doesn’t speak your native tongue. And it’s free!
  • For the classic, yet pricey, language learning tool, you can also check out Rosetta Stone – probably the most well-known way to learn a language.
Tourist vs. Traveler
Compliments of Land of Travel

Day 2: Determine your needed income level

“Money has never made man happy, nor will it, there is nothing in its nature to produce happiness. The more of it one has the more one wants.” – Benjamin Franklin


Now that you have an idea of where you plan to live after making your great escape, it’s time to get serious about your financial needs! How much do you need to make to afford your new standard of living?

This isn’t how much you want to make, it’s how much you need to make. If you’re living in Thailand, that may be $1,000/month. Meanwhile, if you plan to keep your apartment in NYC, anything under $100,000/year may be unreasonable. While you ideally want to at least replace your income, it’s good to know what the bare minimum is before you eagerly quit your job and discover that you can’t make ends meet.

How do you determine your needed income level? To start, I would recommend looking at the cost of living in the country you’re planning to live visit and calculate out how much you’ll need per month. Then, multiply that by 1.5. Why? Because it can be difficult for Americans to live comfortably at the “average” standard in many parts of the world. By adding this minimal buffer, you’ll give yourself some leeway if needed.

Daily tasks

  1. Determine what your monthly expenses will be. Based on your chosen location, how much will you spend for food, lodging, entertainment, travel, clothing, internet, etc.? Numbeo is a great free tool that can help you determine the cost of living in a particular country.
  2. Decide on your actual desired income. Now that you know what your costs will be, add in your desired monthly savings, include any loan payments or mortgages, and account for one-time travel expenses. Now, take this number and multiply it by 1.3 in order to account for health benefits and taxes – which you are responsible for paying on your own when self-employed.
  • Ensure that you’re freelance proposals focus on value. I highly recommend that you sign up for this free 7-day course on Charging What You’re Worth! I’m just finishing it and have learned things I’ll be implementing into my own freelancing moving forward. The sooner you discover how to maximize your value, the sooner you’ll be able to charge premium rates.

Success story

Kim André Langholz is from Denmark and decided that he wanted to embrace the nomadic lifestyle. His first stint was a 5 month adventure to Spain where we worked with a travel company. But, after returning to Denmark, he decided he needed something more flexible that would allow him to work from anywhere – so he started a freelancing consulting company. As we all do, he had an incredibly difficult time getting started, but he persevered!

After sending 132 handwritten letters, he landed his first three clients. He now earns enough for him and his wife to travel the world. You can read about his startup story on Reddit.

Getting started with your first few clients can be incredibly challenging and requires a significant amount of perseverance. But don’t give up! Like Kim, find a creative way to reach out to as many people as possible and, eventually, clients will start trickling in.


How to make money as a digital nomad
Compliments of Sharon from DigitalNomadQuest

Day 3: Take a hatchet to your expenses

“Wealth is the ability to fully experience life.” – Henry David Thoreau


Although you should always keep an eye on your expenses, when deciding to quit your job and pursue your own venture, this is absolutely critical.

As a freelancer consultant your income won’t be based on clocking in every day, it will be dependent on the needs of your clients and your ability to deliver. That means that there will be substantial ebb and flow. Sometimes you will have more than enough work, other times you’ll be struggling to keep yourself busy for a couple of hours a day.

Additionally, there are no sick days or vacation days when you’re self-employed. Although you can work as much or as little as you want – when you don’t work, there’s no paycheck.

This actually isn’t a bad thing. It’s just different than what most people are used to. And, it also means that you need to be very smart with your finances as you make the transition. One of the best ways to do this is to minimize your expenses. Reducing what isn’t absolutely necessary so that you can focus on paying for what matters most – your freedom.

It can be difficult to cut out the cable or tell your friends that you can’t go out to $30/plate dinners as often, but a few sacrifices now will certainly give you peace of mind later on. And consider this temporary. Once you discover how to managing your finances as a digital nomad, you’ll be able to loosen up on your spending embargo.

Daily tasks

  1. List out all of your monthly expenses. This should include your mortgage, student loan payments, monthly restaurant and going-out costs, cable, internet, phone, car payment, etc.. Anything that you pay for on a regular basis should go on this list. For some people this might include shoes, iPhone apps, or nail salons.
  2. Figure out where you can cut or reduce expenses. Take a look at the resources below for helping tips, but find as many places as possible where you can minimize the costs associated with your business.
  3. Work on client projects. If you don’t have any projects, continue applying. We’ll discuss optimizing your online presence more next week, but experiment with different techniques and wording to land those clients – remember to focus on how you can benefit them.

Success story

Who says digital nomads have to be single twentysomethings? Since 2010, the Boyink family has been traveling across the US full-time in an RV! Thanks to Mike’s fully remote business as a website developer, all he needs to succeed is a laptop and internet connection. You can learn about more of their story on where they discuss their experiences and tips for affording a full-time family on the road. If you’re ready to escape the suburban “American Dream”, check out their site for inspiration!

What I love about the Boyink’s is that they’ve realized that the American Dream isn’t their dream. Too many people assume there’s only one way to live and then trap themselves into this lifestyle – even if it isn’t what they enjoy. It’s amazing how much money you can save, and how much fun you can have, once you decide to pursue your dream.


  • It’s almost un-American to turn off your cable/satellite. However, you can save a tremendous amount of money – and get used to limited television while traveling! Instead, spend  $99 a year for Amazon Prime and watch moves on Netflix. Two inexpensive alternatives!
  • Additionally, if you still want to go out to eat and enjoy the town, cut costs by using Ebates for cashback shopping and discounted coupons through Same level of entertainment – for far less.
  • T-Mobile may be the best phone service provider yet! Not only are their plans month-to-month and relatively inexpensive, but you can also text and use data from almost every country in the world – without paying extra! Pretty epic for digital nomads.
  • If you have student loans with interest rates above 3.5%, consider refinancing through LendKey. You may be able to save a few thousand a year on interest.
  • Finally, if you want to get real creative while traveling, you could build your own “camper” like these nomads did while traveling New Zealand.
Save on monthly expenses

Day 4: Begin saving for the transition

“Where large sums of money are concerned, it is advisable to trust nobody.” – Agatha Christie


The absolutely most important planning you can do (outside of developing a freelance skill set and client base) is saving up for the transition. Consider this your escape fund.

When I left my full-time job I was making about 50% of my day-job income by freelancing in the evenings and on weekends. This meant that I was able to scale up quickly once I transitioned to being 100% self-employed. However, there was still a period of transition.

Regardless of how successful your freelance business might be, having at least enough to cover your expenses for 6-12 months will keep you at peace during the transition. If you lose your biggest client one week after quitting your job, you will certainly be happy that you still have these funds saved up.

Add as much to your escape fund as possible! How do you do this? First, anything saved from reducing your expenses should go into this fund. Second, because you’re still employed, anything that you earn from freelancing should also go directly into this savings account. If you earn 50% of your income as a freelancer for the next 3 months, you’ll have 45 days of savings right there!

But be smart with this money. Don’t gamble it away in the stock market or throw it at some sketching business venture (including one of your own). This is money that you’ll need to have easy access to during your transition, so keep it available.

Daily tasks

  1. Establish your escape fund. To ensure that the fund grows, keep it separate from your regular checking and savings account. To do this you can either create another savings account with your bank, or use another secure investment. Personally, I hold my security fund in Betterment, which gives you 2-3% stable returns on your savings! Regardless of how you set this up, make sure that you have an automatic transfer so that the fund grows every month before you have the opportunity to spend it!
  • Work on client projects. Expect to spend 30-90 minutes a day for the next three months either working on projects or finding new clients. Implement what we discuss throughout this series to improve your odds and feel free to ask questions in the article comment sections!

Success story

Sometimes you can cover the digital nomad lifestyle using semi-physical storefronts. Take Francis Shenstone of He owns a chain of 6 pop up greeting card shops across the UK (along with selling online) – but has the ability to manage his business completely remotely! Hence, for the last two years he’s been traveling non-stop.

Regardless of the type of business you decide to establish, make an effort to have your finances in-line before you start traveling extensively (even if you decide to live in another country right away). Once you have your business processes and teams developed, you can easily transition into traveling as much as your heart desires.


Compliments of Money Q&A

Day 5: Discover how to travel inexpensively

“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do.” – Mark Twain


You don’t have to spend much time surfing the web before you hear of people who travel the world for free.

Although you may not be able to eliminate all of your travel expenses – you can certainly make the most of a few services and techniques to substantially reduce the cost of your travel. I wanted to quickly share a few strategies here – although we’ll share more details in future articles (and add plenty of resources at the bottom of this section).

First, make the most of credit cards – especially the initial sign up bonuses! Signing up for 1-2 cards can give you enough points to fly just about anywhere in the world for free – roundtrip. My wife and I are using points for our trip in Costa Rica, used points to cover most of a Europe trips flight, and have traveled around the US for free – all thanks to credit card points. Here’s a list of the best travel reward cards. Just remember to always pay off your cards and track 1) the sign up bonus, 2) the ongoing reward rate, and 3) the annual fee.

Next, make the most of loyalty rewards programs – especially for lodging. For example, Marriott offers a free night after your first two trips; gives you a free night after paying for 10, and AirBnB will give you $40 just for signing up! Although most of your time will be staying in long-term housing, these are a few of the many programs that offer rewards to travelers.

Finally, use cashback sites like Ebates, Giving Assistant, and Swagbucks when buying through any hotel/airline chain to receive cashback on every stay. Although it’s not a ton, I’ve earned over $100 back from my lodging purchases this last year.

In short, as you plan your escape, don’t think that money has to be a limiting factor. If you get creative you can make the entire experience of living and working abroad far less expensive than your current situation.

Daily tasks

  1. If you want to travel with credit card miles, plan now. You have to meet minimum spending limits and then wait a few weeks before gaining access to credit card sign up bonuses. Therefore, if you are at all interested in traveling with miles, you’ll want to get started soon! Here’s a list of some of the top credit card sign up bonuses.
  2. Look through some of the best freelance profiles. We’ll talk more about optimizing your online presence next week. However, you can still benefit from looking at some of the portfolios and gig descriptions of those at the top. Whether you’re using Upwork, Fiverr, or some other platform, do a quick search within your  niche and look at the top results. How can you emulate them to improve your own profile?
  3. Work on client projects. Keep at it! The more time you invest into client projects now, the more you’ll earn, and the more prepared you’ll be for your transition. If you’re still struggling to land clients, reevaluate your niche and portfolio – maybe you need to do a few more projects for free.

Success story

Traveling doesn’t have to be expensive. Nora is a full time writer who is also a full time traveler – talk about living the dream! And what’s more amazing is that she doesn’t spend a fortune. In fact, in 2011 she spent a total of $173 on accommodations – for the entire year! You can learn more about her story on

With a bit of creativity and willingness to volunteer and/or make the most of credit card rewards, it’s amazing how far you can go on the cheap. If Nora doesn’t inspire you, I don’t know who will!


  • You can view the top credit card offers here and then discover how far the miles will get you on United, Delta, American Airlines, and Southwest. Generally speaking, if Southwest flies there (Central America/Caribbean) they often have the best rates.
  • Jump over to Airfare Watchdog and set alerts for your favorite routes or search for the cheapest flights from a specific city — sometimes you can find round-trip flights to Europe for under $400, or flights to Central America for under $200!
how to start travel hacking
Compliments of

Day 6: Maintain focus on your day job

“Integrity is doing the right thing, even when noone is watching.” – C. S. Lewis


In three months you could be working from Europe, Ecuador, or your backyard. That’s exciting!

But don’t let this enthusiasm distract you from being productive in your current workplace – for several reasons. First, it’s unethical to take advantage of your employer. Second, if you get fired this week you lose the security that comes with making the transition while fully employed. And third, you want to leave your job on good terms! Maintaining positive relationships with past bosses gives you a fallback plan, a reference if ever needed, and potentially a future client. So make sure that you put in the time necessary to succeed.

That being said, you don’t need to be an overachiever. In other words, if you’re expected to put in 60 hours a week in order to get a promotion, don’t worry about it. You’re focus is to do what’s expected for your current role, not work yourself into a future role. So, give your boss what’s fair, but don’t allow yourself to be guilted into overtime – as that’s your freelance time.

Finally, don’t tell your employer you plan to leave! This is very important. Until you are 100% confident that you will be leaving, don’t talk about it at work. It’s amazing how fast word can spread around an office and, the moment that you’re viewed as someone ready to exit, advancement opportunities quickly disappear. Although this isn’t bad if everything works out, what happens if one month from now you decide that you don’t want to become a digital nomad? Your career has already been stunted.

My belief is that it’s fair to give 30 days notice and be willing to work with your employer to make the transition smooth for them as well. I ended up staying around part time for 3 more months after “quitting” to help with a few projects before taking off on my Costa Rica adventure. It doesn’t hurt to leave on good terms.

Daily tasks

  1. Make sure that you’re putting in 100% at work. Are you daydreaming in the office or checking your emails to respond to clients? Reevaluate these activities to make sure that you are giving to your employer what you originally agreed on.
  2. Work on client projects. One of my favorite things to do to ensure that my clients are “wowed” by my work is to ask myself after every project, what could I do in 5 minutes to make this noticeably better? A quick 5 minute addition, revision, or bonus can really impress a client.

Success story

I thought sharing Maggie’s story was perfect on the day that talked about staying focused as work – as she’s a location independent career coach! Imagine that – even someone who helps people excel in their corporate job can become digital nomads.

Maggie transitioned from her corporate training position in 2006 to become a full-time career coach. Although your business is based out of NYC, she lives in the Florida Keys with her family and spent a year extensively traveling across Asia, Europe, and Mexico before her son started school. She’s been quoted in Forbes, the WSJ, and a variety of other news outlets. You can see more of her story at


  • Find a great to-do list app that you can download and use to track your ideas while at work – that way you can focus on work without forgetting or daydreaming.
  • Read this LifeHack article on how to stay focused at work.
How to excel at work
Compliments of Catherine’s Career Corner

A wrapup of week two: It’s time to get serious

As week two comes to an end, hopefully you’ve landed your first job or two – even if it’s just a $5 gig on Fiverr. But if you’re still having trouble, don’t sweat it. Next week we’ll discuss how to optimize your online presence to land clients and make sales.

Just remember, even if some of these topics aren’t relevant to you and you decide to skip over them, commit to the two hours a day. It doesn’t matter whether you’re practicing, researching, or contacting potential clients, commit to spending two hours a day to growing your business and you’ll be in a very good place when this series comes to an end.

If you would like to view the rest of the series, visit the introductory article How to Quit Your Job and Become a Digital Nomad in 90 Days or view the latest article in the series here.

Thanks again for reading and feel free to share any thoughts, recommendations, or ideas in the comment section below.


Rob is enthusiastic about everything related to money and investing. A financial analyst and instructor, he enjoys using what he’s learned from 10 years of studying business and money to help others achieve financial stability. He founded Money Nomad in 2014!

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  1. My desire for location independence is a little different than other people’s. I have a disability and cannot drive, though I have other skills and am a speedy learner. I am living off SSI, but could really use extra income. It would be nice to eventually earn enough not to need that anymore.

    1. That’s the beauty of remote work, you can do it from anywhere — even your own living room! And next week will have a lot of great information for you on how to make yourself visible online so that clients find you.

      If you haven’t found a skill or two that you want to try to monetize, I would recommend starting there! If you put in a couple of hours a day, you’ll certainly become a success!

  2. This would have come in handy a few months ago! 🙂 It’s amazing how much of this week I can relate to. We’ve downsized our house, cut expenses, created a personal finance forecast and were very careful about any kind of spending – trips, gifts, big and unnecessary purchases before I started my journey. I love all of the advice and the success stories. I am definitely going to check out – Charge What You’re Worth.

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