In Spring 2020, millions of workers around the world started telecommuting for the first time due to the COVID-19 pandemic. Some can’t stand it and can’t wait to get back to the office. Others had secretly wondered about it for years, and now they find they have a taste for it.
At the very least, telecommuting gives you geographic flexibility to live and work anywhere, and often time flexibility to choose your own hours as well. For some, working from their current home is enough to make them happy. But many workers have started asking bigger questions: “If I don’t have to live in this city — if I can keep working and earning from absolutely anywhere — where in the world would I like to live?”
Those questions offer a first glimpse into the notion of lifestyle design, or intentionally choosing the exact city or town you want to live in, the hours you want to work, and other details making up your personal ideal life.
For example, my family and I spend 10 months out of the year overseas — my current home base is in Brazil. I set my own hours, do work I love as a laptop entrepreneur, pay minimal U.S. income taxes, and even get free housing. But it took a lot of work to get here.
Does your perfect lifestyle involve becoming a digital nomad or laptop entrepreneur as well? Follow these steps to untether your life from a specific location, and start writing your own rules for how you live and work.
Create Long-Distance Income Streams
You don’t have to have a new source of income lined up to move to a new country or state. Many people take a leap of faith to move and figure out income once they arrive where they want to live, or find ways to earn money while traveling full-time. But to become a digital nomad, able to live and work anywhere in the world, you need ongoing income.
Fortunately, you have many options to create location-independent income.
Negotiate Telecommuting With Your Current Employer
Negotiating this perk got a lot easier in the wake of COVID-19. Even the staunchest opponents to remote work had to embrace it if possible; in most cases, the alternative was not working at all.
And now that they’ve tried it, many of those previously antagonistic employers have undergone a change of heart. Some found the drop in productivity they dreaded never happened. Others realized the potential cost savings of ditching their physical office space.
Talk to your employer about telecommuting full-time. Set measurable productivity metrics to demonstrate that you can work just as effectively outside the office. If your employer resists, offer a phased trial period, starting with one or two days per week and gradually expanding if you continue meeting your performance goals.
Physically parking yourself at a desk at work does not mean you’re accomplishing anything. Modern employers should be extremely clear on what they expect from their workers, and have precise ways to measure their results. If you and your employer aren’t clear on those measurements, it’s high time you change how you both do business.
Find a Job That Lets You Telecommute
Not everyone likes their current job, and even those who do may not get the green light from their employer to telecommute full-time. In that case, consider looking for a new job.
A telecommuting-friendly job could be another position in your current field, or you may be ready to change careers. If you don’t already have a specific career in mind, start researching jobs that let you work remotely for fresh ideas. A great first step is to check out opportunities on Flexjobs.
Today there are more jobs than ever that let you work from anywhere. Find a career path that appeals to you and that fits into your lifestyle design, and pursue it relentlessly. It may require new professional certifications or even a new degree, but that’s the price of creating your ideal life.
Start a Virtual Business
No one says you have to take a job from someone else to make money remotely. Why not create your own employment?
Consider starting a side business while working your full-time job to help fund your nascent startup and get it off the ground. In particular, virtual businesses often come with low startup costs and high upside potential, while of course letting you operate them anywhere in the world. As it starts earning more money, you’ll gain confidence in your ability to generate income from anywhere.
And remember, you don’t need to replace your current job’s income. You only need to cover your living expenses — which you can trim far lower than you spend now, especially if you move to a low-cost-of-living area. Even as you build your online business income, start working to cut expenses and grow your savings rate.
Invest for Passive Income
Passive income keeps rolling in whether you’re sitting at your desk or lying on the beach. Start investing to earn more of it, and increasingly cover your living expenses. With enough passive income, you reach financial independence and can retire early.
While there are endless ways to generate passive income, start by exploring the most common passive income sources. I personally invest in a mix of dividend-paying ETFs, rental properties, private REITs such as Fundrise, and private notes to real estate investors I know.
Note how many of those revolve around real estate, which lends itself to generating ongoing income. While not everyone has the time or interest to invest directly in rental properties, you have plenty of indirect ways to invest in real estate for passive income.
As a fun exercise, start tracking what percentage of your living expenses you can cover with passive income each month. When you reach 100%, congratulations — working just became optional.
Do a Trial Run
Before selling all your earthly possessions and moving to another country, you’d better make sure this lifestyle is actually a good fit.
Start with a two-month test run to ensure you don’t make major life changes only to reverse them after a few months, potentially saving yourself a great deal of money, time, and heartache.
Work Remotely
Begin your trial run by simply working remotely in your home city for a month or two. You may find you absolutely hate the loneliness, the lack of camaraderie, and the need to structure your own workday with no supervisor standing over you.
Or you may love the freedom and flexibility. You could work from home of course, although I personally don’t like the blurring of the lines between my personal and professional lives. It’s much harder to mentally “leave work at work” when you work from home.
Instead, consider coffee shops, cafes, or coworking spaces. For years, I worked out of coffee shops, first traveling around the U.S. then later overseas. At a certain point, I got sick of eating cafe food for breakfast and lunch every day, and grew tired of the bland music and endless noise. Today I work out of a coworking office space, which I love.
Regardless of where you work remotely, the point is to try it on for size. If you find it’s not for you, then no harm done — you can switch back to working in person, potentially staying at your current job. If you find you have a taste for it, you can move forward with becoming a digital nomad with confidence.
Create a Daily Remote Work Routine
Without the structure of an office to report to, you need to build your own daily routines if you hope to succeed in working remotely.
Put some thought into the exact sequence of work you should undertake every single day to stay productive. Telecommuting and being your own boss sound sexy, but they require enormous self-discipline and motivation. Not everyone is cut out for it.
The more you can create good habits and routines, the more you can lean on them rather than self-discipline. You don’t need a supervisor to tell you to brush your teeth each morning and night, and you don’t need to muster motivation to do it. Create good work habits and ingrain them until they become routine.
Measure Your Productivity
Whether you continue working for someone else or start your own virtual business, you need to prove your productivity. It’s one more reason to get clear on your success metrics before you stop working in person.
Not everyone has the drive needed to work remotely without a supervisor pushing them. Discover whether you have it before setting off on your digital nomad adventure, because if you can’t perform at the same level remotely, you have no business telecommuting.
Take a Working Trip
Once you try working remotely for a month or two in your home city — and prove to yourself you both enjoy it and excel at it — try taking this experiment on the road.
Spend a few weeks living and working in a new city. Book an Airbnb — perhaps within easy walking distance from amenities like groceries, entertainment, and coffee shops or a coworking space — and see how you enjoy living in a new town.
It could be the city you plan to move to, or somewhere easier to reach. But you need to get out of your comfort zone, your home city, to make sure you actually want to move away as a digital nomad.
You may find that you enjoy traveling and working in short stints, but like returning to a home base in your current town. I have a friend who practices that lifestyle; he lives in Boulder, but averages a week out of every month visiting and working somewhere else. He visits friends and family across the world, and seeks out great skiing and hiking, all while telecommuting.
Prepare to Embark as a Digital Nomad
Still want to set out into the world as a laptop entrepreneur or digital nomad?
It’s a fun life, but it takes work to untether yourself from home. Start laying the groundwork to travel abroad or domestically, and watch the world open up before you.
Form a Plan for Your Current Home
If you own a home, you’ll need to either sell it, rent it out, or continue paying to maintain it out of your own pocket.
Word to the wise: landlords face far more headaches and expenses than most people realize. You can’t just subtract the mortgage from the rent to calculate cash flow; you need to subtract for long-term average expenses like repairs, maintenance, vacancy rate, property management fees, property taxes, and insurance. And you also can’t rely on tenants to treat your home with the same respect you do — expect more wear and tear.
Most homes bought retail, to live in, don’t create great cash flow as rentals. Still, you may decide to accept poor cash flow in order to keep your home for future use or as a fallback option. Just make sure you run the numbers accurately so you understand the true profit or loss from keeping it as a rental.
If you lease your current home, you need to coordinate move-out with your landlord based on when your current lease expires. Don’t be afraid to negotiate a short-term lease renewal or going on a month-to-month lease in the meantime.
Plan Your Initial Itinerary
You don’t need to know where — or whether — you want to set up shop semi-permanently. But it helps to know where you want to spend the next few months.
Plan out an itinerary, and book your flights and accommodations. Leave yourself as much flexibility as you like; everyone has their own travel planning preferences, from booking every detail in advance to leaving them open-ended for flexibility. Websites like Kayak can help you will all your arrangements.
Research Digital Nomad Visas
Clever, nimble governments around the world are increasingly seeking to attract digital nomads with special visas. These visas require you to prove ongoing, independent income, and they let you stay longer than typically allowed under tourist visas.
It makes sense: you earn money from elsewhere and spend it in their country. It’s a simple and effective way for the host country to import wealth!
For example, Estonia launched its digital nomad visa in 2020 to attract earners from other countries and stimulate their pandemic-damaged economy. But they weren’t the first country to try to woo people who earn money from elsewhere. Several other European countries have launched visas to attract laptop entrepreneurs, including Portugal, Germany, and the Czech Republic.
Even some U.S. states have initiated magnet programs to attract digital nomads. Vermont launched a Remote Worker Grant Program in 2019, offering up to $10,000 over two years to encourage remote workers to move to the Green Mountain State. It was so popular that they ran out of funds, and the program is currently on hold pending more funding. Farther south, Tulsa, Oklahoma, opened a program called Tulsa Remote that offers $10,000 in the first year for digital nomads.
Form a Plan for Health Care
If you continue working a full-time telecommute job that provides health insurance, look into coverage while abroad (assuming you plan to travel abroad). Overseas coverage varies by insurance plan, and if it’s included, your insurer typically reimburses you for expenses afterward at an out-of-network rate. That may mean higher out-of-pocket expenses for you — and don’t count on prescription drug coverage while abroad either. Check with your insurance company about your specific health care plan’s international coverage.
If you can’t count on employer health insurance, your options vary based on where you plan to live. Start researching international health insurance if you plan to travel overseas. Alternatively, read up on health insurance options without employer coverage, many of which cover you both in the U.S. and abroad.
Whatever you do, don’t just shrug your shoulders and let your health coverage lapse. No matter your age or health, you never know when you’ll get hit with an expensive health care bill.
Open a Mail Service
Digital nomads still occasionally receive important snail mail. It helps to have a U.S. mailing address that can forward your mail to you, both physically and digitally.
I use a service called St. Brendan’s Isle based in Florida. They scan all unopened letters and packages, which I can review within my online account. For each parcel, I direct them to either shred it, open and scan it, or forward it to me physically.
Transfer Your Phone Number
Want to keep your current phone number? No sweat. You can transfer it to Google Voice, where you can then receive VOIP phone calls and SMS messages.
I took this a step further, paying for a premium Skype service that gives me unlimited phone calls to U.S. and Canadian phones from anywhere in the world. I then combined both services by setting up forwarding from my phone number on Google Voice to my Skype account, and registering that number as my outgoing phone on Skype.
You’d be surprised how useful it is to keep your phone number working from anywhere in the world. My old college roommate, for example, texted me out of the blue last year after 15 years without contact, asking if it was still my phone number. I no longer had a current email address or phone number for him, but we re-established communication because he was able to reach me on the same phone number I’ve had for 20 years.
Tips & Ideas for Cheap Long-Term Travel
My family lives overseas with free housing, free comprehensive health insurance, and free flights back to the U.S. every year because my wife works as an international educator. But there are infinite options to live abroad inexpensively.
Research how other expats live and work to gather dozens of ideas. Get creative, and make it work for your unique vision.
Find Cities or Countries Where Your Dollar Goes Further
Cost of living matters. Exchange rate matters too, but don’t confuse the two — a weak currency helps reduce cost of living, but doesn’t guarantee it, and two areas on the same currency can still have dramatically different costs of living. Look no further than comparing San Francisco to Tulsa.
To kick off your search for particularly high-quality-of-life, low-cost-of-living countries, read through this list of countries where you can live the good life on $2,000 per month.
Test Drive Cities Before Moving
Just as you gave telecommuting a trial run before leaving your hometown, you should similarly try out cities before committing to live there.
We all form an image in our minds of how a city will look and feel, based on photos we see and articles we read. But rarely do our mental images align evenly with the reality of living in that city.
Spend a week or two visiting a city before making the leap to move there. If it doesn’t draw you in, try visiting other places after talking to people who know the region. You don’t have to get it right on the first try. Experiment until you find the perfect place to call home.
Book Accommodations Where You Don’t Need a Car
Driving is embedded in American culture. You might just assume you need a car, wherever you move. But in many parts of the world, driving is not only impractical but expensive and even inconvenient.
My wife and I intentionally chose our current home for its walkability and bikeability, so we didn’t need to buy or lease a car. We walk or bike everywhere, from grocery stores to bars and restaurants to retail shopping. On the rare occasions we need to go farther afield, we take an Uber, and occasionally rent a car from Getaround for long weekends to visit tourist towns within driving distance.
The average car owner in the U.S. spends $9,282 per year according to AAA, between the car itself, gas, maintenance, parking, insurance, and all the other hidden costs of car ownership. Consider going carless to save money and force yourself to exercise more in the process.
Consider House- and Pet-Sitting for Free Accommodations
Across the world, thousands of people need others to watch their home, pets, or both while they travel. This means you can stay at their homes for free, provided you water their plants and possibly feed their pets.
Explore services like Trusted Housesitters, Mind My House, and Nomador for examples.
Alternatively, you can also look into house swapping services, global networks of people who open their unused homes to strangers to stay while visiting. Check out Home Exchange and Love Home Swap to learn more.
While you obviously can’t set down roots in these homes, you can use them to stay for free while you explore new regions to decide whether you want to stay long term.
Final Word
The world is full of alternative ways of living that most people never even knew existed. I interviewed a woman once who lives for free by long-term pet-sitting. She spends three to six months at a time in each location before moving on to a new town to pet-sit.
Another couple I interviewed used their savings to buy a small apartment building to generate income, and bought a used houseboat in Europe. They spend a few months parked on the rivers or canals of a city like Amsterdam, then move on when the weather turns cold or they just get bored. The longer they spend in Europe, the more friends they make in a sprawling network across the continent, and they often revisit favorite cities for weeks or months at a time. And they never want for visitors from the U.S.
Becoming a digital nomad or laptop entrepreneur is easier than ever before. Although it takes some planning and work, what it requires most is simply vision. Most of us have trouble imagining new lifestyles, but once you break the mental boundaries hemming in your vision of what’s possible, you can design whatever lifestyle you like.
Where would you live in your wildest dreams? What specifically is stopping you from living there, at least for a little while?
