Digital Nomads: Setting a Course for Success in Today’s Workplace

By Becky Simon | December 15, 2017 (updated November 17, 2021)

Not so long ago, there were two kinds of workers: full-time office workers and full-time temps or freelancers. Over time, though, a grey area has emerged between these two work metaphors: Advances in technology and the increasing digitization of many roles have enabled more full-time workers to telecommute from home and more freelance contractors to tackle sophisticated gigs for varied clients. Additionally, technology is enabling a generation of freelance “digital nomads” who take their mobile devices and work from afar, doing entry-level as well as more complex work from exotic locations. In this article, you’ll learn how these digital nomads persuade clients and managers to allow work offsite, and what tools and practices fuel their success.

Defining Today’s Remote Workforce

Long ago, the risks of telecommuting for a full-time employee resembled those of an overseas assignment for a corporate giant: Would your work be noticed, would your name be known, and would you wield any real responsibilities from your remote outpost? These days, those questions have faded to black. More and more full-time employees covet the flexibility of telecommuting for a single employer, while more employers are also hiring freelance contractors who work offsite. These days, remote work is becoming as much the rule as the exception. In fact, according to Gallup data, 40 percent of all Americans work remotely, and both traditional freelance and contracting are becoming more common.


Jennifer Worick

Jennifer Worick, a 49-year old jobs columnist at The Seattle Times and a book publishing consultant, says that over her 15-year career as a freelancer, she’s seen a shift from individuals seeking a freelance lifestyle toward corporations trying to pitch their “cool factor” by offering one to contractors as well as full-timers. 

“In Seattle, where I live, Microsoft really led the way. They realized it’s a win-win for everybody for them to allow remote work,” she says of her freelance work there, which has involved a mix of work-from-home tasks and in-person meetings. 

As a publishing consultant, Worick says that she and her business partner went from a locally-run concern between two friends in the same neighborhood to a virtual operation when her partner moved overseas — first to Mexico, then to the UK. The duo helps writers with manuscript editing, book proposals, and marketing positioning to pitch publishers. It’s virtual work, she notes, but the increasing mix of cloud-based tools means that today, it’s easy to collaborate across continents.

“My partner and I share files through Dropbox and Google Drive, we communicate over Slack, and we use WhatsApp and Viber for free overseas texting with one another — these tools are alternatives to Skype,” she says. “And of course, old-fashioned email also works fine when we’re interacting with writers or sending completed remarks on their projects and manuscripts.”


Types of Workers

Here’s a look at who constitutes today’s remote workforce:

  • Traditional Freelancers: Freelancers are self-employed people with multiple clients who work from home or from a local community space (a coworking space, etc.) Sometimes these freelancers work from the road, too, like their roving digital nomad peers. But generally, traditional freelancers work from home, or they take on contracts with businesses in their local community. Freelancers perform their services without benefits as “1099” workers — shorthand for the fact that employers fill out 1099 forms for them disclosing their status with the IRS. Some 1099 workers do go onsite for projects at companies, but in a “temping” mode with specific beginning and end dates. According to the Freelancers Union, 50 percent of all workers will freelance by 2035.
  • Telecommuters/Work from Home Full-Timers: These team members work for a single employer and perform their duties at home either some or all of the time. While employers used to resist telecommuting (for fear workers wouldn’t show productivity), they’re now more receptive. Gallup data indicates that the volume of employees who work from home at least 80 percent of the time has risen significantly, from 24 percent of workers in 2012 to 31 percent in 2016. The Society of Human Resource Management projects that 75 percent of the workforce will work from home at least sometimes by 2020, while London Business School states that 59 percent of executives surveyed believe more than half of all workers will work from home by 2020. 
  • Digital Nomads: So-called digital nomads are freelancers (with multiple clients) who kick freelance up a notch. They opt to travel frequently and work remotely, and often choose countries with low costs of living or inexpensive living situations, such as couch-surfing, house-sitting, Airbnb, or digital nomad-focused housing designed to function like a work-friendly hostel. Digital nomads may prioritize working to live (choosing work that supports their passions) versus living to work (finding a full-time employer and bowing to the schedule it requires), and use freelancing as a way to subsidize passions and travel — or, if they’re lucky, to fulfill their mission-driven sense of how to spend a life. Digital nomads are empowered by smartphones and the technology infrastructure available through cloud-based technologies. In fact, by 2035, one billion workers are expected to fall into the digital nomad category.


Todays Workforce

Remote Workers Cross Many Demographics

There is a wide range of freelance and digital nomad incomes, and they depend on a person’s experience and expertise level and business sector. But some research indicates the typical work-from-home employee is 49, college-educated, earns $58,000, and most likely works at a smaller business (with fewer than 100 employees). Depending on the market where the person lives, this can be a high or low income, but one thing is certain: Without a commute, dry cleaning bill, and lunches out, working from home saves money.  

Happiness and Customizing Schedules

Those who telecommute or freelance from outside an office may also value happiness over money. There’s a correlation between how much work-from-home employees earn and their happiness. When they have the ability to influence their incomes (such as by accepting or rejecting assignments, projects, or hours), work-from-home folks are happiest earning $75,000 to $99,000. Digital nomads, who are overwhelmingly young or millennials, often opt for happiness over income, and choose their work locations with cost of living and leisure in mind. Additionally, many work-from-home professionals eschew the eight-hour day and five-day work week, opting perhaps to work more days per week but for fewer hours.

Benefits of Becoming a Remote Worker

The flexibility (real as well as perceived) of working remotely is both a benefit and necessity, at least according to some experts. Farai Chideya, writing in The Episodic Career, describes the modern workplace as shifting from one where individuals form long-term relationships with full-time employers to one where individuals may work in multiple seemingly unrelated jobs across a lifetime (hence, the “episodic” career) or one where people become “slash” professionals who perform multiple related duties — such as caterer/cookbook author or journalist/professor or bookkeeper/tax consultant or B&B owner/wedding planner. With today’s workers spending less time in long-term, full-time jobs than their forebears, they are more self-aware of their marketable skills and approach the need to demonstrate flexibility in the workplace as both a given and a differentiator for themselves. “Job hopping” is no longer detrimental, but rather advantageous.

It’s against this backdrop that full-time as well as contract workers seek out remote positions: This work style is a more accurate mirror of many professions and professionals’ trajectories through them than the old metaphor of commuting to an office to work for a single employer. And employers have grown more comfortable with allowing remote full-time and contract work arrangements. In the next section, we’ll take a look at why.

Why Do Employers and Contractors Alike Enjoy Remote Work?

  • Autonomy: Whether you’re a freelancer by choice or a telecommuter at a large corporation, autonomy is seen as a privilege. If a freelancer finishes a project by noon on a Wednesday and wants to take the afternoon off, no one’s stopping them. If a telecommuter just delivered a report and wants to get away from the desk (with mobile device in hand) to walk the dog, they can. The freedom to ebb and flow on your own schedule is a benefit.
  • Productivity: Nine out of ten people who work from home feel like they get more done than at the office. It’s not surprising, since so many offices are shrinking their footprint and stuffing more workers into smaller square footage. They don’t just feel more productive — research indicates they actually are getting more done. The firm ConnectSolutions found that 77 percent of remote workers accomplish more in less time thanks to fewer distractions (meetings, watercooler talk, and noisy coworkers or work environments). Remote workers take fewer sick days and request fewer vacation days, too, meaning they put in more work days overall  — a benefit most managers can get behind.
  • Different Work Styles: Introverts, the deep thinkers and focused concentrators of the workforce, thrive on having long periods of time for concentration and without distraction. While they can pivot between team meetings and group projects and their beloved solo time within a corporate office, many report greater fulfillment in an environment where the default setting is solo and silent rather than social and boisterous. People who do rote, repetitive tasks (working in call centers, managing databases, coding, bookkeeping) hold jobs which they can easily execute from home.
  • Flexible Scheduling: Classic nine-to-five office hours aren’t ideal for all people. According to a study of adult sleeping patterns, 20 percent sleep late while 10 percent are at their best extremely early relative to this schedule. For folks with these circadian rhythms, a work-from-home or flex schedule can help them set their hours around when they thrive. Similarly, households with children or seniors may be able to use the flexibility of work from home to better balance care needs. As adults age, they may seek less and less friendship and social life at work — for an empty-nester in their late 50s with plenty of social engagements in the neighborhood, it may be appealing to bypass the forced socializing that goes with an office job.
  • Location Independence: Whether you’re a freelancer who roams regionally or a digital nomad who powers up a laptop in hotel lobbies, choosing the environment (coffee shop, coworking space, bar) that suits your mood or type of work is one of the pleasures of remote work. In a survey of 24,000 workers conducted by Polycon and Future Workplace, the overwhelming majority (98 percent) said a “work anywhere” culture is preferable to a fixed space employment arrangement.
  • Geographic Distribution: Today’s workplaces often involve interactions across multiple time zones, both within a company and beyond it. Remote workplaces make staggering shifts and regional or time-based management much easier for companies and their team members. Technology also simplifies the process of  “passing the baton” between teams around-the-clock.
  • Recruiting and Real Estate Benefits: Companies can pitch remote work options to prospective employees to entice them to apply, and they can use remote work perks as a retention tactic, too. Additionally, since many employees now lament the modern shrunken workspaces that have grown popular with corporations, a work-from-home option solves the corporate problem of expensive and cramped real estate by offering workers the telecommuting privileges they want.

Overcoming Corporate Resistance to Remote Workers

If you work for a corporation as a full-time staffer or frequent contractor, you may see clashing attitudes from management about if and how to offer work-from-home versus in-office arrangements. Some managers think only facetime guarantees productivity, while others know that granting home-alone time promises better (or at least the same) results while also cultivating happier employees. There are several reasons why companies have shifted their stance on remote workers. For starters, office space (especially in major cities) has grown expensive. When employees are frequently on the road, it makes little sense to park empty square footage or pay for oft-empty flex desks. Additionally, as offices shrink their square feet-per-employee and break down the walls and barriers demarcating private workspace, many employees want or need to work from home to find the quiet required to concentrate. The ability to work from home shaves hours off commute times and makes many employees’ lives more manageable. 

If you’re facing resistance from a contract gig about freelancing or from managers about doing staff work from home, use this cheat sheet to prep your pro-remote arguments. We’ve assembled the top arguments that managers assert against working from home, and the best ways to respond with supporting facts and tactics to make remote work function well for both manager and hired gun. You can also always point out that Fortune magazine recently flagged Flexjobs’ ranking of the top 100 companies for workers who ply their trade from home — a sure sign that work-from-home has gone legit.

Myth: Work-from-home employees slack off and are less productive.

Reality: Workers report more productivity, and outside research backs them up.

Tactic: Put a solid onboarding process in place for remote workers. 

Some nine out of 10 workers reported in a 2016 survey that they’re more productive at home. You don’t just need to take their word for it: Outside measurement indicates that when workers are given the option to perform their duties from home, they’re more productive. Chinese travel site Ctrip researched productivity levels of call center workers and found that those working from home tackled 13.5 percent more customer interactions. 

Companies who successfully use remote teams often take extra steps to onboard their remote workers. Onboarding members of remote teams helps establish processes and policies for accomplishing work and setting expectations about the frequency with which remote workers should interact with managers. This onboarding typically involves training workers on software or shared (virtual) work environments and is typically run via a formal, scheduled, and organized presentation or call — just like it would be for in-office workers. Managers need to remember that workers consider desking from home a privilege, so provide clear expectations to make sure employer and employee play by agreed-upon rules. 

Myth: Out of sight, out of mind.

Reality: You can sometimes get more virtual facetime on a screen than in an office. 

Tactic: Train management on how to handle and oversee remote workers.

Middle managers often place in-office restrictions on projects, which effectively creates roadblocks between work-from-home full-timers or freelance project talent. You can’t really blame them: Managers tasked with herding a team toward a goal are themselves part of a management team pursuing even larger goals, so they’d like to keep an eye on all the people moving the parts that constitute a project’s deliverables. 

Mid-level managers are typically concerned about productivity and budgets. Fortunately, by providing these managers with training on cloud-based technologies and empowering them to play a role in telecommuter and work-from-home onboarding, they can keep their eyes on the balls remotely. Of course, some of these measures need to come from corporate, but if you’re facing manager resistance to working from home, discuss your interest or willingness to check in frequently. 

Remote workers surveyed have said that they think the ideal amount of contact with a remote manager is once a day or even just once a week. This might work for freelance, but an antsy manager at your full-time job may expect more contact — or at least to see that each team member is just one click away and is “live” on Skype, Slack, or an instant messaging platform. Reinforce to managers that you’ll gladly be digitally available, and be sure to offer quick responses if or when a manager reaches out to you. On the money-saving front, remind your manager that working from home reduces the need for corporate reimbursements for carpooling and keeps the department’s physical footprint smaller (thus leading to savings on office real estate costs).

Myth: There is no “WFH” in “Team.”

Reality: Remote workers are happy, productive, and therefore loyal to the team.

Tactic: Suggest team-building, periodic facetime or phone time, an annual or semi-annual retreat, or periodic travel to corporate headquarters.

Some managers feel that team cohesiveness falls apart in the absence of frequent facetime and water cooler huddling. This is a valid risk, and some work-from-home pros do admit that they don’t feel as bonded to colleagues as their in-office counterparts. But is bonding with colleagues always the point if a collection of remote workers and contractors are still achieving group goals? Research from the University of Warwick indicates that happy workers are 12 percent more productive. Other research indicates that multi-time zone workplaces are often happiest, which means that even if employees and contractors worked from inside hometown offices they’d still have to collaborate with colleagues remotely. While some workers sit inside the office walls and some workers sit outside of them, managers will still need to assemble and lead teams

If you’re making the case to work remotely and encountering manager resistance, remind them that most contemporary work-sharing platforms allow one-to-many communication (all members of a team can speak in front of one another with leaders) as well as one-to-one contact (workers can dialogue directly). This means that the breakouts and chatter following an all-hands meeting are intuitively replicable with technology. Also, make it known you’re willing to participate in periodic facetime, visits to the head office, or annual travel to corporate headquarters. 

Corporate Challenge: Technology concerns.

Reality: Traveling employees as well as remote contractors are both equally likely to encounter connection failures.  

Tactic: Choose iterative technology environments and train workers and managers.

Remote workers (especially roving digital nomads) may run into challenges completing work and collaborating due to dropped phone calls, spotty internet service, computer problems that can’t be quickly resolved with an onsite IT team, and the vagaries of working from co-working spaces, coffee shops, and hotel lobbies. The same problems may arise when less tech-savvy middle managers aren’t trained adequately on the technologies that regularly support remote productivity (instant messaging platforms, for instance). 

If you’re facing concerns from an employer or client about your ability to make progress from unpredictable locations, remind them of work-sharing technologies that you can both use to check in throughout the day to keep a project moving. For instance, you can use Dropbox or Google Docs to log in (when a connection is available) to edit or transfer documents, and a manager can log in later from their time zone to handle responses. Additionally, remind them that you’re willing to train on the best ways to use these technologies and that perhaps you and managers could do this together.

Corporate Challenge: Cybersecurity concerns.

Reality: With more data than ever stored in the cloud, security is a concern for all workers. 

Tactic: Involve IT in decision-making about platforms that make sense for projects with a fully or partially remote team.

Remote workers (whether telecommuting for one employer or several) are vulnerable to security breaches that differ from in-office concerns. These workers may use a mix of Wi-Fi networks (the home Wi-Fi, networks in coffee shops, co-working spaces, etc.) as well as a mix of personal and work-configured email accounts, for instance. However, remote workers aren’t the only folks using this technology — office staffers also use digital devices and mobile phones in varying environments. 

If cybersecurity is a concern, involve IT professionals in choosing and assessing risk of cloud-based platforms. Additionally, get their input on best practices to prevent data breaches or losses. For instance, remote workers could use a dedicated corporate issued laptop for work, and the company can ensure that documents and collaborative environments are configured with passwords, firewalls, and other safeguards. Many digital nomads draft documents on a personal laptop, then copy them into a shared work environment or send them via email for a staffer to configure in a protected content environment. 

Corporate Challenge: “Tone” on calls, IM, and email.

Reality: Tone is a challenge whether you’re in the office or working remotely. 

Tactic: Vary communication methods and occasionally hold “live” conversations. 

Managers, remote staff, and in-office staff alike all worry about the tone of their emails and instant messages, and this fear translates when workers are collaborating via technology and across time zones. Some 41 percent of work from home laborers and 42 percent of in-office workers worry about tone in email communications, according to Cyberlink and YouGov. 

One worker’s terse email reply might be their way of providing quick feedback and keeping a project moving amid a busy morning, while another’s terse reply might convey an angry attitude. One manager might like a quick reply from a worker acknowledging receipt of a message, while another might not want all that inbox clutter. Whether working with the same team year after year, or a new project lead on a 1099 assignment, it’s hard to know how to interpret electronic communications that don’t provide the real-time clues evident in person, such as body language, tone of voice, or pauses in communication. Offices with frequent electronic communication and a prevalence of remote workers might want to counter this uncertainty by occasionally encouraging phone calls or video conferences so that team members get to know one another’s tones. They might also encourage both employees and contractors to explain their electronic communication style at the outset of their work relationship. Another tip: Encourage smart use of email subject lines, perhaps flagging which notes are “FYI” and which require action and whether it’s urgent. 

Corporate Challenge: Can everyone WFH?

Reality: No, not everyone can work from home, but most people can work from home a day or two a week.  

Tactic: Identify tasks that you can perform remotely and what percentage of the workweek they consume. 

Remote work isn’t effective for every single position in a company. Some people need to work collaboratively side-by-side with their teams to iterate projects, and some professionals deal with highly confidential material. Legal, human resources, and many business roles involve private or even classified files. And certain industries can’t have key personnel working from home – for example, a semiconductor company employee can’t maintain a clean room in his/her garage, a biologist can’t keep petri dishes outside the lab, etc. However, most employees spend a portion of their week performing administrative duties, dialing in to conference calls (which could be done from home or the office), or writing reports, briefs, or analysis that requires some “thinking time.” Even secretaries and office support staff can work remotely with phone call forwarding and other simple maneuvers. If you’re agitating for partial work from home privileges, audit your workweek and flag tasks that you could capably handle from home. Then make the case to management that, say, 20 percent or 30 percent of your duties are “location agnostic.” 

Companies and Industries Paving the Way for Flexible Work

Today, remote jobs are seemingly everywhere. Back in 2006, even before the rise of smartphones and better cloud-based apps for communication, Best Buy debuted a “flexible work” program that yielded a 35 percent jump in productivity. Not only did employees enjoy flexibility, but their employer saw a better bottom line. In recent years, some employers such as IBM, Yahoo, and Aetna famously called their telecommuters back to the office — with much grousing and backlash. Many critical articles asked if these companies went about managing remote workers the wrong way and reported on employee resentment. 

Fast forward to the present, and each year Flexjobs tracks 47,000 companies that employ varying percentages of remote workers. Among the top 15 employers for 2017 are household-name companies such as Amazon, Kelly Services, UnitedHealth Group, Hilton Worldwide, Convergys, Xerox, and Kaplan. Even IBM has re-entered the ranks of the telecommuter and remote work-friendly employment scene.

What Job Roles and Sectors Are Conducive to Remote Work?

Generally speaking, according to an infographic on remote workers created by Highfive the bulk of remote jobs fall into the services (18 percent), management and business (14.5 percent) and office/administration (13.9 percent) categories. According to Flexjobs, industries including medical/health, computer/IT, customer service, education and training, sales, finance, and government all deploy a significant proportion of their work via a remote workforce. According to Glassdoor research, remote jobs with the fastest wage growth include solutions architect, business development manager, web designer, and recruiter — all white collar positions that can be performed from a mix of home office (phone, internet) and cloud technology (contact management, document sharing, project management, etc.). 

Look to Small Businesses

Small businesses (those with fewer than 100 employees) are often among the most significant employers of flexible work positions. This is perhaps because small business owners know that providing work flexibility makes up for the lack of cash bonuses, stock options, or other benefits that a larger company can offer — which can be the key(s) to retaining top talent., a site dedicated to remote job search tools and resources, offers examples of businesses hiring in the space. Many are small outfits, such as TinyPulse, an employee engagement company, Vault Cargo Management which boasts a work-from-home team, Aha! Company, and beyond. 

What Is a Digital Nomad and the Digital Nomad Lifestyle?

Digital nomads (also nicknamed “MoBos” – mobile bohemians) are freelancers who work from anywhere. They work to live, not live to work, opting to travel and enjoy experiences or design their life with a sense of mission. Some of them use freelance gigs as “day jobs” to support non-paying activities and experiences, while others are quite intentional about designing a career they can manage from anywhere. They frequently live a simple life and are mindful of the cost of living in the cities where they’re living or visiting. Here are other characteristics common among digital nomads:

  • They’re Mostly Millennials: Digital nomads trend millennial or on the younger side of this generation. After all, if you plan to roam the globe working as a freelancer, it’s likely you may be young and free of location-dependent life choices such as raising children, owning a home, or other factors. 
  • They Gig Online: Digital nomads who begin roaming the globe without pre-established freelance gigs often turn to “gig economy” options including Fiverr, elance, Odesk, Guru, Freelancer, and other profession-specific sites. These venues may offer projects that don’t pay well in their home country, but which when performed abroad go further economically speaking. 
  • They Tackle Services Business: Online teaching, consulting, and writing are among the many services digital nomads can perform from anywhere, which reflects the reality that many remote workers (but especially those who stay on the move) tend to gravitate toward services industries.
  • They Live in “Best Cities for Digital Nomads”: The website Nomadlist tracks the best cities for digital nomad lifestyles based on “internet speed, cost of living, weather, and fun” — a different mix of priorities from other lists tracking best employers or best real estate markets. Thai cities (Chiang Mai, Bangkok, Pai), Bali in Indonesia, Ho Chi Minh City in Vietnam, and European locations like Budapest and Berlin regularly top the listings. With the exception of Berlin ($2,021/month), all cost $1,350 per month or less to live in. That’s not bad for a short-term explorer with a laptop and clients.
  • They Travel in Packs: Just as Airbnb revolutionized the travel industry, digital nomads have given rise to several businesses which offer “work lodging” or “overnight coworking” in key spots around the globe. Outsite, DigitalOutposts, Couch Surfing, Second House, and Refuga are among the businesses offering reasonable short-term (by the week or month) housing that typically includes a private bedroom, a shared kitchen, and communal workspace with like-minded nomads. Coworking spaces also attract digital nomads

Preparing to Become a Digital Nomad

As with most freelancing, the nomadic edition requires that you manage cash flow — either by launching with a proper savings cushion or a couple of steady clients that function like permanent part-time employment. If you’re prepping to hit the road, clean up your balance sheet (reduce debt, clean up your credit), try to line up “passive income” (rent out your home, car, other assets while away), and choose your mobile technology thoughtfully. You’ll want to make sure you have a thorough understanding of how to access Wi-Fi and other technologies abroad, and also prepare for how to keep work moving while in an “on the move” period. (For instance: Pre-plan your access to Wi-Fi, phone and computer charging opportunities, quiet places for Skype/video calls etc.)

Sustaining Life as a Digital Nomad 

The rules for a sane and fruitful digital nomad lifestyle in many ways mirror those any freelancer would follow, but with a few particular twists. Because digital nomads travel and may treat work as a means to an end, versus an end in itself (work for work’s sake), they nonetheless need to master these skills.

  • Managing Insurance, Primary Care, and Taxes: Not having a permanent home base can cause complications at tax time (to whose government do you pay taxes?), when you have medical issues (if you lack a permanent primary care physician), and with insurance options/coverage. If you live outside the U.S. beyond a minimum number of months per year, you may be able to avoid buying health insurance in America, but then you’re still left to find coverage that will travel with you. 
  • Managing Retirement Savings: Self-employed workers don’t enjoy the employer-provided 401k match that some full-timers get, but they can establish IRA accounts and fund them handsomely — and also lower their own taxable income when making contributions to non-Roth versions of these accounts. If the digital nomad lifestyle is going to become permanent for you, the sooner you begin saving for retirement the better.
  • Maintaining Community: Freelancers enjoy their freedom, but sometimes they miss the instant camaraderie of a full-time job. These freelancers may seek out community by working from a co-working space or enlisting in group activities or other routines with friends to make sure they don’t vanish into their bathrobes. But digital nomads who freelance and change locations frequently may need to look at other options for finding community, such as a virtual community for fellow rovers. Puttytribe is one such group, and there are numerous Facebook and other communities. 
  • Keeping Up with Digital Nomad Best Practices: Connect with all the other digital nomads at the annual Nomad Summit, where you can hear TED-like talks on brand-building, moving an offline profession online, and of course work/life balance. If you can’t afford the fee, this group has a Facebook community. Or consider hitting DNX Global where you can hear about required nomad life skills and more esoteric matters, like finding your passion and giving back while making a living. 
  • Positioning Yourself Professionally: If you’re working remotely, create a digital footprint that describes your expertise and include references/testimonials or work samples. You’ll also want to provide contact information you can easily respond to (perhaps email or instant messaging is preferable to, say, that mobile phone that shuts off in India). 
  • Understanding How to Build Your Day: Like all freelancers, you need time “on” and “off” the clock. If you like to reset your rhythm around the local culture you’re visiting, make sure to track your work hours and demonstrate that you’re on top of tasks. Also, set expectations with clients regarding when you’re available online, via phone, or Skype. There’s no reason you can’t enjoy surfing at high tide or a late night in Spain followed by a next-day siesta (these experiences are why you’re a digital nomad!), but if you want to keep your reputation aloft, you’ll need to plan. 

Quiz: Are You Ready to Become a Remote Worker?

Working remotely doesn’t suit every personality. Will it work for you? Take our quiz and see where you fall on the spectrum between corporate full-time cube jockey and globe-trotting e-lancer. There are pros and cons to the security of a full-time office job and the promise of variety and excitement found in the freelance lane. Answer yes or no to the following questions and see where you should hang your shingle. When you’re done, add up all the “yes” answers to see if working remotely is right for you. 

  • Do you work to live, rather than live to work?
  • Do you consider yourself organized?
  • Do you maintain a credit score above 720? 
  • Is variety the spice of your life?
  • Are you skilled at time management?
  • Are you handy with mobile and travel technology? 
  • Do you have virtual storage space where you save and backup work and files?
  • Are you more improvisational than perfectionist?
  • Have you defined your top three marketable skills?
  • Have you developed a digital footprint (LinkedIn, personal website, social media)?
  • Have you developed an online portfolio? 
  • Are you skilled at budgeting?
  • Do you have at least one anchor client or proven referral source? 
  • Are you familiar with Skype and other video chat services? 
  • Can you get work done anywhere – coffee shop, bar, copy shop, convenience store?

Score 5 or Less: Don’t quit your day job

You’re either just straight-up fond of fluorescent lights and a daily commute, or you’re too new in your field to feel confident or competent for the self-promotion and unpredictability that often accompany a remote-work lifestyle. That’s OK. Some 50 percent of all workers are expected to work remotely by 2020 according to London Business School research, but you’ll likely count yourself among the other 50 percent in the office managing these digital nomads or full-time telecommuters while enjoying the 401k match and office parties.

Score 5-10: You’re a day tripper joyriding in the freelance lane

You’ve worked from home for your full-time employer or are fluent with a few freelance side hustles, but you’re just as comfortable in a work office as you are in a home office and prefer keeping “work” and “home” separate. That said, you’re not a total corporate cog and you’re skilled at personal hustling: You know that even full-timers within a large company need to think like entrepreneurs to get ahead, so you network and keep your resume fresh and virtual portfolio active just like your self-employed pals do. Ultimately, you value security and structure over the virtues of untethered work-from-home freedom, but you might ditch a cube for the right reasons – if you could keep your pay/benefits while working from home or if you had a steady anchor client that paid reliably within a mix of freelance projects, for instance. 

Score 10 or More: You’re a digital nomad

You’re comfortable with your own brand, and you’re so used to working with others via technology that you see no need to limit your skills to just one employer. You enjoy exploring your professional skills by spreading them across multiple projects, and you like exploring your workplace, too, changing scene by working from the road, co-working spaces, or digital nomad lodgings in exotic locations. You may be a millennial (or hang out with them) comfortable with the concept that freelance offers its own kind of security, since a continual flow of projects means you’re never overly reliant on just one employer’s business cycle or industry volatility. You’ve learned time and money management skills and work/life balance, too, and you’ve developed an instinct for sniffing out which projects make sense in terms of time, money, professional advancement, and personal interest. 

Remote Worker Toolkit

The following technologies now make it possible to do most work remotely. Whether your employer or client invites you to use them or you educate a manager about how these technologies can help with productivity, you’ll likely use at least half of these tools in your remote work life. 


There’s no question that you need an email account, but the question is which platform? Some clients and employers collaborate within a Google Drive environment, which means you’ll need a Gmail account. Other work environments will provide you with an office email address. And if you’re a full-time freelancer, you can choose any email platform you want, but preferably one linked to your website (, so that your or address doesn’t travel into work contacts’ junk mail folders. There are many solid free or inexpensive email programs, so play around before committing, and check how well you like the programs’ inbox management and archiving tools, scheduling tools (email invites to contacts), and other bells and whistles. Get more tips for tackling email issues, by reading Conquer Inbox Overload with these Email Management Best Practices.


Instant messaging platforms are useful, but team chat is even more useful for remote workers. Programs such as Slack, HipChat, and Facebook’s Workplace platform let multiple people interact in real-time within a group or one-to-one, which reduces superfluous email exchanges.

Video Conferencing

Video meetings can help bring a personal touch to teams that work remotely or if you’re a permanent remote worker trying to maintain social ties with in-office managers. Google Hangouts, Youtube Live, Zoom, and Skype all allow video interactions. 

Online Portfolio and Digital Footprint

Depending on the norms in your field and how hard you’re looking for new work, your online portfolio could be as simple as a LinkedIn page with testimonials and work samples, or as complex as a professional website with your bio, work statement, resume, and examples of work. These days, there are many free or inexpensive web design programs (Wix, Weebly) for those who want a template-based digital address. You can use social media (Facebook, Twitter) to make accounts for your business, differentiating what you discuss on those accounts from what you share on a personal account. Additionally, you can join industry groups where people look for remote workers and freelancers, and create a passive listing that drives work your way., a media portal for content professionals, lets freelancers post their profiles in a Freelance Marketplace for a small fee; there are numerous trade and industry-specific sites that could become part of your digital footprint. 

Cloud Collaboration Software

If you’re sharing documents with others and multiple parties need to edit, remark, comment on, or adjust them, you can use online storage sites such as Box, Google Drive, or Dropbox. Each of these tools lets you share text documents, spreadsheets, and other document formats. Sites like Smartsheet lets you do all of the above, run reports, assign tasks, and collaborate with other team members.

Project Management

If you’re tracking tasks — or your tasks are subject to tracking — there are several project management tracking technologies that can help. Among these technologies are JIRA, Smartsheet, and others.


If you’re tracking a team’s work in progress, or your own, you can use TodoIst or iDoneThis. You can also use online timers to track work hours.

Development and Design

If you’re a software developer or graphic designer, there are several cloud-based resources that let you host, showcase, share or research code online. GitHub, InVision, Cloud9, CodePen, and Skitch are among the sites that help roving coders.

Scheduling or Quick Feedback

Remote workers who collaborate with teams must frequently “herd cats” to schedule meetings or calls at a time that works for a majority of players, or sometimes they need quick group feedback (a yes/no/maybe vote) on a decision. Free tools such as Doodle let multiple people vote on their preferred options, and survey tools such as SurveyMonkey allow you to put together a questionnaire quickly so you can get key feedback before moving forward with a project. There are many such tools designed for contractors and managers in specific industries, which can let a freelancer keep set hours and opt-in if schedule requests appear outside of them. For instance, MindBody is a tool for spas and wellness studios that lets massage therapist contractors or spa staff accept reservations remotely. Fitness instructors, coaches, tutors, contractors, and auto repair shops also use these tools. 

Empower Remote Workers with Work Management in Smartsheet

Resource Management by Smartsheet is a powerful resource management software that helps to effectively manage the who, the what, and the when behind projects.

With Resource Management by Smartsheet, you can more easily build the best team for a project, keep project schedules and budgets on track, and confidently forecast business needs.

When teams have clarity into the work getting done and by whom, there’s no telling how much more they can accomplish in the same amount of time. Watch a free demo to learn more about Resource Management by Smartsheet.



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