Digital Nomad 101: Should You Travel Alone or With a Group?

Hannah Miller

Have you been considering how to become a digital nomad? If you have, you know it’s no easy task. Think about changing your lifestyle for a second and you’ll probably come up with a dozen obstacles off the bat. The main problem: there’s no one path to becoming a digital nomad.

While there are an array of step-by-step guides, marketed to help you figure out how to become a digital nomad, there’s no one fixed path to the destination. Every digital nomad has a different style, different personal goals, and a different income stream. Choosing to make the leap towards an out-of-the-box lifestyle is a huge life decision. Can someone who has never worked remotely, OR traveled extensively, become a digital nomad? Is it actually possible to get started without relevant travel/work experience?

Believe it or not, most digital nomads start out with very little self-organized travel experience, usually transitioning out of office jobs and “normal” suburban lives. Although every individual has a slightly different approach, most people take one of two paths to getting started as a digital nomad: either diving in solo or via an organized group program.

Each launch method comes with its own set of pros and cons. Five digital nomads, from both group and solo travel backgrounds, came together to help us pin down the benefits and drawbacks of each one.

How to Become a Digital Nomad: Starting Solo

Having read websites and blogs until your eyes glazed over, you’re (mostly) confident about working and traveling around the world. Relying on personal research and prior travel experience, some new digital nomads take the leap on their own. Solo digital nomads set their own pace and budget, plan their own lodging, create their ideal work environment, including wifi and equipment setup, in cities of their own choosing, and are in control of every step of the process. While this method does provide more flexibility, solo digital nomads may experience a tricky trial and error period as they find their feet.

Brooke Siem

An author and freelance writer, Brooke has been traveling full-time as a digital nomad for years. She’s currently located in NYC, working from her home office or a cafe. Her work style requires quiet and concentration, so she travels with ear plugs, Bose headphones, and a white noise app.

The Sueiro Family

Jess & Will stumbled into digital nomadism before they knew what it was. Jessica Sueiro worked as a designer before deciding she wanted a more flexible schedule to enjoy life with her children. She launched her own graphic design agency and has been a digital nomad for over a decade now. She and her husband, Will, just launched their second digital nomad business, WorldTowning. They work wherever they are, from cafes to airports, or laundromats, and are currently based in Europe.

Pros of Starting Solo

Gaining Confidence

Self-started digital nomads gain the confidence to handle anything the future throws at them. Brooke Siem found that starting solo helped her to trust in her ability to work in different environments. “As a creative person, I wasn’t sure if I was going to be able to do my work anywhere. I’ve learned that with the aid of my ridiculous headphone setup, I can get it done wherever I go, which is a powerful thing.”

Privacy, Flexibility, & Independence

Those who start solo are in complete control of their schedule, finances, destinations, and living conditions. They can choose to live and work privately, to pack up and leave on a whim, or take a rest day at home. As Jess Sueiro puts it, “We are free to go, live, and be our authentic selves!” As a family who values privacy and free time, starting solo was the best option for the Sueiros.

Zero Preconceptions

Jess also pointed out one unusual benefit of starting the digital nomad life solo: “We had no preconceived idea of what the digital nomad life should look like. I think this is an advantage, because we were able to create what felt right for us, rather than what others before us had done or what others said worked for them.” Starting solo allows travelers to start on the right foot, crafting a life for themselves based on personal preferences.

Cons of Starting Solo

Reduced Community Support System

Jessica Suiero  points out the reality of the effect of reduced community support: “That means financially, creatively, and on those days where you just need a pep talk, there might be no one there to give it. If you are a digital nomad within a group setting, you have so many more resources to take advantage of and minds to bounce ideas off. Starting out in a new land can be very daunting; however, if you are sharing the experience with other digital nomads who share a common goal, you can support each other in ways that are unavailable for solo digital nomads.”


Brooke Siem points out that lonliness is real: “Today, for example, I literally have not spoken to another human. When you don’t have colleagues to interact with, you have to search for social outlets, and making new friends in a new place is exhausting in itself.”

Research-Heavy Planning Phase

Solo digital nomads have to do all their own research, book their lodging, and find a decent internet connection, alone; which can be challenging.

To make it easier, Brooke Siem recommends that new digital nomads, Start in a country or location where people at least have basic conversational skills in your language. It’s hard enough to adjust to a new life, but when you can’t communicate with anyone, it’s isolating. The work stuff, you’ll learn. One day you’ll slack a little too much and drop the ball because you’re having a great time wherever you are, and then you won’t make that mistake again. That’s the easy stuff to learn. Battling the loneliness is harder, especially if you’re not working in a co-working space. So, go where you can understand people, get used to your new life, and then head to that exotic locale.”

How to Become a Digital Nomad: Starting in a Group

In an organized group program, new digital nomads trade in some of their freedom for the ease of a pre-planned journey with a community of other digital nomads. Programs such as WY-CO, Unsettled, and Hacker Paradise take care of housing, workspaces, and activities, leaving new digital nomads free to explore and interact within a built community.

These programs can run anywhere from a few weeks up to a year in length. Some are location-based, providing a beautiful international base from which to use co-working space, gain professional development, network within the program community, and explore the local area. Others provide trip itineraries with round-the-world experiences, yoga, language classes, cultural day trips, and other events. Each group program offers a slightly different set of amenities.

Costs tend to range from $500-$700 per week, all-inclusive. All of the programs are BYOW (bring your own work) – this is a way to improve and knuckle down on the digital work you’ve already begun, not a beginner’s workshop. Keep in mind that most group programs are application-based, meaning that each participant is individually vetted for suitability to create the ideal digital nomad community.

Pros of Starting in a Group


Most group program alumni will tell you that community tops the list as the biggest benefit of their experience. Paulina and Aviv, Unsettled alumni, say that “The community aspect of starting in a group setting can really offer you the support and inspiration that you need when you’re just getting started, especially if you’re solo… As Aviv and I continue to think about how to make the digital nomad experience a sustainable life experience for ourselves and for families, the community inspiration we received in the Unsettled group setting plays a major role.”

Facilitation / Simplicity

Group experiences with companies such as these allow new digital nomads to sit back and relax as the program leader organizes lodging, travel details, and experiences. Rachael Rife, We Roam alumni said that, “The budget I was planning to spend on accommodation was what WeRoam charges as the monthly fee, but their package includes many added benefits like community and all the logistics being taken care of.  It seemed like the perfect way to glide into being a digital nomad with much less effort and time than I would have to put in with solo travel.”


With this new community of digital nomads comes countless opportunities for collaboration. In learning how to become a digital nomad, spend time working with others in the facilitated group work settings most programs provide. Most programs set up events and workspaces in which to meet other digital nomads with experience that could boost your own projects. Paulina & Aviv appreciated that, “The community aspect of starting in a group setting can really offer you the support and inspiration that you need when you’re just getting started, especially if you’re solo. The networking and the facilitation adds a special spark to the entire experience”

Encouragement to Push the Boundaries of Your Comfort Zone

With all the travel details taken care of and a community support systems, some digital nomads find it easier to push the boundaries of their comfort zones. Micki McNie, a Hacker Paradise alumni, pointed out that, “I went places that I would not have chosen to go on my own like SE Asia, and that renewed my love of travel and pushed me further out of my comfort zone which is exactly what I needed.”

Cons of Starting in a Group

FOMO & Overstimulation

With so many opportunities to participate in the community, fear of missing out and overstimulation can become an issue. Finding the balance between work and play in order to find your productivity peak zone is really important. Rachel Rife offers the following advice: “You can’t do it all and you have to find your personal balance. It takes extra diligence to pull off this lifestyle and not let work and health slip.”

Paulina adds this: “Starting in a group cultivates that magical sense of community and everything that comes with community: events, eating out, late-nights spent talking, excursions, and so much fun that you don’t want to miss a thing! Learn to balance your priorities quickly while staying flexible and spontaneous and everything will work out. Balance is key!”

Strict Schedule & Cost

Micki McNie began to feel the strain of a predetermined schedule: “After four months of group nomading I wanted the freedom to stay or go as I pleased rather than being tied to an itinerary. And I also needed a little “me” time since at heart I’m an introvert.”

When participating in a group program, digital nomads have fixed costs and a fixed itinerary. While this does free up time to work on projects and relax, it can feel restrictive to some.

Group Compatibility

Micki McNie points out how important finding your tribe is, within the larger groups: “I find that groups tend to drift towards becoming party groups and if staying out drinking isn’t your scene it’s easy to feel excluded. The size of the group matters because in a small one you’re kind of stuck, but in larger ones you can find the people you mesh best with.”

Solo vs. Group: Questions Help Make the Choice

When it comes down to it, the best launch method is the one which you’ve customized to fit your own personal preferences. Travelers who value flexibility and quiet time might find that being a solo digital nomad works best for them. On the other hand, if you’re worried about “doing it right” and handling logistics, a group experience might be the way to go. Here are some questions to consider before going solo or joining a group:

What does your work look like?

The digital nomads interviewed prove that working from the road can look wildly different from nomad to nomad. Some own start-up businesses, others are freelancers, one is a life and health coach with a husband who runs a restaurant chain from afar, while another invests in real estate. The work you do may help to define what digital nomadism looks like for you. What kind of work set up do you need?

If your work requires privacy, high-quality wifi, and set working times, the flexibility of solo travel is the best bet. However, work that revolves around collaboration and flexible hours will thrive in a group setting. The Ultimate Digital Nomad’s Buying Guide will help you build your mobile office.

Pro Tip: Whether you start solo or in an organized group program, the Setout Collection provides the perfect selection of bags for digital nomads. Get packing tips from experienced digital nomads here.

What are your personal preferences for travel?

Do you prefer quiet evenings or do you like organized events? Would you rather be in control of where you’re going next, or are you okay with being along for the ride? Keep in mind that group trips focus on community and experiences, often causing burnout for the introverts among us. At the same time, going solo can be too lonely for travelers who value community. Consider your must-haves for an ultimate digital nomad experience to determine where you best fit.

Individual personalities can affect your immersion experience as well. Introverts might lean towards going solo, but may struggle to build a community on their own. Try stepping outside of your comfort zone and participating in a group.

Are you an extrovert? If so, the idea of built in community might appeal to you, but it may not be the challenge you’re looking for. Try going solo, diving into cultural immersion, and making friends across borders wherever you go.

Would you rather dive into full immersion, or ease in slowly?

Digital nomad groups take the hassle out of planning, but on the flip side, solo travel provides the opportunity for full immersion. If you’ve traveled before, are confident with logistics, and want the full immersion experience, a solo start is the way to go. However, if you’re worried about handling the details on your own, consider the group experience as a way to learn from others and ease into taking control.

Do you prefer financial flexibility or a reliable budget?

How reliable will your income be? Do you have money set aside for a group experience already, or will you be paying as you go? Joining (and staying in) a group will be easier if you have the bank to back it up. If month-to-month budgeting is your style, going solo will allow for flexibility during the transition period to living and working internationally.


While every digital nomad has a different “origin story,” most start out on their own, or via an organized group program.

A group program might be for you if:

  •  You’re looking for an organized, all-inclusive international experience from a week to a year in length
  • You’re looking for community and an environment in which to develop professionally, make friends, and ease into the digital nomad lifestyle
  • You have a steady or fixed income
  • You value community, simplicity, and collaboration

However, some digital nomads may struggle with the fixed schedule, social overstimulation, and lack of flexibility.

Starting solo might be for you if:

  • You prefer taking planning into your own hands
  • You value flexibility in schedule, privacy, and the independence to explore at your own pace
  • You are seeking to stretch your budget further

However, solo digital nomads may also deal with loneliness, a research-heavy planning phase, and a reduced community support system.

There is no “right” way to take the digital nomad leap; your choice depends on personal preferences, work suitability, and personal goals.

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