Digital Nomad Lifestyle: 14 Years, 50+ Countries of Real Talk

And I will take my life before I sit in traffic to go to an office job again.
I’m Loren Ross, founder of LRoss Marketing Consulting & Digital Nomad Lifestyle.
I’ve worked from coworking spaces in Medellín, tiny cafés in Vietnam, and Airbnbs across Europe.
I’ve dealt with internet (and power) outages, 3 AM client calls, visa problems, and serious loneliness in beautiful places.
This guide gives you the real version of what this lifestyle actually looks like.

The digital nomad lifestyle means earning your income online while living in different locations around the world. Instead of being tied to one city, you use remote work to:

• Experience new cultures
• Choose climates and time zones that work for you
• Design a life with more freedom and flexibility
• Outrun the voices in your head
  

But it’s not a permanent vacation. 

I tell people all the time

I’m seldom 100% working, but I’m also rarely 100% travelling. 

I exist in the tension between the two, and for me that tension keeps my life interesting. 

Keeps things from feeling stagnant.

Over 14 years, I’ve seen three main paths:

• Freelancers & Solopreneurs – Writers, designers, developers, consultants. Maximum flexibility, but income can be unpredictable.
• Remote Employees – Full-time staff with “work from anywhere” policies. More stable income, less control over schedule and time zones.
• Entrepreneurs & Business Owners – E-commerce, agencies, online courses, digital products. Harder to build, but can be very rewarding long-term.
  

Each can work. None are effortless.

The Upsides

• Geographic Arbitrage
  Earn in a strong currency while living somewhere cheaper. I’ve lived in places like the Dominican Republic for around $1,000/month while earning US-level income.
  • Pro tip – don’t talk about this in front of local people. You’re essentially boasting about how you’re gentrifying their neighborhood. Keep it to yourself, locals don’t want to hear about how much money you have and how cheap everything is in their hometown. Read my article here about whether digital nomadism is colonialism for more on this.
• Self Reliance
  50+ countries will force you to adapt. You become more resilient, self-reliant, and comfortable with uncertainty—skills that will can help you. This is if kept in check – see more on the downsides below.
• Self Discipline
  If you can grow a career while seeing the world, you’re going to learn a lot about self-discipline. Lots don’t learn, burn-out and return to the suburbs – but for those who can stick it out, it’s a real level-up. See my 5 productivity tips for digital nomads here.
• Seldom Boring
  Working from beach towns, mountain cities, or buzzing capitals can spark new ideas and make work feel less like “grind, repeat.”
  • If you’re someone who gets easily bored with jobs and life in general – this lifestyle could suit you well
    

• Loneliness
  Deep relationships are harder when you’re always moving. You have to actively build community and look after your mental health.
  • There is a sweetness to the melancholy of loneliness, which is important to dip into from time to time, but don’t get stuck in it – that shit is dangerous.
• Too Self-Reliant
  This plays into the loneliness aspect. You can actually start becoming a bit too isolated and confident in yourself and begin to believe that you don’t need anyone else, which is a lie.
  • Being able to do whatever you want whenever you want, wherever you want is nice for a few months – but you will get tired of it. If you have a deep desire to explore the world and don’t want to burn out, then you need to recognize your reliance on others, and adapt to other people’s needs (trust me)
• Time Zone Fatigue
  Clients in the US, you in Bali? Get ready for 3 AM calls or midnight meetings. It’s doable, but it’s tiring.
  • Writing this at 7:30pm from Thailand – before my meetings tonight – was up till 2am last night… it’s part of the job man.
• Income Instability
  Some months are great. Some aren’t. Most successful nomads build multiple income streams so they’re not relying on a single client, job, or platform.
  • This is for more advanced folks, when you’re starting out find something you’re good at that you’re getting good reception on and triple down on it, then you can diversify IMO. The entrepreneurs with the least amount of income stability are the ones who start a project do it for a year or two, then quit that to build another one, and so on and so forth.
    

For a deeper dive, see my full pros and cons guide.

You don’t need to be a genius or a programmer, but you do need a few non-negotiables:

• Self-Discipline – No boss, no office, no one checking if you’re online. You’re responsible for your own output.
  • You may not be a master at this, I certainly am not – but you will get better and you do need some of this to get going. 
  • Tip – best way to learn anything is to do it. Put yourself in a situation where you have no other choice but to be self-disciplined. 
• Basic Tech Confidence – Using online tools, troubleshooting WiFi issues, managing files in the cloud / Google Drive.
• Adaptability – New languages, currencies, and systems are constant. If you hate change, this will be rough.
  • This stuff can overwhelm me, but it’s generally quite stimulating – while you can learn this, I believe this is something that’s a bit more baked into your personality – be honest with yourself, do you really like that much changing? If not, then you can always take the slowmad approach.

From 14 years on the road, these skills matter most:

• Internet Management
  Learn how to check speeds, choose reliable areas, and use backups. Here’s my guide on getting fast WiFi anywhere.
• Time Management
  You need a structure that works without an office. I use time-blocking and location-based routines plus these remote productivity tips.
• Financial Discipline
  I recommend 3 – 6 months of savings at all times, unless in life or death situations. That buffer lets you make smart choices, not desperate ones.
  • For most people you will have to take a step back in lifestyle when starting your new career. For young people out there – if you’re in a job you hate, don’t buy a fucking car you can barely afford, don’t buy a house you can barely afford, the less debt you have the more freedom you have to make a career switch down the road.

Best Digital Nomad Destinations (From 50+ Countries)

Shortlist from my own experience:

• Bali (Canggu/Ubud) – Big nomad scene, decent internet, lots of cafés and coworking. Crowded and touristy, but great if you want community.
• Chiang Mai, Thailand – Affordable, reliable internet, easy to meet other nomads. Ideal for budget-conscious beginners.
• Cape Town, South Africa – A great introduction to sub saharan Africa for Americans / Europeans, like Medellin – need to be a bit more careful here – but it’s beautiful.
• Lisbon, Portugal – Beautiful, creative, international. Costs have risen but still a solid European base.
• Medellín, Colombia – “Eternal spring” weather, growing nomad scene, affordable if you’re smart about safety.
  

If you want a more detailed comparison, see my guides toSoutheast Asia on a budget and thebest cities in Europe for digital nomads.

A glimpse of my digital nomad life, one memory from every country on this journey.

You don’t need to quit your job tomorrow and fly to Bali. In fact, I recommend the opposite. Here’s a simple 12-month roadmap:

For a more detailed version, read my step-by-step guide on how to become a digital nomad.

This is the best way to do it looking back – but I didn’t follow any of those rules really. I just jumped – for some people that’s the best way to do it.

For me, yes.

This lifestyle has given me:

• Freedom to design my days
• Experiences across 50+ countries
• Skills, resilience, and perspective I never would have built in a cubicle

But it’s also meant:

• Lonely nights in beautiful places
• Client emergencies at 3 AM
• Constant decisions about visas, money, flights, and logistics

The digital nomad lifestyle isn’t an escape from work. It’s a different way of combining work, life, and growth. It’s incredible if you value freedom and are willing to trade comfort and predictability for it.

If you’re seriously considering this path, start with realistic expectations. Read the full pros and cons, build your skills, and give yourself enough time (and savings) to experiment properly.

But most importantly, fucking do it man – it’s never going to be the perfect time.For more honest insights, tools, and stories from the road, you can follow along at @officialdigitalnomadlifestyle on Instagram and YouTube.