Digital Nomad Getting Started and Planning

By Robert C. L.

My mentor John Smith says, “Meticulous planning is key to start.” He’s right.

Reducing expenses, earning online income, and visa research enabled my nomadic lifestyle.

But it wasn’t easy.

This guide shares my real-world tips so you can turn the digital nomad dream into reality.

I provide practical steps from budgeting to work options that helped me.

If you want to travel the world and work remotely, keep reading to start your exciting journey.

Table of Contents


Digital nomad getting started and planning, what to know?

Embarking on a digital nomad journey involves…

meticulous planning, assessing skills, financial preparation, and…

… embracing a supportive community, setting the stage for a fulfilling and successful nomadic lifestyle. (1)

What is a Digital Nomad?

YouTube video

Source: Tom Gregory Tech

A digital nomad is someone who EARNS A LIVING working remotely, usually…

… in a freelance or location-independent online business role. (2)

This allows them to TRAVEL EXTENSIVELY and live a NOMADIC lifestyle.

As a digital nomad for 3 years, I’ve enjoyed the FREEDOM of working from anywhere with an internet connection.

It’s allowed me to visit over 15 countries while maintaining my income online.

The pros of this lifestyle include:

  • Location independence – WORK FROM ANYWHERE with wifi
  • Flexible schedule – NO 9-5 SCHEDULE, work when you want
  • Travel – IMMERSE in new cultures and locales
  • Lower cost of living – CUT EXPENSES by staying in cheaper destinations

Potential cons:

  • Isolation – LACK OF COMMUNITY without a home base
  • Connectivity issues – UNRELIABLE internet can disrupt work
  • Tax/legal challenges – COMPLICATED visa and residency rules
  • Income instability – FLUCTUATING client work and pay

Assess if this lifestyle suits you.

It requires self-motivation, an online income source, and comfort with uncertainty.

But for remote workers seeking adventure, it offers unparalleled freedom.

My tips will help you transition smoothly.

Essential Steps to Become a Digital Nomad

Digital Nomad Getting Started and Planning

1. Assess Skills and Experience

Becoming a digital nomad requires honest self-evaluation.

What skills, education, and work experience make you a strong remote worker?

Many digital nomads have backgrounds in software engineering, writing, marketing, teaching, or design.

Determine your strongest marketable skills.

Then research potential online gig work or freelancing in your field like web development, copywriting, virtual assistance etc.

Identify gaps in your abilities that need strengthening.

Knowing your expertise makes choosing the right remote job easier.

2. Financial Planning

Create a budget reflecting the lower cost of nomadic living.

Analyze your current finances to build savings for the transition.

Where you live largely determines how far your money goes.

Eastern Europe, Southeast Asia, and Latin America are affordable destinations.

Research expenses like:

  • Transportation: $150-300
  • Housing: $500-1000
  • Activities: $150-300
  • Misc expenses: $100-200

Pick locations balancing cost and your career.

Building financial foundations enables stress-free nomadism.

3. Building a Portfolio

Craft an impressive online presence and diverse professional network.

Building a portfolio highlights your skills and experience.

Maintain robust profiles on LinkedIn, GitHub, Upwork, and Fiverr.

Curate relevant work samples like writing clips, coding projects, and designs.

Proactively connect with other digital nomads through Facebook groups and Slack channels.

Position yourself as an expert by blogging, vlogging, or podcasting.

Supply compelling proof of your capabilities.

4. Choosing a Nomad-Friendly Location

Nomadic living means diving into new cultures.

Prioritize destinations with strong WiFi, access to coworking spaces, and nomad communities.

Many nomads love Colombia, Portugal, Thailand, and Mexico.

Evaluate countries with digital nomad visas like Estonia, Croatia, Costa Rica, and Czech Republic.

These provide legal long-term stays.

Alternatively, colivings like Sun Desk, Outsite, and Roam provide built-in communities.

Pick locations that excite you both personally and professionally.

Digital Nomad Getting Started and Planning 2

5. Logistics of Nomadic Life

Embrace organizational skills for stress-free travels.

Secure necessary permits, licenses, visas, bank accounts etc.

Use travel insurance to protect health and belongings.

Schedule routine medical care when stateside.

Leverage VPNs and international SIM cards for internet access.

Use Wise or TransferWise for money transfers.

Address tax obligations.

Streamline logistics through services like Remote Year or Hacker Paradise.

Proper planning prevents headaches.

6. Selecting Nomad-Friendly Jobs

Choose remote work allowing location independence.

Software development, digital marketing, writing, customer service and design are excellent fields.

Use established job boards like We Work Remotely, RemoteOK, and FlexJobs.

Consider freelancing on Upwork, Fiverr, or Toptal.

Schedule overlapping hours with US teams.

Be open to unusual schedules respecting time zones.

Secure long-term clients for income stability.

Stay vigilant for new opportunities.

With proper diligence, digital nomadism can be a sustainable lifestyle rather than a vacation.

In closing, evaluate your skills, budget wisely, craft an impressive portfolio, pick suitable destinations, streamline logistics, and choose location-independent work.

Prioritizing these steps positions you for an adventurous remote work lifestyle.

The world is your office with proper diligence.

Welcome to your new life as a digital nomad!

Pros and Cons of Digital Nomadism

The digital nomad lifestyle offers unique benefits coupled with distinct challenges.

Evaluating the pros and cons allows making an informed decision about remote work.


  • Travel and Experience New Cultures – Become immersed in foreign lands while working remotely. Digital nomads can satisfy wanderlust and experience the world.
  • Lower Cost of Living – Nomadic living reduces expenses compared to Western countries. For example, renting an apartment in Chiang Mai, Thailand costs ~$500 per month versus $2000+ in Los Angeles.
  • Adventure and Growth – Digital nomadism pushes comfort zones, fosters independence, and creates enriching cultural exchange. Stepping outside routines sparks personal growth.
  • Location Independence – Work remotely while living anywhere. Digital nomads can relocate based on cost, weather, interests and visas. Location flexibility is a top perk.
  • Improved Work/Life Balance – Blur the lines between work and travel. Sightsee after finishing the workday. Schedule work around passions. Digital nomadism makes integrating work and life easier.


  • Unreliable Internet – Remote work relies on steady internet. Developing countries often lack connectivity. Internet outages severely disrupt productivity.
  • Loneliness and Isolation – Frequent moves limit developing local connections. Time zone differences reduce real-time communication. The solitary lifestyle has downsides.
  • Lack of Structure – Abundant freedom makes creating structure difficult. Missing routines around sleep, fitness, and work lowers motivation.
  • Legal Constraints – Visa requirements limit stays to 30-90 days in most countries. Managing extensions and paperwork is tedious.
  • Tax Complexities – Digital nomads deal with IRS obligations and foreign income taxes. Navigating different rules gets complicated fast.

In summary, digital nomadism allows adventure, lower living costs, and travel perks.

But problems like spotty internet, isolation, and legal constraints challenge the lifestyle.

Weigh these pros and cons before pursuing remote work abroad.

Tips for Thriving as a Digital Nomad

Digital Nomad Getting Started and Planning 3

Traveling the world while you work from your laptop is a dream lifestyle for many.

However, living as a digital nomad takes savvy planning.

These tried-and-true tips will help you find balance on the road to adventure and success!

Connect with Others through Social Media

Setting up a digital life begins online.

Use popular social media sites like Facebook and LinkedIn to build your network BEFORE you travel.

Join digital nomad Facebook groups to meet other location-independent workers in each new place.

Group members often share affordable housing finds and insider tips on the best coworking spaces.

Coworking is key for staying social—the people you meet may become lifelong friends or even future clients!

Find Jobs on Top Nomad Boards

Sign up for popular digital nomad job boards like RemoteOK, WeWorkRemotely, andNODESK to browse thousands of remote listings.

You’ll find positions in fields like writing, programming, design, and more.

Post your skills and availability too, as many Digital Nomad Community members hire via these boards.

With persistence, you can LIVE and WORK anywhere in the world!

Protect Your Health on the Road

Being your own boss gives freedom but also responsibility.

Research international health insurance options to get covered if accidents happen abroad.

Some digital nomads like SafetyWing which offers affordable short-term plans perfect for location independents.

Otherwise prepare to self-pay for any medical costs.

Your health is important—don’t risk ruining your Remote Life by the chance of a broken bone!

Maintain Work-Life Balance

On the open road, days blur together easily.

Establish CLEAR work hours to avoid burnout.

At close of business, put away laptops and engage in local activities.

Whether hiking, dance classes or simply chatting at a cafe, staying social helps mental health.

To sleep sound, adjust to new time zones gradually.

Consistency leads to SUCCESS as a digital nomad!

Manage Money Motionless

A credit card with NO foreign transaction fees means smoother finances global.

Charles Schwab is popular for its International banking.

Watch out for ATM fees abroad—withdraw larger sums less frequently.

Budgeting gets trickier traveling, so automate savings.

Starving artists see Rome, but Smart Money travelers keep thriving long-term!

Embrace Local Adventure

Instead of tourist traps, immerse in locals’ daily rhythms.

Follow blogs by long-term residents in upcoming destinations.

Ask locals directly for authentic, off-the-beaten-path experiences.

Whether cooking classes, neighborhood parties or photography walks, unique encounters create Memories to last a LIFETIME.

Plus discovering hidden gems boosts wellness and inspires your own unique perspective and stories to share.

Are you ready to start living your dream as a borderless entrepreneur?

With efficient work habits, a supportive community and the wisdom in these tips – you too can thrive as a DIGITAL NOMAD.

Digital Nomad Success Through Hard-Won Lessons

Digital Nomad Getting Started and Planning 4

Master Time Zones For SUCCESS

AS A DIGITAL NOMAD FOR 5 YEARS, I’ve learned difficult LESSONS.

Early on, I missed calls and meetings while working EASTERN TIME from ASIA.

Now I CLEARLY BLOCK MY CALENDAR when UNAVAILABLE and communicate my hours.

Mastering TIME ZONES is KEY to thriving remotely!

Isolating Your Workspace Maximizes Productivity

NOISY COWORKING SPACES initially destroyed my focus.


Having a distraction-free workspace BOOSTS output tremendously!

Always DOUBLE CHECK Internet Speeds

I learned the HARD WAY in COLOMBIA when a place had speeds too slow for VIDEO CALLS.

Now I TEST speeds first to avoid issues.

FAST, RELIABLE internet is NON-NEGOTIABLE for digital nomads.

Balance WORK with Exploration For JOY

OVERWORKING is easy without office hours.

Now I schedule sightseeing between tasks, like working from a CAFE with LANDMARK VIEWS.

BLENDING work-life maintains happiness.

Staying Connected through COMMUNITY

ISOLATION originally challenged me.

Now I attend digital nomad meetups and video chat with LOVED ONES daily for vital SOCIAL bonds on the road.

Investing in relationships strengthens well-being.

In summary, remote work abroad has PITFALLS.

But with SKILL, resilience and wise planning, YOU CAN THRIVE as a digital nomad.

Keep PUSHING your comfort zone – the REWARDS are priceless!

Frequently Asked Questions

How can someone get started with the digital nomad life and build a successful digital nomad career?

Starting a successful digital nomad life takes time, skill set building and hard work.

To lay the foundation, focus on finding a job that allows remote work or build a portfolio of your work online.

Websites like online job boards can help a digital nomad find remote jobs to gain experience and save funds for future travels.

Pursuing a niche skill set through self study or virtual training opens doors to more location independent work.

Starting small with entry level virtual assistant jobs or teaching English online…

… are great ways for new digital nomads to ease into the lifestyle while learning.

Being patient and persistent is key, as success does not happen overnight in the digital nomad career path.

What types of digital nomad jobs or businesses have a good work life balance?

Common job options for digital nomads include…

… web development, graphic design, writing, coding and digital marketing, which…

… all allow productive work from anywhere in the world with an internet connection.

Many professional services like virtual assistance, accounting, customer support…

… and project management translate well to remote work too.

Online businesses selling products, courses or services provide flexibility, especially for location independent entrepreneurs.

Digital nomads also build location independent businesses…

… through freelancing, such as photography, video production or online tutoring.

Work life balance varies per individual, but the digital nomad lifestyle in general…

… fosters more control over work and travel compared to traditional careers.

What locations are popular among digital nomads and offer a lower cost of living?

When researching possible places to base their operations, digital nomads often…

…. consider destinations with a lower cost of living…

…. like Chiang Mai, Thailand, Medellin, Colombia, Lisbon, Portugal, Tbilisi, Georgia…

… and Ho Chi Minh City, Vietnam.

These spots remain popular thanks to their lively expat communities, nice weather, affordable housing and culture.

Other factors drawing digital nomads abroad include fast, reliable internet connectivity and visa situation ease for long term stays.

Comparing costs factors like accommodation, food and transportation online…

… helps determine the most sustainable locations for maintaining a budget while traveling long term.

How do experienced digital nomads stay productive while working abroad and dealing with issues like time zone differences?

Experienced digital nomads share tips for tackling challenges that come with the location independent lifestyle.

Tools like Trello, Asana or Google Calendar help plan and track tasks across time zones.

Good organization of files, documents and workflows keeps projects on track no matter where you work from.

Collaborating with a team of digital nomads in different locations ensures someone is available during normal business hours.

Working offline when the internet is unstable prevents delays.

Taking breaks to avoid burnout and scheduling fun activities maintain the work life balance needed to stay productive with a virtual job overseas.

How do digital nomads handle long term finances, taxes, healthcare and banking while traveling the world?

Part of the planning process for a successful digital nomad life includes…

… researching solutions for healthcare coverage, taxes, banking and long term retirement savings…

… as you work abroad or move between countries.

Digital nomads utilize international health insurance plans, tax planning strategies…

… for multiple locations, foreign transaction fee free credit cards and bank accounts…

… supporting international wire transfers.

Services like PayPal, TransferWise and crypto currencies help receive international payments and manage finances on the move.

Investing in long term assets ensures financial security in the future.

Asking the guidance of experienced digital nomad communities helps…

… newcomers properly manage these important considerations.


Embarking on a digital nomad journey requires thoughtful planning but promises immense rewards.

Evaluate your skills, build savings, craft an impressive portfolio, and choose nomad-friendly remote work.

Join communities for connections.

Leverage technology for productivity on the go.

With proper diligence, you can start living life to the fullest as a digital nomad.

The world is your oyster if you’re willing to take the plunge.

Let me know in the comments if you have any other tips for getting started as a digital nomad!



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