Become a Digital Nomad: 5 Challenges Everyone Faces When Starting

Hey, friends! Andrae Smith here, and over my years as a career and business coach for aspiring digital nomads, I've helped hundreds of clients navigate the path from 9-5 office job to remote worker/entrepreneur. Making the transition to a location-independent lifestyle is an incredible journey, but one that comes with its own unique set of challenges.

Having guided so many through this process, I'm extremely familiar with the hurdles you'll face along the way. In this article, I'm going to walk through the five biggest challenges to becoming a digital nomad that virtually all of my clients struggle with at first. But don't worry, I'll also share the best strategies I've found for overcoming each one. With some preparation and the right mindset, you'll blast through these obstacles. Let's dive in!

Challenge #1: Not Knowing Where to Start (Needing Career Clarity)

Here's the frst major roadblock my clients run into: They know they want the freedom and flexibility of the digital nomad lifestyle, but they're completely unsure of what they should actually do for work. There are dozens of potential paths like freelancing, starting an online business, finding a remote job, or mixing income streams. The options can be overwhelming!

The key is taking a step back to get hyper clear on your skills, interests, values, and the lifestyle you want to live. Do you crave the schedule freedom of freelancing, even if it means inconsistent income? Or would you prefer the stability of a full-time remote role? Are you looking to provide a specific skilled service like copywriting or coding? Or do you want to create your own info products and courses?

During my intake process, I have clients complete a comprehensive self-assessment evaluating their goals, personality types, strengths, background, and more. From there, we can start mapping out potential digital nomad career paths that could be a great fit based on their individual needs.

Challenge #2: How to Properly Exit Your Job (Creating a Transition Strategy)

For clients currently employed in a traditional role, figuring out the logistics of leaving their job the right way is always a significant challenge. You don't want to burn bridges and eliminate any possibilities for freelancing with your former employer, getting hired back down the road, or even just ensuring positive references.

We work together to craft a detailed exit strategy, starting with determining how much of a financial runway you need before quitting. Most experts recommend 6-12 months' worth of living expenses, at minimum. From there, we map out a transition schedule that allows you to give proper notice and keep relationships positive by not quitting abruptly. Oftentimes, I advise clients to start their digital nomad career path as a side income stream while still employed. This gives you a chance to test it out and ramp up before cutting ties.

Challenge #3: Overcoming Income Fear (Achieving Financial Peace of Mind)

Of course, leaving the security of a stable paycheck behind is terrifying for my clients. Not having a regular, predictable income stream is one of the biggest fears around becoming a digital nomad. I totally understand this anxiety! After years in a corporate job, inconsistent cash flow feels extremely unsafe.

This is why I put so much focus on creating financial runways and diversified income streams from Day 1. Having a healthy amount of savings buys you tremendous flexibility and peace of mind as you build up your nomadic income sources. This might require cutting expenses and living frugally at first. I also guide clients through money mindset work to reframe income fears and adopt an abundance mentality.

In terms of income itself, it's extremely rare these days for digital nomads to rely on just one income stream. Whether it's a mix of freelancing/online biz revenue and remote work, affiliate income, investing, or other passive revenues, creating multiple cash flow sources is critical. That way, you don't live and die by one client or job. Establishing diverse income arms from the start prevents a ton of stress and uncertainty.

Challenge #4: Building a Location-Independent Career (The Nuts and Bolts)

Once we get clear on your ideal digital nomad path, the real work begins! If you're starting an online business, we go through the whole process of ideating viable business models, building a brand, creating websites/funnels, developing service offerings or products, marketing, sales, and more.

If you're looking to land a remote job, we revamp your resume/LinkedIn to position you as the perfect hire for remote teams. We tap into remote job boards, virtual networking opportunities, and outreach campaigns to get your name out there and interviews lined up.

For freelance clients, I guide you through building a stellar personal brand, pitching and proposals, lead generation, optimizing your rates, and all the blocking and tackling needed to win high-value clients consistently.

Having worked with so many clients across different digital nomad paths, I have frameworks, action plans, resources, and communities to plug you into to ensure you build a real, sustainable, profitable location-independent career or business. We take it step-by-step during our coaching, removing any guesswork or wasted effort.

Challenge #5: Landing Your First Client/Remote Job

After all the preparation and work put into challenge #4, you've taken massive action but still face the final barrier - actually closing that first client or getting hired for a remote job. This is such a critical milestone, but also presents its own unique obstacles.

You're typically dealing with companies or clients who may never meet you in person. You need to master virtual communication, remote interviews, and find ways to really allow your expertise and value to shine through digitally.

Fortunately, I've helped numerous clients in this exact scenario and continue refining processes to set you up for success. We optimize your remote personal brand through things like savvy LinkedIn optimization, portfolio/resume/case study creation, video interview training, virtual networking tactics and more.

The key is adopting the right strategies, mindset, and resiliency. It may require applying to dozens or hundreds of remote roles and pitching a high volume of prospective clients. But each "no" gets you closer to your first "yes" if you learn from the experience. When you do land that first remote job or high-value freelance contract, it's an incredible feeling. You see proof that the nomadic path works and the momentum kicks in.

Bonus Challenge: Hitting the Road as a Location-Independent Traveler

Even after building a thriving remote income and getting over those initial client/job hurdles, there's a whole other aspect to tackle - the actual logistics and lifestyle of traveling the world. This is its own fun set of challenges that most of my clients need guidance around.

Questions like: Where do I start my nomadic travels? How do I find affordable housing in different locations? Do I need any special visas or documentation? How often should I plan to move around to new cities/countries? What are the best tools and systems to manage distributed teams and clients remotely? What's the best way to stay productive and focused while constantly on the move?

Having lived as a digital nomad myself for years, I incorporate tons of insights and resources to make this part as smooth as possible. We map out travel hacking tips, craft ideal "nomad budgets" depending on the countries/lifestyles you prefer, build communication processes to stay on top of your work, and troubleshoot the nuances that come up. I share lessons learned the hard way so you can skip the headaches!

What to do next?

Look, at the end of the day, is becoming a digital nomad challenging with a lot of moving pieces to figure out? Absolutely. Is it also an insanely rewarding and life-changing experience if you put in the work to make it happen? 100%.

By being prepared for these major challenges upfront and putting in place the right foundations, you can avoid many of the headaches and speed up your journey. But even with perfect preparation, guaranteed there will still be plenty of ups and downs, mistakes made, and lessons learned along the way. That's all part of the adventure!

Remember, I'm here to guide you every step of the process as you define your digital nomad path, build a sustainable location-independent career, and take those first liberating steps into the nomadic lifestyle. If you found this article helpful and you feel you need some personalised clarity & guidance to get this kickstarted — connect with me here on LinkedIn or simply get in touch with me!

If career clarity is what you're missing, be sure to grab a spot on the next intake of our 30-Day Clarity program - it's everything you need to get clear, focused ad ready to make this dream a REALITY!

I'm cheering for each and every one of you to achieve the life of your dreams.

Now, who's ready to take on these obstacles and become a digital nomad extraordinaire?

Let's get to work!

Andrae Smith Career & Online Business Coach for Digital Nomads www.workwanderers.com