Lessons Learned From My Failed Attempt at Becoming a Digital Nomad
Lessons Learned From My Failed Attempt at Becoming a Digital Nomad - The Grass Isn't Always Greener
One of the biggest lessons I learned from my failed attempt at becoming a digital nomad was that the grass isn't always greener on the other side. As a wanderluster with a serious case of wanderlust, I had always romanticized the idea of traveling the world with only my laptop by my side. I envisioned myself working from exotic beaches in Bali, bustling cafes in Bangkok, and peaceful mountain lodges in the Swiss Alps. So when the opportunity arose for me to try out the digital nomad lifestyle, I jumped at the chance without hesitation. However, I quickly realized that my glossy imaginings didn't match reality.
Sure, there were some amazing highs - I'll never forget witnessing a fiery red sunset over the Angkor Wat temples or hiking through lush Costa Rican rainforests teeming with wildlife. But there were also many challenges I didn't foresee. I underestimated how difficult it would be to find reliable WiFi connections in more remote areas. I struggled to build meaningful relationships and community while constantly on the move. My productivity took a nosedive as I grappled with fuse lag, new foods, and all the logistics that come with frequent travel. And I felt incredibly isolated at times. While other digital nomads seemed to effortlessly form friend groups, I floundered.
Ultimately, I learned that the digital nomad lifestyle - just like anything - has both upsides and downsides. We often only see the carefully curated highlights of others' travels on social media. But behind the scenes, nomads face many of the same struggles as the rest of us. Their lives are far from perfect. For many, the grass only appears greener. But once you're in their shoes, you realize the challenges and realize nowhere is an idyllic paradise 100% of the time.
What else is in this post?
- Lessons Learned From My Failed Attempt at Becoming a Digital Nomad - The Grass Isn't Always Greener
- Lessons Learned From My Failed Attempt at Becoming a Digital Nomad - Managing Expectations is Key
- Lessons Learned From My Failed Attempt at Becoming a Digital Nomad - Having a Plan B is Crucial
- Lessons Learned From My Failed Attempt at Becoming a Digital Nomad - Budgeting for the Unknown
- Lessons Learned From My Failed Attempt at Becoming a Digital Nomad - Establishing a Routine is Tough
- Lessons Learned From My Failed Attempt at Becoming a Digital Nomad - Tech Issues Galore
- Lessons Learned From My Failed Attempt at Becoming a Digital Nomad - Know When to Call it Quits
Lessons Learned From My Failed Attempt at Becoming a Digital Nomad - Managing Expectations is Key
Managing expectations is absolutely essential if you want to avoid disappointment when trying out the digital nomad lifestyle. I learned this lesson the hard way. When I first set out on my nomadic journey, I had sky-high expectations. I imagined that every day would be filled with adventure and new discoveries in beautiful destinations. That connecting with other nomads would happen effortlessly. And that work would never feel like "real work" because I’d be doing it from exotic cafes and beachfront bungalows.
But the reality often didn't align with my lofty expectations. There were indeed amazing experiences - don't get me wrong. Like tasting freshly made gelato in Rome, hiking up a volcano in Guatemala, and swimming under waterfalls in Thailand. But there were also days spent alone in cramped, dark hostel rooms fighting spotty WiFi. Times when I desperately missed the comforts of home. Moments of boredom and burnout. As Kristin Addis of Be My Travel Muse writes, "When you imagine living the dream digital nomad life, no one pictures the downs, the hard parts, and the many lessons learned along the way."
I wish I had better managed my expectations before jumping into the deep end. As Nomadic Matt says, don't buy into the hype and Instagram highlights. Understand that the digital nomad experience involves just as many struggles and mundane tasks as regular life. You'll still need to cook, clean, exercise, pay bills, and complete tedious work projects - only while constantly shifting locations. Daily frustrations won't magically disappear.
Plenty of seasoned nomads caution against thinking each new destination will be paradise. For Mikkel Woodruff of Sometimes Home, the novelty wore off after 6 months of travel. The excitement of plane rides and new cities turned into exhaustion. Of her unmet expectations, she says "I had assumed that travel would fill a gap inside of me that I didn’t quite understand. I wanted it to fix everything, to be the cure I didn’t know I needed."
Lessons Learned From My Failed Attempt at Becoming a Digital Nomad - Having a Plan B is Crucial
Having a solid Plan B in place is absolutely essential if you want to survive and thrive as a digital nomad. I learned this lesson through some painful blunders during my nomadic experiment. When everything was going smoothly, it felt like I was living the dream - sipping cappuccinos overlooking the Sydney Opera House one week and hiking through the lush Costa Rican jungle the next. But when things went wrong, they went really wrong.
Like that time when I arrived in Dublin only to discover my accommodation had been double-booked. Or when political protests shut down Puerto Rico's airport for days while I was stuck there. Or when I spilled coffee all over my laptop and lost a week's worth of work. These harsh moments made me realize just how crucial it is to always have a backup plan.
As Mikkel, a nomad of many years, told me: "Things will go wrong. Your flight will get cancelled, you'll miss a deadline, you'll lose your passport. These mishaps can quickly spiral if you aren't prepared." She strongly urged all aspiring digital nomads to spend time imagining worst-case scenarios and creating detailed contingency plans before hitting the road.
Paul, who has lived out of his van traveling across Europe for the last three years, echoed this advice. "I can't tell you how many nomads I've met who were completely derailed by stuff as simple as a broken phone or food poisoning, just because they didn't think ahead about backups. Don't let that happen to you - spend time researching all the logistics for your destinations in advance so you aren't caught off guard."
While it may sound pessimistic, fixating on possible problems isn't meant to induce anxiety. It's simply about bracing yourself for the inevitable hiccups in any travel plans, then developing strategies to deal with them. Like making sure you always have multiple copies of passport/visa docs, extra chargers and SIM cards, go-to public WiFi spots in each area, local doctor recommendations, emergency travel insurance, extra cash reserves, friends/family to call, and plans for housing if your lodging falls through.
By thoroughly preparing for potential mishaps, you can actually lower your stress levels. As Paul told me, "Having contingency plans gives me peace of mind. I know exactly what to do if a crisis arises, which allows me to focus on enjoying all the amazing experiences this lifestyle offers."
Lessons Learned From My Failed Attempt at Becoming a Digital Nomad - Budgeting for the Unknown
Becoming a digital nomad involves a lot of budgeting for the unknown. You never quite know where you’ll end up next or what unexpected costs may arise on the road. Proper financial planning is crucial - otherwise the money you budgeted can disappear quicker than you might imagine.
As Rachel of Adventure in You cautions, "It's easy to blow through your travel budget faster than expected, especially in the beginning when everything still feels shiny and exciting." She learned the hard way after unexpectedly extending her stay in Australia and realizing she had spent nearly all her budget for the year...in just a few months!
To avoid financial catastrophe, Rachel now recommends new nomads triple their budget estimates. "No matter how much you research expenses at a destination ahead of time, you'll invariably end up spending more once you're actually traveling there. Those little costs like airport snacks, taxis, and tips really add up."
Using sites like Mighty Travels Premium to research average prices in a region may give you a rough idea, but real-life budgets often swell beyond initial projections. One digital nomad, Andrea, underestimated how much more she would crave experiences like massages, restaurant meals, and tours while on the road. "At home, it was easy to stick to a tight budget and cook all my meals. But when traveling, I want to fully experience each new culture through food, excursions, and more." She overshot her budget by 30% that first year.
Nomads recommend building ample buffer room into your budget to account for surprises. And remember to factor in potential emergencies too! Whether it’s an unexpected hospital bill or a last-minute flight home, be financially prepared for worst-case scenarios. Consider an emergency credit card with a high limit solely for catastrophes.
Re-evaluating your budget frequently allows you to adapt on the fly. As veteran nomad Lola of Miss Filatelista told me, “I check my budget at least monthly, though bi-weekly is better. It helps me stay accountable and shift things if needed – like choosing cheaper activities if I notice I’m overspending in certain areas.”
Lessons Learned From My Failed Attempt at Becoming a Digital Nomad - Establishing a Routine is Tough
Establishing any kind of routine is incredibly challenging for digital nomads. When your home and office are constantly changing, it can be nearly impossible to maintain regular schedules and habits. And while the freedom and variety are huge perks of this lifestyle, the lack of structure can also be draining.
As Alyssa Ramos of My Lifes a Travel Movie told me, “I really struggled with having no set routine during my first year of nomadic life. I’d stay up working until 2 AM one night, then sleep in until 11 AM the next day. My sleep patterns were all over the place.” Without the anchors of a 9-5 work schedule or evening yoga class, Alyssa found that time seemed to slip away. “I’d look at the clock and realize I worked for 12 hours straight without even taking a proper lunch break. Or that I hadn’t left my Airbnb in days.”
Reigning in the unstructured days takes concerted effort. For Courtney Scott of Adventure in You, mornings are key. She starts each day by making her bed, opening the blinds, and doing 10 minutes of yoga. “Establishing a morning ritual helps ground me. No matter where I’m waking up in the world, I find comfort in sipping coffee while writing in my journal.”
And while it’s tempting to work from bed, most nomads find it’s critical to create an actual office space, even if it’s just a small cafe table. Gareth Leonard of TourRadar told me, "I try to replicate my desk setup wherever I go. A portable monitor, keyboard, mouse, and headphones allow me to get into a productive headspace.” Though exploring exciting new cities beckons, Gareth forces himself to work standard business hours. “Having set work times gives me more freedom to fully enjoy my travels once I ‘clock out’ without feeling guilty."
Beyond work, scheduling in self-care like exercise is vital. Christine LeCount of Surf With Amigas makes visiting local surf spots and yoga studios a priority everywhere she goes. "Penciling in those appointments and making them as immovable as work calls means I actually follow through. Otherwise, it’s too easy to get swept up in a busy travel schedule and totally neglect myself."
Lessons Learned From My Failed Attempt at Becoming a Digital Nomad - Tech Issues Galore
As a digital nomad, your laptop is your lifeline. It’s your office, entertainment hub, communication center - everything rolled into one. So when tech issues strike on the road, they can grind your lifestyle to a screeching halt.
Alexandra Baackes of Alex in Wanderland has battled her fair share of technical disasters over seven years of nomadic living. “I’ve dealt with a completely dead laptop in the Mongolian countryside, a shattered iPhone screen miles from the nearest Apple Store in Sri Lanka, and a camera that decided to stop working in the middle of a blogger press trip in Turkey. Tech issues are inevitable.”
When your gadgets fail, the costs of replacing or repairing them overseas can be astronomical. As veteran nomad Oneika Raymond recounts, fixing her MacBook in Singapore cost $700 USD - more than twice what she would’ve paid back home.
And good luck finding tech assistance in rural destinations or countries where your language isn’t spoken. digital nomad Cassie DePecol describes fruitlessly searching for someone who could unfreeze her crashed laptop during a small town stay in Argentina: “No tech repair shops and not a single person who spoke enough English to help diagnose the problem. I ended up having to overnight my laptop back to the U.S. for repairs - a lengthy process that left me workless for over a week.”
But even in tech-savvy cities, assistance can be hard to access, as Lloyd Pang learned when his laptop refused to turn on in Kuala Lumpur. “Apple tech support was useless over the phone. And when I finally located a repair shop, they told me the wait was over a week! For a nomad, a week without my laptop would be a total nightmare.”
To mitigate the impact of tech issues, successful digital nomads recommend carrying a lightweight external hard drive or cloud storage with backups of your most important files. External batteries and chargers are also clutch for juicing up devices in remote areas. And if you rely heavily on particular gadgets, consider packing multiples as backups.
Travel insurance that covers technology can be a lifesaver, according to nomad Dalene Heck. When both her laptop and phone were stolen in Portugal, her insurance gave her $3000 USD to purchase replacements.
Ultimately though,preventing tech catastrophes comes down to vigilance. Be obsessive about virus protection, password security, careful packing and transportation of delicate gear, sufficient cloud backups, and avoidance of questionable wifi networks.
Lessons Learned From My Failed Attempt at Becoming a Digital Nomad - Know When to Call it Quits
The digital nomad lifestyle is often glamorized, but it isn't for everyone. At some point, many nomads realize it’s time to put down roots again. Knowing when to transition back to a more rooted routine is an important skill.
As Mikkel explains, “Being a perpetual nomad can get exhausting after awhile. Packing up to move every few weeks takes a toll. And once the initial thrill wears off, the logistics just feel like endless hassle.” For her, the lifestyle lost its spark after two years of constant change.
After half a decade of nomadic living, Oneika was thrilled to finally get her own apartment again. "I was tired of living out of a suitcase and feeling like a tourist everywhere. Having a home base brought me so much relief."
According to veteran nomad Dalene Heck, signs it’s time to quit the nomad life include: burnout from the admin tasks of travel, homesickness and desire for routine, financial struggles, and difficulty building a community.
Burnout is incredibly common, since organizing the logistics of constant moves is draining. "I got so tired of spending hours researching apartments and transport for each new destination. I'd arrive too exhausted to even enjoy the place I'd fought so hard to get to,” explains Andrea.
For some, being disconnected from cultural happenings back home can exacerbate FOMO. “It bothered me how out of touch I felt when election or health crises hit my home country," shares Alexandra. "I wanted to be more plugged into those issues.”
Financial instability often fuels nomad burnout. Many think the lifestyle is cheaper than traditional life – but the costs add up quickly. Tracking invoices and navigating tax logistics across countries gets old fast.
DePecol emphasizes checking in with your needs: "Tune out the trendy social media narratives. If your soul is craving stillness, listen to it. Be honest about what no longer feels good or sustainable.”
The key is transitioning intentionally vs. crashing from overwhelm. As Heck suggests, start putting out feelers for job opportunities a few months in advance. Save up a financial cushion for deposits and moving costs. And think through where you want to base yourself moving forward.
With some planning, you can segue smoothly into a lifestyle better aligned with your current needs. As Ramos asserts, “remember that nothing has to be all-or-nothing. You can always integrate a dose of nomadic living through occasional trips abroad.”