YOLO-ing So Hard and 10 Things to Consider Before Diving in Head First into the Digital Nomad Lifestyle
What (who) is a digital nomad?
I’ll start off by saying from the very beginning, I don’t believe there is an actual specific, clear answer to define what/who is a digital nomad. Originating from different backgrounds, cultures, socioeconomic statuses, and geographical locations amongst a multitude of other diversities, humans are all unique in their own ways. The difference between “us” and “them” is we have the ability to see the world in a way most of the population can’t. We have an intense urge to discover every little thing this planet has to offer.
Nowadays, the term “digital nomad” has become globally recognized, and whether you love or hate the lingo, it’s the best way to describe the growing group of individuals with the freedom to work from pretty much anywhere, as long as there’s decent Wi-Fi. It’s a much sought-after lifestyle, but there’s A LOT more to it than what meets the eye.
Based on my own experience as well as the experiences of other successful digital nomads, I want to share with you how to travel the world and make a living while getting paid to do something you truly love. On that note, be sure to think twice before taking on the risk, and tough grind of life in the land of blogging – seriously, choose another remote job – this one is so much more work than you will initially realize. I promise. Don’t say I didn’t warn you.
So, what’s up with this whole digital nomad thing? What are the misconceptions? The realities? What is the actual TRUTH behind this lifestyle? These answers will be different for everyone, but one thing is certain, if it’s what you truly crave in life, it will be the best step you ever take. Grab a seat, I’m prepared to tell you everything you ever wanted to know!
Digital nomad versus location independent living
But first, I’d like to briefly discuss a somewhat controversial topic. I’m not going to get into this longstanding debate, and I don’t think it really matters, but most would say a digital nomad is someone who works from their laptop, travels full-time, and doesn’t have a home. However, we believe living as digital nomads and living location independent lifestyles are interchangeable, and technically, the latter is the category we fall into as we’ve made a home base here in sunny South Florida.
How does one become a digital nomad?
You’re probably asking “What type of job can I do that allows for the digital nomad lifestyle? What types of jobs can be done remotely?”. I won’t get into specific digital nomad job options in this post (part two will include this information), but I will say the priority is to find and secure some type of remote work. That’s the first step.
Fundamentally, becoming a digital nomad really only requires 2 things:
1. The ability to make money remotely
2. The ability to travel
First, we’ll explore the ability to make money remotely. A blog by itself isn’t a business model. You begin with tedious, mundane tasks. You learn skills such as copywriting, SEO, social media management, web design, amongst countless other projects. Next, rather than generating passive income upfront, you generate active income through freelancing. Lots of freelancing. And in my case, a multitude of other business ventures. It’s really all about the “whatever it takes” mindset. And if you don’t have it, don’t even think about going the digital nomad route. After you’ve built an initial foundation, you’re finally able to get into the fun, passive income opportunities.
Next, we’ll answer “How does one work and travel?”. Sorry to crush your dreams, but, you don’t. When it comes down to it, both need to be looked at as totally separate entities. Just because you can technically work from a hammock on the beach doesn’t mean the Wi-Fi will reach. Also, sun, sand, water, alcohol, and electronics definitely don’t mix well. Trust me, I know firsthand. As a digital nomad you’ll certainly be working and traveling, but most likely not both in synchrony.
10 facts to consider before diving in headfirst
- You will likely work more than you did at your bullshit corporate 9-5-ish job. Sipping cocktails by the pool while leisurely browsing the web on your cell phone and engaging in some social media interactions is sadly not the reality. You will work significantly more than the standard 40-hour workweek. Specifically, if you are a start-up business, or are building a portfolio.
- There is ALWAYS work to be done. Your to-do list is never complete. There is never a time where you feel as though you reach an endpoint. For every one task I check off my list, I add at least 5-10 more.
- Working for yourself isn’t all roses and rainbows. Some digital nomads still have bosses and set schedules. However, we do not. There is no clear line between work and non-work hours. It’s the best thing in the world being my own boss, yet it’s also a curse. That family gathering everyone’s expecting you to attend? The annual holiday event you never miss, no matter what? Your typical Sunday Fun Day boating with friends? These all quickly become things of the past in the beginning stages. It’s super easy to get sidetracked and relax and enjoy life because you can. It’s just as easy to become lazy and lackadaisical. But it’s more important to manage yourself intelligently and focus on your work, and your income, yet very few have the discipline to do so.
- Work hours are not clearly defined. I can’t tell you how many times I begin my day working, and I PROMISE that I’m going to take a break, spend time with friends or family, get something, anything, else done, and next thing I know its midnight and I haven’t had lunch or moved an inch from my laptop screen. Work hours get unstable quick. And whether it’s remaining disciplined and staying on task, or forcing yourself to take time out for other aspects of your life, these are all just added responsibilities of this lifestyle.
- You’ll be asked often, too often, how you make money. Although there’s nothing tackier in the world then this dreaded question, you’ll be stunned at how often you’re asked it. And then even worse, is the question that almost always follows about how much you make. There is literally no other career where it is acceptable to ask about a person’s cash flow, but for some unknown reason, people are interested in the finances of those who are not living a conventional lifestyle.
- Your “circle” becomes small, and new friendships don’t usually progress further than the acquaintance stage. The “where are you from, what do you do” small talk conversations become redundant and the inevitable goodbye that comes upon packing up for your next destination can be even worse. For those vacationing, it’s great! For digital nomads, these goodbyes, the lack of a close-knit circle, and the perpetually fleeting friendships can become overwhelming. In our instance, we have each other. But it isn’t always like that and it’s definitely something to consider when weighing out the pros and cons of this lifestyle.
- There is a false notion that you live on a perpetual vacation. And this has got to be the most frustrating misconception because as described previously, digital nomads are likely busting their asses five times more than those making this irritating assumption.
- Starting out as a digital nomad can be demanding if not discouraging. The amount of work it takes before you actually even begin to work is intense. You’ll spend just as much time applying for assignments as you will completing them. I think we all recognize hunting for a job can be super time-consuming, and obviously, when applying for work opportunities, you aren’t paid. And if you are like us and have chosen the bloggers path, the hours spent teaching yourself how to make a blog a successful, legitimate business are countless. And the learning never ends.
- The process of becoming a digital nomad is not effortless, but in some ways, it’s not challenging either. Wait, what? As we know, there are thousands of options and avenues to take to live this lifestyle. Nearly anyone wanting to work remotely and become a digital nomad could essentially do so. So, what’s stopping someone? Excuses? This brings me to my final consideration.
- You’ll be told you’re lucky. I beg your pardon. Lucky? Nothing I have or have accomplished has been attained by luck. I’m lucky to be from America and have the right to obtain one of the strongest passports in the world. And I am grateful and truly appreciate that freedom. Aside from that, nothing about my lifestyle is luck. It’s conflicting to be idolized for your accomplishments, but to feel defamed because the general population assumes your success is by virtue of luck. What’s worse is people think they can’t achieve the same success because they aren’t “lucky”. It’s something you will have no choice but to grow accustomed to. People just inadvertently don’t understand this.
So, what exactly is the digital nomad lifestyle like?
My intentions in bringing the realities of being a digital nomad to light were not to put a damper on this way of life. It’s awesome! I just want to be real in saying it’s not nearly as glamorous as it’s made out to be. And it’s different for everyone. For me, it’s waking up at the crack of dawn because I WANT to, getting hours of work completed before most 9-5ers even start their day, and then scheduling in any free time I may have to travel, have fun, and just live life. When I’m working, I’m in full force work mode. When I’m traveling, I’m in play mode. It’s the only way to be thoroughly productive, but also enjoy yourself and this life you’ve created.
If I could turn back time, I would choose this route, without hesitation, over and over and over again. There has been no other path to make me feel as exhilarating and free. I love that I work for myself. I love the flexibility, and the reality that I can jet off to anywhere I please with little notice or care while still being productive in my work.
The fantasy of a digital nomad doesn’t have to be a myth anymore. You no longer have to sacrifice personal happiness for a paycheck or wait to travel until you’ve retired. But it will take patience, discipline, and a boatload of hard work. There isn’t a right way or an easy path. There’s only your path. You have to find and make a way. But I promise you, if you persevere and faithfully invest in yourself, you’ll be able to live a life most would kill for. It’s not perfect, but nothing in life is!
Hopefully, I’ve connected with you on some level in identifying an assortment of “need to know” aspects of this way of life. And if you’re not totally put off by what I’ve described, are you still down to become a digital nomad? What are your thoughts and plans? Let us know in the comments!

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