Six Lessons From A Successful Digital Nomad

I have to start an article like this with a disclaimer:


Everyone’s success story is different.


What led me here, can also lead you to your success. It also may be the complete opposite route that you’ll actually end up taking. Regardless of your outcome, understanding how other people have found success will be detrimental to the speed at which yours begins. I’ll prove this later.


The long form story is below. The short form goes as follows:


Free work + Yes Man + A Little Luck = Success


Let’s break that down.


I started with a free Wordpress blog where I talked about health and the dominantly plant based lifestyle that I lived. I had about five articles on my blog when I saw that Wanderlust Yoga Festival was hiring writers to cover their Stratton event. The rules were simple, each writer would get four days of free entry into the festival in return for one article per day, due the next morning. I strongly believe what set me apart from the crowd in my application was this: I told them exactly what they wanted to hear. Since my lifestyle blog was not the type of writing they would be interested in, I specifically said, “I know that the articles on my blog are not the content that you are looking for. For this event, I would write about the experiences that will resonate with yogis and motivate them to buy a ticket to the next festival.” The festival ended, the editors loved my articles and I went home.


This is a pivotal point of my story. Had I continued to push hard for my writing career, it would have come to me much sooner. At the time I was incredibly naive and had no idea what I was doing. I didn’t even think to ask if I could cover another event, if they were hiring contributing writers or if there was any other work I could help them with.


Lesson #1: If you want something, ask for it.


There is no way to say what could have happened if I had the courage to ask for another opportunity, but it’s obvious that I wasn’t mentally prepared to be in the position to take it.


I came home from Wanderlust and settled right back into my routine as a waitress. It took me almost a year and a half to get published again. Given that I was studying biology with a chemistry minor, my time was limited. I was in my senior year of college and it only made sense to go full force on finishing my degree.


I graduated college, and lost for what I wanted to pursue as a career, I kept waitressing. I stumbled upon Elite Daily at the end of 2015 when they were first growing their empire. At the time I’m pretty sure Gerard Adams still owned it. I applied to be a contributing writer and was accepted. In hindsight, this sounds absolutely crazy but at the time it didn’t seem like a huge accomplishment. Elite Daily was just starting out and they were accepting almost anybody as a contributing writer. There was no pay, just the chance to be featured on a larger platform.


I had four articles published:


By the time my fourth article was published, they started sending us emails about what writer had the most viewed articles. The top articles were on topics that I wouldn’t be interested in writing about (think X-rated subjects) and I realized that this path wasn’t going to be for me.


I lost sight of my writing path and kept focusing on waitressing. This has taught me a valuable lesson.


Lesson #2: What you put time towards, you become.


At the time I needed money and the only way I knew how to make it was to waitress. Instead of putting time into searching out leads, building my portfolio or networking, I was picking up extra shifts. This was a pivotal mistake. What did this make me? A really good waitress and a really average writer. I knew that waitressing and restaurant work was not my path. It would have been a much better business move to spend my time growing myself emotionally and skillfully as a writer and not as a waitress.


My ah-ha moment came when I googled “Top Three Freelancing Websites”. The first website that came up was Upwork. I made a profile and started to try to get writing work. My first job was to write 100 product descriptions for an online boutique (including lingerie) for $37.50. The job took me about five hours and averaged me out at $6/hour after Upwork took their 20% fee. Every job I picked up after was low paying and not ideal. I knew that if I sucked it up now, my profile would grow.


For the first time in my life, I worked while on an airplane. Then, I worked from the hospital room after my sister had her baby. Regardless of the crummy pay, I was hooked.


From June 2016-November 2017 I had 29 jobs. I made less than $2,000 but I was convinced that I could make it work. It’s important to note that at this point, I had sold everything that I owned and started to backpack the world. I had thought that I would be able to travel substantially and work online at the same time, but after one month spent adventuring and off of my computer, I came back to find that Upwork was no longer my friend.


Upwork, as I assume, runs on an algorithm. The freelancers that make them money, via their 20% fee, get boosted. Since I hadn’t made them any money in a month, they had demoted me in their algorithm and getting work was almost impossible.


I was backpacking Europe when I started to come to terms with having failed at my dreams. I had less than $200 to my name, couldn’t buy myself a plane ticket home and was completely unsure of what I was going to do with my life. To be honest, it was a bit of a dark time as I stumbled around trying to find my way and remember why I had started such a tough journey in the first place.


Then I struck gold. I traveled to Croatia and met my first (!!!) digital nomad. He had just started traveling and was going to be living in Split, Croatia for a few months. He knew about co-working spaces and had a pretty good plan for how he was going to live and work. I was full set on staying almost immediately and my bank account was reminding me that I didn’t have the money for a bus ticket anywhere else.


This is when everything changed.


Lesson #3: The content world is fast paced and hungry. 


By staying in one place for an extended amount of time and having a set office space to go into Monday through Friday, I was able to create momentum.


I could submit over five proposals a day, answer clients immediately and give them a twenty-four hour turn around time. It wasn’t an immediate success but about four weeks in the ball was rolling. I could tell that I was coming back into the Upwork algorithm.


I soon found that there was a ton of work to be done and that if I could get it done fast people seriously valued me.


I currently work seven days a week, answer clients within twenty-four hours or less (usually much, much less) and complete projects within a day or two of starting a contract. This is without question my largest reason for success.


Although my story may not replicate yours, my success formula can.


The final three lessons of my digital nomad story, come directly from this formula:


Free work + Yes Man + A Little Bit of Luck = Success


Lesson #4: Start small, work big.


If you are just starting out as a content writer, don’t put your rate to $20/hour. Start at $8-$9/hour to get momentum and grow your empty portfolio.


Lesson #5: Say yes to anything that comes your way.


I still rarely say no to projects. A project has to be totally underpaid (Ex. A 15,000 word ebook for $170) or out of my expertise (Ex. Technical writing about engine valves) for me to decline. I plan to continue to say yes to everything that I can until my time is completely full and I have to prioritize.


Lesson #6: Knock on every door in front of you.


Go after every single idea that pops into your head as a means of finding clientele and growing your skills. Try all the options. Repeat your attempts two or three times. Don’t fear asking for more work or a referral. Knock on every door and talk to every person until one of them opens up and you find a pot of gold.


When you are serious about starting a content career, you’re going to know it. There is going to be nothing else that you want to spend your time on. All inflow will be in the form of podcasts and videos that better you. For months, I solely listened to podcasts interviewing successful entrepreneurs. I listened to their stories, learned from their lessons and applied them to my own life. This granted me the ability to avoid mistakes and to get advice from top dogs in my industry. 


All outflow will be a direct representation of your growth as a content artist. Find platforms to grow an audience. Write, post pictures or videos there every single day. Represent yourself and your talents with pride.


If this dream is calling you, find your path and go for it.


Like, now.

Three Resources I Used To Become A Digital Nomad