Digital Nomad Obstacles

by | May 8, 2017

It’s really easy to get discouraged when you are pursuing a dream – especially when you don’t have a clear picture of what that dream is and what steps you need to take to reach it.

I have loved the idea of moving to Europe and/or becoming a digital nomad with frequent stays in Europe for years now. But it always seemed impossible. And wouldn’t I find the guy of my dreams sometime soon? Better not make any concrete plans, since Prince Charming would find me soon and we’d travel the world together.

Well, Charming is still MIA, and I realized I could do this travel thing myself. I also realized two weeks of vacation a year is not nearly enough for all the travel I want to do, and I was spending 25-30% of my budget just getting to Europe, plus the days of jet lag. So I started taking courses to up my digital skills to help make a nomad life possible.

But I still have many obstacles in my way.


I know I will need a solid buffer of cash before I will feel comfortable leaving my fulltime job. But I am also making far less than I’m worth at the company, and a discussion about salary hasn’t happened 2 months after requesting it. Coupled with depleting my savings to help my sister buy a car (she’ll pay me back eventually), my upcoming 2-week trip to Europe, and spending money on training, and my finances, while not terrible, should be healthier. Once my trip happens in early September, I can start putting aside that money for a much longer trip!

Housing and Belongings

I just signed a year lease. My sister and I moved to a new place so that a good friend could move in with us (and we could potentially add a 4th person later on). That makes my rent actually quite reasonable, but still something I would have to pay, even if I’m not here. At the end of the lease I would still need somewhere to put my stuff if I wasn’t living here. I can see getting rid of some things, but I don’t think I can pare down my 75ish boxes and furniture to a couple boxes in someone’s basement. Having a home base here in the States wouldn’t be a bad thing, but it would drain my money faster.


One of the reasons why I can see myself keeping a home base here is that most of my family is in the area. I have 8 younger siblings, and my parents and all but two are in the area – and it would be especially hard to leave my two nieces. So I can see myself splitting my time between here and Europe – coming home for a month or two at a time would be much nicer if I had my own place. But still, money – for keeping a room in an apartment and plane tickets back and forth.


Depending on where I want to live in Europe, it may be impossible to work there legally. Most digital nomads aren’t in one place for long enough to worry about that, and just stay on tourist visas (but moving from place to place can be a lot more expensive). I was thinking this would kill my dream outright, until I found out about a freelancer work visa in Germany that is difficult, but not impossible to get. While living in the UK or Ireland would have been preferable (hello, English language!), Germany is a great alternate choice for me, for several reasons. One, since most of my ancestry is German (various branches of my family immigrated to North America between 1700 and 1900), I’ve always been interested in the country and culture. Two, due to this, I’ve actually been studying German, so this would help both my comfort level in the country and improve my skills with the language. Three, it is very centrally located for exploring the rest of Europe. Four, I love castles, and Germany has many beautiful ones to visit!

Current Job

I’ve been with my company for three years now and my skills have improved greatly during that time. I also have a casual dress code, short commute, and great coworkers. While my salary and vacation time is lacking, this job does give me more time and emotional freedom to pursue freelancing on the side that a stressful new job with a longer commute would not. It would be great to work for my company remotely in the future, and they have approved my trip to Europe, so I am reluctant to leave, even for a job that may pay a bit better and help me save money.

Business Under Construction

I have not officially launched my freelance business and have therefore earned $0 with my new skills. Will I be able to make a living as a freelancer? The last freelance money I earned was writing for a magazine 4+ years ago, and that was just a couple hundred extra a month. I will want to be fully established with several clients before I can even think of moving it to fulltime, not to mention the needed money buffer.


All of this points to it being at least a year until I make the leap to digital nomad. But here are some steps I will be taking:

  1. Launch my business so I can start earning money and paying myself from it
  2. Start saving more every month
  3. Get rid of more stuff
  4. Use my trip to evaluate where I would want to live in Europe

What obstacles to becoming a digital nomad do you face?

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