One of my pet peeves is when people tell me how I am so “lucky” after they learn I work remotely. While I absolutely have many privileges that I benefit from, it’s generally not people from developing countries with restricted passports who say this to me, it’s my fellow US citizens.

Here’s the thing. It might not have been visible to my friends, but I worked on making this switch for a very long time. It was a very conscious, planned decision, and it did not happen accidentally. I didn’t just apply to a remote job on a whim and get it, and no one magically reached out to me with a job or project offer (I wish)!

Building my savings and getting my bureaucratic systems in place to leave took a bit over two years. Getting myself stable enough as a permanent resident of Berlin so I can travel longer-term without my visa getting revoked took 6 years.

I’ll talk mostly about those two years before quitting my job, because applying for permanent residence in another country doesn’t apply to most digital nomads and wannabe nomads.

My Background, i.e. Life as a Muggle

I moved to Berlin in August 2011 to be an au-pair. After rapidly realizing that au-pairing and children as a whole were not my thing, I quickly got a freelance gig teaching English and applied and was granted the freelance visa for Germany. After 3-4 months teaching English, I stopped this and got an internship helping out with data entry at a business school for creatives. I got more responsibilities, became a Project Assistant there and worked with them for two years.

As this was a freelance gig, I also had other clients. I worked as a Project Manager for a company in Dubai I got through a friend, I did workshops on living abroad for tech trainees preparing for internships in the UK, and I was even in a Febreze commercial (that one did happen accidentally).

How The Digital Nomad Seed Was Planted

I first heard about the whole concept of working remotely when a friend from my university stayed with me and mentioned how he was working remotely while doing a 6-month Eurotrip, funding it partially by taking gigs on Upwork (previously Elance). He told me about a guy running a digital nomad/entrepreneur blog called Location 180, that I followed and read profusely. I also made an Upwork account and started browsing the types of jobs there.

I needed a couple years to ponder the concept in the back of my mind and absorb information before it even seemed like something realistic I could put into action. Plus, I had three more years I needed to work for German clients/employers to get my permanent residence.

Okay I lied – I did accidentally become semi-remote once. Sort of.

I started to outgrow my position at the business school, so I applied for a part-time freelance customer service job at a language learning app and website startup in Berlin. I got it, and in the interview they told me they didn’t care if I came to the office, I just had to be there for big meetings.

I had another gig at a relocation company for expats in Berlin at the time, but work here came and went, so I started testing out my new remote capabilities during the down times.

I did a week in Innsbruck, Austria, working from a hotel while a friend from high school was doing some Olympic prep training there for bobsled, so we could hang out in the evenings.

I spent a month living in Budapest with my girlfriend at the time who was from there.

Eventually, I got up the courage to ask for permission to work remotely for three months, so I could do a roadtrip around the entire US. My boss agreed, and off I went!

Finding good wifi while traveling in a car throughout the States, often on couches and in some sketchy motels, proved to be a bit difficult, but I did it, albeit with a few hours less than usual on my invoices.

…and back to the office I go.

After three years in Berlin, I got an open visa which allowed me to do any type of work, salaried or not. At this point, I was bored. I loved the freelance life, but my days went so slowly because my work was not challenging. An immigration lawyer also told me it would be better for my permanent residence application if I got a normal job.

After a brief crisis, I started applying to regular jobs. I got the university job as a Registrar and stopped doing the remote thing.

Is digital nomad life sustainable?

I actually quite liked the university job, but I knew I wanted to switch back to a life that allowed more travel and a sustainable career. I wanted to earn more money than I always had as a freelancer, as I was just scraping by back then. I wanted to be able to pay the better statutory health insurance in Germany, and I needed to be able to pay a bit into retirement (for my permanent residence, but also because it’s a good idea).

Networking with Nomads

Using that seed that had been planted by my friend sharing the Location 180 blog and Upwork with me years ago, I went down a few internet black holes. I stumbled upon the Digital Nomad Girls group, and realized they had a meeting coming up in Berlin soon. Everyone in the group seemed so cool, I had to go.

I remember being super nervous when it was time to head over to the DNG meetup. I wasn’t a digital nomad yet, what would they think?! They all seemed way more successful than me, and more well-traveled! At the time, I had only traveled around Europe and the US (okay and Dubai a bit). I pushed this out of my mind and decided to just focus on getting to the front door of the cafe the meetup was in.

I walked in, and everyone was immediately cool and welcoming. We chatted about traveling, I talked to Jenny, the founder of DNG who happened to be half German, about how she sorted out all the German bureaucracy to go remote. I quickly learned that most digital nomads seem to question whether they are digital nomad enough. 

Meeting people who worked remotely in PERSON made such a difference to me. If you’re thinking of going remote, this is my #1 advice.  

Before, it seemed like something randoms on the internet did. Not me. They must be a type of person different than me. When I met people at the digital nomad girls meetup though, I realized they were normal people like I was, and that made it all seem possible. 

I started reading all the posts in the Digital Nomad Girls facebook group and on Jenny’s blog. I made a big effort to network with other digital nomads, so that the lifestyle would seem more possible to me. I went to local digital nomad events in Berlin, and I joined other groups and found more blogs. I started a Queer Women* Digital Nomads group to connect with other queer women who were or wanted to do this remote work thing.

Eventually Jenny started offering retreats and a year later, I decided to go to the second one. I had about 8 months until I would get my permanent residence at this point. I planned to quit my job and go to Asia in early 2018, so it was time to get a bit more serious.

Digital Nomad Girls Retreat

This ended up being another life changer for me. The masterminds at the retreat helped me refine my plans, and it was so, so helpful being around a group of women with such varied expertise and experience levels. There were a couple other women who were also planning to go remote on a similar schedule to me, and we made out own mastermind to help keep each other accountable after the retreat.

I ended up being great friends with a lot of people from this retreat, and watching their journeys helped my own.

Also on this retreat was Taylor Lane from Remote Like Me, who had just started a remote career coaching company. I joined her Facebook group and went through all her blog posts and resources, which really upped my remote job game.

Re-thinking my job search as a digital nomad

Taylor tells it like it is, no sugarcoating, and I really appreciate that in a sea of other digital nomads trying to sell you the dream without much substance beneath it. Taylor knows her shit. I watched her videos in her Facebook group, and redid my resume. I didn’t even consider that the way I apply to jobs, and my boring-looking resume, should ever be updated, as it seemed like one of those things that were A Certain Way for REASONS.

I got used to the idea of applying for remote jobs with videos instead of cover letters, which was TERRIFYING at first, but now gets me interviews almost every single time.

Taylor has a free masterclass on how to find your ideal remote job, which is a good starting point. You can sign up here.

how to find a remote job

Taylor also offers a course that’s more in-depth if you get on well with her free stuff. I can also highly recommend her group and the resources in the files there. She also offers a mentorship program on her website that gets rave reviews if you want more support during the process. If you want to get a remote job rather than do freelance stuff, she is the one to go to. Even if you don’t want to go remote, she’s just generally on the ball with career advice.

What is a virtual assistant exactly?

Around this time, I also noticed another one of my queer nomad peeps I met online, Hannah Dixon, had a business training virtual assistants. I saw a free challenge she offers, the 5-Day VA Challenge, come up and hopped on it. In the challenge, we have to break down who we want to work for, what we can offer, get our online presence set up for this, and learn how to pitch clients. You can get an accountability buddy, and we get templates and tools to come up with our info, and a whole community cheering you on. 

This was another game changer for me, as it connected me with other people trying to go remote right NOW to talk with. It also forced me to vocalize my ideas instead of just silently wondering what kind of remote work I could do. While my first 5-Day VA Challenge was very different than what I ended up doing, writing out what I wanted to do, and getting ideas from others about what they planned to do, really helped me see what was possible. I still talk to a lot of these people today, and have met some in person. A lot of us actually work remotely now, and some of the people I started this journey with have even referred me to clients.

Here’s a post (not mine) with 100+ skills you can offer as a VA, to give you an idea of the type and variety of work.

Building my remote work toolkit

Another thing that helped me with the logistics of going remote is Hannah’s VA Starter Kit. I bought this course, which goes over all of the tech of working for yourself. I have always been pretty good at tech, but working for myself remotely was a different setup than I was used to.

I learned the best (mostly all free) tools online for making quick social media graphics, basic tools for creating color palettes and figuring out image sizes, what I could use to time myself online and create reports, suggestions for invoice software, and lots of helpful advice on what to charge and what types of payment structures to offer. I still go back and refer to this course today when I am trying to refine my skills and packages.

If you’re not fantastic at tech, Hannah also offers a WordPress course, which I imagine is also super helpful. Pretty much all my clients have their websites on WordPress these days, so knowing how to use it is very useful no matter what role you’re after.

Hobbies as a Way to Build Experience

Luckily I have been a blogger since 2008, and have my blog on WordPress, which gave me a lot of practice.

People complain a lot to me that they are never able to get experience because no one will take a chance on them to GIVE them that experience. Honestly, my response to that is make your own experience.

Even before I knew what a digital nomad was, I had various projects that were my hobbies. I cannot tell you how many times my food blog got me a regular, totally not related to food or blogging job, just because the interviewer thought it was cool. During a period I thought I’d do a marketing internship, it also got me lots of interviews, even though I had never had a job or position or university courses in the subject before.

This doesn’t mean you have to be a blogger, but do SOMETHING you are interested in. I created an eBook about how to get the freelance visa in Germany and put it up for sale on a WordPress website. I did it because people would not stop asking me about it, and I no longer had time to let everyone “pick my brain”. This also gave me experience making an eBook, with how self-publishing a book on Amazon worked, and later, how to set up WooCommerce and sell my book myself, without the Amazon fees.

I hosted meetups for queer couchsurfers in Berlin, a vegan pub crawl, a vegan pancake pop-up in a tiny house with a friend, and spoke at some freelance events on the freelance visa in Germany. This gave me experience with advertising events on Facebook, marketing the events, making the social media graphics for them, and some project management. 

I organized an alumni group for my university and ones like it in Berlin, stalked all the alumni I could find in my area to invite on LinkedIn, and created an email list for us with some meetups. This gave me experience using the email software, reaching out to the right people, and also connected me with some cool people.

All this stuff is on my resume. No one gave me the experience, I took it.

So, if you don’t have any experience appropriate for going remote on your resume, go make it! None of this cost me any money (okay, the website hosting cost me money, but I earned it back in affiliate sales). Speaking of, there’s another thing I learned: How to do affiliate marketing on a blog. Boom! All these skills ended up being the basis for my client work today.

Tip: I use Siteground for hosting on all my websites, and they are the best host I ever used *wink wink* (yes it’s an affiliate link but also it’s the only host that doesn’t make me want to die when something breaks).

TL;DR – What’s the take away?

Now that you read my whole story on how I prepared to become a digital nomad, you may be wondering where to start. If it’s not already clear, my biggest recommendations are:

  1. Start networking and building community with the people you want to be. 

I cannot stress this enough. I don’t care if you’re an introvert, or you’re shy, or whatever. Get over yourself and try it. If you hate them then at least you know, and you never have to see these people again because they are nomads. Go find some other introverted digital nomads or drop shippers or grant writers or whatever. Find people in your area on the Facebook groups and suggest to meet. Meeting it person makes SUCH a difference as you realize they are just awkward humans like you. 

Without my digital nomad network this whole thing never would have seemed possible. My nomad friends got me out of so many moments of doubt throughout this process, clarified things that were blocking my next steps, and have referred me to many clients now. They also provide my community, so I don’t run back to a cubicle out of loneliness.

Some great free groups to start:

Sorry dudes, a lot of these are women-focused. I was in the ones with men, but usually end up having to leave because some of the guys in there are so mean to people, and they tend to be more anti-gay or mocking gay people on the rare occasions they post. I do feel for you all as the women’s communities are so supportive and it doesn’t seem like there’s a supportive space for dudes. So if you’re a dude reading this looking for that, maybe you should start one and don’t let all the snarky assholes in.

2. Get skilled up

I had a decent amount of applicable skills and work experience before going remote due to my hobbies and real life work experience. If you are still mostly computer and social media and tools clueless, first thing you probably want to do is get skilled up.

Here’s some useful courses I can 100% vouch for because I know the people personally:

5-Day VA Challenge – This is a FREE 5-day course that helps you work out what services you could even offer, how to set up your online presence, and how to get your first clients. I’ve done it three times and can def vouch for it. It’s also great for making community with others trying to make the jump to remote freelance work.

The VA Starter Kit – I bought this myself and still refer to it. This will help you in much more detail with all the logistics and how-tos of going remote. You also get access to the 5-Day VA Challenge forever even if one is not running soon. Honestly I think this is useful to anyone trying to be more tech and social media savvy at any job.

The WordPress for Beginners Kit – If you don’t even know where to start with building a website or working on clients’ websites in any fashion (even if it’s just loading up or writing them blog posts), this is for you.

How to Find and Land Your Ideal Remote Job Masterclass – This one is totally free and well get you started if you prefer a remote job instead of freelance work.

The No Bullshit Road to Remote Work – Taylor is my friend, but I’m also her fangirl because I love how straight-forward she is in a sea of bullshit, while somehow also managing to be kind. She is thorough, and offers actual, actionable steps to get you where you want to be.

Navigating the Post-Grad Pivot Workshop – Sami is a friend of mine and has been a career coach for ages before starting her own business around it. If you have graduated and are wondering WTF to do now check out this FREE workshop from her.

LinkedIn Mastery for Solopreneurs – Another great course by Sami. Did you know Linked In still has an algorithm that doesn’t suck, i.e. you can actually be seen there? Do you still just think of it as an online CV (I totally did). Sami goes over how to make the most of your LinkedIn profile in depth and how to turn it into a sales funnel for your services or product, pus loads of features you probably didn’t even pay attention to.

Find the Jobs, i.e. Figure Out What the Jobs Even Are

Everyone’s first question is – where can I find remote jobs? Realize this is a complicated question, as it depends on your skills and experience, same as a regular non-remote job. That said, there are some websites and groups I recommend for job postings. I also find these useful just for getting an idea of what types of jobs are out there.

Work From Home (without selling anything!) – She vouches all the jobs before posting in the group so there are no scams.

Where to Find Remote Jobs – The Ultimate Guide for Digital Nomad Girls

Top 30 Freelancing Platforms for Digital Nomad Girls

Remote Job Boards for Every Industry

50 Digital Nomad Girls Share Their Online Jobs (to help give you an idea of what’s out there)

Remote Like Me’s Weekly Roundup (not free but Taylor hand-curates a list of 30 jobs you get every Monday)

When it actually happend for me

So there you have it! That’s what I did during my two years while prepping to go remote! I got my first job from a friend I made from the queer nomad group I run and maintain, and referrals from other nomad friends I made during this networking period. The actual switch to working happened way earlier and easier than planned, but it’s only because I laid the groundwork.

Do you have more questions about preparing to go remote? Hit me below in the comments!

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