Why you will fail as a digital nomad

As a seasoned digital nomad with, frankly, not that many skills, I have some experience with finding remote work.

My number one tip, and the one that I constantly tout on Reddit is this:

Don't leave until you have a skill.

Ideally something futureproof. When I first slipped on my walking boots and bought that dirty ticket on a plane that probably didn’t meet all the safety regulations I had no idea what I was going to do long term.

I started in England, did a quick TEFL course so I could teach English online, and off I went. Now, about ESL schools (English as a second language), looks promising, doesn’t it? Back in the day companies were offering sometimes twenty-five dollars per hour. Cool. Until Jimmy comes along. Jimmy doesn’t like learning English. His parents make him sit there and he mumbles back whatever you said over and over and over.. “Jimmy, what’s your favourite colour?” You say. “Jimmy, what’s your favourite colour”, Jimmy mumbles. And so it goes on. After the class, Jimmy rates you 1 star. Now your overall rating is below the company's allowed rating, which can never drop below 4.99 out of 5 stars, lest you be culled.

Now you have no income. These kind of jobs are easy to get and easy to lose, oversaturated and, essentially, a trap. I have been stuck for years just managing to make ends meet working across various ESL schools, forever praying that a ‘Jimmy’ doesn't enter my classes.

You are probably thinking, “pfft, in my spare time I’ll become a world-class coder, everyone will want me!”. You might become a world-class coder, I thought a similar thing, I learned Salesforce, A CRM system. I got my certifications, built a portfolio, and started applying.

Here's the thing, company’s actually don't care that much about certifications, they care about experience. You may have five exams under your belt and 100 personal projects, but you have never WORKED for a company as a programmer, administrator, project manager etc.

So why should a company risk hiring somebody with no actual work experience, who lives abroad where it is difficult to mentor them? They shouldn’t. You, remotely accessing their business unsupervised is a terrible idea.

But I’m already abroad, stuck in this situation, what do I do now?

Thankfully there is a solution to this woeful life of misery. Start with an entry-level position remotely. I did this with an IT startup. Just get your foot in the door. I started basically as a researcher/admin. I would hunt for jobs the company could take and occasionally schedule meetings and reply to emails.

Then, through sitting in countless standup meetings I identified areas of weakness. Our customers had no way of seeing how far into the project the IT company was, they had to email and wait for a vague, brief reply back from one of our engineers.

AHA! This was my moment to strike, Salesforce! I started bringing it up in meetings, “Man, it sure would help if we had some kind of.. customer portal… where customers could track the progress of the project they were paying for…” and so I brought up Salesforce, which I knew had a function for this, I made a demo, walked the CEO through it, he liked it and so we got Salesforce, I implemented it and became the Salesforce administrator for the company. I have since left the company and am no longer really working in SF, but I still get recruiters calling me, and it’s because I have experience, when I only had certifications, I couldn’t get so much as a rejection email.

Experience matters.

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