financial freedom as a freelancer or digital nomad

10 Steps to Becoming a Digital Nomad

The date: January 2015, Location: Atlanta Ga. It was here I began on my quest of being a Digital Nomad, working for myself and being truly independent.

I was working for a dick of a boss who had the worst concept of a business model known to man. I do not say this lightly, I had worked in the industry for many years and risen to great heights. In truth, greater heights than I could have expected had I stayed in my native country of Great Britain.

Don’t get me wrong, I love my country, but when I was leaving college in the late ’80s early 90’s on the back of a recession, the opportunities just weren’t there, at least not in the city I was in. So I had done well, but it was time to do it differently. I was thinking of being a Digital Nomad and working for myself – but how?

bad boss becoming a digital nomad

Background Story – the start of being a Digital Nomad.

Late 2001 I packed my bags and moved to Florida, USA. There followed an amazing career arc and progression that was very lucrative indeed. Fast forward 15 years and I have to admit that I was getting a bit, well…..burnt out. I had worked for many years in the ultra-competitive Logistics and Supply Chain industry. I had seen it all and done it all and ended up in Regional Management traveling extensively, which I loved. Eventually, I relocated to Atlanta on the company’s behalf.

becoming a digital nomad

There came a point in which my experience and expertise brought me out of direct Management and info a related field as a Director for another company that a friend worked for and had recommended me for the position. It was great for about a year, then due to some rather lax Management and unresponsive business owners, boredom set in.

Fortunately, I got headhunted again, to oversee local operations for a smaller company. I wrangled with the offer – going back to operations now I was out wasn’t a thought I eagerly relished. However, driven by the tedium of my current position and the rather substantial salary being proffered, I accepted – against my better judgement.

becoming a digital nomad and earning a large salary

It was the worst career decision of my life! I lasted 6 months then quit. Either the business or I was going to suffer, and I didn’t like the thought of either, so I left. Once I had done so it felt like a weight had lifted. I had been truly miserable in that last, and what would prove to be final, position in the Logistics business. That was where the story started in January 2015 and I took the 10 steps to become a Digital Nomad

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Step 1 – Make the Decision

I enjoyed 3 months to rest and do nothing in particular. Then decided I would never go back to being employed by someone else. It was a conscious decision and one I was 100% sure about. But not that easy. I wasn’t a big saver, never had been, and 3 months off work had depleted my savings to the point of being non-existent. So I had some planning to do if I was to reach my goal of becoming a digital nomad.

make money from nothing as a freelancer

Step 2 – Plan your strategy

  • Be brave enough to make the break, decide that you want to be a Digital Nomad then plan some steps.
  • Plan your exit strategy, try and stockpile money and resources
  • Avoid the temptation of going back into the job market just because its easier
  • You can do it, don’t let anyone tell you you can’t
  • Be resourceful, build income streams, focus on survival
  • Elicit help from friends, colleagues, family where possible

Step 3 – Determine how to make a living

I did a quick assessment, I had a house, a car and a little bit of cash, not much. The easy option would have been to return to the job market, take a position with a fat salary then there would be no issue. Apart from the obvious drawback of going back into gainful employment in an industry I just flat out didn’t care about anymore.

I couldn’t bring myself to do it.

resist job temptation

So using the resources I had, house, car, laptop and internet connection I researched how I could make money for myself. By myself. Answerable to no-one but myself.

I knew it was possible, and along the way, I learned something.

It’s terrifying!

Step 4 – Recognize it is not easy. Acknowledge it can be scary.

That’s the part no-one ever tells you about going it alone. It is really scary going it alone. Something you will realize as your work through your steps to becoming a Digital Nomad. As an employee you get your salary check every week or month, even if you take a sick day or go on vacation. Being self-employed you get paid only for your own input and effort. It is a very nerve-wracking thing in the beginning.

But something happens along the way, your confidence and faith in yourself increases, not overnight but slowly, by degrees. Then suddenly you look up and you’ve survived a whole year. You paid the mortgage, the lights are still on, you made it! I believe that the point of reaching the 1-year mark does something to the psyche.

Suddenly it’s not so scary, because well, you made it a year, and if you made it for 1 year, you can make it for another year, right? RIGHT! So now you are a Digital Nomad or starting to be, keep following the steps.

success becoming a  freelancer

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Step 5 – Assess skills and resources.

I already mentioned earlier that I’d done an assessment of my situation. Coming to the conclusion that my assets were, my home, car, laptop, street smarts, and past employment history. I had skills I could market, but it’s not easy to leverage those and jump in to being a well-paid consultant overnight.

In that assessment, I realized that being self-employed and self-sufficient meant facing some truths. The bills and overheads had to be covered and, in the interim, pride had no place. Anything that would pay money was viable – apart from anything illicit or illegal if course.

freelancer multi tasking digital nomad

Step 6 – Explore every opportunity you can

The bright side of being self-employed in 2015 was that we now lived in a world of online opportunities, crowdsourcing, and gig work. Multiple platforms were now available that would pay you money for your time, knowledge or labor.

Sometimes not a lot of money, but like I already said, pride has no place in the beginning. Making money and paying bills is the priority. It’s all about survival for the immediate moment. The steps to being a Digital Nomad are not always easy or glamorous.

What did I try?

multiple income streams digital nomad

Everything! I signed up for Uber and other gig-working or crowdsourced platforms. I started to drive for a living and was pleasantly surprised. The people were really nice. Mainly, I stuck to the day time hours as I didn’t want to deal with the drunk night time bar crowd.

I found that on the whole people were very courteous and polite. My clientele was a mix of students, business types, and people going to and from the airport. Uber’s pay isn’t massive but it was a place to start. After a while, I signed up with Lyft to and did both concurrently.

In home hours I spent a lot of time online and taught myself to build websites with WordPress. A quick few ads on Craigslist advertising budget web design and I had some customers. A few hundred bucks here and there for websites topped up my Uber and Lyft earnings nicely.

freelandce digital nomad web design income streams

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Step 7 – Diversify your income streams

We are now up to mid-2016. During this time I found an Atlanta based company called Roadie – like Uber but for packages rather than people. That was when things began to take off. Layering the different platforms on top of each other, managing them to maximize output and income and doing web design was more than enough to cover my bills. It was a great feeling.

I made enough money to rent a car from Uber, not cheap but it saved wear and tear on my own vehicle, and was a great tax write off along with the massive mileage I was doing. My tax bill was virtually nothing.

reduce taxes as a freelancer

The final layer came in 2018 when I partnered with a local guy that owned his own courier company and paid well. I also found an additional Roadie like company that realized I had a management background and wanted me to travel to different cities and manage their ad hoc distribution operation for companies doing promotions.

I was doing so well by this point I was able to ditch Uber and Lyft – the lowest paying and most time consuming of my endeavors. Now I was starting to see progress. But I wasnt TRULY a Digital Nomad yet, I had a few more steps to do.

Step 8 – Consolidate, assess, reassess

It was time to consolidate. I’d made it over a year. I was free of the shackles of a boss, corporations, and shareholders and I was truly self-sufficient. But now what? I’d make the break and built an income but I knew that I didn’t want to drive around or deliver packages every day for a living. So I began to experiment to obtain more income.

Platforms like –



Citizen shipper



Web design,

Social Media Management



Anything to try and build my income stream and to gain more independence. The idea of being a Digital Nomad is easy but the steps are hard. It takes application, adaptability and the willingness to change tactics along the way.

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Step 8 – Aim for financial freedom

I also decided that it was time to sell the house. The market had gone up a lot since I’d bought so the sale of my property gave me a nice nest egg. Around this time I decided to move back to England and be closer to my family. I also decided that I didn’t want the burden of owning property anymore.

As I had been a homeowner for so long I was concerned this might give me feelings of insecurely or of being adrift – it didn’t. I found that as long as I had enough money to live on, I couldn’t care less about owning a home. Another step closer to truly being a Digital Nomad.

financial freedom as a freelancer or digital nomad

Coupled with the fact that I wanted to travel more it seemed like the sensible thing to do. Once I moved back to the UK I managed to partner with a couple of companies that were creating professional logistics training (my old wheelhouse!) and now I work with them as needed providing consulting services and helping to develop their training programs.

Step 9 – Continue to build on existing skills

I also write professionally as an extra income stream – I no longer drive people or packages to their destination. I started a blog as an offshoot of writing and found it to be good therapy and fun to do. 

Now after 3 years I am in the fortunate position of being able to divide my time between the UK and the USA and travel more or less anywhere I want. This coming year is 2019 and I plan to travel and blog much more about locations visited. It wasn’t easy, but I had lots of fun along the way.

digital nomad freelance blogging

Step 10 – Making it!

For anyone wanting to make the break and work for themselves, it can be done! If I can do it anyone can and in this age of technology it is much easier to find potential customers for whatever service it is you’re offering. It’s not easy, it is scary, and sometimes you wonder what the hell you were thinking but trust me, it’s worth it in the end.

Last words

I’d love to know how you made the break and quit the day job, and what it is you do now. Please leave a comment and share your own experience or contact me HERE.

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1 Comment

  1. Nice post. I was checking constantly this blog and I am impressed!
    Very helpful info particularly the last part . I care for such information a lot.
    Thank you and good luck.

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