How I’m Learning To Become A Digital Nomad

Aspiring to any new state can be a challenge. And a career change is no different. But it can be easy to feel out of your depth and like there is either too much information – or not enough.

If you always feel like you are failing, or you forever get the impression that you’re climbing a mountain, instead, realise that you are grabbing life by the horns, facing up to uncomfortable things, and giving it a go. Good on you.

Perhaps the world’s greatest self-development guru – Anthony Robbins – says:

“There is always room in your life for thinking bigger, pushing limits and imagining the impossible”.

If you realize the truth of this, you understand that it’s all one big journey towards a better you…and that there will always be mountains. And hard though they may be to traverse, they are the rocky paths to the realization of our better, more successful selves. Equipping yourself well with the knowledge and techniques you need for ‘climbing’, however, is vital.

How I'm Learning To Become A Digital Nomad


In this post, I’m going to discuss how I’m trying to get to the top of my current mountain and get closer to successfully earning an online income sustainably. My strategy is based around 3 main areas:

1. Surrounding myself with the right people

I t was Jim Rohn who said:

“You are the average of the five people you spend the most time with.”

I believe this to be one of the most powerful pieces of information a person can be in possession of.

If you understand this  simple truth –  that the people around you will change YOU – then you understand that your success, your emotions, your future even, is influenced by those you spend the most time with.
If you doubt that for even a moment, take time to think about the five people you spend the most time with in your life. You’ll soon come to see that there is a ring of truth to it.

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No man is an island


In light of this I decided (back when I had determined that I was going to make this career change) that one of the first things that I needed to do – as soon as practicable – was to surround myself with people who were doing what I wanted to do.

This was particularly important for me because, at this point in time I had never even met a digital nomad before. Even though I had determined – beyond doubt – that I wanted to become one.

This is why I chose to begin my travels in ‘cheap and cheerful Chiang Mai’ – the Southeast Asian capital of digital nomadism. I was not disappointed. Let me explain why:

Surrounding myself with the right people (in real life)

During my few months in Chiang Mai, I had more occasions of meaningful interaction in that space of time, than I have perhaps had in years. I actually had valuable conversations with people who were working on the road (or trying to!). Many of these developed into ongoing friendships and connections which I continue to this day. For some tips on this check out my post on how to meet people while working and travelling.

Prior to heading off to Chiang Mai, I knew that while I was doing the best that I could with the resources that I had (which is all any of us can really do), I was not even grazing the surface. And turning up in Chiang Mai and immersing myself in a community of people who were succeeding in the ways that I wanted to succeed was like the most amazing reverse brain dump. Matrix-style.

For all the amazing benefit of our virtual capabilities, and the immense amount of learning that can be done by watching and interacting with other people online, we remain physical beings. As such, communication has no finer form and is no more instinctive than when it is done face-to-face.

Surrounding myself with the right people (virtually)

In saying that, personally I have found that the rule holds true virtually as well as in real life. I remember for quite some time I didn’t have much of a social circle – or a circle of colleagues. The nature of my day job caused me to be alone almost constantly. And my work day would often begin when most other people were just coming home at night.

I remember thinking that in order to even make up the five people necessary for this rule to hold true, I would have to start looking at people that I was spending time with virtually.

It was then that I realized that I was spending upwards of three hours a day “with” Pat Flynn, John Lee Dumas and other online business podcasters. It’s no wonder that my life has taken the course it has! Aside from that, I was also spending a lot of time on YouTube following many influential You Tubers, and many aspects of my life now are a reflection of that.

The message I really want to get across here is this: Surrounding yourself with the kind of people that you want to be is possible – even if you don’t know them personally.

Some of my favourite ways to surround myself with good online influencers include:

You Tube 

You Tube is a great place to find and connect with producers of visual content. More established You Tubers often collaborate with each other, bringing you even more insightful content. You Tube is particularly useful for finding ‘How To’ videos which can instantly answer specific questions on a variety of issues. I have used it to find out how to edit photos on Pixlr, solve tricky issues with software, learn how to do keyword research, and much more.

Online Forums and Facebook Groups

This is one of the best ways to be able to interact online with people quickly and be able to offer and receive a lot of value – with little commitment or time needed. I have joined some excellent Facebook groups, and find that I enjoy giving information to other people, as much as I appreciate being able to ask questions, and have them answered by others.

pats first kindle book group
Learn from others and share your experiences

Some of the best groups include the following:

Pat’s First Kindle book – this is a Facebook group started by Pat Flynn of Smart Passive Income, and has a really excellent community of self-published and would-be authors who interact through questions, success stories and cautionary tales. Perhaps my favourite Facebook group ever. Just request to join.

Ultimate Travel Group – this is a Facebook group for travel bloggers, and was started by Aileen Adalid of I Am Aileen Travel Blog, which has been featured on BBC Travel and National Geographic. It is a great place for travel bloggers and other travellers who work on the road (and have a blog) to get discovered. There is a very easy-going feel to the group. However it is well structured, with certain days being dedicated to particular themes, and this method works to make a really valuable resource for the bloggers who use it.


These days there seems to be a podcast for almost every topic under the sun. When it comes to online business podcasts, in particular, there are some real stars that are engaging, entertaining and providing consistent value.

Podcasts are a powerful medium for learning

These are some of my favourite podcasts:

Smart Passive Income Podcast – Although I have tried, I have never found a better online business podcast than Pat Flynn’s Smart Passive Income Podcast. For those of you who have followed, firstly his blog, and then his podcast and other ventures, I’m sure like me you recognise why he has  has seen such success. It provides consistent value, a bevy of interesting guests, and Pat Flynn himself is the nicest of hosts, providing great value for his audience over the years.

Problogger Podcast – A relatively new addition to the podcast scene, Darren Rowse creates value-packed practical podcasts for improving your blog. The podcast’s tend to be shorter bite-sized nuggets of wisdom someone who has been blogging for a decade.

Travel Like A Boss Podcast – This podcast is hosted by the celebrated Chiang Mai-based digital nomad Johnny FD. Johnny FD Interviews a lot of location independent entrepreneurs who are travelling while working. It provides a perspective on earning online and travelling that is a lot more attainable for the beginner than other similar podcasts.

2. Self-Directed Learning

I wish I had been more clued-in in the past to the importance of self-directed learning, the way I use it now. I have always enjoyed learning new things, did well in school, and was excited – rather than bored – by learning. However, I was always taught that conventional education was superior – and that obtaining official certification in the form of a diploma or degree, was the way to go.

I wasted a lot of time, obtaining qualifications which, while useful in their own way, have not equipped me nearly as well as they should have, considering how much time I put into them. Had I been in the know, I would have educated myself then the way I do now.

The benefits of self-directed learning is that it is far more fluid. When you are able to determine for yourself what you learn, and change that at a moments notice according to your needs, you are able to educate yourself a lot more efficiently, and not just according to a standardised curriculum.

As I said before, I adore learning and the time in which we live has made self-directed learning so wonderfully exciting and easy.

These are my favourite ways to learn online:


I always go for the free option first. It’s amazing what you can get for free if you look. If you are familiar with the Kindle platform, then you will be aware that Kindle allows some of its authors to offer their books for free for a couple of days every few months. This is done to allow the authors to get exposure for their books, and as a marketing tool.

This is also your opportunity to get many new titles for free at some time or another.

free kindle books on amazon
Plenty of free titles on Kindle

I am definitely not suggesting that you should stalk the Kindle store for every new title that comes out.

However, if you regularly check for free Kindle books on offer, you will find useful reads in a variety of topics like self-development, earning money online and more. There are also online forums and Facebook groups, that will often notify members of free e-books when they are available for free download. Furthermore, a lot of blogs and websites give away free e-books to grow their email list, and especially on some of the more high profile blogs, these free ebooks offer excellent value.

Of course there are always paid options and – especially on Amazon Kindle – the prices rarely go above five dollars for most books. Therefore it is easy to amass quite a collection of e-books at very little cost which can be invaluable learning tools.

Some of my favourite Kindle titles include:

Digital Nomad Escape Plan: Chang Mai Handbook by Michael Hulleman – This is the best e-book I can recommend if you are preparing for your digital nomad debut in Chiang Mai – or really if you are planning to visit Chiang Mai for anything more than a month. Written by a bona fide digital nomad who writes from his personal experiences living and working in Chiang Mai.

How To Write A Book That Doesn’t Suck (and will actually sell!) By Michael Rogan – I really love the relaxed tone of this book. It is a really good guide for someone who is planning to create their first e-book and just needs a bit of guidance. He includes some priceless tips on how to best communicate your message to your audience in a way that will appeal to every reader.


I’d have to say I actually prefer audio books over e-books. Be aware that many Kindle e-books give you the option to buy the audio file for the book as well. If you find that you are able to listen to audio books easier than you are able to read e-books, consider going that route. This is a perfect method of learning on-the-go.


In the last month I have attended three free webinars online, and from each one of them I got lots of valuable information that is helping me get closer to my goals.

Clickbank training webinar you can do it too
Screenshot from recent free Clickbank webinar – I learnt so much

Webinars are popular among many for expanding their online business. It enables business owners to grow their email list and connect more closely with their audience by giving them value and taking an opportunity to be heard by their customers and create rapport. This increases trust, improving the chances of creating more loyal customers.

From the standpoint of someone looking to improve their knowledge in a certain area, free webinars equals free information.

Because Webinar hosts often offer a product that you can buy at the end of  the webinar, they do their utmost to provide genuine value throughout the webinar, in an attempt to impress upon you the value of signing up for their paid program. You are under no obligation to buy any product, but you still get lots of value, regardless.

Attending free webinars is one of the best ways that you can learn more insider information from experts – at no cost.

Online courses

I started taking online courses years ago. I began by signing up for a site called which offered free courses on a variety of subjects. I found the frame work a little clunky. But at the same time, the course content was legit.

alison free courses
Learn for free

To this day, you can access free courses on Alison, as well as from other online course providers. Many bloggers offer free courses nowadays as well, as one way to grow their email list and get in front of more potential clients. Courses such as these can be perfect for anyone wanting an overview of any aspect of the online space.

It enables you to find out more about a topic before you decide if you actually want to spend on getting more in-depth training in that particular area.


I have this past year become a big fan of Udemy. I have found it to provide me with the right level of skills, at prices that I can afford.

I have taken a number of courses, covering topics such as affiliate marketing, course creation and e-commerce. Going forward, I have plans to take even more of those related to earning a location independent income.

What I love about Udemy is the way they offer so many practical courses directly related to the needs of the budding online entrepreneur. So many of the course creators are people who have themselves created sustainable income online using the methods they teach. Many even offer short free courses which are a fantastic way to discover if you like the teaching style of the presenter before you purchase one of their paid courses.

Another thing that attracts me to Udemy is the option you have to take very niched courses. Sometimes you don’t need to learn to be an expert – you just need to acquire an isolated set of skills. Udemy allows you to do that very cheaply.

 3. Experiential learning

At the end of the day, it’s all theoretical until you actually start doing something yourself. And not until you begin doing things yourself, do you formulate your own specific processes and your own particular approach. This happens because you are able to reflect on what you have done and choose courses of action based upon your experience.

Remember, things that are true for others are not always true for you, and sometimes you hear a lot about one side of an equation and not the other.

Experience – even failure – is a pathway to success

As long as you give yourself some room to play with it, it can be fun. This is why it is a really good idea to experiment in the online world at least a little before you rely upon it exclusively for income.

This allows you to freely fail (and thereby learn) bringing a much more carefree approach to the exercise. They say it’s good to fail – and quickly – and after this success is more likely to come. Once we overcome the fear of failure then the true learning begins.

So I do that too. I try and fail and try again. And I’m learning a lot a long the way.

Let me leave you with this quote from one of the most successful writers of today – J. K Rowling:

“Failure meant a stripping away of the inessential. I stopped pretending to myself that I was anything other than what I was, and began to direct all my energy into finishing the only work that mattered to me. Had I really succeeded at anything else, I might never have found the determination to succeed in the one arena I believed I truly belonged”.


Are you learning to make your living online? Are you an aspiring digital nomad? Let me know in the comments below how you equip yourself for the challenges of this lifestyle.

5 thoughts on “How I’m Learning To Become A Digital Nomad

  • January 4, 2016 at 5:12 pm

    I am making a part-time income from blogging and hope to increase that this year. One tip is to value your readership and your worth, and don’t undersell yourself when pitching to companies. Show them what you can do for them! Great tip about surrounding yourself with people you like and that really matter.

    • January 5, 2016 at 5:37 am

      Hi Melissa, it’s nice to hear that you hare my perspective on the value of surrounding yourself with the right people. Glad to hear that you are making a part-time income blogging, and best of wishes with your blogging efforts in the New Year. I absolutely agree with you about valuing your readership and your worth. Thank you so much for stopping by, commenting and adding value here!

  • March 10, 2016 at 4:15 pm

    Great summary of your resources. I can relate with you by having a 9-5 career that just feels really isolating, which is why I think we are both looking for a better way. I agree with you that there are a ton of resources out there for directed self-learning. It takes a lot of effort but I feel it’s completely worth the feelings of achievements you get from them.

    Right now I’m checking out Side Hustle Nation, Thrilling Heroics, Digital Nomad Community, and other small blogs. I enjoy Pat Flynn’s blog a lot too!

    At the moment, I’m working on web dev skills and implementing mailing list on a few websites I’ve built. I’m also trying to surround myself with like-minded people as well since no one in my immediate friend circle has this kind of passion.
    Tim recently posted…My 3rd Divi Website Is LiveMy Profile

  • June 8, 2017 at 11:49 am

    Aw, sincerest thanks for mentioning my book “Digital Nomad Escape Plan”! The book has done really well on Amazon over the years because of awesome people like you.

    This year (2017) I decided to give it an overhaul –added a bunch of new chapters, gave the cover a redesign, and took it off Amazon to give away to aspiring digital nomads for FREE.

    You can pick it up for free at

    And even after all that, it’s still growing. Another update drops in July of this year. This is to celebrate the reboot of Hobo with a Laptop –I got married, and now it’s a joint project between my wife and I. It’s a lot of fun. We only relaunched Hobo 2 months ago, and it’s gaining traction, fast! You’re a big part of that. Get in touch if you’d ever like to write a guest post, we’d love to have you.

    Once again, a big thank-you to you.
    Michael Hulleman | Author “Digital Nomad Escape Plan” recently posted…20 Years On the Road and Counting, Meet Dave from Dave’s Travel CornerMy Profile

    • September 22, 2017 at 12:37 am

      You’re very welcome Michael, I’m glad to hear the book has been so successful. Congrats on your marriage and the relaunch! I appreciate your offer that I write a guest post – so I’ll definitely be in touch when I’m ready to get into guest posting again. Best wishes!


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