Start Here – The Digital Nomad Journey
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Start Here – The Digital Nomad Journey

Start Here.

“Riley! How do I become a digital nomad?!”

This is the most common question I get. Understandably! My YouTube channel is freakin called ‘Livin That Life’, where I share my journey as a digital nomad. “…Posting travel vlogs is cool and all, but HOW do WE start Livin That Life?!” Well that what this blog is designed for.  To help you get where you want – becoming a digital nomad. Or just creating an online income stream.

Being a digital nomad comes down to one thing – being able to earn income remotely… aka from a laptop.

There are 3 main categories of earning income remotely!

1. Own an Online Business

2. Freelance

3. Work for a company remotely

So which one is best for you? This depends on your personal situation! Such as how much money you have saved, your computer skills, and how soon you want to leave your job. Freelancing is the quickest way to start earning online. But you should strive to create an online business that you own, for the long-term.


The 3 main categories of earning income remotely! 


Category 1: Build an Online Business

  • Everyone should strive towards this eventually. Becoming an owner of a company.
  • The holy grail is creating an online ‘passive income’, which means a business that makes money 24/7, without your direct input. You build a system, and the sales keep flowing in. But not all online businesses are passive. Some require more daily attention and maintenance than others. And of course, like any business, an online business takes full time work and dedication to build!
  • How to know which type of online business to start?
    • Step 1: Go to my page and read through each business model.
    • Step 2: Put some thought into which business model is right for you.
    • Step 3: Commit to one. Sign up for the recommended course & resources, and put your head down and get to work!


Category 2: Freelancing

  • This is usually the quickest way to make your first $1000 online
  • There are dozens of skills you can offer online


Category 3: Take your current job remote

  • Do your research and figure out if your company allows remote-work agreements
  • Start by offering your boss/manager a trial period, like 1 day per week, based on performance
  • If things go well, they might allow you to extend remote time, like a few days per week
  • Look up articles and videos on youtube of people who are doing this for more tips, as I’m not the expert
  • There’s a chapter in The 4-Hour Work Week about this



Step 1: Choose which category suits your current life situation

  • If you want/need to start earning online SOON, like in the next few months, start with Freelancing on nights & weekends.
  • If you think you can negotiate a work remote agreement with your current company, do that. And also start your side hustle on the side so you can quit down the road.
  • If you have time, like 6 months to a year to build something during your nights and weekends on the side of your job, then jump right into building an online business.


Step 2: Life Tip – Get in the habit of going to Starbucks or a coffee shop nights & weekends and sitting down with your laptop for 3-4 hour sessions. This is how online businesses are built. Coffee & laptop time!


Step 3: Get your Mind Right:

“I’m a first time entrepreneur, what books & resources should I read to learn the Entrepreneurial Mindset?” I get this a lot.

  • The quickest and most efficient way is to buy the “67 Steps to Success” course.  It’s basically daily summaries of the best business books. It will save you time and money, and turn you give you a Wealth of Business Knowledge in the quickest fashion humanly possible. Buy it and treat it like a daily class.
  • If you’d rather have just one book / audiobook to get started with the ’21st Century Digital Business / Lifestyle Business Mindset’– get The 4 Hour Work Week on audible. 
  • Set up Life-hacks in your life that will help accelerate everything. Read this: “My Top 5 LifeHacks that Made me a Digital Nomad”


If you are unsure about which path to start with, you can pay to Book an Advising Call with me.  I’d be happy to hear out your story and personal situation, and share my honest thoughts if you are serious and about that action boss.




If you are wondering… UNI OR NAH?

So you’re not sure if College / University is for you? Read by blog about College Alternatives


“I want the digital nomad lifestyle but… It’s a big leap to leave everything behind!”

This is a question I got the other day. A good question!

My thoughts:

Yes it’s never EASY to leave everything behind. The more you got goin on, the harder it is to leave.  It comes down to HOW BAD DO YOU WANT IT.  I think it boils down to that.

You are thinking about the travel life already… You can either, think about it forever, or FIND YOUR EXCUSE and GO FOR IT!

And everyone has their own story, situation and timing… But there will NEVER be the  PERFECT time!!  There will come a time where you get sick and tired enough of not being satisfied, and going for a CHANGE will be easier than the DIFFICULTY and or STRESS that comes with leaving things behind, and possibly burning bridges.

BUT!!!!!  Riley! You are over simplifying it!!  It’s not that easy!!

Yes, I know, because you need to be able to EARN ONLINE FIRST!!!



1) Freelance gigs (can make your first$1000 in 90 days on Upwork if you do it right)

2) Work your current job remotely

3) Build an Online Business (takes time to build up! 6mo to a year at least, part-time) (

So…. don’t complain that it’s hard to leave everything behind if you are not even earning online yet! First things first!!

And when you are making some relatively steady money from the laptop, maybe you will have more confidence to TAKE THAT LEAP!

YES. Some things DO take a LEAP OF FAITH!

“Do I need to be earning online before I quit my job?” — Everyone’s situation is different!  How much savings do you have?  Me and Park saved up $10,000 and quit to move to Chiang Mai BEFORE MAKING OUR FIRST DOLLAR ONLINE.

The thinking was, it would buy us 6-months of full-time work on our online hustles in Chiang Mai… and we got lucky that something worked out! Now am I recommending you do the same? And is our result typical? No, but I’m just saying what I did.

The safest bet obviously would be to be making $1000/mo online first before moving to Chiang Mai or something.

But sometimes you have to say FUCK SAFE because you are that itchy for a change and you just gotta, as we say, ‘GET THE F*CK OUTTA HERE!’ Lol.

Worst comes to worst, your online hustle isn’t making money, so you go back to a JOB! I know many digital nomads who have done that!   And what did they get for trying? Just an amazing 6 months or a year having tons of fun and experiencing a shit ton!

So that’s my rant…. It’s never easy to make a change in life… Whether thats a break-up, changing jobs, changing schools, moving to a new city, etc!

Making a Career-Move towards one of Internet Entrepreneurship is just the same!  It’s a big career move. Not for the scared. It’s not a question to whether you want it bad enough. I think you do. I can’t think of a more flexible career. It’s a question are you determined enough to put in the work nights and weekends to build up your business to make it happen.

– Riley in Starbucks in Bangkok

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