The Nomad Parlay: My 6 stage playbook to travel forever

I’ve been travelling the world indefinitely since 2016

I always get asked:

"When will you stop? What are your plans? Where are you going next?"

The truth is, these are the types of questions I’ve asked myself every day for the last 2,190+ days

How is it financially, legally and practically possible to travel the world indefinitely, whilst working? How far can you actually take the very notion of “digital nomad” or “remote working” in reality?

In 2019 I started to seriously ask myself these types of questions. - Is it possible to build a financial, and legal infrastructure suited to my desire to build wealth and travel the world indefinitely?

The short answer? - Yes.

Some important context

I always wondered if I should take the safe route in life - relocate back to the UK. Buy a nice semi-detached house. Get a comfy fixed low-interest rate mortgage (in 2019) and be considered by society as “normal”?

Or since I have no major liabilities or obligations - maybe I should go all out? Live life to its logical absurdity. Travel the world to far away places. Formulate more of a global strategy to solidify my ambition to continue travelling until something more meaningful presents itself

In 2019 I opted for the latter. Why? Because despite the alluring illusion of “stability” that we constantly sell ourselves in the western world about owing a house and having a state pension - there are no safe options in life. Sooner or later we’re all going to end up in the same place, eventually

The way I look at it - life is a game. It’s a game of risk engineering, strategy, luck and downright gambling

At this point, I’ve placed my bets on the assumption nothing is guaranteed and you shouldn’t bother minimising your risks. Instead? Maximise your opportunities

I’ve essentially framed my life choices with a simple question: If I’m lucky enough to reach the age of 85, how will I look back on my time?

Will I be happy knowing I succumbed to the pressures of society by ‘keeping up with the joneses’ and playing safe? Or will I be thankful, whilst I still have the ability to walk, that I grabbed life by the bollocks and did all the things I’ve ever dreamed of doing, whilst I still had the ability to do so?

It’s simple, really.

People who want to work remotely should know that nothing about being a nomad is practical. The longer you keep going, the more complicated it becomes in many ways. Especially when you want to 'future proof' what you’re doing and keep one step ahead of potential regulations

So, with that little bit of context in mind: I wanted to share the types of stages I’ve personally experienced on my quest to travel forever

1st Stage: The overzealous newbie

You’re overwhelmed by the possibilities of being a digital nomad. You significantly over-prepare, over-think and over-plan. You’re enthusiastic for absolutely everything and everyone. - It's probably the first time travelling alone so you're probably terrified, nervous and think you’re going to get scammed, robbed and kidnapped all in equal measure

2nd Stage: The slowmad

You’ve been a Nomad for a bit and you become more accustomed to being in control of your own schedule, taking your time and slowing down. You’ve opted to spend months in the same place, opposed to mere days or weeks. You learn most people in the world are nice, kind and caring

3rd Stage: The inflection point

After a while, you’ll fall in love with a few particular places. You make good friends. This is when you begin to realise you’ll probably never be able to go back to where you’re originally from and endure a normal office job ever again - this is when it gets confusing, and a little more scary because you’ve arrived at the inflection point; you realise this is no longer a phase, it has become the norm

4th Stage: Wait, is this legal?

Your attention turns towards the idea of trying to legally solidify your position in a select few countries which compliment the life you want. After all, hundreds of visa extensions are going to attract unwanted attention at immigration (been there, done that). Travelling starts to become an economic, cultural and opportunistic scouting operation opposed to simply leisure

5th Stage: Go big or go home (literally)

You start investing in different countries to obtain residency permits. You organise your business affairs in a format which takes advantage of different jurisdictions which represent your ideals and values from an ethical, entrepreneurial and social perspective

6th stage: Planting flags

You rotate around the world in each jurisdiction you’ve nominated to be your “home” - maximising your opportunities and taking advantage of the benefits whilst still exploring and venturing to different parts of the globe at the same time

I’ve only recently arrived at stage 6

When you invest large portions of your net worth into different countries, with different economical infrastructures and politics - it can be a little daunting. However, I started this journey in 2019 and it’s starting to become the new normal for me

I’m currently trailing the process of “residing” in a carefully crafted selection of countries which fit into my perception of an 'ideal life'

Essentially, I’ve designed my life around how I want to spend my time on this planet. All whilst keeping an eye on a few key metrics, such as;

• Sun - How much?
• Daylight - How many hours per day?
• Seasons - Taking advantage of different seasons (weather/ tourism, etc)
• Timezones - Optionality to work with companies in US, Europe, Asia, etc

As well as more broader questions around the economical, ethical and political environments of each country (banking, taxes and IP rights)

I've also designed my options to avoid dependencies, and ensuring I have multiple options at any given time

As the world evolves and changes over time, I’m almost certain I’ll re-jig and organise things differently as time passes and new opportunities present themselves.

After all, the whole point of this is to enable unlimited upside in the form of opportunity cost. Being super liquid, infinitely flexible on geographical location and having a diverse selection of economic jurisdictions gives a little more of an established advantage in the long run

If you’d like to learn more about the details of how I’ve actually done this, feel free to reach out. I enjoy talking about it.

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Darcey.