Weekly Wednesday: Don't Rock Up and Live, That's a Mistake

This is a Part 1 of Series for People Considering Working Overseas Who Are Not Following a YOLO Philosophy

I spent a few weeks casually reading

The AmerExit subreddit.

It occurred to me that some people coming to this newsletter might not understand the planning and strategy needed to make a switch to the Expat lifestyle.

Although this newsletter focuses on opportunities in the professional education sector, including online opportunities for Digital Nomads, the general steps to prepare to make a move like this are very similar for all professions.

In Part 1, we will review some key concepts regarding employment and visas. As long as a handful of people do a FREE subscription, I will do a Part 2.

Share this with anyone you know who might be interested in working abroad.

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After reading Reddit, I want to add a few disclaimers:

• All advice is based around having the highest chances of success; If you have a cousin who won a golden ticket, that is not something I will consider as a practical solution; advice is not only anecdotal; advice is based on rules and common practice

• The goal of all advice is to achieve financial success and to improve your options; advice is not meant for people looking to retire or claim some other type of status

• I will never recommend anyone surrendering their passport, but I will cover permanent residency programs in more detail (Part 2 or Part 3)

• With very few (like you need to be a millionaire to do this) exceptions, you cannot relocate without a home base. If you have no residence connected to your nationality, your journey will be short-lived, and you will be in legal trouble after about two years

• That means you need a legal mailing address, a driver’s license or alternate ID connected to the address, and someone to receive all your mail, legal notifications, tax info, credit cards, etc.

Understanding Status

The highest level of status is being a citizen. Without being a citizen, you are on a lower tier for things like due process of the law, borrowing money, entering into contracts, etc.

When you decide to embark on an overseas journey, you will be in a situation where your ability to move forward is based on how you treat people, how hard you work, and what level of risk you are willing to take.

This extends to your family if they are coming with you.

In most cases, if you follow a roadmap or path to citizenship, you will stop at being a permanent resident. Very few places in the world have true citizenship opportunities that are worth the effort.

I have gone through this process in the USA, from visa to green card, to citizenship, and a passport. The USA has the best process I have encountered for citizenship. However, the USA is tough for things in the middle, and in the middle is a sweet spot for most people.

To move to another country and legally work, you need a visa. There are visas based on traveling and studying, but you are not likely to find any stability in life with one of those visas. Also, visas built around travel and education do not last forever, and usually exclude family members.

Normally, you need a work visa that a company sponsors to get legal working status in a country.

If you want to be a long-term resident somewhere (and maybe work towards citizenship), getting a job is the best first step you can take.

There are a few exceptions, which I’ll outline below—but keep in mind, this is not a complete list. Countries frequently change their residency rules, and that alone should serve as a warning. If you're considering a country that has a pattern of shifting its residency requirements every few years, your long-term plans could be at serious risk.

Imagine doing everything by the book, securing your residency, only to have it revoked down the line. Unless you have full citizenship—or deep pockets and a skilled legal team—these are battles you’re unlikely to win.

Other Ways to Get Residency Besides Working through a Work Visa Process (Countries Listed are a Few Examples and Need to Be Reverified Every 30 Days):

1. Retirement Visas
Countries: Thailand, Colombia, Portugal
If you're over a certain age (usually 50+) and can prove a stable monthly income or significant savings, many countries offer retirement visas.

• Thailand: Offers the “O-A” long-stay visa with proof of income or funds.

• Colombia: Pensionado visa for retirees with stable pension income.

• Portugal: D7 Passive Income visa (great for retirees with non-work income).

2. Digital Nomad or Remote Worker Visas
Countries: Croatia, Portugal, Colombia
These are for people who work remotely for a non-local company but want to live abroad.

• Croatia: Offers a digital nomad visa for up to a year.

• Portugal: Offers the D8 “Digital Nomad” visa (recent addition to their program).

• Colombia: Launched a digital nomad visa in 2023.

3. Residency by Investment or Golden Visas
Countries: Portugal, Singapore (indirectly), Thailand
If you have capital to invest, some countries allow you to buy real estate, invest in local businesses, or deposit funds to gain residency.

• Portugal: Golden Visa program (currently evolving; check latest updates).

• Thailand: Offers the “Thailand Elite” program with upfront payments.

• Singapore: Has a Global Investor Program for high-net-worth individuals.

4. Residency through Study Programs
Countries: Singapore, Portugal, Colombia
Enroll in a recognized university or language program and get a student visa that can sometimes lead to longer-term residency options.

• Portugal & Colombia: Offer post-study paths to stay longer.

• Singapore: Offers top-tier education with potential for work pass transitions.

One huge misconception is that you can rock up and live somewhere if you have enough money to stay and look for a job. That is a huge mistake.

Local vs International Contracts

Here is a common situation. This is not theoretical. It has happened to me. It has happened to friends. And, it will happen to you if you show up as a tourist and apply for jobs.

You arrive as a tourist. Maybe you are a teacher. Maybe you work in IT. You meet some people, and after a week find some jobs. The application process begins, fast forward, and you have a job offer. The contract comes, and bang, you have a transferred visa and can start living as a legal resident.

A few weeks later, you meet Tim. Tim has the same job as you do. Tim seems to also have more money, a better home, better insurance, and is always planning for long summer holidays. You, on the other hand, have 14 days off a year.

Why is Tim getting a special deal? Because Tim has an international contract. Unlike the USA, most countries allow for multiple levels of contracts, based on multiple arbitrary rules.

Recently, as part of the work I do for my subscribers, I went through a new employment application process that an international school was running. I wanted to see what questions they were asking. Here are a few to note:

• Full family status with details

• My Age

• Religious background and details of religious identification

• Required a recent photo

• 10 years of criminal background checks from every country I have lived in

• Copy of Diploma attestation (will cover this in Part 2)

See, in Tim’s case, he did something like that process, but longer. Tim’s application included probably 6-8 hours of data work (if you are organized, this can be reduced to 2 hours usually).

Tim was able to negotiate as well. He could say ‘No’ and look at another job/ competitor. This employer sought Tim out, they wanted him.

You are a local hire on a local contract. You need the employer to go to immigration for you, sponsor you, pay to have your paperwork transferred, etc. You have very little leverage. You can fill a spot quickly and be cheaper, but you are not going to get the same contract. The employer needs overseas employees, and they know those people will cost more. They have two budgets, and you are categorized by the location you applied.

Can you ask to be an international hire on an international contract? Yes. And, this is how that works in most places if you are moving from a local to international contract:

• You prepare all the paperwork while in Country A

• You work with HR locally and review everything

• You then leave Country A and go to the cheapest neighboring country you can legally get into, Country B

• You wait in Country B for a set amount of time, you also find your embassy or consulate, and complete additional paperwork

• You find Country A’s embassy and consulate, and complete pending paperwork

• If you need a background check, this can be done in 1-2 weeks for about $300.00-$600.00 a person; I have done this myself (More on these in Part 2 or Part 3)

• Finally, Country A gives you the green light, and you can leave

OR,

You can simply look for jobs while living in your actual country of origin, save thousands of [insert currency], and go to Country A on a sweet international contract. HR in Country A will walk you through it all, and your fees will be much less than doing an international paperwork rollercoaster.

But, You Don’t Care, You Need to Leave Now!

If you decide to go to a country as a tourist and look for a job (aka Rock Up and Live), follow these steps carefully:

• Have a round-trip or outbound ticket (round-trip back to your country of origin is better)

• You only state on paper that you are a tourist, never allude to your employment plan

• Take minimal items with you, do not make it appear as if you are relocating

• This includes if you are taking a family

• Purchase travel medical insurance, so you can avoid using any local government resources

• Your hotel/accommodation bookings need to cover every day of your trip (most of the time, these can be cancelled after you are in the country)

• Get a local rental phone when you land, you will need it to find a job, no one is calling your iPhone from California

These are all the steps a well-planned traveler takes, but also the steps a person looking for a job would take.

Any indication of visa or process subversion will reduce your future chances of success. There will be no due process or ability to ask “why” if your visa is rejected. Most of the time, immigration will look at things you did that indicated you were lying about simply wanting to be a tourist, but then magically found a job.

Most Countries Block Competitive Labor

I have had interviews for tech jobs, and even been flown into countries to interview for tech jobs, where I lost the job due to workforce protection laws. In the EU, Singapore, etc, you will not be employed if they have a citizen who can do the job. It is not based on merit, portfolios, etc. Even if a failing company needs cutting-edge tech, the company has to prove that the local talent cannot do the job.

This is another reason the rock up and look for jobs approach is normally not recommended.

Not only do you often need to be literate in the local language, but you need to have skills they do not have, and will not lie about having.

“Hey James, can you build AI apps in Python?” James says “Yes”. And then you don’t get the job. James has no idea what AI is, James just wants to keep his job.

Also, in industries that have these types of regulations (Human Resources is a big one nearly everywhere), you will likely have poor working conditions if you do get hired. Why? You have nothing to negotiate with. They have James ready to pretend he can code, and you will get deported as soon as your visa is cancelled.

Most places in the world move you out within 30 days. There are many pressures used to discourage any recourse you might plan. And, if you overstay your visa, and try to leave, prepare for living in the immigration holding area for a few days and paying a big fine.

So, what is the solution? This is the reason I have my newsletter, you need to find a job first and get the sponsorship first. You need to arrive with a contract, some agency in your life, and these contracts come with more negotiating power.

How Do You Negotiate without Due Process

When an employer wants to bring in foreign labor, they need to have a reason to do so. Labor protection is standard everywhere I have lived, even in the UAE, which has an 80% expatriate and 20% indigenous population.

The employer gets to request visas. The government expects the employer to meet quotas, and that includes the frequency of visa requests.

Here is what that looks like from a financial standpoint (these values are not real, they are only here as an example; costs are usually higher):

The immigration office also has to staff and prepare for this volume of work. Now, one universal thing, government offices do not like to work, much less work more than they planned to.

Not only does your employer need to keep you until the end of your contract to reduce their financial burden on recruitment, but the immigration office is going to stop allowing them to get new visas if they are constantly having people quit/fired.

This means, on an international contract, they will work to keep you for at least two years, and then work to release you on good terms (even if you are James and can’t code) during year three.

Investment for local contracts often excludes housing, expat-level healthcare, and other benefits. Local contracts tend to be cheaper and easier to rollover.

Your plan may be to start working and stay long-term. Employers who initially sponsored you are more than happy to work with you on that after that first contract. It is cheaper to keep you going and working towards residency (assuming things are going well, etc).

Also, if you need more money, and your employer cannot meet your needs, working with them on transferring your visa to a new employer (assuming all contract terms are met) is the same as moving your international contract to a new company. Except, you don’t need to leave the country and wait.

Some countries allow you to move fluidly after getting your work permit. However, most industries looking for non-local talent are very tightly connected. Your boss can blacklist you, and there is very little you can do about it. I read stories about this often, and even read people plotting online to take the job, take the sponsorship, and then ghost their employer.

That is a bad idea, because your only leverage is your value to help solve a problem and keep long-term costs down. Looking like an unhinged liability is not appealing.

Achieving the Goal: Next Steps to Moving Out and Into Something New

The first thing you need to do is find an agency or company that is placing people like you overseas.

Currently, I only focus on International Schools. If you subscribe to the FREE tier, you will see the jobs posted every week.

The paid tier receives the jobs a day early, but the job list is the same on both tiers.

Even if you don’t work in education, you will likely find the job descriptions and information useful. 90% of all jobs in a country have the same immigrant visa requirements. You can research living in any location by finding professional jobs in that location.

Many professionals I know in the USA have done simple certifications (not expensive degrees) to move into international education. The savings rate for many is higher with a lower salary because schools provide housing, etc. Also, schools provide education for children, which is astronomically expensive in most places. You do not want to move to Japan and place your child in a Japanese public school unless they learned Japanese at home from the age of 1.

As an example, a teacher can earn $65,000 a year teaching English Literature internationally. As long as they completely avoid the EU, which offers a negative (yes, negative) savings rate, they can save $20,000.00 a year and have a free ticket home every summer.

I have a recent Salary Survey Linked Here.

Maybe you want to look for other jobs or attempt to be a Digital Nomad. Either way, you need an authoritative resource, not social media comments, for something like this. For example, if you want to go for a special visa in Thailand, find a law firm in Thailand that walks you through the process.

Or, if you have a tech job or corporate specialty, find multinational companies, and get registered while in your country of origin.

I have friends who are in fields like construction, and they have a special skill set. They sourced US companies working on large projects in China, and they got on board. Truthfully, it was not a location most people were interested in, so some of the normal requirements for education, etc, were waived.

My point is, they did not just rock up and go. They established themselves in their home base and then found a job.

I often read statements like this, “We are planning to leave in three years. We are saving and getting things ready.”

That is not going to work unless you can buy a residency visa, and if you have children, afford $15,000-$30,000 a year per child in tuition.

You cannot plan to simply immigrate without permission or a plan.

But you can plan and get this done by changing your mindset to focus on career first and residency later. If you want to leave in three years from now, I would:

• Look over about 100 different job postings

• Make a list of common requirements wherever you want to go

• Check the target locations’ immigration website and read all the rules

• Pay for X or ChatGPT Pro and query your scenario against the known rules; both have been accurate for immigration rules, health care, etc, on a worldwide scale. Paid versions will give you references and sources

• Find all the services you will need to get your paperwork completed

• Create a budget to pay for all the paperwork and overhead

• Enroll in certificate programs that level you up to meet base requirements (do not go into debt)

• Pay off all the debt you have. Managing debt overseas is tough; student loans are the exception. You can kill those quickly working overseas

• Slowly sell off your possessions and discipline yourself to a nomadic lifestyle

Those are the first of many steps, but essential. Even if you don’t end up moving, you will find freedom in completing the process. It’s weird. Sometimes, the harder you work to leave, the better your current situation becomes.

I am Looking Forward to Writing Part 2!

What’s on the Paid tier?

The paid tier has financial information, strategies for negotiating contracts, a deep dive into worldwide healthcare, etc. I like to tell people that for $50.00 a year, they can save 10 times that with the advice I give them. The truth is that when my techniques are used for salary negotiations, even in the USA, I promise you will get 7%-12% more than you thought you could.

I also have amazing memes, but those are always free.