I left the US in 2010. Here’s what worked for me and what I wish I had done differently.

I grew up in an urban area and started working when I was 13. In my 40s, I decided to leave the US. Since then, I’ve lived in three countries, visited several others, and no longer have to work.

I combined the “pile of money” approach with “create an online income.”

Short version

Useful things I did:

Lived frugally and saw it as an adventure
Created an online business
Learned Spanish before leaving
Chose an easy place for my first move
Traveled full time for a couple of years
Chose another place because I loved the culture
Visited most places for months before deciding

Things I regret:

Waited until my 40s to get serious about financial independence
Dawdled when fixing up real estate
Chose a location just because I spoke the language, ignoring red flags

Long version

Here’s what I did and what I think about it now.

Worked as a contractor, not employee

I stopped working for a single employer when I was 23. Instead, I juggled contract jobs, most of them tech-related.

Multiple contracts meant a safer income, because I didn’t depend on one employer.
I made more per hour than in a standard job.
I could try different contracts to find the work I liked.
I often had no vacation or sick leave and was denied health insurance.

What I think now:

The job-juggling taught me to adapt to new situations and accept risk.
Since medical care was expensive, I learned to stay healthy and treat ailments myself.
I had no health insurance for years because the Medical Information Bureau made an error in my record. I should have more assertively investigated why I kept being denied. An accident or illness could have left me bankrupt due to one person’s typo.
I should also have been more assertive when negotiating pay. The book Overcoming Underearning eventually set me straight.

I worked on the cutting edge. Image by Rama & Musée Bolo.

Avoided debt

I worked while I went to college. The jobs gave me in-demand skills and helped save me from student debt.
I quit university after a bachelor’s degree because my student job was already full time, and an advanced degree wouldn’t get me better jobs, just debt.
I had a mortgage for awhile. But beyond that, if I didn’t have the cash for something, I didn’t buy it.

What I think now:

Avoiding consumer debt was smart, but I had almost no credit history as a result. It would be hard to get an emergency loan.
When I was living abroad, I had trouble proving my identity to US government sites because they expected me to have a credit history. Apparently, a real American uses debt.
I should probably have used a credit card that I paid off each month.

Improved my Spanish

I had studied Spanish in school and kept learning it as an adult. I used workbooks and flashcards, watched Spanish-language TV, and volunteered with Mexican immigrants.
I spoke it at a B2 level when I moved to Mexico, and life there brought me to near fluency.

What I think now:

Becoming bilingual in Spanish was one of the most useful things I’ve done.
It made my first move abroad easier, helped me see from different perspectives, and meant that I could socialize with anyone, choose any doctor, go to any show…
I avoided paying foreigner prices and didn’t have to hire translators or other help.

My Spanish study included more than 200 hours of the soap opera *La fea más bella*

Had a hands-on frugal lifestyle

In my late 20s, I bought a cheap fixer-upper that had two rental units. I lived in the small unit while renting out the big one. Rent for the big unit paid most of the mortgage.
I did most of the renovation myself, usually enjoying it, and sold the house for a profit.
With the house money, I moved to a cheaper area. I bought several acres of woods near a college town that had the kind of contract jobs that I usually did.
I parked a $3000 trailer in the woods and lived for almost free, heating with wood from my land. This helped me build a modest pile of money and take risks with my business.
Later, I had contractors build the shell of a small passive-solar house, and I started completing it.
I usually bought clothing from secondhand shops, had boring used cars, rode a bike… My main splurges were tools and food.

What I think now:

I should have been more focused on profit and speed when fixing up the rental house. However, I wasn’t sure at first if I wanted to live in it or sell it.
The same goes for the house in the woods: I should have finished it more quickly, especially once I realized I wanted to leave the US but the house still wasn’t done.
In both cases, living cheaply meant that I didn’t have to accept every job or client – I could choose the ones that were best for my future.

Created an online business

From my contract jobs, I chose a niche I enjoyed that paid well and could be done online.
I started a service business in that niche, getting most customers through a blog. That was in 2007, when blogs still got traffic.
When I had enough customers, I quit my last contract job.

What I think now:

Creating the business is the best thing I’ve done to improve my life.
It let me choose interesting projects, do the work to my standards, get paid according to the value I delivered, explore cool ideas, and build something useful.
It took off quickly. Three years after starting it, I was able to leave the US.
Eventually, my business gave me the freedom to choose almost any country.
The business was also social, which helped during the nomad years. I always had my colleagues, clients, and conferences.

Made exploratory trips

While my business was young, I tried running it from western Europe during a long trip. It was 2009, and fast internet access was a challenge. I also didn’t like the many rules of the places I visited.
Later that year, a conference brought me to Australia, which made it easy to visit Thailand, which convinced me I wanted a “developing” country, not western Europe.