The plan is simple: Travel the world while working remotely for a year. Pay for it with the money I would have spent on taxes.


My departure date for the 330 Day Challenge is today; February 11th, 2019. I am writing this while sitting on a plane en route to Florianopolis, Brazil.

I have known about this plan for the past year and have been making life decisions based around this departure date.

In the article below I will walk you through every aspect of planning that I did. It is more than likely I forgot a few things, so hopefully I can use your comments to remember what I have missed.

If everything is planned well my hypothesis is that my entire trip around the world should be cheaper than my life in California. The following is how I laid the groundwork for this trip.

My Personal Tax Situation

Pulling this off has everything to do with taxes so lets start there.

A little about my tax situation:

I own 50% of a company that is an LLC that is treated as an S-Corp. I am paid $36K/year and the rest comes as a dividend at year end.

This is a strategy commonly used to pay less in payroll taxes.

I want to say that THIS IS AN ABNORMAL SITUATION FOR MOST PEOPLE. If this isn’t you, I explain further down more common employment situations.

However, there is still a solution for me to be able to take advantage of the FEIE.

In the last month of the year depending on how much money the company makes, I will raise my salary to the maximum amount of earned income I am allowed to exclude under the FEIE. So my salary will jump from $36K to $104,100 if all goes well.

Yes, I will pay payroll taxes on the extra income, but the federal income tax savings will be much larger than that amount.

There are no penalties for waiting to increase my salary either. I will also be able to lower it back to where it was the following year.

The other hidden benefit is that if I end up having to come back to the US for some reason before year end, I won’t raise my salary at year end and won’t be responsible for paying the increase in payroll taxes.


What About State Income Tax?

I have ended my apartment lease, car lease and health insurance in California and have cut all ties to the state.

I signed a lease at a friends place in Florida that has an extra bedroom and have been staying there for a few weeks before I leave. I will pay him $50/month in rent.

I am now a resident of Florida. If things go crazy abroad and I need to return to the US, I will return to Florida.

Getting this part correct is extremely important. More information can be found here: Eliminating State Taxes

The best part about this is that there is no limit for the amount you can save by changing states. With the FEIE there is a limit.

Since Florida has 0% income tax, I will save every dollar I would have given to the state of California.

Why pay the sunshine tax when you aren’t enjoying the benefits of it?


A More Typical Tax Situation

Most readers will say “cool story bro, but my situation is different”. They will probably fall into the category of employee or freelancer. Luckily for these readers – it is far simpler.

Employees have it easy:

You go and work and make your money. At year end you can deduct up to $104,100 from your income. If you are on salary you will have a large tax refund headed your way or if you are a freelancer you will have a very small tax bill at year end.

Here’s an example. You have a social media consulting business you can run from anywhere.

You decide to pack your laptop, passport, some clothes and go.

In 2019 you spend 337 days backpacking through SE Asia and the other 28 in the US. In that time, you make $125,000 profit in your business, with all actual work being done out of the country.

Normally you would pay ordinary taxes to the IRS on all $125,000 of that profit (this is changing slightly under the new tax plan). But with the foreign earned income exclusion, you will only pay the IRS ordinary taxes on $20,900.

This is a massive tax savings. Probably in the range of $15,000-$25,000 per year, depending on what your other income looks like.

State taxes would work as explained above and could net you even greater savings. More information can be found here: Eliminating State Taxes

Preparations & Logistics:

Now that the boring stuff is out of the way, I will walk you through how I dealt with common excuses for not being able to do it and other logistics you may need to keep in mind.

What will you do with your apartment?

I have known about this plan for the last year. I was able to structure a month to month lease with my landlord and once I knew the official date, I gave them notice of when I would be leaving and had no issues.

TOTAL SAVINGS: $1,050/month

What will you do with your car?

My  car lease ended a month before departure. I was able to get the leasing company to extend my lease an extra month so I could drop off the car and head to the airport.

TOTAL SAVINGS: $240/month

What will you do about your important business mail?

I am using I have changed our business address to their Florida location and am paying them $15/month to collect everything and let us know if anything urgent comes in.

They will scan me the contents of anything I need and can shred anything I want destroyed immediately.

Everything is managed through a fairly friendly user interface. There are many companies that do this, so just find one that meets your requirements.

TOTAL COST: $15/month

What will you do with all your stuff?

I am a 27 year old bachelor so it’s safe to assume my house was built on Craigslist. I was happy to give back to the site that made my decor so unconventional (read: used/gross).

Within two weeks I had everything I owned gone. You could always go the less extreme way and find a storage unit for between $50-100/month as well.


What will you do with your phone? Don’t you need to have access to cheap rates to talk to US customers?

I switched from Verizon to a T-Mobile plan. This allows me to step off the plane in any country and already have phone access without crazy daily fees.

If interested in more details on what to do with your phone check out THIS article.

TOTAL COST: $60/month

Will you continue paying for your health insurance? Will you get supplemental insurance?

I want to start by saying this was the hardest/worst part about planning this trip. Everyone’s needs are different so my solution is not a one size fits all.

I have cancelled my California health insurance since I no longer live there. That is a $350/savings.

Instead, I replaced it with a Florida Blue Cross policy for $310/month and supplemented that with World Nomads Standard Plan policy for $113/month.

This World Nomad policy is only good for two months. I am going to try it out and make sure any claims are handled before committing to it for the remaining 10 months.

Yes, this is expensive. More than I thought it would be, that’s for sure. However, one accident could wipe out everything I own in just a couple days of medical treatment. In my view, that would be worse than shelling out $423/month for one year to have peace of mind.

Also I chose Blue Cross and World Nomads because they are two of the industry leaders in what they do. When you need to make a claim, dealing with a second rate company could be a nightmare.

The main items that matter to me and that this will cover me for are:

  • Charges in excess of $7,900 (my deductible) in the US. If something really bad happens and I want to be treated at an American hospital I can be and won’t be bankrupt after.
  • Emergency medical services up to $100,000 and dental up to $750. This covers my favorite activities of surfing and scuba diving (up to 50 meters).
  • World Nomads provides a list of 200+ activities so it’s worth checking to see if your hobbies fall on the standard or explorer plan (more expensive). They even have Tuk Tuk racing on this list. Unfortunately, it is not covered on the standard plan but it is on the explorer.
  • Emergency evacuation is covered which means if I break my leg and want a US doctor to operate on me, my flight back to the US is covered and the procedure will be covered because I have US health insurance.
  • Trip cancellation is covered in case I get sick or if someone in my family dies while I am on the road.
  • Baggage and personal effects are covered in case my laptop or cell phone are stolen or lost.
  • Plus a bunch more!

These are the important things to me, but be sure to do your research as every plan out there is different.

TOTAL COST: Extra $73/month

How will you be sure you stay compliant with the IRS guidelines?

It is very important to track the amount of days you stay out of the country. Remember, the burden of proof is always on the taxpayer not the IRS.

With this in mind, I will keep a google spreadsheet tracking dates and flight times. This will also provide a great amount of peace of mind.

A year is a long time. How will you make sure you have social interactions?

I will be living with friends for the next 5 weeks that I met while on a co-living experience last September. From there I will be attending another co-living experience in Peru for a month.

Hopefully, from there I will have a small network of nomads I can travel around with.

For more on different co-living options check out THIS article.

What paperwork/shots etc. did you have to deal with before departure?

Since I am starting in Brazil, there are no shots necessary. It is a good idea to always research your destinations beforehand so you are sure you are safe and compliant.

For Brazil I did need to get a Visa, so one online application, $40 and 2 weeks later I was approved and legally allowed to enter the country.

I also had to renew my passport because it was due to expire in the middle of the trip. I think its better to get those pesky tasks over with while still in the US.

Financial Breakdown:

When taking the taxes and my lifestyle in California into consideration – this is how much money I have to spend each month. I should end up saving more money than I did while living in California.

Tax Savings
Federal Taxes$18,194
State Taxes$7,707
Apartment$12,600 or $1050/month
Car$2,880 or $240/month
Health Insurance-$876 or -$73/month
Total Savings$42,257

That leaves me with $3,521 each month to spend. This does not consider the money I spent on groceries, gas, dining out, etc. living in California. I am pretty sure you can live quite nicely on this sum of money abroad. After all, my trip depends on it!

Next Steps

Throughout this blog series, the other contributors and myself will walk you through how I structured my taxes and life to make this possible. Hopefully this will inspire someone to do the same.

Part 3: Month One on the 330 Days – COMING SOON

Please post comments or questions and I will answer them as openly as I can.

Also, if you are interested in connecting with other people who are attempting this join our Facebook Group.

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