Paying tax for freelance work while travelling
Having freelanced myself in South America I could give you a sound advice BUT you would first need to answer some questions.  1) How long do you plan on being in South America? At the end of 2017 will you be back in Ireland or still being in South America? In other words was is your country of residence for tax purposes on Dec. 31 2017 ? That is the key element to consider. Link 2) In latin America you can freelance with a legal working permit BUT in all these countries more than 50% of the economy is under the table. In all these countries expatriate work under the table. The question you need to answer is then: Who will be your employer, a company or the owner of this company? Working undeclared in Latin America is very common, what are the risks? The legal risks depend on the country and their laws. In which country will you travel? How long will you stay there? You will have a tourist visa or a working visa? 3) An important detail, your health. Check how long you can be out of Ireland without loosing your social health benefits in Ireland? In my country, if I am abroad for more than 180 days, I loose my national health coverage. Evaluate the amount of days you will be out of Ireland and where you want to be on Dec. 31th. That could change a lot of things in your life.
Working in my current sales role, I find myself listening to hours of business podcasts a week while travelling. Some of my favourite podcasts at the moment are:  PNR With This Old Marketing Futureproofing with Kelsey Ramsden The Brutal Truth About Sales &amp; Selling If you are paid by foreigners then it is quite possible they don't file anything with the IRS. All of this income you are required to report as business income on schedule C.  There are opportunities on schedule C to deduct expenses like your health insurance, travel, telephone calls, capital expenses like a new computer, etc... You will be charged both the employees and employers share of social security/medicare, around ~17% or so, and that will be added onto your 1040.   You may still need a local business license to do the work locally, and may require a home business permit in some cities.  In some places, cities subscribe to data services based on your IRS tax return.... and will find out a year or two later that someone is running an unlicensed business.  This could result in a fine, or perhaps just a nice letter from the city attorneys office that it would be a good time to get the right licenses. Generally, tax treaties exist to avoid or limit double taxation. For instance, if you travel to Norway to give a report and are paid during this time, the treaty would explain whether that is taxable in Norway.  You can usually get a credit for taxes paid to foreign countries against your US taxes, which helps avoid paying double taxes in the USA.   If you were to go live in Norway for more than a year, the first $80,000/year or so is completely wiped off your US income.  This does NOT apply if you live in the USA and are paid from Norway. If you have a bank account overseas with more than $10,000 of value in it at any time during the year, you owe the US Government a FinCEN Form 114 (FBAR).  This is pretty important, there are some large fines for not doing it.  It could occur if you needed an account to get paid in Norway and then send the money here... If the Norwegian company wires the money to you from their account or sends a check in US$, and you don't have a foreign bank account, then this would not apply. "I am a proud member of the BA frequent fliers' club (Executive Club). Their service is superb. Their avios (aka miles) are quite useful. However, that is if you're not flying with British Airways, because if you do - you'll pay enormous amounts as ""taxes"". I've used their avios on Air Berlin, American Airlines and Iberia - several times each, and their prices are very reasonable (including trans-Atlantic flights, although I mostly used it for domestic flights in the US and EU). If you only fly BA - their club charges ridiculous amounts for taxes and you would probably want to be in one of their partners' clubs. Depending on your traveling pattern - I'd suggest American Airlines (if you travel a lot in the US) or Qantas (if you travel to far East). I'm not familiar with other partners' clubs, so can't tell. So whether or not the 50K avios worth the investment is really up to you - it depends greatly on your traveling pattern and where you can use them. If only on BA - not sure if it is worth the trouble (although you do end up with about 50%-70% discount of the regular price when you buy miles tickets)." The plan is perfectly valid and legal as tax rules currently stand. There is no limit to the amount you can rollover or convert to Roth. Assuming your 401(k) is traditional pre-tax, you'll have to pay income taxes on the amount you convert above personal exemption + standard deduction, which is currently about $10k/year for single filers. The other caveat is you'll need funds to live off of while your conversion money is seasoning for 5 years in your Roth IRA. If you start the conversion while you are still working, you'll be paying taxes on it in your marginal bracket, which will negate much of the benefit of the pre-tax 401(k). If your living expenses are low, you can convert about $10k/year without federal income taxes, while living off capital gains from a taxable account which have a 0% rate in the 15%  income tax bracket (goes up to about $37k/year). You can use the ITR 1 and declare the income from freelancing as income from other sources. As part of freelancing, certain expenses can be deducted provided they are directly related to work and have proper records. Please consult a CA who can advice you on how to do this. The Actual income shown should be less of the expenses. "1. What forms do I need to file to receive money from Europe None. Your client can pay you via wire transfer. They need to know your name, address, account number, and the name of your bank, its SWIFT number and its associated address. The addresses and names are required to make sure there are no typos in the numbers. 2. What forms do I need to file to pay people in Latin America (or any country outside the US) None. 1099s only need to be filled out when the contractor has a US tax ID. Make sure they are contractors. If they work for you for more than 2 years, that can create a problem unless they incorporate because they might look like ""employees"" to the IRS in which case you need to be reporting their identitites to the IRS via a W-8BEN form. Generally speaking any foreign contractor you have for more than 2 years should incorporate in their own country and you bill that corporation to prevent employee status from occurring. 3. Can I deduct payments I made to contractors from other countries as company expense Of course." "New York State is one of a few states that will go after telecommuter taxes (such that some people may end up paying double tax even if they don't live in NY).  There are a few ways that you can avoid this. If you NEVER come to NY for work, and your employer can stipulate that your position is only available to be filled remotely, you will likely be covered. But there are a myriad of factors relating to this such as whether the employer reimburses you for your home office and whether you keep ""business records"" at your office.  Provided you can easily document the the factors in TSB-M-06(5)I, you shouldn't have to pay NYS taxes.  (source: I've worked with a NYS tax attorney as an employer to deal with this exact scenario)." "When I have a question about my income taxes, the first place I look is generally the Giant Book of Income Tax Information, Publication 17 (officially called ""Your Federal Income Tax""). This looks to be covered in Chapter 26 on ""Car Expenses and Other Employee Business Expenses"". It's possible that there's something in there that applies to you if you need to temporarily commute to a place that isn't your normal workplace for a legitimate business reason or other business-related travel. But for your normal commute from your home to your normal workplace it has this to say:  Commuting expenses.   You cannot deduct the costs of taking a bus, trolley, subway, or taxi, or of driving a car between your home and your main or regular place of work. These costs are personal commuting expenses. You cannot deduct commuting expenses no matter how far your home is from your regular place of work. You cannot deduct commuting expenses even if you work during the commuting trip."