Taxes have got to be one of the biggest hang-ups I have about going 100% into nomadism. I’ve got American citizenship so the very words ‘double taxed’ make me shudder. I’ve thought about just getting an accountant to handle my taxes when I take the plunge, but is it really necessary? It doesn’t seem that complicated on the surface, but I know that the repercussions can be serious if you do it wrong. I’m planning on working as a freelancer, not necessarily starting a whole new business. How have you chosen to tackle it? Do any of you have pitfalls to avoid or horror stories to share?
I had the same question when I first started out. There are many ways to make mistakes, especially the different types of forms that you will need to do your US taxes only adds to the complexity and chance of errors. I decided to consult a tax advisor for the first 2 years to understand the requirements, potential pitfalls and tips and hints to reduce the tax burden. After the first 2 years, I was able to do the taxes by myself by simply using the tax reports that the advisor did as reference and allowing several hours to become familiar with the instructions of each form. Looking back, I was happy I did it this way.
Hopefully this helps