🇪🇸 Spain - The First Steps

Christina and I have been making our way around Europe for the better part of fifteen years. We got married in France, which either says something romantic about us or something practical about venue pricing, probably both. Since then we've spent time in Hungary, Austria, the Czech Republic, and most recently a lot of time in Spain and Portugal. We love Europe. The food, the culture, the landscapes, the general sense that people have figured out that lunch should take longer than twelve minutes. For years the plan was to eventually retire there. Someday. Later. The vague, comfortable way people plan things they're not quite ready to commit to.

Then "someday" started to feel a little too convenient.

Over the past few years we've been quietly pulling on a different thread what if we didn't wait for retirement? What if we made the move while we were still working? That single question turns out to be a very efficient way to generate approximately one thousand follow-up questions. What visa do we use? Can we work legally? How do we get taxed? Will the US and Spain both want their cut at the same time? The answer to most of these, it turns out, is it depends, which is attorney for keep reading and also maybe hire someone.

We did what any reasonable person does first internet searches, AI rabbit holes, Reddit threads, Facebook expat groups. You can actually find a lot of good information this way. The problem is you have no idea which parts are accurate, which parts are outdated, and which parts were written by someone who confidently had no idea what they were talking about. At some point you need a human being with a law degree to look you in the eye and tell you what's real.

So this week we took the first concrete step and sat down with a Spanish immigration attorney.

The conversation centered on the most likely paths for people in our situation specifically whether we'd be coming over as W2 employees of an American company or as 1099 contractors. The W2 route requires either a company willing to establish a Spanish entity (a heavy lift for most employers) or an Employer of Record (EOR) arrangement, where a third-party organization with a Spanish entity essentially employs you on paper while you continue doing your actual job.

For us, the more interesting option turned out to be something we'd already partially built without realizing it. We formed an LLC last year Cascadia Ascent originally so Christina could take on contract work. Under the right structure, we could both work for our own company, which itself holds contracts with other companies. From Spain's perspective, the LLC is the tax liability, not us individually. The one catch: the company needs to have been in existence for at least a year. Given our timeline, that's probably fine. Probably.

Next stop: the international tax attorney. The paperwork is just getting started.