Success! Last week I landed a gig as an independent contractor for the next 3-6 months, helping to launch a new mobile app that will help medical professionals maintain their required certifications. All remote, from anywhere in the world as long as my work hours overlap their east cost team by at least 6 hours per day. That wraps up the first set of to-dos from my checklist.

Now comes the rest of the list…

• Figure out health insurance. Ugh. I’ve made the same mistake before, but for some reason I didn’t see it coming right at me again. The Colorado Affordable Care Plan (Obamacare) health insurance portal provides all the info needed to make a selection online to cover me while I’m in the U.S. Unfortunately, it also makes your phone number available to a bunch of health insurance brokers who immediately start calling and texting. Ignore. Block. STOP. That’s what my afternoon has looked like. I get that people need jobs, but having someone harass me with questions I’ve already answered online and for which I already have solutions is a huge waste of my time and no way to get my business. Anyway, check.
  
• Set up a new business checking account. Super easy since I had already set up an LLC and received a tax number the last time I was doing contract work, but not as easy as it could have been. In order to make sure I had what I needed when I went to the branch, I called ahead to get the list of stuff to bring with me: Articles of Incorporation, Certificate of Good Standing, and IRS tax number (EIN) for the business. I printed each of these and headed to the bank.
  
  As the account opening process gets started, I proudly lay my papers out on the desk in front of me, showing what a good student I am. “Actually, we have to print the Articles of Incorporation and Certificate of Good Standing ourselves so we know they’re real. The call center always says to bring them, but we can’t use yours.”
  
  “Maybe someone should give the call center that info,” I think to myself. Whatever. Check.
  
• Determine whether I need a tourist visa and get one if so. This one is a little confusing because I have conflicting info. Officially, the U.S. State Department says that U.S. citizens do not need a visa for Colombia if staying for less than 90 days. On the other hand, the brother of a friend of mine, an American who has spent a lot of time in Colombia, said I absolutely should get a visa, if only to save a couple of hours of standing in line upon arrival. It also seems based on what I’m reading on Migración Colombia that if I want to spend more time there – either by extending my stay or coming back later – then having a formal visa on arrival may be to my advantage. Those two reasons seem like good enough justification to go ahead and get a visa. Apparently I can’t apply for it until 72 hours before my trip, though, so I’ve got that step marked on the calendar. Check(ish).
  
• Figure out how I’m supposed to handle taxes. This one is going to take a bit more research. Based on the reading I’ve done so far, here’s what I think I know:
  • The U.S. and Colombia have no “Double Tax Agreement,” which is an agreement between countries to prevent double taxation of individuals and businesses. That means that if I don’t get it right, I may have to pay taxes in both countries.
  • The number of Residency Days in Colombia is 183. Going above that will trigger the need to pay taxes there. Since the trip currently on the books is for only 42 days, I should be in the clear. For now.
    
    Tip o’ the hat to the folks at Work from Anywhere for their free Tax residency risk map that informed me of those first two points.
    
  • Figuring out exactly what I have to pay the IRS in estimated taxes on a quarterly basis to avoid underpayment penalties is a HUGE pain in the ass. This post was delayed by me falling down the rabbit hole on Friday trying to get too detailed on this. Doing it the “right” way requires a through understanding and completion of…
    • Publication 505, Tax Withholding and Estimated Tax
    • A dead end at The Tax Withholding Estimator, which only works if you have a job where they withhold the tax for you, not if you need to do this yourself
    • Form 1040-ES, Estimated Tax for Individuals, which includes a separate form, the Self-Employment Tax and Deduction Worksheet for Lines 1 and 9 of the Estimated Tax Worksheet AND one line (5) that requires completion of Form 6251, Alternative Minimum Tax – Individuals

Halfway through Form 1040-ES is where I threw in the towel on Friday afternoon.

Diving back in on Monday morning, I had an idea. I Googled “short cut to estimated tax payments” and quickly discovered the IRS Safe Harbor Rule. Under this rule, you can avoid underpayment penalties if you pre-pay, on a quarterly basis, either…

• 90% of the taxes you will owe for the current year OR
• 100% of the taxes you owed the previous year
  
  …whichever is less.

In fairness, this rule is mentioned in Publication 505 but only in the context of whether you have to pay estimated taxes, not as a shortcut to calculating what you have to pay. If you are someone who is concerned about not paying the IRS too much in advance, resulting in a refund when you file your taxes, then this shortcut method won’t work for you. If you’re like me and enjoy getting a refund, even if it means you essentially put the money in a 0% savings account throughout the year, this shortcut is gold.

Oh, and don’t forget to include social security and medicare in quarterly estimated tax payments – 12.4% and 2.9% respectively.

With that, I’ll leave you with a clip from my favorite movie: