What It’s Really Like Living, Working (and Paying Taxes) Abroad

Taxes For Expats did my taxes in exchange for a blog post. They asked for no editorial input – as in, I’m free to say whatever I want – just that I mention them in a post if I liked their services! But I’m covering a lot more than that in this long overdue post…

These days, I get a lot of questions about what I’m doing for work, how I’m still traveling, how many hours a week I actually work, and even a few requests for advice on how to do the same from curious folks via email. So here goes. This is an attempt at explaining what my “traveling the world” lifestyle looks like nowadays.

So… What do you actually do?

Despite the common misconception that my parents have been fronting the money for my dilettante, round-the-world travels for the past 3.5 years, alas, they have not. Every time my mom mentions that yet another person from home has insinuated this, I always make it a point to say, “Wait, you guys, that was an option?! Yeah, I changed my mind, let’s do that instead! Set up the trust fund NOW!”

(I know, I’m hilarious. But in all honesty, my ass would’ve been home way before now if I wasn’t actually working and churning out some kind of income.)

Anyway, before I quit my job back in 2015 – whoa, it’s been a long time! – I saved up a TON of money in anticipation of traveling for about 10 to 12 months. Well, we all know how that worked out: Broke up with the live-in boyfriend, moved my stuff out, did not return home, did not pass go, did not collect a regular paycheck… for a while, anyway.

Instead, I met a boy, went to Nepal and India, and got a working holiday visa for New Zealand that I never used… because I discovered freelancing. That translated into more money for more travels – back to Thailand, Europe, home, and now Mexico. The idea that I could make a living online or working remotely while still traveling was always in the back of my mind (to be honest, probably since the days of law school while I sat drinking wine on school nights watching Anthony Bourdain). It only blossomed after reading way too many travel blogs, particularly Adventurous Kate, and seeing that people were actually doing this.

But the travel blogging life is not an easily attainable life. Well, at least not one that pays the bills. It’s a ridiculously saturated market because #millennials and Instagram. You’ve got to do it for free for a while to gain a following and/or search engine results to make any money. And it really helps to, um, post consistently. So yeah, not my forte.

Also, for anyone out there thinking of doing what I did: If you’re going to quit your job to travel, just keep a journal and take pics to help you remember things. If you’re having a ton of fun on the road, hopping hostels every week, sitting on beaches, and making friends on the reg (not to mention the beers you’ll be drinking), you’re not going to want to seek out wifi and sit in the corner on your laptop blogging.

For instance, if you want to see where I really started having fun on the road, you’ll notice that my posts screech to a halt in Vietnam. Know why? Because I was BUSY having so much of that aforementioned fun. And once you get behind in blogging chronologically, it’s super hard to catch up. (See Exhibit A, the 57,6956 unedited photos I have on my external hard drive.) This is the reason that you’ve never read about the 4th of July I spent at the Ramadan market in Malaysia or my unexpected trip to Kosovo or the Uber I got into in Portugal that wasn’t really an Uber… hey, maybe one day!

Answer the damn question, Rachel. What do you DO?

So I just told you what I don’t do for money – travel blogging. So what do I do that actually produces cash?

I write. I blog. I do copywriting. For other people. For businesses. I edit for those who can’t write or don’t have the time to. (I didn’t realize that there were so many folks out there who can run a successful business but can’t write for shit. Or everything they write sounds super formal or uninspired. Or they just want a blog, because hey, every business needs a blog!) I work with a consultant in NYC drafting and editing his written deliverables for clients. (He’s another lawyer who’s not lawyering.) I blog regularly for a sports ticketing company. (Think StubHub competitor.) I write for a wine club. I’ve helped design websites and written copy for landing pages of all sorts of businesses from high-end men’s shoes to bakeries.

So while the travel blogging thing isn’t for everyone, the “digital nomad” thing could be. There is no limit to the work you can get online as a freelancer, contractor, remote worker for a big company, whatever. If you’ve got the talent and functioning wifi, you can work from anywhere. For example, Marko does more business-y, number-related stuff. He builds giant spreadsheets, creates business plans, and – oops, I just fell asleep. (HA, you get the idea!)

Lots of people email me asking about how to do what I’m doing. I personally started with Upwork, an online platform for hiring freelancers that tracks your time, sends out invoices, and lets you apply for jobs. Yes, it’s competitive. Yes, they take a cut. Yes, people will low-ball you. And it can be disheartening at first. But it’s a great way to get started. Just build a portfolio, apply like hell, and keep your rates high. I did it, Marko did it, and my friend Anna did it (check out her guide if you want to get started freelancing online that way).

Also referrals. A couple of Marko’s clients needed some writing. Some of my clients knew other businesses who need a blogger or a copywriter. They like me, they refer me. Word of mouth is even better than finding something on Upwork, so I’d recommend starting with your network at home to see if they or anyone they know needs work done. And if you’re going to quit your job to travel, start freelancing before you quit. It takes a while to build up a client base. Plus, you’re going to want all the cash money you can get your hands on before you leave the country!

Well, what’s the money like?

So nosy. 

I never let the money from my initial travel savings run out before I started freelancing… because I’m responsible! (Though we definitely met people on the road who got down to their last $20 and just slept in their cars in NZ or picked fruit or whatever was in season to make some cash before moving on. Not my style.) I’m a worry wart and pretty anal – some might call it “cheap” – when it comes to money. I have literally always been that way, even when I had a “real” job.

I have spreadsheets that track all my spending from every country… literally every dollar from every day. You can enter your name over to the right for my newsletter and I’ll send you the link to the budget on Google Sheets. It’s insanity!

Just like when I started traveling, I still try to keep my spending to $50 a day, but let’s be real, sometimes that doesn’t happen and sometimes we like to have nice things. Marko and I will spend more on a cool apartment, and I love massages and nice dinners. Still, my monthly costs typically range from $1,200 to $1,800 per month. Everything else, I save!

At first, the sporadic payments from one-off freelancing projects was just a bonus. Like, “Woohoo! That pays for gas and groceries, and damn, New Zealand is expensive and every little bit helps!” By around month six or seven, my freelancing jobs started covering all my travel costs and I no longer had to dig into my savings – like it all netted out pretty nicely and I never had to move anything out of my Ally account where I keep the majority of my funds. (Definitely recommend their online savings account, btw, it gets 2.2% interest, which is way more than most brick-and-mortar banks.) By months 10 to 12 of freelancing, I was able to start saving more and more money each month. But starting last spring, I was able to start saving a significant amount.

Most months now, I’m saving as much as I was as a lawyer in Raleigh. Oftentimes more. No, I’m not going to say a number, nosy, but I’ve set up another retirement account, I’m paying student loans every month, and of course, I’m always saving for taxes!

Because student loans are still terrible and self-employment taxes are a bitch.

Doing taxes on the road.

Ugh. This is why I have the spreadsheets. Aside from the budget sheets, I also have income sheets. They make reporting my income much easier than relying on bank statements or the severe lack of W-2s or W-4s or 1099s or whatever it is people are supposed to send their independent contractors but don’t. I get paid all sorts of ways – Upwork, Venmo, and PayPal, but yes, I record it all and I reported it all and I paid taxes on it all. I am not our president.

Taxes For Expats made it a lot easier for me. Instead of emailing stuff to my dad, who tends to check his email about once a week and not notice that attachments exist, I simply filled out an online questionnaire where you enter all of your income, any possible deductions (they’ll let you know what counts!), expenses, and where I lived for what amount of time.

Fun fact: If you’re a true expat, you can avoid paying federal taxes, but to do that, you have to qualify for something called an FEIE (Foreign Earned Income Exclusion) which means you stayed out of the US for 330 days of the calendar year. And because I love my family (and Marko loves Vegas), I tend to stay in the country longer than 30 days each year. But I’m not sure you can ever totally avoid self-employment taxes… and those are like 15.3%. Woof.

Anyway, Taxes For Expats assigned me an accountant and I filled out their questionnaire and submitted a few tax forms. All online! They reviewed it, I answered a couple of remaining questions my accountant had, and my tax return was done within a couple weeks! I looked at the number, felt sick to my stomach for a bit, and gave it the okay. Then they filed my tax return for me – state and federal – so all I had left to do was pay it. Yes, I’ve already paid. It’s the worst!

Best of all, they prepared all the documents I need to pay state and federal taxes quarterly as a self-employed individual going forward… so that taxes don’t hurt so much next year! 

Taxes For Expats is a little pricier than my (dad’s) accountant back home, but the process was much simpler for someone living halfway around the world and pretty painless (except for the actual paying taxes part). However, if you are a true expat and qualify for the FEIF or earn income abroad in a multitude of complex ways – trusts, foreign-owned companies, bank accounts in other countries, etc. – I think it’s totally worth it because these guys are experts in all those things that make me want to curl up and die.

But like, do you actually work every weekday? Like 40 hours?

Most days, yes. I definitely work harder than I did before at my “real” job because I don’t have that salary “get paid no matter what” money. I actually have to earn everything that I make and there is no PTO, so that’s pretty motivational. Despite what it might look like from the outside, Marko and I are typically pretty boring Monday through Friday. We set an alarm, pull out our laptops, and get to work most weekdays. Sometimes, if we have a lot to do, we work on the weekends – gasp!

But do I actually work 40 hours a week? Um, probably not. I go to the gym when I want, take breaks when I want, go to the beach if I get done early, and take off Friday if there’s something exceptionally fun going on. We move countries every month… or three. Best of all, when friends or family visit me around the world, I can usually get my work done ahead of time and go hang out with them. I’m flying to Italy this year to meet my mom and aunts because I CAN. I just had friends come visit me in Mexico… twice! I’m taking off a ton of time this summer to go to the UK because we got tickets to Glastonbury. I book flights on weekdays. Hell, I booked a flight to Vegas for the same day! I do what I want!

No more asking for time off even though I’ve got the PTO. No more sitting at the office until 5:30 whether I’m done with work or not. I utilize my time how I want. And it’s a glorious feeling!

Was it all worth it?

Quitting the job, leaving the country, traveling around the world, and working online? Yes, yes, 100 times yes! I have zero regrets. I truly love living in a different place every month or so. This “digital nomad” thing is not for everybody, though. If traveling isn’t your thing, if you like the creature comforts of home, if you love your house and your stuff, this probably ain’t for you. And that is okay. You do you.

Of course, I still worry about money, but I think that’s just part of my personality. To me, it’s the freedom alone that makes this lifestyle worth it. I love traveling and I’ve met someone I love who loves it just as much. We don’t answer to anyone (well, except to each other) and we can plan out our lives however we see fit. It’s pretty beautiful.

If you’ve got more questions or want some advice about digital nomad stuff, feel free to leave a comment or send me a message!

So… do you think this lifestyle would suit you?