The epic, epic mountain landscapes of “Ushuaia, fin del mundo, principio de todo” (Ushuaia, end of the world, beginning of everything) in Argentina.

Month Seven of Remote Year: Earth

But more specifically Malaysia, Thailand, Singapore, Australia and Argentina.

Cassie Matias
Go Remote
Published in
8 min readDec 27, 2016

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This month and next I chose to opt out of the Remote Year program. What that means is I’m doing my own thing away from the group for a couple months. I chose to opt out for a couple of reasons:

- Prior to joining RY I had a big trip planned that overlapped December and January
- I wanted to dedicate very special and specific time to exploring Australia and New Zealand

I’ve met up with great people, friends, and friends of friends in every country I’ve been to this month. What’s come up in these meet ups and conversations is the inevitable “so are you working or…?” question. Then I have to explain how yes, I’m working. And yes, I’m doing it while traveling. But no, it’s not a steady thing so my situation is a little more complicated. Also yeah, it can be challenging, especially when all I want to do is explore a new city / country I just got to.

The last time I wrote about what I’ve learned professionally while working remotely was back in Portugal. That was July, month two of Remote Year. It feels like eons ago. While everything from my list of surprises and learnings still hold true today, I’ve gained a number of insights that I think are worth sharing.

Disclaimer: I have a set of marketable and transferable skills that easily allow me to work remotely. I fully understand this isn’t the case for everyone, so take my thoughts with a grain of salt.

Bird parks in Malaysia; spicy food in Singapore; wonderful humans and serene floating piers in Thailand.

Finding Projects

In a word: networking.

I’ve leveraged everything from the extended Remote Year network to friends and colleagues back home, as well as services online that help match you and your skills to potential projects.

Services like Pipeline are great (and a tax write off), as well as The Muse, Remotive Jobs, AngelList, Jobspresso, Authentic Jobs, Scalable Path and Space Chimp. Then there are of course the recruiters looking to fill positions and the local contacts in each city I move to. Although, recruiters prove difficult much of the time because they’re usually looking to fill on-site positions that I’m just not able to take on.

Finding projects isn’t easy by any means. And it’s constant business development, networking and engagement to keep things moving. Sometimes I can slow it down, especially after wrapping several projects at the same time, and other times I’m uncomfortable with the lulls. It’s an endless balancing act.

Client Breakups

Sometimes things just don’t work out. Since starting to freelance steadily in May, and taking on freelance earlier in the year, I’ve had four client relationships end. The common denominator between all of them was communication.

Whether it was a lack of transparency and honesty on their side, communication and collaboration breakdowns between both parties, or entirely my fault, these were all learning experiences. Since I had to end one client relationship prematurely in May, I made sure to tell every client afterwards exactly the type of environment I thrived in: constructive criticism, honesty, and collaboration. If they’re uncomfortable with any of those items, our engagement won’t work. Being up front about that in the very beginning sets expectations and has dramatically improved not only the types of projects I’m doing, but the relationships I have with teams now.

It also notifies all individuals that I want them to speak their minds, know that I won’t take things personally, and that I expect equal contribution in order to come to decisions. It ultimately holds everyone accountable and gives me runway to make some pretty bold moves.

Working Alone

I went from an environment that was so heavily focused on teams, their dynamic and its benefit to clients to now working primarily solo. In the beginning I found it challenging and isolating since I was (and still am) the only one in my RY group that does what I do.

But now 7 months in, I’m much more comfortable. I still prefer working with others, but ultimately I know I can handle anything that comes my way. And if I can’t, well that’s what the honesty and communication parts mentioned above are about. There were a few big turning points in the last few months that gave me a nice confidence boost:

- Remotely facilitating a 2 hour workshop with 4 members of a client team, one of whom was on a cell phone and riding in a cab, while the others were watching me pull together notes, research and synthesize their input in real time via screenshare
- Remotely facilitating a 3 hour workshop between 6 people across 4 continents and 5 time zones from Seoul, Korea, starting at 2am, after a literal entire day of working in an airport and traveling
- Collaborating with a massive client in NYC who was giving an important presentation to fellow C-suite executives, the SEC, general counsel and new board members on their company’s split and they needed to revamp their entire business communication

As for everything else that I have to do—meeting scheduling, invoicing, following up on payments, finding new projects, doing the work, planning the work, responding to emails—I compartmentalize it into sections of my day. Or, if it’s one long series of similar tasks, I move them all to one day out of the week. Also, working on flights is not a fun thing to do so I refuse to do it now, and I never take calls on the first day of a new city arrival. The internet hasn’t been tested well enough yet and I’m usually just too tired.

Getting Paid

Due to the literal entirely digital nature of my relationship with clients, this of course translates over to payments as well. I’ve worked on projects for people across the US, and ended up expanding my roster to include companies in Taiwan, India, Hong Kong and France. Getting paid from US clients is generally easy; it’s the international ones that require a little bit of creativity.

For US clients I’ve used PayPal, Square Cash, bank wire transfers, Justworks and Harvest to receive and manage invoice payments. Paper checks are really out of the question since I’m not around to deposit them. Also, it’s 2016. C’mon.

For international clients this is a whole different ball game. First, there’s the currency they’ll be paying in. And if it’s not US dollars, I’ll have to go and find the best way to convert not only my hourly rate to their currency, but also define what the total project budget will be. Then, once that’s figured out, I’ll have to convert it to US dollars and factor in any conversion / international transaction fees that might be applied to me once a payment comes through. This is the part where it’s a gamble: do I use the current rate for USD, or do I have them pay in their country’s currency? I’m still figuring this one out through a bit of trial and error. (Advice is welcome here!)

Next is receiving payments from international clients. PayPal charges high fees for not only currency conversion (link is for the UK but you get the idea), but also international transaction fees. And these percentages vary per country, with some being higher and some being lower. In a worst case scenario, a project that I invoice for several thousands of US dollars can have several hundred US dollars worth of fees taken out of it at the end. That’s a fairly significant loss on my side.

I know there are products like TransferWise, Xoom, Dwolla and Stripe out there that are intended to help facilitate this process. But they also take out a decent chunk in fees. My current solution? Use a combination of a Simple bank account that can accept international wire transfers and Western Union. Simple isn’t my primary bank, but they don’t charge me anything to receive the transfer and offer a fixed rate to clients to perform a wire transfer regardless of the amount. I’ll take it.

Being a Woman in the Tech Field

I had a conversation last month that addressed what it’s like to be female in an environment where it’s generally dominated by men. And I was asked if I ever felt like my career, personal needs or salary were compromised because of my gender.

I responded with nope, nope and probably.

However, as a female freelancer I’ve become more aware just how much extra I have to prove myself in every meeting, every presentation, every decision. I have to be beyond thoroughly researched, competent and “on” during every conversation, no matter how big or small. Now one could argue that yes, of course you have to because you’re getting paid for your expertise. Arguably more than an employed designer because you’re coming in much more focused for a much shorter amount of time.

But that doesn’t really explain being second guessed during almost every decision that I’ve ensured is backed by research. Or being spoken over and constantly interrupted during a presentation. Or being told the right thing to do, when I was brought in because no one knew the right thing to do. Or having production work delegated to me when I was specifically hired to define, guide and build smart solutions to complex problems.

But I have to say, one of my favorite things is noticing when the tide starts to turn. When the constant interruptions and opinion “offerings” soften and instead become a “what do you think?” with genuine interest in my answer. When I’m being approached with increasingly difficult problems, instead of being asked to make something look prettier. And when I share my work and thought process, it’s not about how pretty the presentation is, but how intelligent and targeted and effective the solution was. After weeks of not standing down, making sure my professional opinion is heard, and that positive progress is being made, I consider it a massive win when I can recognize the considerable ground I’ve gained in a client dynamic.

Achieved a massive life goal by finally reaching Australia; coming in for landing in Buenos Aires, Argentina; the breathtaking beauty of Ushuaia, Argentina.

When it was coming time to reflect on the month, I was honestly choosing between this and something much, much heavier. Basically, what felt like an existential crisis. I contemplated on a few serious questions and reevaluated several viewpoints that I had on not only myself, but my impact on others. Maybe I’ll share it next month. Maybe I’ll instead focus on what Antarctica was like since that’s what my next 12 days will be about (!!!), or what my road trip through New Zealand at the end of next month will teach me (also !!!). I’ll figure it out when I get there.

In the meanwhile, greetings from the Drake Passage & Happy New Year! 🎉

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Cassie Matias
Go Remote

Digital product design consultant in NYC. Member of the Remote Year alumni crew. ±