My usual work space while in Valencia, Spain last month.

Month Two: Remote Work Learnings

Cassie Matias
Go Remote
Published in
6 min readJul 25, 2016

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First, a bit of professional background for context. I went to college in NYC and graduated with a BFA in graphic design about 8 years ago. After college, I “didn’t want to work for the man”, so I freelanced for about 2 years. I did everything from identity work to (self-taught) interaction design.

It was a good and bad decision but ultimately it taught me a lot about hard work, self-discipline and responsibilities. I made a ton of mistakes, learned a bunch, and eventually found myself learning about a whole new world of design. I eventually wanted to “work for the man”, and found myself working at a super small studio in midtown Manhattan for a year and a half. Since it was so small, I did a little of everything—answering phones, setting up for client meetings, designing, interviewing, teaching interns and managing vendors. After a year and a half there, I moved onto a larger company in SoHo where I worked for 5 years.

Here is actually where I became a real designer.

I learned about UX design and many of its methodologies. I learned about UI and digital product strategy. I learned how to present to clients and run research testing sessions. I properly learned how to work in teams where everyone was held accountable for their own work, and of course the overall project. I worked with developers across the world and was taught how to QA the build of apps and responsive sites. I learned more about finance, healthcare, media, entertainment, sports and education than I knew what to do with. I learned some important components to selling work and qualifying leads, managing large budgets, keeping scope in check, monitoring the overall pulse of my team and managing expectations for everyone.

Then I quit.

Saying that freelancing makes me nervous would be the understatement of the year. It’s not easy, but I also never expected it to be. I knew what I was getting myself into. Almost. The only variable I had never played with before was my location while also freelancing. In the last couple of months, I’ve had some surprises and learned some things.

Surprise #1: No one cares where I’m working from.

Literally, no one. Actually, that’s not entirely true. The clients that I have are asking at least once a week where I am. Not because they want to keep tabs on me, but because they want to know what cool city / country / continent / background they get to hear stories about and see. Several of them get a kick out of seeing a new background behind me every time we do a Google Hangout. Others just want to know where I am in the world because they either have questions about said city, or because they have a travel story they want to share during a call. Either way, it’s a pretty easy ice breaker and a sure fire way to generate conversation for relationship building. As long as I continue to deliver good work for them, they couldn’t be happier.

Surprise #2: If you’re saying things that sound smart, people will definitely eavesdrop.

To be clear: I’m not saying this is an issue at all and no, this isn’t me bragging. I actually feel pretty humbled by it, especially since I consider what I do fairly normal. Apparently though, that’s not the case. When I’m in presentation mode, I’m entirely focused on the material, the reaction of the client and listening for feedback. So I have a tendency to tune out my surroundings and become extremely focused. I’ve had people wait until after my call is over to comment on what I’ve said while in co-working spaces, airport waiting areas and coffee shops. I usually get asked what it was I was presenting, or what it is that I do, or just flat-out told that I sound like a badass. If nothing else, it’s a confidence booster and a good way to talk a bit more about what my working hours consist of. And a reminder to take calls that need to be confidential in a private space.

Surprise #3: I’m learning what I like and don’t like to work on.

I don’t know why this is a surprise, but it is. My last 5 years were spent doing cool projects on complex problems with super smart teams. I was fortunate enough to be able to go between 21 different accounts in that time, do a variety of projects, and cover 6 different industries. I worked on everything from short, 3 week projects to long-term, years long engagements. I thought I knew what I liked.

Turns out, when I’m entirely responsible for the work that I do, who I work with, and the nature of the problem I’m being asked to solve, it’s a whole different experience. At this point in time, I can safely say that I really enjoy meaty, strategic, complex work that forces me to cover a wall in Post-Its for a few days, create crazy diagrams and build out robust decks that include proposals for 6 month, multi-team design plans.

Learning #1: I can communicate, design and deliver good work from anywhere.

Literally, anywhere. In July alone, I’ve had Google Hangouts in my Portugese housing with construction happening outside, presentations in a co-working space in Lisbon, written emails in an airport in Istanbul, done calls for business development while walking around San Francisco, constructed competitive landscape 2x2s with a ton of Post-Its in Portland, created PDF decks on an 18 hour Amtrak train ride down the west coast of the US, and done screen design on a 14 hour plane ride from Turkey. Next weekend I’ll be sketching out options for content strategy while commuting to Morocco.

I don’t need a whiteboard, tons of sketch paper, a big desk or a fancy office to get my work done. As long as I have a power outlet, some noise cancelling earbuds and access to wifi, I can get just about anything done.

Learning #2: When scheduling calls, always provide your time options in the time zone your client is in.

Since I’m bouncing around quite a bit, I can’t expect my clients to know what time zone I’m in. I barely know what time zone I’m in. Even if I provide my anticipated itinerary for the month, it’s still asking a lot for them to remember it. So even though it forces me to do the math, and triple check it for accuracy, I always provide meeting time options for where they are. Adding PT or ET or MT to the end of the time block is also a hugely important thing. It just helps clarify that I’m catering to their schedules more than my own. Mine is pretty flexible already.

Learning #3: Something will always go wrong with the meeting connection when you need it.

Whatever can go wrong, usually will. Whether someone has a fan blowing by their computer because it’s 95º out and it causes weird sounds in their microphone, dial-ins don’t work, clients have never used Google Hangout before, Chrome randomly decides to not allow you to have sound in a Hangout or Skype won’t let you log in out of nowhere one day, one of those things will happen. Or all of them. In one day. Maybe all in the same call. Basically, have a backup plan. And then a second backup plan. And then probably a third and a fourth.

For me, I can choose between Google Hangouts, Skype, Appear.in, WebEx or Google Voice to get in touch with clients. And I end up needing to use something different for each one for a variety of reasons.

Learning #4: I am the intern, the designer, the project manager, business development, the billing department and the secretary.

Since I’m working solo right now, I have to do everything. Oftentimes all of the above roles in the same day. Sometimes, within the same hour. It’s a lot of different levels to balance and a lot of different hats to wear, which took me some time to adjust to. It results in long days, late nights, early mornings and a strong self-awareness to know when to turn it all off.

This is only the first couple of months in a 12 month long endeavor to better understand myself professionally. I’m sure I’ll learn a ton more things, so I’ll probably post another similar piece in the future.

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Cassie Matias
Go Remote

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