Remote Working, Take Two

I recently returned from a two week trip across Japan with my good friend. There’s no showing off here: it was an incredible opportunity and I’m endlessly thankful for being able to tag along. While we were traveling, I was dabbling in design work for my business when time (and wifi) allowed.

It also happened to be the first time I’d been so far away from my business partner, the ever-talented Bryant Hughes. On most days, he’s based in Chicago while I’m in Denver.

During the Asian adventure, I scribbled (a lot) on the topic of remote working. I gathered fairly extensive thoughts from select colleagues and integrated their quotes into a lengthy post about business, design, and creative.

But when I tossed it online, I felt blah about the whole thing. It felt fake. Like I was trying to write about something on a pedestal, even though plenty of people know more about the topic than I do. As if my “ah-ha” moments over the last year and a few nicely placed pull quotes from talented creative folk would somehow make my thoughts matter more.

Well, I realized they don’t.

I scratched that approach and decided to write this off the cuff. My goal is to simply explain what brought our creative business to this place, where we’ve been over the last year (as a company and, to an extent, personally), and noting what works and what’s constantly under review. This topic should be shared and learned from by all, in my opinion.

Bryant and I ran our own businesses for many years before meeting happenstance last year. We worked on a few projects together, enjoyed our relationship, and kind of both thought: Huh, this may be beneficial long term. Our small shops were at the same place with fairly well-sized clients and patterns that were becoming well established.

However, we wanted growth. We wanted to be valued for the work we were doing. This meant better relationships with clients; people that appreciated and understood the work that goes into design and developing something from scratch. This meant a back and forth where we could be, at times, pretty brutally honest with each other.

It certainly also meant larger and longer term projects. We’d both been in “mom and pop shop” mode for some time, dabbling in larger projects when possible while realizing we had to grow in order to go after that work more consistently.

So, almost a year ago (early this year), we made it official. Remote working relationship: start.

Deciding to work remotely wasn’t without a lot of back and forth. And questions. And pondering. Then more questions. How will we work day to day? Who takes the lead on what? How will I know you’re actually doing anything?

Working remotely brings up quite a few topics that we’d never faced as a unit before.


Kicking off a new business is hard enough under one roof, but we had to start relying on different communication methods to get things done. Without the luxury of popping over to one another’s desk, keeping the pulse shifted.

We started relying heavily on Google Docs for company planning and document writing. It’s there that we first put together an “Internal” folder that holds everything from contracts to always-evolving agreements to notes on company ethos.

Without constant face to face dialogue, chat became the goto source for staying in touch. Whether it’s Mac Messages or Google Chat, we’re almost constantly in communication. As a quick aside, I remember visiting my friend Ian Coyle a couple years ago and recall him describing how much he would chat with his partner, Duane. He proceeded to show me their chat transcript for just that day and I laughed. Woah! But now, I get it.

As a way to project manage ourselves and our clients, we looked to Basecamp, a tool we’d both used prior but that was suddenly more important than ever. At times we’ve also used a couple of 37signals’ other products as needed. The luxury there, of course, is that anyone can pop in at anytime and keep track of things.

More recently, we’ve started a meticulous weekly admin call on Skype to run through projects, todos, and leads. This levels us both up with what’s been happening and gives us an opportunity to gauge the upcoming weeks. Skype isn’t perfect, but it’s surely a fast way to hop on a free call. And if that’s giving us trouble, we’ll flip over to Google Hangouts for another try at the connection, or to take part in a multi-person video conference.

When it comes to screen sharing, Screenhero has been pretty incredible. We can share screens with ease and the connection always seems to be far superior than anything we’ve tried. Reviewing a code issue or talking through design feedback happens a lot easier this way.


The expectation of the day-to-day, at least for me, was a pretty significant grey area at first. I know I checked my Harvest hours a lot more than I ever do now, making sure it looked like I was doing the work I set out to do.

I quickly realized that it was no longer just me and I was accountable for my days. I hadn’t logged black and white hours in quite some time (relying mostly on per-project rates), so getting into that mindset was an adjustment. It made me a little grumpy at first. And I still don’t love it.

But a funny thing happens when you are being counted on: you either take the baton and run with it or you fall on your face. You either deliver or you disappoint. And I kind of like that pressure. Nay, I like that pressure very much. Thankfully, we both do.


The nebulous nature of remote working is somewhat elusive in a defined manner, but we think it comes out of a few pretty sturdy beliefs.

First, that a person works best in his or her own chosen environments; not in a cubicle stressing about when the boss will come back around to check in. This might mean a big monitor at a home office or a small laptop at a coffee shop smiling at friends who walk through the door. It shouldn’t matter the place, but what comes from being in said place.

Second, that working remotely allows life to happen in a way that otherwise may not. Meaning that running an errand or visiting the gym can happen at any time, just as long as he or she can flex time. It harkens back to the accountability piece. Get the work wrapped and be around for others within reason. This requires situational awareness.

Third, that a specific company ethos is lived out. For us, it boils down to a few key things that include travel, health, family, and friends. We take pride in our work as much as we take pride in the time we invest in our lives, and creating a remote environment that celebrates those attributes is important to us both.

Having a clear vision of the framework that surrounds a remote working situation seems crucial after the last year. Without knowing why we were doing things, or how we expected one another act, we’d constantly wonder what we were doing.


Being upfront with your colleagues should be a staple; don’t get me wrong. But by honesty in this case, I mean really getting to the bottom of issues, situations, or otherwise important topics that come up: either with client work or interpersonally.

A good example that comes to mind relates not only to our communication but also to the ethos and lifestyle we have defined for our company. It has to do with the trip I took to Japan and the issues that were presented that we’d never talked through.

About 10 days in, I started feeling more disconnected than I would have liked. Leaving the states, we’d roughly discussed that I would be working on this and that, but no hard and fast expectations were set for how that progress would be communicated back to Bryant. Having to catch wifi at a Starbucks before linking up with trains wasn’t ideal to be present with everything that was sitting in my inbox.

And at the same time, I never really clearly defined what these two weeks were: a total disconnect or a remote working trip. Looking back, that’s my fault.

Soon after I landed in Denver, I sleepily got onto our admin call and the same things that started to creep up in my head were being presented to me on the other end of the line.

I started feeling that…
This was pretty frustrating last week…
I wasn’t entirely sure about…
Next time we should…

Truth be told, he was right. We had a bit of an uncomfortable (at first) conversation about how “vacation” and “remote working” must be defined for our company in the future. Whether that’s with the two of us, or with future employees. It was a meaningful discussion that had to happen in order to process and grow from.


Perhaps our least experienced area is in the realm of hiring. We’ve read books, asked colleagues, and eyed from afar when we see job postings. But really, we’re learning along the way. Who do we hire first? Should we “trust” a recommendation from either of us? Do we put out a global search? What’s asking too much, and what’s offering too little?

Then there’s the other can of worms that relates to most creatives’ desire to own the work. To touch every piece along the way and hesitate to give away too much influence on a project if at all possible. As a partnership, we haven’t crossed that bridge yet.

Matt Crest, owner of Denver-based Artletic, gave me something to ponder on the topic:

I had to mentally shift and let go of doing 100% of the work on every project. I still feel great about all the work that we put out and happily put our name on it, but I had to let Artletic become more than just me. That was a process, but it’s helped shape how I view the company. Letting go and delegating has led to reducing the stress I put on myself.

I’m unclear exactly how this will play out for Bryant and me, but I imagine it will be a process of sorts as well. Finding the right fit, at the right time, with similar lifestyle aims and general ethos will certainly make it easier to let go of the reigns.

When the dust settles, it seems remote working comes down to a mindset that balances the vigor for doing quality work in a particular profession with being able to live out a life the way you choose it to be.

When you find others that feel the same way, even better. Build something. Live happier. Feel more freedom. Have gratitude that it’s even an option.

For us, this is a freshly cracked topic that will surely present more wins and new challenges down the road. The conversation remains alive and well in hopes we gain insight from those also willing to share their takeaways.

The surface has only been scratched, but there’s plenty of content to come.

I felt the recent video by 37signals shows the attitude of remote working rather well. It (visually) hits on a lot of the things we often discuss. While it’s most definitely a CTA for their recent book, the remote argument is well made.

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