Rise and Grind: The Benefits and Challenges of Working Remotely

Category: Culture

Written by: Doug Black

Posted on: November 12, 2019

I don’t always make good decisions. Ask me about the near mullet in high school. Or the decision to call mozzarella sticks a “healthy choice” in front of my in-laws. Or letting a friendly stray kitty come in our house “just the one time” (I suppose I’m ok with that one).

But, one decision I’ve not regretted was this: work remotely. It seems it’s all the rage nowadays, for companies to offer some days as remote work, or even fully remote jobs. And, though I’ve worked in a number of jobs where I was required at a physical location, having the privilege to work from the comfort of my home, or traveling with family, or sitting in a Philly restaurant eating a cheesesteak and listening to people talk about the Eagles is something I couldn’t see giving up.

As a developer, and now the Engineering Lead, at Primitive Social, working remotely has served me and my family well. Let me share some of the positives and negatives:


No Commute

I’ve traveled to work in many different ways. I’ve driven in deadlocked traffic along Philadelphia corridors. I’ve taken public transit for hours. I’ve biked and walked in sun and snow (especially so I can tell my kids not to complain about a short drive to school)

One lesson I’ve learned: I hate it.

Not that I don’t love traveling, or want to be stuck in my house all day. But, commuting to a job is just not for me. I found it really hit me in two areas.

First, I almost always found myself distracted when I came in. Whether it was the driver who cut me off, the driver who knicked me on my bike, or even just the anticipation of getting the work day started, I always had to take some time to orient myself to the day ahead. Working in my living room gives me the chance to orient myself to the day while I prep breakfast for the kids or run on the treadmill, then enjoy my ten step commute to my standing desk.

Second, it took time from working. The most difficult thing for me was getting excited about the work ahead of me and then having to sit in traffic. I love what I do, and I hate wasting time. Now, I can grab my laptop, grab my coffee, and code and coach the minute I’m ready to do so.


Daymond John in his book “Rise And Grind” talks about finding balance. In his early years, he said balance was pointless; he was young enough to where he could work 16 to 18 hours a day without even thinking about it. But, as he got married and started a family, he sought to make a way to find some balance between life and work. “Sometimes”, Daymond writes, “It’s a little less work and little more life.” One of my main goals over the past few years has been finding more of this balance. Sometimes this has meant making sure I’m available to pick my girls up from school, or being available to help my wife do a school project in the classroom she teaches in. Other times, it has meant being available to meet with entrepreneurs in my community or attend a neighborhood meeting.

The only way I’ve been able to make this happen has been moving to the remote life. As long as I can find wifi and a place to sit, and can get to work on building some excellent software, the space and time is my own.

Get Stuff Done With the Best People

Some work is undeniably bound by location. I’ve worked in a number of different jobs, ranging from “Pizza Technician” at a major restaurant chain to managing a miniature golf course to running a homeless shelter. It would be difficult to build teams outside of the direct proximity of any of these locations.

One of the glorious things about doing the work I do now is that I get to work without those restrictions. Our team can be made up of the most talented individuals from around the world. Remote work gives the opportunity to build the best team with the best talent, without having to worry about proximity. In fact, I couldn’t be a part of the amazing team at Primitive if I couldn’t work from Philadelphia!




I am a natural introvert. I enjoy my screen time, and the quiet, with a good book and a bucket of coffee. When I first started working remotely, I loved this, and most days I still do. But, some days are just rough. I require a bit of human interaction to remind me I’m not alone. Those are the days I grab my laptop and head out into the world. In the summer where I live in Philadelphia, this usually means a park with wifi, near the water. In the winter, I find a great coworking space or coffeeshop, or hole up with some other close friends who work from home.

Losing Time: Work Too Much

There’s something oddly comforting about the 9-to-5 grind. You have set expectations when the day begins or ends. I’ve remembered 4 PM meetings in offices where everyone anxiously looked to their watches, watching closely for the second hand to glide past 12 so they could make their way out.

So there are some days where I start early, and before I know it, my girls are walking in from school. The sun is down, and much of the day is gone. It made me realize: working remotely has no boundaries except for the ones I make for myself. Self-discipline has become an absolute essential in making the day a balanced space.

Losing Time: Interruptions

The other side is distraction. The are just some days where I can’t get my head in the game. When I was working in an office, the team would continually prod each other along when we found ourselves distracted (though, there were many times where we distracted ourselves, so I imagine it balanced itself out).

Some days, it’s the constant flux of neighbors walking by, or waiting for a package from Amazon, or having the TV on in the background with junk food programming that gets me. And without having another physical presence in the room to knock me out of it, it can be easy to fall into distraction.

With any employment situation comes pros and cons. For me, the pros of remote life heavily outweigh the cons. It’s all about discipline and self-awareness that allows me to make it work. What about you? Have you tried working remotely? What do you like or hate about it?

Want to join a great team (hint hint)?

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