The Problems with Remote Work

Coworking spaces have been booming over the past decade. These spaces are valuable to Digital Nomads or other Remote Workers and telecommuters who do not have a stationary office. According to StackOverflow’s developer survey, 53.3% of respondents said the ability to work remotely was a top priority when applying to new jobs. According to Deskmag, the number of coworking spaces has been growing at a rate of ~20% per year and will likely continue to grow at that rate until 2020 at least. Remote.co (great resource overall) has also published a survey of remote workers and the companies that employ them with valuable insights into what works and what does not.

I’ve worked remotely since 2014 and have loved most of it. I’ve done this while working at 2 person startups to much bigger companies and a lot of in between. Disclaimer: I haven’t worked as a freelance only developer, but primarily with companies for extended periods of time. Not all of this will be applicable to full time freelancers!


The Problems

So what happens when you take a worker out of the office environment and send them on their own to work at coffee shops and coworking spaces? The first, and the one that most companies talk about, is that there’s an effect on that employee’s connection to the company and company culture. The second problem, is that the employee loses the connection to their location and professional network. If you don’t have that social structure of “work-friends” around you, it gets a bit lonely (especially while exploring a new city) and makes it difficult to network.

Connection to Your Company

The problems about being connected to your company seem a bit fluffy, so let’s come up with a concrete problem: knowledge silos.

Knowledge silos occur in organizations when an employee in one part/team has information that would be helpful to another but doesn’t know to share it. A great example comes from the Masters of Scale podcast episode 6 with Eric Schmidt. He talks about being unable to project sales numbers at some point when an engineer overhears him. The engineer is able to pull up the projected sales numbers right away because he happened to be the engineer who worked on those analytics tools. Schmidt didn’t even know to ask the engineer because he didn’t know it was a possible solution. That is a knowledge silo and they can hamper innovation, produce redundant work, and prevent efficient solutions to problems. They’re an even bigger problem when workers aren’t in the same office space.

Connection to Your Location

The other side of this same problem affects the remote worker more than the companies that employ them. I spent about 8 months last year hopping around new cities every month before I finally settled in Austin, TX for a bit. You know what was one of the hardest things about moving around so much? Not knowing anybody in the cities you are moving to.

It is frustrating since I know how popular remote work is… just go to a slightly removed coffee shop during the week and you’ll see at least 2–5 people in there silently hacking away at their computers. Yet it still seems taboo to walk up to other remote workers and see if they just want to grab lunch or a beer after work. I’ve gone to networking events, joined social sports leagues, and picked up new hobbies but the fact is digital nomads live a fairly different life than traditional employees.


These are the some of the things I see as the biggest problems for remote workers and digital nomads. I’m going to post again shortly on some solutions I’ve thought about to these problems. In the meantime, let me know what you think!

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