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What are the most difficult things about working remotely?

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In my experience, there aren't that many downsides to working remotely. Yes, it gets lonely sometimes, and yes it may sometimes be frustrating for you to organise yourself, but you're free. At least more free than the your office-bound relatives.

I've been remotely for the most part, since 2015, with exceptional cases when there was no other way and the project was too interesting to let slide.

I've experienced many of the states of being a remote worker but there are two things in particular that I find difficult.

The lack of peers

The lack of peer interaction is one of the most pressing issues. Now, I’m a web developer but I’m sure this applies to many professions in the knowledge work spectrum. You might say that you interact online, but most of the times you’re a lone wolf. Indeed, this comes with its benefits, but as humans and as professionals, we need that feeling of proximity and of kindredness that only physical presence can offer.

To cope with this I frequently work from coffee shops and attend various community events. This also exposes you to people from various fields and who have no interest in just being nice with you for the sake of it.

They have no office politics to navigate.

Getting organized

This is the biggest one.

The fact that you need to look at the work that lies ahead of you and plan it throughout the day, then also execute on that plan, could bring even the hardest of us to tears.

I have days where I just stare at my notebook, waiting for it to fill itself. I use a physical notebook to get organised, so that I can also switch the context I’m in, and get out of my head and out of my laptop.

One of the best choices I made, back in 2012, was to write everything on paper. This led to me amassing a small fortune in filled notebooks. Every idea, every thought I deemed important in the past 7 years was written in one of the notebooks in the stack below.

Notebooks stack

Now, when I catch myself staring at the notebook not knowing what to do, I don't fight it. I just roll with it and start doodling. I simply put my pen on the paper, look around and start by drawing a line, until I get in the mood to write something useful.

Then I revert to my Bullet Journal (rapid logging) + Pomodoro setup and start cranking at it. I only set around 5–6 items I’d like to do in a day and try to stick to that list.

Whenever I'm in the mood, I also do time blocking. Time blocking is a great habit/technique but I just can’t seem to convince myself to do it enough. Maybe I should try harder 😅.

The less difficult things

Difficulties for remote workers don't begin and end with what I outlined above. If they would, where would the struggle be? How could we sing hymns to the remote heroes?

A set of notable mentions comes below.


Due to the lack of body language, communication is more difficult online. We're wired to infer a message from the tone of voice, the body language and other cues that tell us whether someone is happy, sad, satisfied or discontent about something.

This makes project management tools, email, texting, realtime chat and even voice chat a bit inefficient, compared to in-person communication.

But there are, of course, solutions to improve communication. The first one that comes to mind is video calling.

Video calls can bring back the visual and auditory cues we need in order to make ourselves understood and understand the other person.


Someone once said to me: "There's nothing like a good in-person meeting with a whiteboard and some markers".

They were right. This type of "working together" is the best in class. Fortunately, there are tons of solutions out there, that when combined can yield similar results to in-person collaboration.

You can combine voice calling via Skype, Slack, GoToMeeting or Zoom with a whiteboard app or a remote-desktop session to get the same results.

You can even go so far as to create a video call and point the camera at a physical whiteboard which one of the participants could manage — they would then also become the moderators of that discussion.

It just requires a little more tech than usual.

You should also know that when collaborating online you're at the mercy of the Internet Connection gods. In a physical setup you'd only depend on the level of involvement and attention of the participants.

Tool mismatch

You might think that this is a self-enclosed category but it's not. It's also related to communication.

In a physical setup, someone might hear your WTFs and ask "What's up?" and you could tell them you get this weird error when starting the app. You'd then quickly realise you're trying to run the app on Node 11.x and the version it was built for is 10.x

But there's nothing preventing you from asking for help, when you realize you're wasting too much time on some weird error nobody else seems to have.

This actually taps into one of the best practices of working in basically any environment: ASK FOR HELP!!

As long as you've tried it on your own, did a bit of digging on Google and still found no solution, talk to someone and walk them through what you did. They will be more than happy to help.

As long as you're not being lazy and asking people about anything and everything without looking it up yourself, first, everyone will be happy to help. At the end of the day, you're all pushing towards the same goal, hopefully.

Timezone mismatch / lack of synchronous communication

This is a tricky one. One of the dangers of working in distributed teams is that you might have people whose schedules don't overlap. Not even one small bit.

This is how team members end up passing work from one to the other without having a common context. When some of the team members finish working, the other part of the team starts work, and emails get sent when work ends, and get replied the next day.

You can quickly end up with a 5-day stream of emails just to clarify a couple of implementation details and some tasks that literally take two hours to clarify and implement.

My recommendation is that you get people in timezones with a minimum of two hours overlap. Four is amazing but whatever is above four doesn't make any difference.

You need to be able to have synchronous communication if you need to. Just gather everyone in a video call or a Slack channel and set the damn thing straight.

If you're in a situation where you have to work with timezones that don't overlap, don't fret, there's a solution for you, too.

Whenever something needs to be clarified, someone must shift their schedule (usually everyone involved). You have to wake up earlier, and your coworkers have to spend a bit more time in the office.


This article was not written to talk about "truisms". It was written to provide solutions. If it did help you in any way, it would mean a lot if you could share it with your friends. If it didn't, do let me know using the contact form, I'm open to update the article with your knowledge and would love to give you proper credit for your contributions.

I’d love to hear your thoughts so feel free to reach out in the comments (once they're ready) — see better build half a product, than a half-assed product — since one of the goals of WeRemote is to educate professionals and companies about remote work, freelancing and everything in-between.

Community contributions

This section comprises contributions to the article by community members. It's a great opportunity to put community members in the spotlight and learn from them.

Iuliana Jackson

As I was a freelancer until a month ago, when I joined Omniconvert, the thing that really was f****g with me was the lack of separation between me as a person and me as a professional.

And that was also affecting how I was perceiving my house — like a full office. Even if I was done with work and watching TV, in my room, I didn't feel like "I am home" because Jira notifications were popping and my phone was ringing and I just couldn't find the power to say no to it.

But it was fun tho.

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