Working remotely is becoming the big dream for many. However, if you've never done it before, it can also be a nightmare. Here are the main issues I came across when starting my first remote job - and how I conquered them.

Landing a remote job sounds like the epic personal freedom you've been looking for – there's no need to go to an office, your work hours are flexible and you can do your stuff from home, a coffee shop, or even a beach. On the other hand, having a classic 9 to 5 office job is also freedom, just a different kind - it's the freedom and convenience of having limited distractions, more discipline and your teammates constantly in your reach.

Before I joined Teleport, I worked “normal” desk jobs with set hours, and always looked forward to one day having that magical remote job instead. Immediately after joining Teleport as a remote team member, I started to struggle. Here's why.

1) Time management and discipline is suddenly all up to you

There are definitely some distractions in an office as well, but I found it can be a lot worse when you’re on your own. A guy I used to work with used the word anatidaephobia - the fear that somewhere, somehow, a duck is watching you - to explain why being in an office is motivating in itself. You do work because:

  1. other people around you are working
  2. at least one of those people would definitely see you if you were to slack off.

duck“Do you work for Facebook? No? Get off it then.”

When you work remotely, there is no duck. There is nobody to remind you to do your stuff and there are no people around you to act as a motivating factor. You might think you'll be great at disciplining yourself on your own if you've never had to do it before, but then again I also think I can do a double backflip. Hold my beer.

How I overcame it:

If you're like me and easily distracted, you need to find your duck and establish some serious disciplinary rules to make sure you don't go off track. Team Teleport uses Asana for task management, which is great, but doesn't really do much to actually push you (besides sending an email every day about your overdue tasks, just to subtly mock you for your laziness).

My duck has been Toggl – a free time tracking software that I use for both work and personal projects. It's great for working from home, because:

  • You can see see how long it takes you to finish certain tasks - this way you’ll be better at anticipating how much time you’ll spend on similar things in the future, and plan your time accordingly.
  • You can see how much time you've actually spent working that day. Breaks from work can add up quickly - closely tracking your time prevents lost hours.
  • You can see when to take a break – you've done a few hours of something – probably time to take five.
  • You can connect it with a bunch of tools including Gmail, Asana, Trello etc.
  • When you're tracking time for what you're currently doing, the tab with the time ticking away is always in sight. It's a good motivator.

toggltabIt's watching you. Judging.

Physically writing things down is also a motivator for me - even though I have my daily tasks in Asana as well, I make an actual list every single morning of things that need to be done that day - it takes about five minutes, but it’s like my own little stand up meeting to get me into the mood. And there’s nothing better than finishing off a day and seeing everything on the list crossed out.


2) Distinguishing work from everything else gets harder

When you work from home, the strict lines you (probably) used to have between your work life and your personal life become a lot less clear – you're in a comfortable and familiar environment that you also do all your day-to-day personal home stuff at and that, again, takes away from the concentration that you're supposed to put into your job.

In the first months of working remotely, I didn't even bother to really get up in the morning – I suddenly had the chance to do work from my bed and man, was I going to use it. The amount of business video calls I made wearing a nice shirt paired with pajama pants is staggering.

How I overcame it:

There are four main things I've started doing that help me separate work from everything else, even if I am in an “everything else” environment.

1) Even though most of the time I don't actually have to get out of the house for work, I act like I do. I wake up, have breakfast, shower and get (at least somewhat) dressed. It puts me in a mindset of something important happening and gets me prepared for work.

2) I always try to have a real workspace wherever I am. I now refuse to do work in bed or on the living room couch – I have a designated space at home and even though I spend a lot of time traveling, I make an effort to get one when on the road as well – most hotels have at least a few rooms with desks, all you need to do is ask.

In August I was in Edinburgh for a month for the Fringe festival and lived in a massive apartment with 10 other comedians. It was outrageous, loud, and covered in pizza crumbs and comedy show flyers. My bedroom had very little furniture, but I made an effort to build myself a little work corner, which made focusing a lot easier.

workspaceI photoshopped out the 5 bottles of Irn-Bru I drank every single day

3) I have proper lunches – I take an hour for lunch and get away from my desk for it. Whether it's going out to a coffee shop or just into the kitchen and actually making some food, I get up and treat lunch like a break. I don't eat at my laptop and I don't work while I'm eating.

4) I cancel out any external noise - my blocker of choice is loud music from massive headphones, but a pair of simple earplugs work as well if you prefer silence.

Basically you need to make your brain understand that whether you’re at home, at a hotel or on the road, work time is still work time in a designated workplace with work related thoughts.


3) Communication gets a lot more complicated

The great thing about everyone being in the same office is that your coworkers are constantly there – if you have an issue, you can just walk over to whoever you need and talk it out on the spot. It's different with a remote team – not only do you have to keep in mind the different timezones your team members might be in, but online chats also don't convey emotions or mindsets that well – it's just text.

In my first remote months I struggled a lot with being unsure about whether I was understanding my teammates correctly or interpreting their emotions the right way and acting accordingly.

How I overcame it:

I got lucky because our team genuinely values the importance of real face time, having regular online meetings every week and actual meetups every now and then to see each other's pretty faces.

However, being lucky doesn't mean you should work less on creating good communication. Whenever I have a topic to discuss with someone, I try and make it a call so it's an actual spoken conversation rather than just typing. Video calls are even better - a face-to-face interaction means real engagement and attention and you can actually see the person’s expressions and body language rather than guessing.

I've also gotten over the fear of needing additional information and asking if something is unclear – good communication is crucial when you don't get to actually be in the same physical space as your teammates. Don't understand something? Ask. Not sure what to do? Ask. Think someone got something wrong? Tell them. Don’t ever be afraid to clarify or speak up.


The time it takes for someone to get on a call with you or type out the answer is always going to be shorter than the time you’ll be spending fixing your mess-up because you didn’t ask. Nobody will mind, and if they do, it just means you’re working with crappy people.

All in all - you might not be the kind of person that has a problem with being let out of the cage, making your own decisions and managing your own time - I’m not saying everyone is. However, if you are, all you need to do is stick to it and be very conscious of what you’re actually struggling with. There’s a solution for most of those roadblocks and you can learn to work independently - it might take a bit of time, but it’s worth it.

What are some of the challenges you’ve had to face with remote work? Do you wear pants when you work from home? How have you managed to create a work environment outside of an office? Tell us in the comments!


Elen Veenpere is part of the Teleport team, spending most of her time writing all kinds of content for everything Teleport. When she's not busy typing, she likes to travel around the UK doing stand up comedy and drinking coffee.