How to Work Remotely and Live to Tell the Tale

Two of the most common questions I get while talking with my peers is why and how I work from home.

I always get startled by the amount of people that feel confused by the concept of remote working. It has been a long way, but some people still neither trust nor respect it. Movements like We Work Remotely by Basecamp (née 37Signals) have brought the idea of remote working closer to many, but I still get sceptical nods and “it’s not for me”s when I suggest it.

Is remote working the best solution for you, though? Let’s go through the good, the bad and the ugly bits of it, together.

My experience as a remote worker

Since 2005, when I started working as a designer, I have been dreaming about working from home. I mean, you have Internet access, lots of food and every day is no pants day, what more could you possibly need?

Since I always wanted to try it and I also wanted to try freelancing, I decided to leave my job and try both in 2010. Up till then, I was doing the usual thing; wake up, have breakfast, put on clothes and (maybe) makeup and drive through heavy traffic to be at work at 10am. It wasn’t terrible, since my commute was fairly short, but I felt it wasn’t ideal either.

Since 2010, I work from home full-time. There were some bumps along the road, but for the past 4 years I’ve been doing it with a moderate amount of success. Sure, there are times that I just want to hit my head against the wall, but all in all, working from home was a rewarding, life-changing experience for me.

Let’s clear up some facts beforehand:

  • Yes, I spend more time talking to my cat instead of people on most weekdays.
  • Yes, there are days that I don’t even get out of my pyjamas.
  • Yes, I cook lunch for two almost every day. Sometimes twice per day.
  • Yes, I put on weight since working from home.
  • No, I don’t feel particularly bad about it, because I’m also fitter than ever since I started exercising regularly.
  • No, I don’t work from my bed, I’d fall asleep in a second. Most days I don’t even work from my sofa. I work from my desk, in my office.
  • No, I don’t go to the beach every day after work during summer, even though I could do that.
  • No, I wouldn’t change my lifestyle for the world.

Is remote working the best solution for you?

Well, it depends.

Do commute costs and long hours on the road drive you crazy? Are you a homebody like me? Can you live with staying for hours inside your home? Do you have a family you want to take care of? Are you averse to wearing pants?

Then congratulations! Remote working is going to be awesome for you.

But. There are many downsides to restricting yourself in a rectangular walled box for hours on end. Be prepared to feel lonely, even if you insist you’re an introvert and you don’t need people to feel good. If you’re working in a team, you’ll lose about 90% of their everyday hustle and bustle. Say goodbye to your hard working metabolism, since remote working usually means sitting on your butt for hours on end, which makes you work twice as hard to lose weight.

Still with me? Awesome. Now fasten your seatbelt, because you and I together are going to make remote working werk.

Work that discipline muscle

If you want to start working remotely and keep being productive, you need discipline. There will be noone at home to look over your shoulder and check your progress, so it’s all too easy to lose yourself in a whirlpool of email newsletters, YouTube browsing and fighting over Twitter. Discipline is your top priority.

Establish a routine to help you with that. Write down your day-by-day schedule if you need to. I use a 12-month daily planner to write down the 3 most important things I want to achieve at work and at home every day. This kind of high-level planning works for me, but if you need more fine-grained control of your time you can check Jessica Hische’s Ultra-Schedule.

Working from home means being constantly distracted by chores and family members. Fight that. Assign time after work to chores and be vigilant with your relatives. Back when I was still living with my parents, I had to have a talk or two with my mother to make her understand that no, doing the laundry wasn’t as important as finishing that Skype call.

If you can, turn a separate room of your house into an office. When I started freelancing, my desk was right in the middle of the living room, which was a nightmare. Minimize friends and family visits and treat your personal phone calls as you would do when working at an office; keep them short and to the point.

If you think that putting on clothes makes you feel more disciplined, do that. At first, I used to put on clothes, shoes and even makeup, but then I realized that it had no effect on me. Nowadays, I mostly work in sweatpants.

Maximize your time

Working from home may create the illusion that your free time will increase since you’ve stopped commuting. Unfortunately, this isn’t the case.

Sure, your commute is now just seconds long and your lunch breaks can be a lot shorter but no matter how vigilant you are, distractions will always creep in. For me, these distractions include house chores and my cat. Walking past a room, I’ll decide to make the bed, or maybe do a quick load of laundry? And this cat is so. Friggin’. Cute.

These can add up over time. To combat this, I dedicate my Pomodoro breaks to chores. So I work 25 minutes, then walk around the house doing chores for 5 minutes, rinse and repeat. What I love about this is that if you are strict about it, at the end of your day you’ll have accomplished tons of work, plus your home will be in relatively good shape. Win-win! Now you can pet your cat to your heart’s extent.

If you work in a team, take advantage of your coworkers’ commuting time. Since you don’t have to drive yourself to work, you can use this time to catch up with your overflowing reading list or experiment on a feature without creating bottlenecks.

Lastly, be protective of your free time. The fact that you stay in a room all day by yourself makes it very hard to work long hours. Make your work count and stop working when the time comes. Take a proper lunch break and eat on a table, not in front of your screen.

Communicate to ease cabin fever

I’ve been doing the working from home thing both as a freelancer and a startup employee. I find it is easier to do when freelancing, since you (probably) don’t have a team to interact with on a daily basis. Working remotely with a team is another thing altogether. The key word here is communication.

Even if you enjoy alone time “in the zone” like me, don’t be the person that disappears for hours on end, because the quality of your work will suffer. Share your progress early and often. Ask your coworkers for input; at first, it will be mayhem and you’ll regret asking for feedback, but after a while you’ll start to notice patterns that will help you evolve and iterate.

The biggest challenge while working remotely is keeping up with your team’s culture. Don’t just communicate with them regarding work, but try to learn their interests and hobbies. I’m lucky enough to work with great people who are interested in a variety of things, so we have separate Google hangouts for gaming, design, and trashy YouTube clips. We also have a habit of creating Spotify playlists for every occasion. These may sound silly, but it’s amazing how much you can connect with your team through that.

Of course, you shouldn’t get caught up in communication. Some days, your coworkers will be too funny to ignore, or an interesting conversation will make you type like a mad. Don’t let communication take up your time. Try to create a silent bubble around you during your most productive hours so you can do quality work.

Take care of yourself

Working from home means moving a lot less, so you have to make up for it. Since you have no water cooler to go to or teammates to annoy, you’ll just find yourself sitting on a chair for hours on end. This will make you put on weight, hurt your back and feel miserable in general.

Now, don’t groan, but you have to start exercising. I’m not even suggesting it as an option, that shizz is obligatory. Enroll in a gym, start running, find your old football mates and start a league, or take dancing lessons. Playing Kinect games doesn’t count. The key is to move at least an hour per day, even if that that’s just walking around the block.

Another important thing is not to let yourself sit down for too long. I’m not into the “sitting is killing you” bandwagon and I hate standing desks, but you have to realize that your lower back won’t be the same after a few years. Take regular breaks while working.

Working from home also means working mere feet away from your fridge, so it’s getting easier and easier to grab a snack. Resist the temptation. Fill your pantry and fridge with healthy stuff and try to stay away from delivery pizzas and frozen meals. Cooking isn’t that hard, really. Don’t forget to drink plenty of water!

Stick with great tools

Remote working can be really difficult without the proper tools. Below you can find a list of my favourite apps, which I pretty much use all day. The list is slightly design-oriented (because that’s what I do, man) but it can easily adapt to any kind of remote work.

  • Droplr ($4.99/mo) or Cloud (freemium) or another screenshot/file sharing app. Being able to quickly send screenshots of what you’re working on is a must-have while working remotely as a designer. Most of the time, describing a design decision with words just won’t do. You’ll have to show people a picture so they’ll get what you mean. Droplr also lets you share files and screen recordings, which is great for presenting interactions.
  • An online chat service to communicate. In Workable, we use Google Hangouts as a part of our Google Apps suite. You might prefer Messages, Campfire, Hipchat, Slack, or plain old Skype. I’d suggest going with an app that offers both text and video chat to avoid keeping two apps running all the time. No, Facebook Messenger won’t do.
  • A prototyping/collaboration service to share your progress. In Workable, we use and love InVision. Seriously, there’s a hidden shrine somewhere in our offices dedicated to it. The sheer amount of features is mind-blowing: you can upload mockups, add comments, create full mobile mockups and check them on your phone, even collaborate live on a screen with your coworkers. I don’t want to sound biased, but it’s such an amazing service.
  • A timer app or even a plain kitchen timer to keep track of time. As I’ve repeatedly mentioned above, I’m a huge fan of the Pomodoro technique, which suggests working for 25-min increments and taking 5-min breaks. It’s the only thing that works when everything is a distraction and my mind is all over the place. It also helps when I must work on a task I’ve been avoiding for ages.


Working from home is something that keeps me happy and healthy. Stress is a big issue for me and relocating would be a huge lifestyle change that would cause tons of it. I can’t deal with that. I need to give my 100% to my work.

And I can only do that when working inside a sunny apartment, in a noisy neighbourhood of the busiest city of the biggest greek island.

In the words of a great scholar, let’s do this.

Disclaimer: This is a reference post which will be updated regularly with things I’ve missed, so if you have any remote working questions, shoot me in the comments below and I’ll be happy to answer.

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