Everything you Ever Wanted to Know About Remote Work, Part 0: The Dark Side

8 minute read

Photo by Hannah Wei on Unsplash

Psst: I kicked off a remote work/nomadic lifestyle series (yay!). The first part is ready: Everything you Ever Wanted to Know About Remote Work, Part 1: The Ultimate Guide to Finding your Remote Dream Job. I’m almost done with the second part “Everything you Ever Wanted to Know About Remote Work, Part 2: Hacking the Job Interview by Never Taking One” (I never had a single job interview in my life! Find out how I pulled it off).

Sign up to the mailing list at the bottom of the article if you’d like to be notified once I release them!

Welcome to the Dark Side

First, let’s start with a prologue: what challenges remote workers/digital nomads are facing? This is the single most asked question I’m getting on twitter, so I decided to finally answer it.

My aim is not to discourage you, but rather to paint a realistic picture of challenges you might face if you decide to go remote. Not all of them might apply to your situation, but it’s good to know about them anyway.

Here are a few things I wish someone told me before I got started with remote work:

Do NOT Believe the Hype

Coding in the infinity pool on a tropical island, gentle breeze, bottomless mojitos, traveling all the time - there is no shortage of digital nomad cliches on social media.

I’ve been working remotely for well over a decade, and I could flood Instagram with some cool images I snapped during the years myself.

However, working remotely can be difficult every now and then. Loneliness, impostor syndrome, stress, lack of motivation, ‘wtf I am doing’ days, chasing clients, feast or famine, or burnout are all too real.

Do not believe the hype generated by sensationalist social media accounts: it’s better to be skeptical and being pleasantly surprised than the other way around.

Get Ready for Loneliness

According to the State of Remote Work 2018 Report by Buffer, loneliness is the number one challenge remote workers are facing.

To combat this, you need to proactively spend a good deal of time on networking: going to meetups, looking up and joining activities, hitting up people online, meeting them for coffee (virtual or IRL) and more.

Even if you put a non-negligible amount of time into these activities, the ROI will be questionable at best: digital nomad relationships are almost exclusively ephemeral.

Staying on the top of it all might be frustrating and energy-draining in the long term.

Hi, This is Trinity, Can you Hear me?

Even though there are a myriad of tools facilitating collaboration on-line, they still leave something to be desired.

Even if that weren’t an issue, some companies require set times for standups, meetings or even real-time communication via Slack or similar.

To me, this kind of defeats the purpose of working remotely: what’s the point if you are tied to your desk anyway?

Motivate Thyself

The onus is on you to stay motivated and productive during work hours.

While you are free from your pointy-haired boss peeking over your shoulder in the office, you have to find ways to motivate yourself and pump out quality work even on those not-everything-is-awesome days.

Location, but not Time Independent

Most companies require you to be present when everyone else on your team is around. So if your company is in say, Boston, they will assume you are around 9-5 EST (give or take a few hours).

This poses a problem if you’d like to stay in Asia, for example (in which case you would need to start working in the evening and finish at dawn).

Talking to other remote workers I found that most companies don’t allow you to be in a different time zone (they might allow a hour or two behind/ahead, but not much more).

So, even though you are not tied to a particular place, you might have to choose a location inside a narrow vertical strip around your brick-and-mortar office.

Traveling Like a Boss #not

You might think that hopping between all those exotic destinations is commonplace, but according to the State of Remote Work survey, 78% of remote workers are working from home (I talked to a few Automattic employees during a retreat, and they agreed - almost all of them are traveling only when on holiday).

This makes sense - you have your own setup, reliable Wi-Fi, kitchen, you can take a nap whenever you want, be with your family and have a greater degree of freedom.

Even if you decide to go nomad, you won’t travel nearly as much as you think you will - constant setup, finding reliable wifi, the hassle of figuring out all the things in your new location all the time can be frustrating - especially if you want to put in a good amount of work over large swathes of time.

In the beginning your wanderlust will prevail and you won’t even notice these challenges. However, the excitement will eventually wear off.

Coworking Spaces to the Rescue?

Don’t expect coworking spaces to replace the camaraderie of the office.

Coworking spaces are rising in popularity, and they look like a place of deep work and great socialization.

As always, the reality is different from the Instagram images though: people come and go, just when you get to know someone, they’ll move on (or you will), you’ll still have to put a ton of work into building and maintaining relationships.

Most of the time everyone will sit around with their headphones on and you will feel alone in the crowd.

Be Picky

Be very selective which jobs you accept.

It’s going to be difficult in the beginning (especially if you are cash-strapped), as you’ll just want to accept anything & everything and get down to it.

I recommend you to resist the urge. Your future self will thank you (and me) profoundly.

It’s infinitely better to put more time into the preparation, collect a few offers and choose the best than just going with whatever you get.

Money, money, money

Sounds trivial, yet I see so many people crash and burn for this reason: money.

Have enough money stoved away that makes you comfortable if you run out of jobs - for some people this could be few months of living expenses, for others might need to have enough for two years to feel warm and fuzzy.

Worrying about money can really kill your productivity and mood, and it’s an awful place to be in (it forced me to make some crazy decisions in the past, and I have observed similar behavior for other people.)

Let me debunk some common myths and cliches:

‘But money is not everything’ - Correct! But if you are not sure how are you going to pay your next bills, or buy food, or the lack of it might force you to give up your lifestyle, then it will mean everything to you in that moment (been there, done that.)

‘The love of money is the root of all evil’ - the emphasis is on the love part. Don’t love money - it’s just a tool that enables you to put food on the table. Having enough of it to be comfortable is a different matter entirely.

‘Fuck money, I’m following my passion’ - to the extent that you are OK living under the bridge and beg for food? OK, in that case this section is not for you I guess.

When 40 !== 40

40 hours in the office !== 40 hours working for yourself.

The first scenario has tons of fuck-around time thrown in as an unofficial (?) perk (coffee, breakfast, water cooler chat, lunch, idiotic meetings, plain old procrastination), paperwork is taken care of, sick time and paid vacations are a thing. As long as you show up, you get the same amount of salary.

This is very different if you are a freelancer: you can’t bill for having lunch or filling out paperwork - things that are perfectly normal and accepted in the office.

Time Flies Like an Arrow and Fruit Flies Like a Banana

Don’t underestimate the amount of time spent on creating systems to be productive, taking care of your food, health, workout, setting up and maintaining your hardware/software, job hunting, networking, paperwork and other admin tasks, chasing clients for payments and other yak shaving.

These are non-issues in a 9-5, but as you will find out once you start freelancing, these tasks do exist.

Sharpen your Saw

In a 9-5 it’s accepted to ignore blogging, (serious, not full-of-cat-photos) social media presence, continuous learning, standing out from the crowd, working on open source software and making yourself externally visible in other ways.

You’ll have to do at least some (preferably more, or all) of these once you become a remote worker.

A Renaissance Soul

You’ll need a wide range of skills as a self-employed person.

If you are hired as a Javascript engineer in a ‘standard’ company, that’s what you are going to do daily (doh).

However, if you are a freelancer, you need to be well-versed in so much more - communication, (copy)writing, networking, marketing, sales to name a few.

Most programmers are not ‘naturals’ when it comes to soft skills - something to keep in mind.


There are so many more things I could talk about (let me know what would you like to hear), but this should be enoug to get you started.

TL;DR: Remote work is work with different rules. The upsides might outweigh the downsides (like they did in my case), but I saw a lot of people getting fed up and burn out after buying the hype and realizing the reality is very different from the social media version.

Make sure you know what are you buying into, and working remotely/becoming a digital nomad can be one of the most rewarding things you will ever do (like in my case). Ignore the warnings like this blog entry, jump the bandwagon or FOMO your way into this world and you might be in for some nasty surprises.

Let me know your pet peeves, tips, and experience in the comment section below!

Hey There! Can I Write to you?

Don't Be a Stranger! Sign up to the newsletter to get notified about new blog entries, interesting stuff I bumped into on- and offline, books I'm reading etc.

You can also hit reply to talk to me - I'm replying to all emails personally!