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Gage Henderson
Gage Henderson

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Remote Jobs: How-to, and the Downsides

I've always wanted to work a remote job. My current job is in Portland, Oregon, but I live somewhat far away (about a 1 hour commute). Remote work has always sounded like a good fit for me, I feel like I am good at managing my time, and can hold myself responsible for things.

But it seems like the type of thing that is "too good to be true". What are the downsides? I feel like if it really was as awesome as sitting at home and coding all day, everyone would be doing it!

Also, if I do end up looking for a remote job, what should I be looking for? What should I avoid? Any guidance on landing a remote job would be super helpful.

Top comments (24)

k4ml profile image
Kamal Mustafa

This is my 8th year of working remotely. If there's one wish I could have is going back to work in physical office, but due to where I live that's not going to happen anytime soon as that require me to relocate to the capital 400KM away and double (or maybe triple) the cost of living. The primary reason I stay with remote job is my kids. This job allow me more time with my kids, at the expense of my own social interaction but I'm fine with it. Few times a year attending team meetup or conferences in the city are enough and already exhausting so it also good having time and space to wind up before the next event coming up.

I think you need very strong reason to work remotely and it can't be just, oh it look cool, I can spent all days coding at home etc. That won't keep you for long.

callgage profile image
Gage Henderson

Wow this is a very different answer than I was expecting!

So the lack of social interaction is the largest downside in your experience?

I'm extremely introverted (as I'm sure most developers are) and I really cherish my time alone. But I also know how detrimental too much alone time can be. I'm sure after a while it definitely would get to me as it has the past.

k4ml profile image
Kamal Mustafa

Partly, yes. On the third year I think I started having some kind of depression due to lack of social interaction. So I started going out, established local user group and try to have regular meetup. It help a lot at that time. But the effort didn't last long, everyone busy and I don't have the energy to keep it running.

These days I just keep a group of friends from my circle in telegram group. That help me a bit to still have someone to talk about our field. The non-work social interaction is different and at least to me, not really full-filling. I mean, at the end of the day, you still need someone to debate vim vs emacs, right ;)

bbrewder profile image
Brian Brewder

It really is as awesome as sitting at home and coding all day :). I've been working remotely part-time for about 13 years and full-time for a little over 1 year. I love working remotely and would only seriously consider remote jobs if I were to look (unless I became desperate, of course). I only fill the tank in my car about once a month or less. No rush hour, no wasted time in the car, no driving in dangerous weather, no road-rage at all.

The ideal remote position has the entire team working remotely (managers, developers, testers, etc). It can be challenging if you are the only remote team member. The team should use Slack (or something similar) to communicate, including both formal meetings and informal chatting, joking, etc. There is no physically banging down doors, so everybody on the team needs to be willing to watch the shared communication channel (Slack or something else) and respond reasonably quickly.

If you are considering it, you should be sure that you can commit to it. It seems you have the right attitude, but if you live in a shared space (family? roommates?), you need to get buy-in from everybody else in the household. They need to agree that when you are working, you are "not at home". Get this agreement before accepting any remote job.

It's nice to have the flexibility to go pick up your kids from school and whatnot, but it either needs to be part of your typical day and the rest of the team knows you will be gone for that time or it needs to be infrequent (ie, no more than once or twice a month). If you have kids and your spouse works, they need to be in daycare, at least if it is expected that you actually watch and entertain them (you can't work and watch young children at the same time).

You also need to have an office with a door that you can close. The office can be used for other things, but it can't be a shared space. This is important to not only be able to have a space you can work without being distracted, but also a place that you can leave when you are done working for the day (it's important to have some psychological barrier between work/home life). The further and more isolated this space is from the rest of the household, the better (fewer distractions, more distance between work and home).

You will probably want to participate in Meetups and user groups as well as go out to lunch or dinner once or twice a month with friends that are in the same profession as you. I haven't missed being in the office much. Perhaps this is due to my team's good use of Slack, or that I attend professional events, or maybe it's because I'm more introverted than others, but I don't feel like my social life is lacking due to working from home.

jimsy profile image
James Harton

This reminds me of when I first started working remotely and I didn't have a separate office space - my desk was just wedged into the corner of our dining room. My ex-wife's mother came around to visit with my wife and kids one day about 2pm in the afternoon. They sat in the dining room while she drank a cup of tea with my wife. After about 10 minutes of them sitting there while I was quietly working away in the corner she turned around and said "James! You're being so rude to me!"

Make sure that everyone who enters your home knows that this is your workspace.

callgage profile image
Gage Henderson

Super useful reply thank you! Everyone seems to be advising towards a fully-remote team, I never even thought about that but it totally makes sense.

Fortunately I do have an office space, I use it to code and home and make music, which I can see becoming a distraction - Might have to move that equipment somewhere else.

And I do have roommates, luckily they are all usually at work from 9 - 5.

jimsy profile image
James Harton

I have done a lot of remote work both as a contractor (Auckland <-> Portland) and as an employee (Auckland <-> Wellington). The biggest problem I experienced is poor communications. You really don't want to be the first/only remote worker for an organisation where everyone else is in the same office. Companies that have a lot of remote workers will understand that they need to invest more:

  • As a senior dev I am expected to pair with/mentor less experienced developers. Often I had to organise for my team to have good headsets so that they could hear each other properly while on a call or remote pairing session.
  • Make sure that they buy you a really good headset unless you already have one. It makes a world of difference.
  • Make them buy good quality conferencing equipment otherwise you'll be attending stand ups or planning meetings where someone just dials you in with their laptop speakers/microphone and not get that all you can hear is "mumble mumble mumble laugh".

You'll need to change your behaviour too. Social interaction in an office just happens as a by product of you all being there but if you're not there then you have to dial up the volume. If your company uses a tool like Slack then you need to spend some of your time being visible and probably funnier than you really are to make sure that people remember you're there.

For a couple of years I was living by myself and working remotely. Sometimes it is just really, really lonely. A local co-working space really made all the difference for me; I got to talk to peers and make new friends. Some of them are friends for life. You should definitely investigate whether there's a space near you. Otherwise there's always local cafes, just make sure that the owners are happy with you working there and that you spend money while you're there.

Working remotely is hard. But it's not as hard as a crushing commute or an office where you don't really fit in. You get out what you put in.

Good luck!

callgage profile image
Gage Henderson

Thanks for the reply.

A local co-working space really made all the difference for me

I didn't even know there was such a thing as a "co-working" space! I feel like Portland is likely to have some I'll have to look around🕵️

You'll need to change your behaviour too. Social interaction in an office just happens as a by product of you all being there but if you're not there then you have to dial up the volume.

Makes sense. Never thought about that.

codevault profile image
Sergiu Mureşan • Edited

I have partially worked remote in the past and one thing that is really different is the environment. At work, you see everyone typing away at their keyboard, coding, making progress, testing and that motivates you... at home, well, in my case, you hear a lot of kids playing outside which won't give you the same motivation to work hard.

Although, if you have the right mindset, you will find motivation.

drbearhands profile image

I second this. Adding to it that humans are social animals and need contact with others. To alleviate this problem you might want to search for a shared office space, it does wonders for me.

coreycondardo profile image
Corey Condardo • Edited

What are the downsides?

Humans are designed to be together, there is no replacing in person time. With that said, video chats and slack can do a great job feeling like community exists.

Local networks will not be strong. Your network will likely be National, not local. This means losing a job means another local job won’t be as easy to come by.

It’s harder to get close hands on help remotely - but if you’re aggressive and work hard to get help you can succeed. It’s just not great for folks who lack autonomy skills.

Communication skills have to be expert - you can’t be a mediocre communicator and work remotely.

Travel should be required at least a few times a year to build in person relationships.

Working at home can be a drag. Separating work from home life can be nice!

Also, if I do end up looking for a remote job, what should I be looking for?

A company who has a remote culture. Being on a remote island when others are in an office is hard. Being completely distributed encourages a remote culture to be formed and everyone is on the same page.

Any guidance on landing a remote job would be super helpful.

I think you probably need to be slightly over qualified. It’s hard to assess potential hires remotely so I find the more qualified the more likely you are to succeed.

You didn’t ask but the upsides are huge.

Get a job outside of your local economy, be paid better than locals
Work for companies that don’t exist locally (ie if your local city or town has no startup scene)
Skip commuting and get hours per day of your life back
Flexible schedule usually is a given - it’s too hard to keep track of local employees so trust is critical and usually expected. This means some benefits of flexibility are usually given.
Your own office however you want it to be! A fully stocked kitchen, and perhaps outdoor working space - whatever your house can accommodate!

Source: 3.5 years at fully distributed company

imben1109 profile image

I just find there are a lot of remote jobs posted on stackoverflow.

Actually, I do not know what define remote jobs. I do not know if the salary is attractive.

Sometimes, I just think the interaction or communication may not be good enough as same as face-to-face.

k4ml profile image
Kamal Mustafa

Salary will depend on your location, and sometimes that what make it attractive. For example I have friend working with US company. Even if he only get 5K/month (average salary when I googled) that already translated to 20K local currency, which is a lot ! On the minus side he has to work odd hour - 9PM to 5.00 AM local time.

karloabapo profile image
Karlo Abapo

The benefit of working remotely is the location independence. But having to work at odd times and a subjective salary defeats the purpose.

mortoray profile image
edA‑qa mort‑ora‑y

A lot of people are not able to work remotely. It's a different discipline than working in the office. Your motivation has be primarily internal.

You face physical isolation for long periods of time. You miss out on lunchtime with colleagues. You miss out on social events. The entire human aspect of a job basically disappears. For a lot of jobs they become unbearable when that happens. For a lot of people that kills their motivation.

Time management is a separate, compounding problem. You need to be able to actually put in some working time. If you're a productive person you'll find that you can get more done in less time, compared to an office. However, you still have to manage expectations of being available for colleagues.

I've worked remotely for about 8 years now and I'd have a hard time going back to office work. I'd be okay with going into the office once a week, but more than that would impact my productivity and lifestyle too much.

Finding remote jobs can be challenging. Beyond just proving you can do the job, you have to prove you can work remotely with that company. I find it's an additional hurdle to having an in-office job. Some positions are better suited to remote work -- alas, these aren't usually programming positions.

callgage profile image
Gage Henderson

Really interesting insights. I feel pretty confident in my ability to self-motivate & manage my time, but I know I just can't predict how I'm going to handle it if I work a remote job. Seems like I may just need to dive in the deep-end to see if I can swim.

jay97 profile image
Jamal Al

I would say unless u think u absolutely don't need someone to help with work or time management, then go with with a remote job. Downsides of a remote job are not much things that u learn from a remote job, everything u have to learn it urself,and lose the leisure of having coworkers and senior developers to ask and learn quickly from. U will need very strong will power to push urself to work and learn bcz as things progress, u will lose ur drive. Human interaction is another downside as u will be spending most of ur time alone.
I would say that if u could work partially remote that is the best, cuz then u enjoy that of both sides.

kurisutofu profile image

I've just started a remote job and it was really hard to find where I live (Japan).
That has always be my dream too and the only thing that could be better would be if that was a programming job instead of technical support but I tell myself we can't have everything ;)

But so far, I find working from home really nice.

I had a 1 hour and 20 minutes commute and I calculated that given a period of about 4 years, because of work added to the commute etc, I would actually be spending time with my wife for a little more than a year ...
I may sound corny but that was the main reason I wanted to work from home.
Now, as soon as I'm done, I can enjoy being with her and even during work, I can talk to her. She's basically a colleague sitting next to me (she's freelancing at home too).

So to me, I don't miss the office at all but keep in mind it's been only 2 months.
In 2 years from now, I may be saying different things :D
(Hopefully in 2 years, I will be back to programming and from home!)

Sorry for the long comment ...

limnaior profile image

Doing this for more than 10years, living in Greece, working remotely in London. Large part of the company is spread accross Europe and Canada.

The first and most important thing you need to establish is trust with your employers and the team. Sounds easy but it is not at all. Trust that you're actually working (especially when you're stuck on something) and trust that they still value you as a team member (in other words, they don't forget you in meetings or other activities). Mind, that each side cannot see physically what the other side does and that makes trust establishment hard.

Downsides according to my experience:

  • Communication. Not easy to communicate over text messages or phone or even voip meetings.
  • You don't really have the isolation you believe at home. There is always (always!) distraction.
  • That feeling, you want to jump in a meeting room and do a proper meeting talking to other people. So it is good to visit office once a while.

Not everyone doing this, because most companies HR policy does not support remote working (I've received a hundred invitations in LinkedIn, but only one supporting remote working). It requires extra effort from the managers and they feel that they cannot control work when employees are not in the office. It is less risky to give you (and pay you) on a project or a task (so it is up to you to finish it on time), rather than hire you as staff.

bosepchuk profile image
Blaine Osepchuk

I've been fully remote for over 10 years. I was the only remote employee in our company for years and it can be tough.

Lots of commenters did a good just of covering the upsides (no commute, etc) and the downsides (isolation and need for internal motivation) but I want to touch on three additional downsides.

  1. People are going to make decisions without you. Lots of decisions--big and small--get made at the water cooler or in the hallway in unscheduled little encounters and you're going to miss all of them.

  2. You may have a very hard time getting a promotion. Outside your immediate team, you are completely invisible to your organization. If my boss's boss is looking for some great tech person to head up an exciting new project, I'm unlikely to even be considered.

  3. You may never really understand the business. There's tons of implicit knowledge that is shared informally in organizations and you'll miss out on all of that. The most valuable programmers to an organization have a strong grasp of the business domain. It helps them make good decisions about that software. If you don't have some way of learning the business remotely, you're going to be disadvantaged.

There are ways to mitigate these problems but you need to be proactive and that might not come naturally to you.

migueloop profile image
Miguel Ruiz

I will start next month to work remotely and It will be my first time. I want to leave a pc 24h hours connected in my current office so people can see me. I don't know if it's a good idea but I'll try not to loose contact with them and overall speed up the get in contact process.

kevincolemaninc profile image
Kevin Coleman • Edited

I have been working remotely for 4 years now and I have worked with 4 different companies during that time. I have been W2 and internationally remote as well as 1099.

One of the big issues that doesn't get a lot of light is the mental health problems [0]. Every year or so, I see someone talk about it on Hacker News.

Things to look for in a remote job are if the company is "remote first". It is not fun if everyone else is in the office and you're not. I have had issues where I disagreed with a co-worker and they walked across the hall to talk to our boss without fairly conveying my arguments.

Another talking point for me is compensation. Many remote companies try to price you at your location. I interviewed with Gitlab 1.5 years ago. They wanted to pay me in Argentina pesos and 50% less than my coworkers in San Francisco. In the last 1.5 years, Argentina pesos have halved in value. If I agreed to those terms, my co-workers in SF would earn $125k/yr, I would of made $30k/yr for the same job.

I tell everyone: I am American and I will only be paid American rates in USD. If they want someone cheaper, they should keep spending their time looking.

Awesome Remote Job is also a really good resource [1].

[0] -
[1] -

callgage profile image
Gage Henderson

If I agreed to those terms, my co-workers in SF would earn $125k/yr, I would of made $30k/yr for the same job.


One of the big issues that doesn't get a lot of light is the mental health problems [0].

I struggle with this on a day-to-day basis already. I'll definitely keep this in mind.

Also, thanks for the resources that github repo is awesome!

bgadrian profile image
Adrian B.G.

I would also suggest rent an office, do not work from home if you do not live alone. Probably it will be better for everyone on the long run.