Remote Work

The future of work? An essay.

“The most exciting breakthroughs of the 21st century will not occur because of technology but because of an expanding concept of what it means to be human”

John Naisbitt – Megatrends
New Yorker Cartoon


There is a lot of reading available about distributed and remote ways of working but a lot of this is written from the perspective of an employer (Basecamp, Automattic etc) and the benefits it can provide to those employers. Things like gaining access to a global talent pool, more productive employees, workforce diversity, lower office costs, more dedicated staff, and broader timezone coverage.

Remote was an early manifesto for distributed work from the perspective of founders, and highlighted the value the practice provides to open-minded employers”

Working Smaller, Slower, and Smarter

I haven’t been able to find much material that’s written purely from the perspective of an employee that provides a balanced view of distributed and remote ways of working. This essay aims to provide an employee’s perspective of how remote and distributed ways of working compares to traditional office based roles.


From the perspective of an employee who works in software development in Australia the most common working arrangements I’ve seen are:

  1. Distributed Jobs: working for a company that is entirely distributed that has no offices: you choose your own work environment and can generally choose work hours 
  2. Remote Jobs: working for a company with offices but you work from home (or in another location) 100% of the time either during your own time or a common overlapped time
  3. Office Jobs: working 100% of the time in an office 
  4. Flexible Office Jobs: working mostly in an office but having flexibility eg. working from home one day a week or as required 

I’ve spent the last year working in a flexible office job, with the previous three and a half years in a distributed job, and almost all my previous experience in office jobs. I haven’t ever worked in a remote job.

I’ll primary focus on comparing distributed/remote jobs with office/flexible office jobs, and attempt to highlight the benefits and pitfalls of these working arrangements. 

The Benefits and Pitfalls of a Distributed/Remote Job

There are lots of benefits and pitfalls of working in a distributed or remote role. I’ve tried to include the ones that I have witnessed during my time working remotely.

It may be less about the hours you work and more about your productivity and output

A lot of distributed companies measure their staff performance on output over hours worked since it’s difficult to monitor when someone is working or not. This is liberating in that you don’t feel like management are watching the clock and that you need to work a certain number of hours per day/week, as long as you get your work done.

The downside to this is, on those unproductive days where nothing seems to work and everything seems much more complicated than you expected, it is hard to show exactly what you did all day.

Also, some remote/distributed companies still have policies to demonstrate when you are online and working: at Automattic we had to be logged into Slack when we were working so people knew we were online and available.  

The downside to being measured purely on productivity/output is after a while it can feel like you’re just some remote machine sitting somewhere processing away:


“Instead of pursuing scale, Jason is more interested in optimizing the output of each individual employee”

Working Smaller, Slower, and Smarter

Matt from Automattic would often discuss keyboard layouts. This came about in hiring questions, during meetups and even your employee profile showed which keyboard layout you used. Matt was a Dvorak keyboard user:

“The big thing for me is comfort. I can now type for long periods of time with no fatigue at all, and that isn’t even an issue I think of anymore.

For my it was a no-brainer because I knew that however long it took me to learn it would be incrementally paid for by the increased productivity and comfort in the future.”

On the Dvorak Keyboard Layout

Whilst remote working is about your output, it can lead to you working a lot longer hours:

“Perhaps surprisingly, working at home can lead to longer hours than they would have in a traditional office setting.”

Vox Recode

You may have a lot more flexible work schedule

Depending on how the company is structured, work schedules can be set to have specific overlap between team members or entirely up to individuals when they work. 

“At 37Signals we’ve found we need a good four hours of overlap to avoid collaboration delays and feel like a team.”

Remote: Office Not Required

When a team doesn’t have standard hours this provides maximum flexibility to employees to work whenever they like. Like to sleep in? Start late work late. Early bird? Start early and finish by afternoon tea.

Whilst there are numerous benefits to have people working overlapping hours, if you have a team that is globally distributed including places like Australia where I live, it can be impossible to have such overlaps, or highly inconvenient for some team members (3am meetings anyone?)

This applies to both team work time overlap and meetings. In the three plus years at Automattic there was only ever one Town Hall company meeting that was within Australian work day hours, with some happening during US Fridays which was Saturday in Australia. 

I found I would often do work on Saturday mornings as most of my team in the US was still finishing their work week Friday on my Saturday morning, and at some point I had considered working Tuesday-Saturday Australian time each week, but I realised this was having a huge impact on my family and friends who go to school or work Monday-Friday in Australia.

This was explained well in a NY Times article, in the context of four day vs five day week:

“You cannot get more “weekend” simply by taking an extra day off work yourself. If we were to take more time off as individuals, we would be likely to spend that time, as the jobless do, waiting for other people to finish work. We are stuck “at work,” in a sense, by the work schedules of our family and friends.”

The New York Times

A flexible work schedule can also mean you can never really escape work:

“The good news is the 9-5 boundaries have broken down; the bad news is the 9-5 boundaries have broken down,” Steve King, partner at small business consulting firm Emergent Research, told Recode. “Most people so far are happy to make that trade-off, to have flexibility in how they live life and work in exchange for sometimes knowing that at 9 o’clock at night you’ll be answering emails.”

Vox Recode

As working environments and work times become a lot more flexible I have found work time can start eating into your home time, as demonstrated by the example above – answering emails at 9pm (or 4am). The problem is when you can’t be fully present and not thinking about work, or when it interferes with your sleep:

As Matthew Walker, one of the world’s leading sleep scientists says:

The silent sleep loss epidemic is the greatest public health challenge we face in the twenty-first century in developed nations. If we wish to avoid the suffocating noose of sleep neglect, the premature death it inflicts, and the sickening health it invites, a radical shift in our personal, cultural, professional and societal appreciation of sleep must occur.”

Why We Sleep

You may eliminate commuting time/expense but also lose its not so obvious benefits 

If you choose to work from home this eliminates the need to spend time and possibly money on commuting to work.

There are benefits of commuting to an extent though, in experience I have the commute to/from work creates a clear division between home and work, and a commute of around 20 minutes each way including some walking is just the right amount of time in my opinion. I use the time on public transport to edit some photos and I have found by the time I arrive home I have forgotten about the day at work.

Many remote workers incorporate a ‘fake commute’ into their daily work routine, myself included, where they do things like walk around the block or walk to get a coffee near their house and upon return they are in “work mode”. I found this works well in theory, however it’s sometimes easy to skip it if say you have an early morning meeting, and it’s particularly easy to miss it at the end of the day when you’re racing to get things done as well as get to the dinner table:

“Working at home does not leave you time to cool off while coming back home from work. For me, the ideal duration of a commute is 15 to 20 minutes. That leaves you some time to walk, and so, do at least a bit of physical exercise, and to change your thoughts a little bit. There were a lot of evenings where I ended up going from a video meeting to a family dinner in 30 seconds, and I must says that it is not always easy to give a good attention to my kids in such occasions.”

The Stress of Remote Working

You may not have to spend money on work specific clothes, but will probably spend more on other things

Working from home typically means a more relaxed work wardrobe, unless you’re in a lot of video conferences and you need to look very presentable, at least from the waist up. 

Whilst this means you can save money by not buying work specific clothes I found my regular non-work clothes wore out a lot quicker since I was wearing them a lot more, and also I found that there wasn’t really a mental differentiation of putting on my work clothes versus being in my home clothes. Some people who work from home still have a work wardrobe for this reason.

I found when working remotely I spent a lot more money on electricity at home for cooling and heating, and also had to pay for a faster Internet connection at home, neither of which were covered by my employer. 

You may always be working or thinking about work which can negatively impact your life

There’s a common belief that we’ve moved beyond the concept of “work life balance” and there’s even a concept of “work life integration” which goes along with remote and distributed ways of working, as well the move towards a “gig economy”:

“The reality, of course, is that my attention is almost always split, and I like it that way. I work at the table where my teenage sons study most mornings. We discuss my work, and their reading. I punctuate intense hours of writing with detox time in the kitchen. I sit on the dock and sip my beer, while answering email on my phone. I take conference calls from the roof top terrace of my hotel in Cuzco. I edit on the train.”

Fuck Work Life Balance

“Another study of home workers from 15 countries found 42% of remote workers had trouble sleeping, waking up repeatedly in the night, compared to only 29% who always worked in the office.

Some 41% of highly mobile workers felt stress “always or most of the time” compared to only 25% who always worked at the office.”

The Conversation

You may suffer a lot of mental health issues and feel isolated and lonely

“Remote work poses unique mental health challenges. And when you don’t see your coworkers in person every day, it’s easy to assume that everything is ok when it’s not. As a remote company, we need to honestly acknowledge the downsides of remote work and do more to help our people thrive in all areas of their lives.”

I enjoy alone time so I was surprised to find my three and a half years of remote working the loneliness period in my life, despite working from home where my wife and I were raising three pre-school/school aged children.

Most days at Automattic I wouldn’t have real time conversation with a colleague for more than a few minutes at the start of my work day since I was the only person in my team in my timezone. I fell into the loneliness spiral:

“Entrepreneurial coach (and Buffer cofounder) Leo Widrich joined us for Episode 7 and shed some light on the ways isolation can affect the brain. The vagus nerve, Leo explained, governs social engagements, and if not sufficiently exercised, it atrophies. This atrophy can result in what Leo calls the “loneliness spiral.”  

As mammals evolved to be in groups, we are very unfit to survive alone. When we are alone for too long of a stretch of time, many people report to feel a feeling that they name “I feel lonely.” And that feeling is simply our nervous system’s alarm system to say, “Hey, if you spend too much time alone, you’re not gonna survive in this world. Go make some friends, go be of a family, go be with other humans.”

Fortunately, frequent meetups, coworking spaces, and non-work-related chatter can alleviate the isolating effects of remote work.”

Eight Lessons from the Distributed Podcast So Far

I found frequent meetups introduced their own problems (see below), co-working spots were expensive and felt “fake”, involved commuting and were hard to use for video conferencing and late night/early morning meetings. Unless you have a large enough group of people working in your timezone work related chatter is non-existent as it doesn’t work well asynchronously.

“Working at home can mean a lot of loneliness. I do enjoy being alone quite a lot, but even for me, after two weeks of only seeing colleagues through my screen, and then my family at night, I end up feeling quite sad. I miss feeling integrated in a community of pairs.”

The Stress of Remote Working

One common opinion for remote workers is that they need to spend time to build relationships outside of work:

“Matt believes that friendships both inside and outside of work can also help.”

Eight Lessons from the Distributed Podcast So Far

Whilst I agree there are benefits to this, having tried doing this for the three and a half years at Automattic I can say it’s exhausting not only working, raising a family but actively developing new friendships outside of work. It’s very easy to fall into this trap:
Why working at home is both awesome and horrible – The Oatmeal

I’ve personally found it’s much easier to develop friendships within an office environment and through social activities that can be organised by colleagues who work in an office together – for example – we have a hiking group at my current workplace where we go hiking together about once a month.

You may need to frequently travel potentially long distances to remain connected to colleagues which has its own impacts on your family and health

“Spending a week away from home can be challenging for many reasons. Some Automatticians are caretakers or parents who leave kids, dependents, and pets at home. Some might be overwhelmed by large crowds. Others fly in from distant locales and must navigate not only severe jet lag, but also nonstop communication in English, which might not be their native language.”

The Importance of IRL in a World of Screens –

My “week” away involved 30 hours of long-haul economy class travel each way, as was often well over 10 days taking this and infrequent long haul flights into account. My last grand meetup at Automattic I missed two whole weekends (Sat-Sun), one public holiday, and a week of school holidays away from my partner and children. 

As someone who is nearly 2 metres tall I also find long-haul economy class travel particularly uncomfortable and trying to arrive jetlagged and immediately be in “work mode” and socialise with ~800 colleagues you potentially haven’t seen for a year is too much. 

You may burnout within five years of working remotely

Automattic had a two-three month sabbatical after 5 years of work and I noticed a common theme from colleagues who had reached this point: overload/burnout.

“After three months of sabbatical, I’m back to work… Some takeaways and things I learned through this experience: I realized how burned out I was.

Back to work – Dan Hauk

Whilst there are many factors that can contribute to burnout, and it can happen to anyone regardless of working environment, I believe that remote work can make you burn out faster due the always-on nature of work, less work/life separation, frequent long haul work travel and jetlag, and also the necessity to multi-task and multi-converse.

For example, when using online chat systems like Slack remote colleagues can’t see if you’re privately chatting with someone else so someone can ask you a question and you can have multiple conversations going at once, whereas in an office it’s obvious if you’re in a private conversation with someone and rare for someone to walk up in the midst of your conservation and immediately start talking with you.

You may be annoyed at people’s misunderstanding of your job

Most people I met didn’t understood how my job worked. It seemed fake to them, or they were envious of you having “the best job in the world” since I could work anywhere anytime, and wear whatever I like, but didn’t understand the pitfalls mentioned in this essay.

A lot of people couldn’t see me going to work, so they would think it’s okay to call me, visit me or interrupt me during my work time, which they wouldn’t do when I was working in an office.

Housing costs are very high in Australia and we’re moving to smaller and more expensive houses so it’s increasingly harder to justify having a dedicated office at home. If you were building a house to live in here in Australia adding a 15-20 square meter dedicated home office for remote work could easily add $30,000-$40,000 to your build costs.

I also found there were times where a home environment wasn’t great as a working environment. A neighbour was demolishing and building a new house right next to our house and I found the demolition and building site noise very distracting whilst working from home.

I also found school holidays particularly hard as my children would be home during weekdays 12 weeks a year and we only have 4 weeks of leave, so there would potentially be 8 weeks where my children would be home on my work days.

Moving house to more suitable accommodation can be expensive in itself and quite stressful when you work remotely as you need to get up and running with your work as soon as possible after moving house since you’re essentially moving house and your workplace at exactly the same time.

If you don’t have a suitable place to work from home, and co-working expenses are too expensive, or not available or too far from home, this means that there’s a whole group of people who can’t consider remote work which reduces the diversity of the workforce.

Benefits and Pitfalls of an Office/Flexible Office Job

You may feel more engaged at work and less lonely

“Contrary to what we might think, research shows that as the availability of laptops and other remote work devices increases, proximity has becoming more important.

One study showed that engineers who shared a physical office were 20% more likely to stay in touch digitally than those who worked remotely. Employees who were in the same office emailed four times as often to collaborate on shared projects than staff who weren’t in the office. The result, for these sorts of projects, was 32% faster project completion times.

Other research finds face to face interaction is essential for identifying opportunities for collaboration, innovation and developing relationships and networks.”

It’s not just the isolation. Working from home has surprising downsides – The Conversation

I find myself more engaged with my work in an office job as I’m surrounded by people who I can interact with and engage with on work everyday.

Whilst I may not be as “purely productive”, I find myself more engaged and feel more effective as I feel like I am working on the right things and working with others to deliver desired outcomes.

“Human communication is fraught with the perils of misunderstanding, miscommunication and unstated assumptions. These perils are are the foundational basic of most relationship problems, What one side sees as obvious, the other can’t even comprehend. For us the only way to knock down his wall of misunderstanding is to get the players together and put them in a structured ritual that involves touching and seeing the technology under development.”

Richard Sheridan: Joy Inc.

Home may feel less like work and you may not need as many holidays away

I found when I worked from home full time whenever I took time off I needed to get away from home to escape the feeling of being at work – which not only had the expense but wasn’t something I felt like doing all the time. When you work in an office walking out the door in the evening and going home feels like you’re not at work, so a “staycation” of say spending a week on holidays at home can be quite relaxing in itself.

You can choose to have separate surroundings for home and office jobs

I currently work in an amazing building at South Bank in Brisbane that overlooks the Brisbane river and has incredible city and mountain views. There is no way I could afford to live where my office is, but through my job I can spend time here each weekday and enjoy the surroundings. I choose to live close enough to my office but far enough from the city to be quieter and greener, so I enjoy the contrast of city/suburbia for my work/home contexts.

“It’s possible to enjoy, like, or even love work, and yet also appreciate life away from work. Appreciate the breaks and the distance from work that rewards us with perspective.”

When did work-life balance become such a bad thing?

You may find an open-plan office noisy and distracting

“But despite the pursuit of collaboration in workplaces, the need for concentration and focused individual work is also increasing.

And research shows that when employees can’t concentrate, they tend to communicate less. They may even become indifferent to their coworkers.

Knowledge work requires employees to attend to specific tasks by gathering, analysing and making decisions using multiple sources of information. When any of these cognitive processes are interrupted, inefficiency and mistakes increase.

Being able to focus on a task without interruption or distraction is an essential foundation for effective work.”

A new study should be the final nail for open-plan offices

We recently moved into a new office building which is in a great location but the floor is large and open-plan which means there are few walls and the high ceilings so noise and conversation easily travels through the office. 

We also have a table tennis table and video gaming lounge, all open plan, and all about 10 metres from my desk. Most people play over lunch-time which gives me an excuse to leave the office, but some people decide to play table tennis or video games during the day which is very distracting. 

Some people also bring their children to work during school holidays which again creates more noise and distraction, and some people even grind their coffee at their desks. 

A lot of people buy and wear their own noise cancelling headphones to combat the office noise but it kind of defeats the purpose of being co-located if you’re sitting there all day with noise cancelling headphones on using Slack.

You may find an office too stimulating and need time out

As an ambivert I enjoy collaborating and working with colleagues throughout the day, but I find by about lunchtime I need to get out of the office by myself and “recharge my social batteries”. Our work has groups that do activities like a fitness bootcamp during lunch breaks however I find if I don’t have some alone time during my lunch break I find I am more fatigued and less engaged.

You may feel weird about walking out of the office early even if you started early and had a productive day

How long people work is an office cultural norm, and many offices, particularly with younger staff who often play video games all night tend to start later and finish later. If you start earlier, you may have trouble with the looks/feeling you get when leaving the office earlier than the majority of people, even when you’ve had a very productive day.

You will probably have a dress code which you may not like

Most offices have a dress code of some description – some of which employees agree with and some who don’t. You can’t wear shorts in our office, but t-shirts are okay. Your mileage may vary – some offices required collared shirts and slacks, even for roles with no customer or client interaction.

The office culture may not be inclusive

Technology companies have a reputation for tech culture which may include table tennis tables, video games and drinking alcohol. As someone who isn’t in to any of these things it can feel less inclusive when most other people in the office are taking part – whereas in a remote environment you don’t feel obligated to participate in such things as you set your own working environment. 

“Recreational equipment such as foosball, arcade games and ping pong tables had the worst impact on employee satisfaction, with 25% of those working in places where these were available saying they found them ‘annoying’.

Hammocks and ping pong tables going into storage – Is this the end of the ‘fun’ startup office?


There are many bold claims about the future of work:

“In 30 years time, as technology moves forward even further, people are going to look back and wonder why offices ever existed.”

One day offices will be a thing of the past: Richard Branson

It’s less common to find such claims about a future where all children are home-schooled and there are no university campuses. There are strong claims about working arrangements, particularly from those with vested interests in building distributed and remote workforces.

Whilst it’s clear there are clear productivity benefits, from an employee engagement and satisfaction benefit I feel like this style of working, at least in a distributed asynchronous team with no overlapping hours, contributed to a huge decline in my mental wellbeing and quality of life. Why did I keep it up? I enjoyed the content of my work, and the flexibility I had. Would I do it again? No.

“In my experience, there’s no replacement for a live, in-person company, with all members working in the same physical location. Being in the same place, with the sounds of your peers all around, greatly increases the possibility of innovation and collaboration. No advanced video conference system has gotten to the point where it’s on par with being in the same physical location as the rest of your team.

I believe we have fooled ourselves as a society into thinking that remote work arrangements are actually more productive and effective, even though we are naturally wired as humans to be in community with one another. There is no better way to be in community than to actually spend time together in the same space.

I know this thinking will be controversial to many, and there are plenty of counterexamples. I’m just not going to spend any part of my remaining days trying to work out how to make distance working part of our practice.”

Richard Sheridan: Joy Inc.

I think that instead of trying to make all our office jobs 100% distributed and remote, I think we should be instead focus our efforts on making our existing office jobs as flexible, inclusive and conducive to productive work as possible.

Some suggestions to move towards this goal are:

  1. Eliminate open plan office designs and instead offer smaller contained separate office environments which offer teams quieter workplaces to concentrate whilst still being able to collaborate and communicate effectively;
  2. Offer flexibility around work hours, working from home as required, and other commitments; and
  3. Ensure workplaces are inclusive to people’s needs.

6 replies on “The future of work? An essay.”

Very interesting. Before reading this I would have said I love remote work hands down, now I’m thinking perhaps it just has much more to do with the actual job and team than whether we’re in an office or not. Also, 90 min commutes are too long 😀

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