I spent a decade of my life working in an office, dealing with ice cold hands, annoyingly loud neighbors and feeling socially worn out at the end of every work day, even though I spent 6+ hours staring at a screen.

After 10 years of this, it finally hit me that I'm not fit for office life.

I also realized that I'm in a perfect industry for remote working. While software development does require human interaction, it doesn't have to be face-to-face most of the time.

Once I realized this, I knew there was no going back. From that point forward, being able to work from my home office was at the top of my job requirements list.

The problem was, the job I had at the time was 100% office oriented. I didn't know a single person in my organization that worked remotely.

So there I was... driving in to the office every morning thinking, "This is just so dumb. It would be so much better working from home, but here I am sitting at a red light on my way in to that cold, dreary office".

I couldn't stand the cognitive dissonance of the situation, so I started to plan my escape.

How to escape the office

There are two ways to become a remote worker. You can leave your current job in search of a remote workplace, or you can transition your role to incorporate working from home.

As alluring as the first option seems, it's not a great option. For reasons I'll go in to later, remote jobs are hard to get hired for, especially when you have little remote work experience.

That means most folks who want to start working remotely need to do so through their current gig. In my experience, almost all tech companies are open to some sort of remote work, so it's an option for most employees out there.

Even if you don't currently have a job, it's usually easier to find a local workplace and transition over, rather than trying to land a remote job with no remote work experience. That's why I'll focus so heavily on it here.

Starting the conversation

Before you can ditch the commute and start enjoying breakfast at home, you'll need approval from your leadership.

Thankfully, any manager worth their salt will want to help their team succeed, and if they understand the merits of remote work, they'll be open to at least giving it a try.

I would start by ensuring they're okay with any sort of remote working. That means they're okay with the occasional "work from home" when your cable needs connecting or that plumber is coming by to fix the sink.

If they're not okay with that, I highly doubt they'll be open to any sort of remote work arrangement. In that situation, I wouldn't recommend attempting any sort of remote working arrangement, and instead I'd start looking for new employment.

Even if you can only find a new on-site job, you can mention remote work as a possibility during interviewing/on-boarding and gauge their response. I've done that once before and it worked out pretty well (until a new manager arrived and the culture shifted, but more on that later).

Selling it

Assuming some sort of "work from home" is allowed, you need to determine how to best bring up the subject.

You'll typically do this during a one-on-one meeting with your manager. It's really the best time to bring it up, because it doesn't put the manager on the spot in front of the rest of the team, and gives them a chance to react and process the idea.

I'd start the conversation by explaining the advantages of remote work for the employer (mainly revolving around your improved productivity).

Explain how it's much easier for you to get work done from home, due to the lack of distractions.

Here's some things I would likely say:

"When I worked from home the other day I swear I was five times as productive as in the office. I think we would really benefit from doing that more regularly"
"I'm able to concentrate a lot better at home, without the distractions of the office"
"I really feel more comfortable in my home office, allowing me to work more effectively"
"It's important for my productivity to be able to work undistracted for large chunks of time, and I'm just not able to get that in the office"

All of these reasons revolve around the benefits of remote working for the manager. A more productive you means hitting timelines and better reports for your manager to brag about.

Start Small

It's important at this step to start really small. I'd aim for working one day from home per week.

Research ahead of time what day would work best for you. Mondays and Tuesdays are usually bad days, because that's when most meetings are scheduled. Fridays aren't always great, since a lot of sprint demos and retrospectives occur then.

Wednesdays can be a great option, as it's in the middle of the week, giving folks in the office reassurance you're there before and after the "day off" (in their eyes).

When you're talking to your manager, explain which day you'd like to work from home and why. This will help reassure them that you've really given it thought and are trying to ensure it won't negatively impact the team.

Assuming they respond positively, reassure them on all the ways you can be contacted when needed.

"I'll be on chat most of the day"
"I'll be sure to check email at least twice a day and respond ASAP"
"I'll give everyone my phone number if they have any urgent need"

The two main concerns for an employer when approached with remote work are:

Will this affect project work?
Will this person disappear from the team?

Being confident and showing you've spent time thinking about it should be all you need to do to allay any initial negative response.

Security concerns

There are special circumstances that I feel are worth mentioning, and they don't have to do with productivity/communication.

These concerns have to do with data.

If the company you work for is in the financial/health sector, or deal with any sort of sensitive data, chances are they have a security team in place.

That team will have all sorts of thoughts on people working outside the office.

I'm not saying you can't work remotely at one of these companies, but be prepared for pushback from the security team if they've never had to accommodate a remote employee before.

Work with them to understand what they fear, and either find a way to work through their concern, or help clarify why their fear is unfounded (just don't belittle their opinion or dismiss it).

Proving yourself

Okay, so at this point, you've gotten approval to work remotely one day a week. This is a huge victory and the first real step towards remote life.

You're goal now is to spend the next month or so proving that:

You're more productive working from home
You're just as available as when you're in the office

You can do this by being overly communicative when at home. Send an end of day recap on days you work remotely. Be active in the group chat.

During your 1:1s with your manager, explain how working from home has really benefitted the project, with specific references to how the extended focus time has helped you solve problems you wouldn't have been able to in the office.

Also, ask for feedback from the team about the state of things. At this point, they probably won't have much feedback, since it's not much of a change for them, but it's going to be important going forward to have this line of communication open.

After a month or two of working one day a week at home, people should be comfortable with it, so much that you can try 2-3 days a week.

Again, have a conversation with your lead about it, going through much the same motions as before. Talk about increased productivity, better focus, etc.

Show how the change hasn't impacted anything, and has likely improved work. Mention how you'd really like to try more days, to see if you can further benefit from the focused time.

Have days picked out based on feedback from teammates. You should be able to float the idea by them and ask for preferences on which days you can be remote.

If all is going well so far, you should be able to get approval to increase your days at home pretty easily.

Now comes the real challenge.

Managing Communication

At this point, you're going to start pushing the boundaries in terms of communication. Once a week was pretty easy, as people could fall back to talking to you in person any other time of the week.

But at three days home, you're spending the majority of the time away from your team, and it's going to increase the likelihood that they need to get in touch but aren't sure how.

To avoid this situation, become even more proactive about communication. You can start by taking some small steps to let folks know you're still around.

If you don't have a daily stand-up, be sure to send daily status via chat/email
- Alternatively, use tools like workingon or idonethis to better manage the communication
If possible, be sure to always turn on your video during meetings. It's much easier for people to remember you're in the meeting if they can see your face, instead of looking at some weird speaker phone thing.
Use you chat status to communicate passively, always updating it with what you're working on at the moment

Having an on-site ally

Even with you doing your best to stay in touch, it's going to be difficult.

Speakerphones will break, the audio quality is going to likely suck, and video connections in conference rooms will be spotty (Sidenote: I've never known a tech company not to struggle with AV technology).

People may be patient with this at first, but after the fifth time in a row of a meeting starting late because of connection issues, they're going to start blaming you for not just showing up to the office like everyone else.

This is where an on-site ally can do wonders.

Someone to help pre-check the AV connections before the meetings, to help troubleshoot communication issues when they come up, and to remember to say bye at the end of the meeting so you're not sitting there at home wondering if the meeting ended or you lost your audio connection.

As important as it is to be a good remote worker, it's equally important to have good "remote" teammates.

Without them, you're going to be trying to steer a battleship with a paddle. It's never going to work and you're going to look like a fool for trying.

Signs of Turmoil

Aside from the technology issues, it's at this point that you really need to start watching out for signs of discontent from your team.

Things like:

Being left out of last-minute meetings, because it's too much trouble to get the tech set up
Off-hand comments about never being around
- Note that this is not the same as people joking when you are in the office that "hey you do exist". People make this joke and it's just a lazy attempt at humor. Forgive them and try and find a better topic to joke about.
No one else is doing remote working (especially if they're not allowed to)
- If you're doing a good enough job at it, leaders should be encouraging others to give it a try. If not, it's probably a sign they've made a special exception for you, but don't trust the overall idea enough.
There's very little communication towards you. Teammates don't talk to you about technology decisions and it's a little too quiet for comfort

All of these are signs that the team is having trouble adjusting to your new work arrangement. Like I said, being a good remote worker is half about you and half about your team.

If you start to notice these things, you need to have a real conversation with your manager about what you're noticing. If there's a specific developer involved, you're going to have to mention them.

The best case scenario is that you're just imagining things, and your manager should do a good job of reassuring you.

The worst thing to do is to play it off as nothing, only to have it blow up in your face two months later when that deadline gets tight and teammates start looking for excuses on the delays. You'll quickly learn who has been subtlety annoyed (or jealous) with your working arrangement.

"Is there something I should know?"

People won't want to open up about their concerns, especially if they don't feel they're reasonable ones. If someone prefers to talk face-to-face, but they're constantly having to do video chats, they may just begrudgingly humor you but inside hold it against you.

In this case, one of the best questions to ask folks, especially your on-site ally, is "Is there something I should know?"

When asked at the right time, this open-ended but specific question can really open the door for feedback. Usually this feedback is second-hand, from someone who heard another teammate talking about you during lunch or that happy hour they forgot to invite you to.

Be prepared to hear negative news when asking the question. Hopefully it won't come, but be thankful when it does, as it's better to hear it in this situation than in an end-of-year review when your promotion/pay raise is on the line.

Again, it's all about being proactive about communication.

A disclaimer

I should mention at this point that a lot of this is "Do as I say, not as I did". A lot of my advice comes from not being proactive enough, hiding away from conflict and having to deal with the fallout a month or two later.

It's really difficult for me to ask for and deal with negative feedback, especially about something I believe strongly about. But it's even more difficult dealing with the situation after it boils over in to real conflict.

So, do the best you can, and push yourself to have difficult conversations. Realize that the hardest part is just bringing up the topic to begin with, and once out in the open, it's a lot easier to manage.

Staying Productive

Say things are still going well and you have a supportive team. Maybe other teammates are giving the lifestyle a try as well, and you're encouraged to see the shift in the culture. That's awesome and something worth celebrating for sure!

In that case, you can shift focus back to improving your work from home flow, in preparation to making it a full-time deal.

Here are the tools I find essential to working from home:

Have an office
- Not a chair at the dinner table. Not your couch in the living room. Have a real office with a real door and a real desk. Speaking of...
Get a good desk
- Standing/adjustable preferred. You won't be walking around as much and it's important not to sit for 8 hours straight.
But also buy a good chair
- You shouldn't be standing 8 hours straight. A good ergonomic chair is really important to avoid back pain.
Hang a whiteboard
- You can get a cheap one of these at a hardware store, usually called hardwood panel boards.
Multiple Monitors
- Please don't try and work from your laptop screen alone. It's just terrible.
External keyboard/mouse
- Another essential bit to having a real workspace.
Solid wifi/ethernet
- This is really important for those video chats
A good microphone/webcam
- Critical for video chats. People will love hearing your real voice, versus a crackly headset mic.

Hopefully you can convince your workplace to pay for most of these things, but don't be too surprised if that's a bit difficult.

Consider it an investment in your career, as you're going to want to keep these tools anyway if you leave this job.

It is funny/depressing to consider that workplaces will happily pay for a parking spot, office space, HVAC, restrooms, desks, monitors, etc, but freak out if you mention wanting a nice mic to help do your job. But that's how it goes.

Some places are really good at this, and it can even bring up the topic of "tech allowances" for all employees. That said, it's probably not worth an extended battle if you find yourself fighting it.

Managing your day

Aside from the tools, you'll also need some techniques for staying productive over the long run.

It's easy to be productive from home one day a week, but once the novelty wears off, you can start slacking and fall behind.

Starting the day

I struggle with this a lot, since I usually don't know where to start. My default usually ends up being the daily morning standup, but that can really delay your start if it's at 10:30 in the morning.

One of the best tricks I know is to leave a problem unsolved for you to finish in the morning. When ending the work day, don't try and finish that last task. Leave a small final step for you to complete in the morning, giving you a good starting point in the morning.

Take real breaks

One hidden difficulty of remote working is knowing how-to and when to take breaks, and for how long.

In the office, these breaks are inherently encouraged by colleagues wanting to grab coffee or go see that new weird art piece in the lobby.

At home, no one is going to stop by (okay, maybe the postal worker), so you need to learn to take breaks yourself.

It's going to feel really uncomfortable stepping away from your desk during the day.

"Am I allowed to do this?"
"What if my manager/teammate reaches out?"
"What if people catch me?"

All these feelings are hidden guilt you have about working from home. The truth is, any break you take will be made up by your increased productivity during the rest of the day. Just make sure people know you're on break and how to reach out if they really need you then.

Here's my "ideal" break plan:

15 minute morning break (assuming I got a good start to the day).
1 hour lunch
30 minute afternoon break

This seems like a lot, but it's really important to make time for yourself. Again, you're making up for it by being much more productive during the rest of the day (right?).

Plus, these breaks are going to be really important to keep you from burning out on screens. Without the commute to the office and the lunchtime chatter, you're going to start losing touch with the outside world.

Allow yourself the chance to make a coffee run, or spend some time outside in the garden. It's going to keep you productive over the long run.

Also, don't spend your breaks checking twitter or doing some sort of screen related thing. Give your eyes a break and get outside.

How to lunch

Aside from starting in the morning, the other struggle I face is how to manage lunch. One hour is just the right amount of time to get hooked in to something else, especially if it's watching a show or playing a game.

Those may seem like the perfect escape from the workday, but I've found myself saying "just one more episode/turn" too many times.

Instead, grab a book and read outside. It's much easier to get back to work after reading a book, compared to competing with the entertainment of a show/game.

It will also stimulate your mind when the afternoon doldrums roll around. It can also give you something to talk about in the team chat room.

Another option is to meet a teammate for lunch. This is a great opportunity to catch up on life at the office, and give them a chance to give candid feedback.

Either way, be cautious how you use your lunch time. Keep it for nourishing your body and mind, not for distracting yourself from your workday.

Closing up shop

If you're like me, you really hit your stride around 4:30 in the afternoon. This surge of concentration has been incredibly effective at getting me in to the flow state and I'm usually a ton more productive than the rest of my day.

I think it has something to do with knowing that I'm almost out of the workday woods. When I think about spending a full 8 hours working, I freak out feeling stuck. But when it's only an hour to two I have to go, I relax and just get working.

The trouble with this is shutting down when supper time rolls around and the kids get home.

You're finally being productive and now you have to stop?

Unfortunately, yes.

If you've struggled to focus throughout the day, you may feel a bit anxious about not getting enough done, making it difficult to close that laptop lid.

If that's the case, you've got to be honest with yourself.

Spend 10 or so minutes thinking about what physical and mental issues prevented you from focusing today.

Did you get enough sleep last night? If not, your mind likely struggled staying focused. Working late won't help with that at all. Resolve to sleep better tonight to make up for it.
Did you eat a decent breakfast/lunch? Hunger can be pretty distracting, so make sure your eating well.
Are you starved for novelty/social interaction? A big reason people spend hours on social media is the need to talk. Make plans to get out of the house and see people, so you're not trying to fit that in during the day.

Whatever it is, be honest with yourself and resolve to fix it tomorrow. Don't try and just push through it for the night, as the problem will still be there in the morning.

Making the final transition

So here you are. You've been at this for several months and you're ready to leave the office life behind for good.

I'd recommend next knocking office time down to one day per week for about a month, then transition to being fully remote.

At this point, you should have other teammates who are remote. If not, I don't recommend this step. It will be too much of an uphill battle to be successful in the long run.

If the support is tehre, have the conversation with your manager about why you'd like to try full-time remote.

Maybe you want to try working from the beach or the mountains for a month.

Maybe you want to visit family in a different country and would love to stay there for an extended period of time.

The conversation will no longer be about how you'll be more productive, but more about how you'll be finding more value in your job.

You're manager really shouldn't care about it at this point, because you've proven to them and your team that remote work is a-okay.

But still go in

As much as I love remote working, I'm a huge believer that you need to see your co-workers at least once a quarter. I've worked on a fully-distributed team that never met in person in the 15 months that I spent there.

It definitely hurt the team.

Team connections got a little loose, conversations became a bit more tense, and in the end the culture eroded and the team broke up. Meeting in-person could have really helped avoid this.

So plan to be in the office at least once a quarter. On those days, plan special meetings for you and your team:

Arrange to have lunch together at a nearby restaurant.
Schedule brainstorming/planning meetings, as they're much easier to do in person than remote.
Organize a hackathon type event, encouraging face-to-face time.

Whatever you do, don't just go in to the office to stare at a computer screen all day.

Living a remote life

Being fully remote really opens you up to travel, as you can work from anywhere with a good internet connection.

One thing I've taken advantage of is extending my holiday visits. Every Thanksgiving for the past several years, I've done two and a half week vacations at my in-law's house.

While I usually take some time off during this, I do spend about half my time during the visit still working as normal, just from a different location.

It's a really great opportunity to spend time with family, without having to use up all my vacation days. My kids love getting to play with their cousins and my wife really enjoys the extra time with her parents.

Plus it makes paying for $2000 in plane tickets a little more worth it (not to mention the hassle of traveling with kids).

If you do decide to take some trips with your newfound freedom, check out nomadlist for recommendations on where to stay/work.

Exit Strategies

That's the guide if things go well, but what happens when it doesn't?

Unfortunately, I've had many experiences in this.

They say that "the only constant in life is change". This is especially true for remote working.

No matter how supportive your manager/team is about your remote working, that can change at a moments notice. Something as simple as your manager getting promoted can cause a shift, especially if your new manager isn't as keen to remote work.

Unfortunately there's little you can do about it, and all your effort to promote a remote-first workplace can be for naught.

You may also find yourself running in to unexpected roadblocks along the way.

Perhaps your manager has been really supportive, but once you try and go fully remote, word gets around and the CTO suddenly takes unwanted interest in your whereabouts.

In these instances, you may need to start looking for a new job.

Fortunately, you now have a ton of experience you can use during the interview process to show why you'd be a great remote worker.

There are a few job boards I'd recommend for finding remote jobs:

I've applied to several jobs through these boards, and have gotten callbacks from many of them. Honestly though, I've never actually gotten hired via them, although that's the truth with most of my jobs.

It's just so much more important to know someone than it is to know about a company.

Perhaps the best thing you can do is get to know folks who work remotely, either through conferences, places like dev.to or by writing/talking about the subject yourself. This will help form the connections that can get your foot in the door when the time comes.

There's also this fact: when applying for a local job, you're only competing with the local market. Not only will fewer people be applying, but your salary requirements will likely line up a lot better with the company.

In a remote position, they have a much, much larger pool of people to draw from. Some of these people will be in lower cost-of-living cities than you, allowing them to live off a smaller salary.

This is just a reality of the marketplace. It's not good or bad, it just simply is.

But, good companies will happily pay extra for the right person, so don't be too dismayed at it. You have very unique assets that can be a perfect fit for the right role.

Be confident in your experiences and your ability that got you where you are today. Rely on the lessons you've learned to get you through tomorrow.

What about you?

What experiences have you had in remote working?

I'd love to say it's all sunshine and lollipops, but I've had my fair share of conflict going down this path.

I'd love to talk in more detail about it, but I also don't want to throw people/companies under the bus, so I won't get in to specifics.

Just know that you will likely face some struggle going through this, that you're not alone, and that it is possible to find a remote job you love.

Just be patient, communicate with folks, and you'll be fine.

Header photo by Mantas Hesthaven on Unsplash

How to find (or make) a remote job