How to Transition to Working From Home

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By Blake Thorne



You’re more likely than your parents to work from home one day.

Or from a Starbucks, a shared working space, you get the idea. In fact, 4.2 million American workers joined the remote working movement from 1997-2012, according to the Census Bureau.

What this means is that many of us who started careers in a cubicle and necktie are switching over to the pajamas and home office.

It’s a big change. And it’s not easy.

Thankfully, the trail has been sufficiently blazed by workers who have been remote working for years, some for decades. Many of those brave pioneers have documented their experiences. So let’s explore some of the best advice from remote workers who have learned what works, and what to avoid.

Be available

The first rule listed by many people who call home the office is to be available. Set clear expectations with your colleagues, supervisors and subordinates about when you’ll be available. Then actually be there. If someone’s expecting you to be working at 2 p.m. and they can’t reach you, it had better be because you’re doing something else that’s work related.

Scott Hanselman, a remote worker and Microsoft programmer, calls it one of the most important aspects of the job structure.

At the same time, Hanselman wrote on his blog, the idea is to hold clear working hours. Don’t fall into the trap of being constantly on call.

“Be Available During Work Hours. Don’t overcompensate and be the person who is online at 5am or answers emails on Sunday. Just make sure that from 9 to 5 you are 100% available via SOME way that your boss knows about,” Hanselman wrote.

Fix your environment

When you can work anywhere, your environment is your responsibility. Everything from your chair to the art on your walls to — increasingly — the desktop and mobile software you use at work is up to you. You have to find what works and put it all together. As it once was said, with great power comes great responsibility.


Chances are, no corporate IT pro is going to come by your house to be sure your email client is running properly. There’s a good chance even that the computer and phone you use are your own, as well. And increasingly, workers everywhere are using cloud-based services that allow you to log in and work from anywhere.

It’s up to you to be sure you’re using the tools that your coworkers are collaborating on, and find others that work for you.

“We use Lync at work, but I also use Skype, GChat, Join.me, straight VNC, Windows Remote Assistance, CoPilot and a dozen others,” Hanselman wrote. “If one doesn’t work for some reason, don’t waste time, just move to the next one. If someone starts to associate you, the remote worker, as a symbol for technical difficulties it will slowly warp their perception of you. Make it easy.”

David Fullerton, VP of Engineering at Stack Exchange, calls Google Hangouts “the lifeblood of our organization.”


“If you haven’t tried them for video chat, you’re living in the Stone Age,” Fullerton wrote on the company’s blog. “We have persistent hangouts for every team available at URLs that everyone knows.”

Stack Exchange has been a remote company from day one and more than half the non-sales staff still works remote.

Fullerton also recommended tools for online chatting with coworkers. Many companies have replaced e-mail for internal communication altogether with tools like Slack (we here at iDoneThis use Slack and obviously love using iDoneThis for asynchronous communication, we think you would too).

“We built our own chat system, but there are good alternatives like Campfire and HipChat out there,” Fullerton wrote.

Physical environment

There’s no right or wrong way to set up your physical environment. This is where personal preferences — and a lot of freedom and responsibility — play the strongest role.

Spend time thinking about what has worked for you in the past, what you like and don’t like about working in an office. Do you thrive in order and cleanliness or messiness? Do you need total silence or a buzz of activity?

Some people work standing up, some people wear a bathrobe. Some — seriously — put on a suit and tie to work from home every day. Find what works for you. Don’t be ashamed of it.

And even if you consider your self the most introverted and shy person you know, don’t discount the value of human interaction.

The Chicago-based company Basecamp (formerly knowns as 37signals, has been a pioneer for remote work and one of its most visible advocates. The company’s leaders have authored two books on the changing way we work, “REWORK” and “Remote: office not required.”

In “Remote: office not required,” founders Jason Fried and David Heinemeier Hansson write that human interaction is one of the most important aspects of work. Though it doesn’t neccesarily have to be from coworkers.

“Fortunately, one of the key insights we’ve gained through many years of remote work is that human interaction does not have to come from either coworkers or others in your industry,” they write. “Sometimes, even more satisfying interaction comes from spending time with your spouse, your children, your family, your friends, your neighbors: people who can all be thousands of miles away from your office, but right next to you.”

Or as Hanselman put it:

“Often just being at home can drive you nuts. I try to get out a few times a week. I’ve worked from the mall, from Starbucks, from McDonald’s (free wi-fi, sue me) and from a park bench. I find that just having people walking around makes me feel more productive. Their movement and energy keeps me focused.”

People around you

Speaking of human interaction. Having friends and spouses nearby can be the best part about remote work. It can also be the biggest detriment. If expectations with people in your physical space aren’t clear and understood, friction will arise.

Set clear expectations with the people around you, especially those you live with. They should understand that you’re at work. Doing the dishes and cutting the grass will have to wait.

Do a good job making it very clear when you’re working, when you’re OK with interruption and when you’re not.

Hanselman, for example, installed a Busylight for Microsoft Lync, which is installed outside his office door at home and lets family know — without asking — whether he’s busy (red light) or available (green light).

Know your expectations

This isn’t the time to be wishy-washy about the kind of work you do. If your boss isn’t seeing you every day — and possibly going weeks or even months without hearing your voice — both parties need to be extremely specific about what you’re doing and when you’ll do it.

Step one is to not pollute the expectations with a mishmash of busywork or unrelated responsibilities. If you’re a boss who likes to micromanage, this might not be the work style for you. Aim for simplicity and clarity, John Mancini, President and CEO of AIIM, told Fast Company.

“Be disciplined and work according to simple rules,” Mancini said. “Clarify those rules and make sure everyone knows them.”

In other words, showing up in a necktie and sitting in your cubicle all day doesn’t count as being at work anymore. When you don’t work from an office, you have to actually be working to “be working.” Otherwise you’re just hanging out at home. When you get the hang of this discrepancy, working remote starts to make a lot more sense.

It even seems pretty great.


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