Having the Chat: Your first step towards remote work


It’s not always easy asking for what you want. Especially from your boss. Fears of coming across as presumptuous or impudent can conspire to keep you where you’ve always been. It’s not that you don’t like your team, or having chats around the ping pong table (or is that too 2014?). It’s just that you would really, REALLY rather spend your mornings doing yoga rather than commuting, making scrambled eggs rather than grabbing a muffin on the go. And, that holy grail of remote professionalism, who hasn’t wanted to work sans-pants? (seriously google it, there’s even a book about it).

Remote work, or telecommuting as it’s commonly known, is not a new concept. In fact the Work without Walls survey by Microsoft in 2011 triggered structural changes within organisations internationally when it was found that  “a fifth of respondents…said they’ve conducted a business call in their underwear.” Yes that was a weak segue. But the figures don’t lie.

Despite the figures, however, some employers baulk at the idea of losing sight of their employees. This is obviously lacking in rationale, as anyone who spends the first hour of work on FB can tell you,

“You can make me sit at this desk but I will exercise my right to waste time DAMNIT!” Sound familiar?

Whether it makes sense or not, you’re going to need to make your employer comfortable with a new arrangement and that means one thing: TRUST.

So where do you start?

Well, firstly, you’re going to want to be on good terms with your employer, and be confidant that your work has been up to scratch. NOTE: Your argument can NOT be “So yea, you know how I come in late all the time and called in sick the day after I was tagged #jelloshots #sleepwhenimdead…yea so I’ll be HEAPS more productive if you just let me work from home.”

Erm. No.

The best way to build trust in your ability to work remotely is to give it a try, so I’ve put together a roadmap for you:

Step One: Question your motivations and suitability.


Are you sure you want this? Why do you want to leave the office environment? And how do you imagine your day looking if you did? The reality of location independence is considerably more challenging than you might expect. You need to be the kind of person that can self-motivate, stay on task, manage your own time effectively, and be able to stay focused when there’s a million distractions such as the laundry and dishes (although you can use those as your break tasks), the tv, your partner or your cat. (NOTE: Cats have evolved specifically to lie on laptops, paperwork, and hide your pens). Oh, and partners look much sexier when you’ve been staring at a spreadsheet for 3 hours.

Step Two: Get your facts straight.

If you’re going to present the concept of going remote to your boss, familiarise yourself with the pro’s and con’s. Here I’ve presented it under headings that’ll convince your employer you have your company values in mind. Keywords people, keywords.


Passion: Remote work offers you more autonomy and flexibility with your schedule, which in turn results in a reduction of stress as you have extra time on your hands, hence greater work/life balance, increased happiness and thus increased productivity.

Profit: They’ll SAVE MONEY if they reduce office space, reduce tardiness and absenteeism as you can’t get stuck in traffic, use a snowstorm as an excuse, and if the kids are sick you can be there for them AND your boss (although to be fair that one sounds a bit stressful).

People: They’ll both retain employees and appeal to new prospective employees, as flexibility is sexier than ping pong tables.

Planet: Reduce CO2 emissions by reducing commutes, one remote worker at a time!

(Although I do think it would be interesting to see a graph with emissions from daily commuting over X number of years VS emissions produced by air travelling location independent professionals. But I digress.)


Distractions, lack of boundaries, loneliness, loss of motivation,


(More genius honesty about working from home at The Oatmeal.)

Step Three: Get to grips with the practicalities.

  1. I’m going to assume that as you’re currently employed you’re probably brainy enough to realise you’ll need a computer and wifi connection wherever you choose to work. Then again, office work can occasionally sap brain-power, so I thought I’d mention it.
  2. How is your boss going to monitor your work? Are you still going to be required to ‘clock in’ online for a certain number of hours or do you have a job scope that allows you to work however you want as long as you get the job done? You might need to present a system that tracks your hours as you work, such as Hivedesk or Hubbstaff.
  3. How is this going to affect your other working relationships? Will you be judged by the other non-location independent staffers? How will you keep up to date on gossip (I suggest Snapchat)? It is worth chatting with everyone you work with, and not just your boss, if you want to stay friendly with your colleagues.  

Step Four:

Write up a proposal. Have a chat. Gauge the reaction. Suggest a trial period.

AND VOILA! Nude work here I come!!!!

…and if things don’t go so well…

Step Five:

Here’s a list of remote work sites for your new job.





And if you’re REALLY ready to take a leap…DON’T GET A JOB.

If you have the financial means to support yourself for a while, why not explore starting your OWN business, so you never have to ask for permission again! There are a number of innovative organisations out there to support your exploration of entrepreneurship, location independence, and the future of work. Check out Coworkation.com, they curate retreats with a perfect balance of inspirational high end locations, exceptional networking potential and outcomes-based workshops and activities. They also have the smartest, sexiest staff.

Signing off, Kirsty for Coworkation  (#nopants).