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I've been working 40% remote (two days from home, three days in office) for just over twelve years. I'm employed as a developer, and I negotiated this arrangement when I joined the company. I have no experience of freelancing or self-employment.

As others have said, the key to making it work is trust and communication. Employers/management need to know that you are being at least as productive as you would be in a conventional office environment. And your team needs to know that you are making a fair contribution to getting things done. Each person in those groups will have a different default belief about what you are doing (working or slacking) in the absence of evidence to the contrary. Understand that, and use communication to address it.

So communicate appropriately. Some people suggest being super proactive on communication as a way of visibly signalling the effort you are making. I'm suspicious of this in a developer role, as you can end-up being thought of as noisy and self-promoting. Recognise that the way you communicate will probably need to change over time.

Find tools that work for you and your team, but don't get too preoccupied with tool selection. Its not the main issue.

Assuming an employer is open to remote working, I'd say that you need to: a) show a realistic understanding of how to make remote working work, and the problems that can occur; b) demonstrate that you are trustworthy and can work independently; and c) demonstrate that you can communicate effectively. This is going to be easier for an existing employer than a prospective one. being familiar with popular tools like hangouts/slack/skype will help.

Scott Hanselman [1] has some useful things to say about remote working. He's a PM at Microsoft.

Finally, recognise that it might not work for you. You might get lonely, or marginalised/overlooked, or just want a change. Don't lock yourself into one way of working for ever.

[1] https://www.google.co.uk/#q=remote+site:hanselman.com



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