How and why did you start working remotely?

I started 9 years ago at Microsoft because I wanted to work there on Open Source but I didn’t want to move to Seattle. I was born in Portland and this is where we’re staying. It wasn’t negotiable. All our people are here.

What advice would you give someone considering a remote job?

Remember that it’s gonna suck. They’ll forget you exist, they’ll ask “when are you coming up next,” and they don’t know how to set up the camera.

How did you convince your company to let you work remotely?

Just pushed and pushed, while trying to provide as much value as possible. Built robots, made roomba cams, tried portals, showed I was dedicated to solving the remote issue.

What are the biggest benefits to working remotely?

I drop off and pick up my kids at school every day.

What are the greatest challenges to working remotely?

I miss major conversations that happen spontaneously in the hallway.

Do you keep a regular remote work schedule? What is it?

Yes, mostly 9-4/5 then a little more from 10 p.m.-midnight.

How do you avoid becoming distracted when working remotely?

I walk around when I’m distracted then come back when I’m ready again.

What is a remote work pain point, and how do you address it?

Folks will ask you, WHILE THEY ARE ON A VIDEO CALL WITH YOU, “When are you coming up next?” What is it that we can’t talk about right now? Why postpone for weeks? Remotes are often second-class citizens.

What gear can't you work remotely without?

• Webcam
• Batteries

What apps or websites can't you work remotely without?

• Skype
• Microsoft Office

Would you consider returning to a traditional office job, or are you remote for life?

I honestly don’t know. It would depend on the job. Likely I’d be remote a few days a week.

How do you stay connected with your local community?

I go to user groups, code camps, conferences, meetups, have lunch with lots of different folks doing different work.

How do you stay connected to your professional community virtually?

Twitter, iMessage, Skype, basically anything but LinkedIn.

What's the best way to develop professional contacts while working remotely?

UserGroups, remote pairing sessions, tech clubs.

How do you stay in touch with friends and family while traveling?

Facetime, iMessage, Skype, WhatsApp

What are your favorite cities in which to work remotely?

New York and anywhere in Northern Europe. Norway and Denmark are fab.