Hi, My name is Sara Rosso and I'm the VIP Global Services Manager at Automattic / WordPress.com VIP - I've been using WordPress since 2006 and working at Automattic since 2010. I'm also a writer, photographer, technology lover, and business & digital strategist, and I've been living in Italy since 2003.
I use a 13" MacBook Air, and often I'm using an external monitor when I'm working from home. I use an iPhone for most things, including most of my photography now, but I like to go back to my Canon 7D for when I'm really interested in getting some shots to print out or sell online.
I always have a text editor open for drafting things and note-taking, and I love TextWrangler because I can have X drafts/files open at the same time in a single window (it hovers around 20-30 at any given time), and it can also be a decent HTML editor. I use Wunderlist to track my crazy to-do lists and a squared reporter Moleskine when I want to flesh out an idea or brainstorm freely. For photo editing I switched to GIMP several years ago and am comfortable there now, even though I've tried Lightroom a bit too. I live in Google Drive & docs (I have a thing for spreadsheets!), and also spend a lot of time in Google Maps because of I'm often traveling and discovering an area - I love creating custom Google maps to help with that.
I think I've got it! I am away from home 40-50% of the year (Automattic is a completely distributed company, so we have no offices) so I need a nimble setup I can stick in my Timbuk2 carryon bag when I go. If there was some sort of global wifi program, I'd be the first in line.
I also really need music for mood changes, productivity, or concentration, but I can't rely on streaming it due to moving around so much, so I still have a healthy local collection & am always looking for new inspiration. I'm really loving the hour-long fixtapes Sol Bicycle company puts out every month for free.
I get a lot of inspiration from people I follow on Twitter and what they share and I use News.me to make sure I get the good stuff even if I'm offline that day. I'm really enjoying receiving newsletters again, especially from those who craft and share things they find online, as when I trust someone's judgement or voice, I know I'm going to get some good information from them even if it's not something in their direct sphere of expertise.
I also get a lot of inspiration from people who are helping others to create or succeed - I think there's a lot of power and good in sharing with others what you know and what lessons you've learned.