10 Lessons from 4 Years Working Remotely at Automattic

4 years ago today I started working full-time for Automattic.

Four years seems like a lifetime, but it’s a pretty short time in my work history, and it’s been the most life-changing job so far for me. I’ve had years where I spent 40+% of my year away from my home base (with only two weeks off), and I told you how I almost stopped myself from applying and sabotaging my own success. Working at Automattic and working in a distributed team has changed how I will look at work and being productive for the rest of my life.

I wanted to share some of my own reflections, lessons, and scenes of working for a startup with an entirely distributed team for the past four years, in no particular order. Some may say Automattic is no longer a startup, though we just raised more funding, but 4 years ago when there…