Let's think about it in terms of expected return on investment. For full disclosure: I am an Automattic employee and love working remotely on the side so much

Let's think about it in terms of expected return on investment. For full disclosure: I am an Automattic employee and love working remotely on the side so much that I devote my private time to promoting it [ https://www.quora.com/How-is-life-as-a-web-developer-who-works-remotely/answer/Artur-Piszek-1 https://www.quora.com/How-is-life-as-a-web-developer-who-wor... ]. Opinions here are my own. The way I see it (and this is my private opinion), Automattic can successfully pull off what it does, because we really filter people who are self-driven and NOT motivated by money. If you want more $$$, Google or Facebook is definitely your best bet. But in Google or Facebook, your role will be tightly defined. In Automattic you have LOADS of freedom and flexibility to try to have a positive impact. We sometimes succeed, sometimes need to work on something else, but the work tends to be very fulfilling. Now, back to the money topic. My salary went up about 6x after joining A8C (yes, that is 600%). Part of this is of course due to the fact that I live in Poland. - I can travel the world without needing more vacation time, - I have company off-sites in Disneyland, Athens or wherever it may be. - I can visit my grandpa during the workday because I don't have to sit in an office all day or move to Silicon Valley. - NOT EVEN ONCE was I pushed to do overtime in Automattic. I did it because I got myself into way to many projects, but I have multiple coworkers that do not go over 40 hr/week I promised you expected return on investment formula. My calculation went like this: - My quality of life will go about 80% up for the number of years ( I just clocked in 4 years at Automattic, so lets use that number ) - To achieve that, my quality of life will go down 40% over 2 months, because of the trial - I have the confidence of about 50% that I can make it. You do the math. I learned that to achieve better results that everybody else, you just need to do a little more upront work. People tend to not do that. The funny part is that after you do that upront work you are usually in a place where you have to work less than everybody else.