A gem of a writeup by Ryan. I read through the whole thing, including the emails he shared. Some snippets below for folks who may not read the whole thing. The

A gem of a writeup by Ryan. I read through the whole thing, including the emails he shared. Some snippets below for folks who may not read the whole thing. The people we let go had joined because they believed in our product and mission. They had done nothing wrong, yet suddenly there was no longer a place for them. I remember letting go of someone I had known since college. She turned to me and said, “I took this job over something that paid more, and now what should I do?” These agonising decisions kept me up at night for weeks, and I know it was much harder on those affected. That group of professional challenges was more difficult than anything else I’ve faced in my career. At the time, I told a teammate that it felt like I was playing seven-dimensional chess because of the complexity of the negotiations combined with so many conflicting challenges at work. I was also juggling personal challenges that were far more stressful than the hurdles at work. It started with absolutely brutal fertility issues that my wife and I went through, beginning in 2016. One of those tests revealed unexpected, terrifying information. I was diagnosed with cancer. I only remember a pair of words from the first conversation with my doctor: “two tumors”. For the next several months, my emotions would sometimes pour out in a tidal wave of tears and yelling. Anger, frustration, fear, confusion — there were so many feelings to contend with. I worried that the team would use my diagnosis as an excuse to throw in the towel, that my health would become a distraction, cause the company to fail and make things that much worse. To this day, I cry every time I go to the cancer center at Stanford. I hadn’t had a headache in 20-plus years and now I couldn’t go through a full day without experiencing crippling pain in my head. By the end of 2017, I was completely worn out. Persistence was my superpower. But now I’ve now come to understand that persistence is a double-edged sword, and my decision not to take a break, to not take more off my plate, hurt me, my family and the company. That was the biggest mistake of my career. depression and burnout can make even small challenges feel like a big deal. I had gotten to a place where I only focused on the losses and couldn’t accept positive things. my daughter looked at me and said, “Daddy, you always look so sad”. She was five. It was the push I needed to change. A successful and healthy transition requires one to live in the nothingness between the end of one period and the beginning of another. FINALLY HIS FIRST EMAIL(feedback to the board member) IS AN EXCELLENT READ.