I currently work at a non-profit in a technical role, earning $90K while living in a very high cost of living area. My commute is an hour each way, and I have a hybrid schedule of two days in the office and two remote, working a four-day week. As I prepare for the arrival of my first child in December, I'm feeling the pressure to advance my career. My wife earns $150K, but her field is at risk of being heavily impacted by AI, so we are focused on paying off our mortgage and aiming for financial independence. With my boss retiring in March, I see an opportunity to transition from my technical role to a more hybrid position that combines technical and people management as a director of operations, targeting a salary of $115K with a three-day in-office and two-day remote schedule. I plan to spend the time before his departure transferring knowledge to ensure a smooth transition. However, I've been looking for director roles externally and have faced rejections after interviews. I hold an MBA and an MPA, which I obtained for free, and I feel like I need to make a move soon. Staying in my current role means I would have to dedicate almost all my free time to studying for the LSAT, which isn't ideal as I want to be present for my family. I'm worried about a few things: 1. If I express to my boss that I can take on more responsibilities, he might either offer it without a pay increase or reduce my hours to part-time. He's difficult to read, and while I don't think he would do that, I've seen nicer people make unexpected decisions. 2. If I stay stagnant in my current role, I could be unprepared if layoffs occur due to a worsening economy. 3. I want to support my wife fully, especially with the added daycare costs of around $30K once we start that phase. We don't have family nearby who can help out more than once a week, and asking for that is a challenge. I'm seeking advice from anyone who has faced similar situations or has insights on how to navigate this.