"I'm a fairly new father (two-year-old son), and I have explored switching careers recently. I am a high school teacher, and I have considered switching to prog

"I'm a fairly new father (two-year-old son), and I have explored switching careers recently. I am a high school teacher, and I have considered switching to programming." "There's a lot to be said for stability and security, but there's also a lot to be said for keeping yourself excited to be alive, with your family." (Absolutely 100% correct. If you are not happy and fulfilled it's not good for your kids or your marriage.) "Switching jobs and switching careers is a lot different as a parent than as a single person." Let me say this (knowing a few people who spent their entire working career teaching and are now rotting away in apathy and mediocrity). If you are going to make the switch now is the time to do this. When you have one child who is 2 years old. Once you have more children and they are older the chance of it happening (especially with the golden handcuffs of a tenured teaching job if that is what you have) approaches 0. The time to act is now. You will also have to decide (because from following the links on your profile it looks like you live in a pretty nice place) whether you are willing to give up that geography for giving yourself possibly a more challenging career path. Obligatory: "And only you can make that decision". I can tell you this though. If you do something that has a bigger upside (financially and intellectually) than teaching it will open up an entire world of possibilities for you and your family that in the end might be more beneficial. You have to think long term. One day your kids will be older and move on. (And in fact they will change once they go through puberty but that's a different story all together). My advice just knowing what I know from what you wrote (and what I see after a quick look) is to consider seriously switching careers. You can always fall back on teaching (so we are not talking about the downside risk of turning down admission to Harvard or anything.)