I'm in a somewhat similar situation, but I'm 50 and the equivalent of a cobol programmer - useful in my niche (financial services), and a lot of general experie

I'm in a somewhat similar situation, but I'm 50 and the equivalent of a cobol programmer - useful in my niche (financial services), and a lot of general experience in the field, incredibly useful to a few firms but I don't know the latest hottest tech stacks so not generally employable. Also not an entrepeneur, so a startup is out (don't have any good ideas anyway). If I go, it'll have to be along the FIRE line, and I haven't figured out what the alternative revenue stream is. Probably consulting back to the industry part-time, as long as I don't take a couple years off and stop being "somebody". I get the panic. It's hard to walk away from the job and the money and the status. It doesn't matter if you objectively don't need it - you get used to it. It's a massive security blanket - not just the money, but the perks, the being coddled by the company. And while hard work plays a part in getting there, you know that some of it's just pure luck. Are you going to just throw it away before you're sure you're done forever? I've been at this level for 10 years now and all of the above just sinks into the bones. It's harder as you get older - age discrimination and all that, and you have fewer years in which to recover if you really do screw it up. Have you thought about the health insurance angle? That's the biggest bind-up of all for me. You can't get decent health insurance without a full-time job. I don't know how much help I am, because no I haven't screwed up the courage yet, and I don't have a good plan. But I understand the boat you're in.