It's good to see someone express this. I really hate working and you've enumerated my concerns about stopping.

The conclusion I came to is that I need about $3M to provide a life-long safety net, then I can try just making enough to cover the "basic needs" and not end up homeless if things go wrong.

Do you have any thoughts about taking a year off? I'm considering doing that once my current employment expires, but I'm concerned that if I taste freedom and begin enjoying life, I may not be able to go back to work.