I'm in a situation getting similar to this Ask HN... I have a family that depends on my income (plus, it's very stable/secure, enjoyable, but unfortunately under market pay). If I find a better job, and things don't work out, we'd have virtually no household income... However, I was able to find a second job (which required honing one additional skill) to pull in $3000/year working a few nights a year... Which helps pay for unexpected expenses.