Quitting Job

In multiple podcasts you’ve suggested to never leave a job or a marriage until we are happy with ourselves.
If after doing the work, creating my own happiness, how would i know its time to move on to other things? I have been contemplating leaving my job for a few months, I want to work from home instead and what holds me back on the decision is the loss of income, health benefits i am currently receiving, and being truth to myself, i do care what my boss would think if i quit. She trusts me a lot and the company is going through tough times so that situation makes me feel guilty of quitting.