There is a saying my dad often reminds me of: “It is far easier to find a job when you have one than when you don’t”. I felt exactly as you did. I weighed similar scenarios as you. I had a former manager continually remind me to start looking while I could. The saying my dad often told me holds true. You have time to think. You have time to say no to offers. You have less in the game to say yes right away. You value yourself more and can leverage that knowledge when negotiating. When you leave or are left, there is a desperation that wiggles in and may lead you to pick something you might have otherwise said no to. I was very unhappy where I was. I now work with an awesome group of people, I am challenged and I am making significantly more than I initially thought I was worth. I only learned that after getting multiple interviews and offers.