I related to this so much! I’m job searching and have been for several months (though I’m currently employed… I admire your planning and courage!) I also knew it would be a longish process — I have a pretty specific list of must-haves and nice-to-haves — but I was not really ready for how much the rejection (or more often the radio silence) would affect me.
I have been dealing by generally trying to be nice to myself, because it’s really easy for me to start beating myself up when I’m getting rejected. Money-wise that mostly means things like springing for a good salad on days I don’t pack my lunch instead of grabbing a cheap slice of pizza, saying yes to drinks or dinner with friends instead of sitting on the couch stewing, and keeping up my gym membership. I’ve also bought a suit (ugh) and spent quite a bit on Ubers so I could be sure I’d get to interviews on time.
Also, Allison, if you’re reading these I would love to know what you thought of the Skillcrush class! (I’m also a nonprofit marketer and could probably stand to build up those skills.)