Q: I can’t stand my boss. Is it ever OK, financially, to quit your job without having a new one first?
—Over it in Ottawa
A: Yes, it can be. But first answer this: What’s your pumpkin date? That’s what Toronto career coach Caird Urquhart asks clients contemplating such a move: “The day you turn into a pumpkin is the day you run out of money.” So, if you have four years of savings, it can be worth it to take eight months off to conduct a thorough hunt for that perfect position you really want—which is generally the amount of time it will take. “While you’re more hireable when working,” says Urquhart, “do keep in mind that you’re also not able to devote the time it really takes to find a new job.” However, if you’d hit your pumpkin date within three months, you’ll be under immense pressure—particularly if you’re older with lots of responsibilities. Only those who are young and have the option of temporarily moving back in with Mom and Dad could take that approach. Good luck!