We meet every couple of weeks, but regularly- it's on my calendar. The regular part is important, as is the on-my-calendar part.
Today, we went back to the first question: do you want to stay in academia and do you want tenure? When I posted those original bits about Molly, it elicited a lot of responses, many of which are worth reading. I do think that knowing what you want in life is one of the hardest things there is. Knowing how to balance short-term frustrations vs. long term goals is tough. Letting your executive function/forebrain make the decisions (no, I don't want to eat that chocolate, no, I don't want to slug or curse the woman at the Department of Motor Vehicles who says "no, I have no record of your existence") is not always easy. Some of the more problematic responses to What Should Molly Do posts are people imposing their wants on Molly.
Molly has decided she wants to be here, and she wants to do what it will take. She then started talking about a problem that her chair wanted her to not write so many grants of a particular type. These grants required matching funds for money to be awarded. I am sure the chair wasn't great about conveying this to Molly, who just saw any money coming as a good thing. "He's got scads of discretionary funds" Molly said. "The matching amounts aren't that much". Well, except that they are. And they have not been budgeted for by the chair, and they have to come out of some other project he's got in line. I said that she has to, in her head, as loathsome as it may seem, be the chair and understand his perspective.
Then she brought up the next problem, which was something about department meetings. And I said: Molly, we can go through each of these problems, and I'm happy to do that with you. But here's an idea that might save you the grief of identifying and living with this list of issues. I quoted my next-door-office neighbor, a former college-football player who decided he wanted to do Something Else, and who, btw, is pretty good and pretty impressive at knowing what he wants): "Is this the hill you want to die on?". Molly got it immediately (she is smart, and quick, and very very good). She laughed and laughed and said: "I'm going to print that one out".