This is a symptom of having nothing to do and no direction in life. I truly believe that Jen has hurt herself in the long run spending all that time in her 20s and early 30s not working outside of the home. I think a job/career can give you a sense of what you're good at, what you like, what you find value in. And if you're wealthy enough to not work, you need something like a long term project, volunteering or specific charity work. Spending her 20s fannying about at home doing pointless expensive hobbies meant that she was always directionless and never gained enough confidence to be a proper adult. At the age of 38 Jen should have a pretty good idea of who she is. And she should be too busy being a mother and deciding what to do with her life to spend all day watching Youtube videos of people who she has nothing in common with.