Vipassana is about directly seeing impermanence, dissatisfaction, and lack of self in all sensations. The point of practice is to elevate your skill in seeing those. Because direct comprehension of the so-called three characteristics can reboot the mind in a way that is very analogous to how we reboot the computer and remove malware.
Vipassana is not about helping you deal with your psychological issues at the level of content. Its not a therapist-substitute. In fact it will often make matters (temporarily) worse, if you actually follow the instructions and do the practice.
Spending your meditation time pondering your "issues" is the biggest rookie mistake you can make. People can do this for years, and never get anywhere in their practice.
If you want to spend some time alone and contemplate your life, thats great and quite possibly useful, but don't call it Vipassana.
This is worth repeating. This is a silent practice, and while thoughts may arise (and very interesting ones, too!) learning to let them go, and remain (mentally) silent was perhaps the biggest obstacle to progress for me personally. Not sure if mental silence is a cause or effect of meditation, but it's the closest thing to real happiness I've experienced.