Hi Kelly,
Money has a transformative power within relationships. Like it has a life and energy all its own. It can mean love, security, success, freedom, power or all those things. It sounds (I am trying to say this gently esp. since you are sincerely trying to figure this out) as though you have been groomed to be an "economic outpatient". Financial independence will put you in the drivers seat of your own destiny.
For self awareness you might want to research stuff like affluenza and psychology of money type websites and books. Try "The Millionaire Next Door" for inspiration on getting a handle on your own assets. This is the author who coined the "economic outpatient" term for second-generation wealthy.
You are in a very common situation. One generation worked hard to "make it" and the second generation is used to having the benefits of parents who "made it". It's a very different viewpoint. I'm surrounded by people who are controlled by their parents' wealth. They would be happier if they felt they could stand on their own two feet. Honest. But they feel they have to (their feelings or their parents' feelings, pick one) uphold the standard their parents have achieved over the years. So the pressure is on to be an "overnight success".
If you choose therapy as an option, try to find someone familiar with money matters through generations. It may help to get a handle on how you feel about money, where it comes from, etc. in order to really get a grip on what you want to achieve and why these feelings are pressing so ####### you right now. Hope this helps, Kelli.
Good luck, Seeker