It sounds like both you and your mother have been living beyond your means for a long time. Also, you've been enabling each other to do that. That's a very hard pattern to break. You really don't know what it's like to have to totally depend on yourself. Where you lived for 15 years was in a property partially owned by your dad.
You refer to where you live now as you being "under (your mother's) roof." So you liquidated two properties that you owned to buy a condo that is not in your name. Or maybe it is, which would mean it's as much yours as hers. I don't know if you get the Suze Ormand Show up there in Canada. She gives excellent advice to people about money matters, especially to people in families where there is excess inter-generational dependence. Do yourself a favor and get her books and watch her programs. (Books at the library are free. Programs are probably accessible on the Net.) You could learn a lot, probably more than you could learn from a therapist. Your mother could learn a lot from Suze too.
I don't think either one of you can make it right now, without a roommate. And I don't think either one of you can find a roommate right now, other than each other. (Since she has no job, and yours is part-time.) So you're kind of stuck with each other. Your mom is just as dependent on you, as you are on her. So just go live your life and see whom you please and stop telling your mother every detail about your life. If she doesn't like it, what's she going to do? Leave you? It doesn't sound like she has anywhere to go or any means to get there.
Maybe you are lucky to have a mom who is willing to at least partially support you for 36 years. I don't think its the healthiest arrangement, but it seems to be what is required for you to pursue your entertainment career. We all have to make sacrifices for our dreams. Everything in life comes with a price. Maybe being on your own would involve you giving up on the career you dreamed of. That may be something you are not willing to do. And you have a right to make that choice.
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