In a predicament. What’s everyone’s opinions on applying to more than one position at a company?

I have tried a career coach, volunteering, upskilling, networking . . . and am currently in therapy . . . nothing is sticking. I have switched roles 6 times in 6 years. I have also done freelancing and tried starting my own business. And the job I have now is sucking the life out of me. I have only been there for 9 months. Not one to whine . . . and yet here I am. I can see the appeal of a mindless job that just pays the bills and I never have to think about a "career" again . . . am I giving up??

I'm 76 years old: too old to go back to school for 2 years and then do the 3000 hours of supervision. I work remotely for a toxic company; along with others haven't been paid in over 2 months. I love helping my clients but the $$$ issue is eating away at my peace of mind. I've interviewed several places, but lack of licensure is a hurdle. Ideas on how to get out of this trap really appreciated.

For background, I'm a cisgender white male looking to find ways to become a stronger ally through action and priviledge.

(I am a transitioning English teacher, so I have plenty of writing experience, but nothing that would be suitable for a writing sample.)

How is that legal? If it's not a numerically required field, what is the best verbiage for how to get around it?

He has derailed work meetings by questioning me, and my boss doesn't interfere or interrupt at all. She didn't question his previous action, which basically took a job duty away from me and appropriated it for himself. I asked her about it, and whether it was permanent. She indicated (vaguely) that it wasn't, but she didn't seem too worried about it. It was his area of expertise, so I let it go. If he wants to reduce my workload, I'll just spend that time posting to FGB! He sent an email today, cc'ing her, and gave me some orders outside of his wheelhouse. I spent at least an hour writing a draft that detailed my level of knowledge and how I didn't need to do what he insisted on, then decided to simply say I'll do whatever our boss says in a reply-all response. The other email would have been sent to my boss's boss and someone else in the organization who supervises my stakeholders, and the supervisor of my stakeholders.... and I wanted to cc' others as well. But I felt that would have been a jerk move response to a jerk move. I'm proud of myself for standing up for myself and keeping it brief, but now I know I really need to discuss it with my boss, and she doesn't have time for this nonsense. What would your next step be, hive mind?