When the Job You Love No Longer Loves You Back

I'm tired. I've been working in the library/education field for over 10 years, and as much as I love it, I think I need a change. I truly love what I do, but more and more, I’m struggling with the reality of working for someone else. I’d love to work for myself.
Lately, I’ve been dealing with some health issues, and trying to keep up with a job that requires me to be in better physical condition has made me take a good, hard look at what I’m doing—and how much longer I want to keep doing it.
The problem? I’ve quite literally trained myself into a corner—or at least that’s how it feels. I’ve spent the last decade educating and training myself specifically for this career. While I do have a few transferable skills, most of them would keep me in a similar field, still working for other people—two things I’d really like to avoid.
One option I’ve been seriously considering is freelance grant writing. With all the funding cuts happening lately, I think it could be a great use of my skills. It would let me work for myself, choose the organizations or causes I want to support, and still use my love of writing. I’d have some human interaction without being tied to a desk all day.
The only daunting part? Learning how to handle the business side of things—like health insurance, taxes, business insurance, budgeting, and marketing. I’ve been diving into those topics, and while I’m slowly checking them off my list, I still have that nagging voice in the back of my head:

1. I’m oversimplifying things, and I’ll get it wrong, or
   
2. I’m missing something important.
   

I just feel like I’m approaching a point where making a change will actually be easy.
Four years ago, my mom (who worked with me) and two coworkers who are like second parents to me all retired, leaving me alone at work. Yes, I have work friends, but it wasn’t the same—especially as we started adding new staff. The following year, though, my niece transferred to our high school, and I wasn’t alone anymore. We’re really close, and her presence made the absence of my mom and those other coworkers much easier to bear.
The problem now? My niece is graduating this year. I’ll be all alone again—but this time, for real.
Yes, I know plenty of people thrive at work without family around. But for me, family is everything. I love the camaraderie we share and the support we give each other. As someone with chronic health issues that can flare up unpredictably, it’s comforting to know that if something happened to me at work, there are people nearby who understand what I’m dealing with.
And honestly… I’d love the freedom to travel and not be tied to a desk or a rigid schedule. Nothing wild! But I got an RV last year that I’m hoping to fix up for weekend trips, and I’d really like to actually take those weekend trips.
I just don’t quite know how—or when—to take that first step.