Am I doing this wrong? Scared vs Strategic

Hi Brooke-

I’ve been a scholar since January and I’ve gotten so much out of it. However I still feel like I’m struggling with the one issue I’ve had since the beginning- should I try to make money with a job immediately or should I focus on making money through my creative work (screenwriting)? I have focused on my creative work because I could and it’s what I wanted to do, but the urge to make money now has never gone away.

I have fallen short of goals I’ve set for my creative work although I remain committed to pursuing them. As you can imagine, I buffer a lot. Calendaring helps me with structure but I can’t shake the money thing. I don’t want to have all my eggs in one basket as I know how risky filmmaking is. Even when I imagine making lots of money doing it, my first thought is always how can I invest it wisely so I’m not dependent on making money that way.

When I look at my thinking, I wonder if I’m scared or if I’m being strategic. The Coppola family, for example, have side businesses to support their creative work (winery, hotels, clothing lines, commercial directing etc). If I’m really honest with myself, that seems like a smart way to go about it. I have a new idea for work I could do that sounds fun, is in alignment with my life goals, and would give me more structure. I think making money on a side job would actually make me more productive with my writing. But then I’m not practicing constraint. But when I think about the buffering I’m doing, I think that working more would make me more efficient and also more ambitious.

All of this falls under a larger heading of what I believe is my core issue- fear of doing things wrong. And also old feelings that I can’t have what I really want and have to settle for what I can get.
I’ve done thought work on it and these are thoughts I like:
Changing my mind is okay.
Having different experiences is great- even failures.
I can do hard things.
I like to make money.
I want to challenge myself.
I am capable of so much more.
This will all be a huge adventure.

Do I just sit with the self-doubt and carry it with me? Continue to do thought work on it? Is my expectation that the self-doubt will go away entirely an obstacle in itself? How can I keep things simple and not over-complicate them? I feel like I shouldn’t be so crazy and scattered this far into your program! Help!