Lather, Rinse, Repeat - What is This REPEATED LIFE Lesson - Trying to Teach Us?

Repeated Life lessons. Kinda like having a recurring dream/nightmare. Having researched the form, I understand we're, "Being told something," by these events/dreams and I'm not sure I'm listening properly or able to act upon this Repeated Life lesson.  A few days ago, I started (but didn't publish) a blogpost on the subject of achievemephobia or Fear of Success, which I suspected I suffered from. Personally, I feel VERY HAPPY with the 'creative life' I've had; as an artist I thought I created some powerful images; as a writer I thought I created some powerful characters; as a commentator I thought I came up with some powerful arguments. But this is all like a kid playing with a toy i.e. there's no serious career in my self-entertainment or life plan(sic).  Additionally, there seems to have been some sort of barrier to my financial success from  my own creative endeavours. Events were cancelled. Trips have gone wrong. Sales have fallen through. Success and fame have been pulled back, just when they seemed to be 'there for the taking'. Career has ended, abruptly. As much as I enjoy what I do, I just can't make enough money from my own creative efforts to continue down this path. So, I take jobs to make money... I know, I know, I know, "I may be the problem," I mean, after all, I'm cantankerous, I'm disruptive. I've been banned from so many forums, because I like to debate every technical issue. It's just what excites me. The debate. I'm never satisfied. When I worked at Sony Cambridge, management used to call me "Loki," - I only found this out after I left. I may be my own worst enemy. But what can I do, other than quietly work for someone else and earn pointless money to keep a roof over my (and my family's) head? I think I have the talent to 'be creative' but why can't I 'make a living' from it? I mean, I have tried to set up businesses, and I do fill in my taxes every year. This 'repeated lifestyle' that I experience no matter what I try, what is it trying to tell me? Though it's a real financial burden for my wife, do I even WANT to be a success and be renowned and be rich & famous for what I do? It's like I'm TINKERING and not really taking the Repeated Life lessons seriously, but I can't find a way to 'use the knowledge' and I 'don't have answers' as some people think I have. I'm at a loss... I wonder if I'm MISSING THE POINT OF MY OWN LIFE, like I'm always 'doing the wrong thing' and can no longer find a way through to the real reason I'm here, on not-yet-Free Planet.