Tender one, I have often thought of doing a Jack Monroe - My Story flow chart but I do like your idea too.I have a great idea! Bear with me... (and if this bloody happens, the idea's copyrighted, ok?)
WHY doesn't Jack do her autobiography like one of those 'choose your own adventure' books that were all the rage pre-internet?
Every time her life stories diverge, you get a choice:
"If jack gets dumped by Allegra and keeps her boobs, go to page 50"
"If Jack fucks up another relationship, go to page 75"
"If Jack sold her lightbulbs, go to page 30"
If Jack arranges a Yummy Mummy play date, go to page 35"
Ok, it's late, I have brain fog (need HRT, dontcha know) and I might be hallucinating.
But you get my drift?
I think it could work...