Paradoxically, having less story dialogue makes this more possible as you can act out in your head how the dialogue went for an event in the story where you picked one big choice or the other.
First, you need a story to work with... Second, it's hard to "act (it) out in your head" when the actual dialogue is saying things like, "But, mommy, I don't want to go" or "Your bags are at the door, boy. Stop whining and hit the road" to a supposed 80 year old man.
It can work if he is written like someone who thirsts for knowledge, moving through multiple universities' graduate programs to take up Master's Degrees and PhDs. Based on this thread's comments, he is not.
Bachelor's degrees take 4 years. Masters and PhD programs are usually about 2 years. So, eight bachelor's degrees, eight masters degrees and eight PhD's would get you there. It would likely, also, get you a severe case of absolute uselessness... Oh, wait... Maybe that's what happened to him... Poor kid.