The opportunities to be successful don't necessarily come when you're ready for them. Though going down a particular path will not necessarily lead you to your dream job, don't discount where you're at now – you may be more ready than you think you are.
Designing for a product that's been around means working within expectations. How do you (gently) break someone free from a timeworn path to discover a new one? Use a few cues from magic to shake things up.
Projects shown in the light of success – like portfolios, or client stories – will naturally emphasize the best, but this doesn't mean it was a smooth process. Most projects will reach a point where something is off or not quite right.