I really want to be the “underdog” or “dark horse” that proves society wrong. I just don’t know what to do currently.
You're not going to do this the way you seem to be going about it, not least since you seem rather keen to prove society right by following its customs and expectations.
Even the premise you began with, that 'the longer it takes, the harder it gets' is upside down and back to front. It doesn't matter that it's a cheap tag line from a lousy movie about a stereotype being poked fun at, but that it is actually not the slightest bit true.
The longer it takes, the more experience of life you accumulate - if you let it. The more experience you accumulate, the more sense you can make of the things around you, and the more easily you can adjust so that others have less difficulty understanding and relating to you.
If there is any trick to this at all, it is to avoid creating unnecessary targets and milestones which probability says you will fail against. That then teaches you the wrong things, because they were the wrong targets and milestones.