Yeah...I know what you mean. I've written an article about that but haven't published it here yet. It's about the difference between knowledge and wisdom.
Knowledge is knowing a lot of stuff, wisdom is about using that knowledge combined with experience and having good judgment.
And even when we have both - as you do - we can be our own worst enemies. It's usually got to do with self-esteem, how we view ourselves against the rest of the world, and it's human nature that that's not always in such a great way.
When there's something at the core of us that feels unworthy or not good enough, it's easy not to take care of ourselves, not to value ourselves the way we value or see others. Part of that can mean not applying wisdom that we've gained and that we've shared with others.
Striving to have a sound and solid relationship with yourself (the general "you," not "you" specifically, Jimmy!) and developing a deep sense of self-respect and self-love is the best way to begin taking your own advice, applying all that wisdom etc. because it means you care enough about yourself to want the best for yourself and your life.
And...these things can be fickle. Life can knock us around a bit, and sometimes that can take chunks out of a previously-pretty-decent self-esteem. Then we're more prone to beating ourselves up, not taking such great care of ourselves etc.
Does any of that feel like it fits for you? Because I think you have plenty of wisdom...it's just that there's something blocking you always using it (and I speak from plenty of personal experience with the same issue!).