Hey Jay, I think that the career thing is just an effort to impress her. Don't take this the wrong way but if she's gonna love you it should be for who you are, not what you've accomplished. To be honest, my advise is two part.

1. If you really want to see her again then don't wait. Keep working on the positive improvements that you're working on cause they are great and you should be proud of yourself for them, but don't let them decide for you when the time is right. Your heart should decide that.

2. If you contact her, hope for the best but prepare for the worst. Make sure that you're ready to face the fact that she may be seeing someone else now or that she may share your feelings. I'm really not trying to rain on your parade and I'm sorry if I did. I think that it's a good thing to see someone again, especially if there was no closure or if there's a chance to re-ignite an old flame. I'd just hate to see you fall into the trap that I fell into. I did the same thing a few years back and I made the mistake of just assuming that things would go according to my plan and I ended up crushed. Just something to think about.

I guess over all I'd say go for it. I hope that this advise is taken as it was meant, cause it wasn't meant to offend. You seem to have a good head on your shoulders so take the advise you get from here with a grain of salt and use your best judgement. Take care and good luck.

ryan