You really don't see the irony in questioning his capacity for empathy while minimizing his hardships and suggesting they're likely all his fault?
I must confess I haven't had something like this happen to me at this level, so maybe my capability of empathy is diminished, but the questions do not imply that it's entirely/likely his/her fault, outside of the fact that you generally can't get into a situation like this without some action on your part. This is precisely why OP is trying to take steps to change his behavior.
Maybe what I should have asked was:
"Care to share more?"
Without the pointed questions.
However, It's mostly positive, as I'm sure Jesse is finding out. I wouldn't trade anything, it's just hard, and that's that. Humbling, really. It's feeling like you've failed yet you've not begun.
I had the privilege of talking with Sean O'Sullivan for an hour or so recently, he coined the term we use today as "cloud". I explained how I felt, and my situation (as mentioned, similar to Jesse). He made a pointed observation about success. Often with success comes great failure, and it's in the failures that we have the learnings, that lead to success. I wrote a little about learning by doing: https://medium.com/love-etc/small-talk-795a6bc9b615#.kc8kopb... - Learning by doing requires failure. Recently, someone who I'll love eternally shut me out of their life because I prioritized my work over them for months and months and months, I didn't listen, I didn't act, but I did learn.
Frankly it seems most of us are not particularly vocal about our failings, maybe some of us are perfect.
All of the times I've failed it's been because of me, and every time I fail, I learn more about what it means to be: me.
Thanks a lot for the thoughtful reply -- wish you the best! As you've put it, it's certainly a journey (no way, don't pick a simpler one!), and it looks like you're ready to be in it for the long haul. 100% agree on your thoughts about success/failure and found your thoughts on smalltalk/education/love interesting.
I have a brother who is trying to learn programming and I wish I could infuse him with the spirit you've learned (I'm sure the hard way) to have. If only there was some way to consistently teach tenacity.