I'm broke and broken

Yeah, it is Chicago, a 38K salary really doesn't go far. To answer some of your other questions, I do have a roommate but even then it's a bottom tier salary for this city. It's mostly a bunch of kids right out of college and in their mid-20's I work with.

Outside of that I'm living pretty cheap. The only thing that temporarily takes my mind off the shame and anxiety is volleyball, and I have some friends to play with in the summer at the beach which obviously doesn't cost anything. I'm really staying away from alcohol right now because it gives me a ton of anxiety, especially the next morning. I'm not really eating out or anything either, but I just feel so bad that food doesn't really even taste like anything anymore so I just eat a lot of salad and fruit.

I don't have much debt, just really low savings. But more than that I just don't have any real career direction. Yeah, things could grow at this job but it's going to take a lot of time and I'm going to be 35 in a couple of months. I'm basically starting where so many people did 13 years ago.

I can survive on this, I'm looking for a 2nd job to supplement it. I can get by.

It's the constant deep shame and anxiety that's so hard to shed. I'm going to be 35 and I have nothing that would make my parents proud. No wife, no kids, no money, no real career.

I used to be a fun guy. What I loved most was trying to free other people from concern and worry. I should have followed that into a career. A few years ago I was a special ed paraprofessional just to try it out to see if I wanted to teach. I thought I had all the time in the world to do things like that and try even though they didn't pay well to find my niche. And then I tried working for a couple of startups that didn't work out.

I think I was honestly in denial about so much of this and how life really works until recently. In a way it's prompted me to work harder because I've finally really truly, accepted where I am in life. And it's 34, broke, and still looking for a career.

All of that is fine, I'm getting in good shape, eating really healthy, working harder than I probably ever have. Good development I guess. I just wish I could feel OK. That every single day wasn't just me pushing through. That I could enjoy something again.

And this isn't like a breakup. I'm still going to be behind in a couple years. I probably always will be. I'm not scared that I won't have enough money to survive, I'm scared that this is how I'm going to feel for the rest of my life.

Makes sense. Are you contributing to an IRA? There's some good retirement savings advice out there, sites such as Retire on My Terms.
Have your parents been judgy in the past?

Nope, I screwed that up too. Always said I would worry about that later. My first priority right now is cleaning up the debt I do have and getting a little bit of savings before I start contributing but that's going to be a top priority.

My parents are a little judgy but not really. That actually makes it worse though. They would have been so proud if I had made something of myself. They had me when they were older too so they're both in their early 70's now. I might never be able to give them that moment. I won't have enough money to get married or have a kid for many years, likely when I'm around 40, and even then most likely not enough to offer a middle class life. But more than that, if I can't stop feeling this way, there rightfully won't be a woman who would want any part of me and I wouldn't want to subject anyone to this either.

I just wish there was something to ease the pain. I can accept and take on the hardships that are coming for the consequences for what I haven't done in life. I just wish I didn't disappoint so many people. And eventually they'll figure it out. My parents deserved so much better than me.

I am that cautionary tale that parents will tell their kids about, the kid who didn't give himself structure and discipline and direction that woke up one day at 35 and realized he's a loser and can't do it all over again. And I can't blame them. I'd tell them the same thing.

Life rarely works out how we dreamed it would...I changed careers at your age, started again at zero. Tackling the debt is your first port of call...then start building again from there...it ain't over till its over my friend.

Thanks, I hope you're right. I hope it's not too late. I'm not going to go out without a fight.

I found a $20 bill on the street while I was walking home today and even though I'm broke, I just felt like I didn't deserve it. I gave it to a homeless guy I passed a little later.

I'm trying the whole gratitude thing, waking up in the morning and being thankful for health and a 2nd chance even though things look really bleak and I'll never likely actually catch up, just kind of keep my head above water at this point.

I think I have to somehow get to a point through hard work and becoming a better person where I actually believe I deserve this life after I've failed so much. I hope I can get there and I appreciate everyone writing that actually cares about my sob story, even though I'm the one who got myself here.