I am 41 years old.
I have been working since I was 15 years old in a variety of retail, food service, and educational jobs. My first job was working as a children’s librarian. At 15, my hometown library trusted me to manage evenings alone in the children’s section of the library and to help shape the lives of children who spent their time with me, reading books.
I graduated high school in the top 10% of my class. I have a bachelor’s degree (education), two master’s degrees (theology and literature), and an abruptly aborted attempt at a PhD (American literature), but I passed my comps, technically making me ABD. I never had a GPA lower than a 3.4.
I have taught every grade, except kindergarten, fourth, fifth, and sixth grades. I was responsible for helping to educate preservice teachers. I taught college classes for fuck’s sake.
Now. Today. In this life. I am in an entry level position, but I work for an amazing company (I would argue one of the best). I wouldn’t give away my career for anything.
I struggle today with this: one of my favorite coworkers who has the same job title that I have now is an 18-year-old recent high school graduate.
I struggle today with this: why did I waste 25 years of my life with higher education to find myself here?
Today I’m finding it difficult to deal with this.
Today I am having a hard time making sense of how this is fair.
Today I am feeling duped by the American Dream.
I followed all the rules in the educational and vocational sectors of our culture. And each time I have to start over. At the bottom. In the entryway. Even out on the doorstep, if you will.
Don’t get me wrong: I love my job. I love my life. I love my coworkers.
Why can’t I just be happy here? Why can’t I just let this feeling rest?
Because I can’t reconcile who I am with what I’ve been socialized to think I deserve, or what I have been socialized to think is owed to me, because I did it “right.”
I am perfectly happy on most days with who I have become and who I am becoming. I am perfectly content most days to be joyful and blessed that I am loved, respected, challenged, and fulfilled by my work.
But today. Today I struggle with being 41 years old. And being here.
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And I think what bothers me the most in all of this is my ongoing struggle with entitlement. I know I am blessed to have all I have. I know I am privileged in so many ways. I know I sound whiny and ungrateful, when I am so grateful for so many people, experiences, and opportunities. I know I just need grace. Grace. More grace.
Reason Breeds Insanity 
I hear you. Thanks for your honesty. I wrestle for contentment too at times. For years I was a touring musician. The feedback is pretty immediate, and was very gratifying for my personality type. All was going well til the day my daughter stopped talking to me. I felt like the biggest loser; my dreams were crushing hers. I got off the ride, and had to eat the humble pie of working a very physical job with almost zero recognition. The tradeoff? I have a real relationship with my kids again, not an arrangement. Keep on persisting, something good is about to happen!