Am I out of touch with the reality of how successful my family is?

Okay, so this may all sound crazy or artificial, but I have a genuine question.

Am I out of touch with the reality of how successful my family is?

So, before, here is a little about me & my family. We are pretty normal people, all of my family members (those who can) work, and no one is really struggling much financially. As a kid, I wouldn't say I got spoiled, but if I didn't get something, I was more upset because my parents didn't want another toy in my room, not that the money was tight. I always knew that my family was okay, always had food on the table, and new clothes, but I knew that we wouldn't afford some things. 

Fast forward a couple of years, and I became, not jealous, but somewhat bitter of my friends and their parents. Their (mostly) fathers had their own companies, and they knew that they could always count on them to hire them. My parents work in firms, so I knew if I wanted a real job, I'd have to get one myself. 

Another fast forward, I'm talking with some girl from my uni, we were sharing what we're going to do for the holidays. I said that I wasn't very much looking forward to holidays because I knew I had no plans, but before I could finish, she asked me if I wasn't excited because I was going to work. I said no, and I don't see a reason to work. I don't spend that much money, and if I want something, I can just ask for it. Then she said that her mom is in debt and she needs to work to support her.

And then it hit me, "Am I really that spoiled? Was I  thinking my family was poor when in fact, they are the opposite?" 

I know that it may sound strange, but share your thoughts, what does it mean to you to be successful or comfortable in life? Am I the crazy one who freezes bread when my dad takes me to the restaurant and pays +100$??