I have been busting my ass at a job I don’t really love for a decade, and I have been very successful. I own a condo in an expensive geography that I don’t think is going to appreciate much, and I pay a ton of property tax.

My sister and my best friend are both trying to purchase quadreplexes and have them be rental units. Neither one of them is even half as successful as I am in terms of income, and I am EXTREMELY resentful. It lights me up with rage when I think that they are going to build wealth by doing relatively little, while I sit here working at job I don’t like for so long. At the same time, I feel like I *should* be investing in real estate, but I’m so incredibly risk averse that I can’t. My condo doesn’t count because I don’t think it’s a good investment and I’m actually thinking about selling it.

I know that I feel resentment and rage and envy, but I don’t really know what else is driving these feelings. I know I have the thought that “I’ve wasted my time” and that makes me feel incredibly defeated and hopeless and worthless. I feel like I traded ten years of my life where I was supposed to be getting married, having a family, and enjoying the best years of my life were squandered away trying to get money that I thought would buy me freedom and happiness and it hasn’t. Now I feel like I’m all alone in this big city with money and so much scarcity mentality and so much fear of losing it, and now others can just swoop right in and surpass me. I have tied money to my self worth in some way, 100%, and I use it to make myself feel ‘good enough’. Well, now if others can just invest in some real estate while having lots of debt and never getting a masters like me and never working their ass off to climb a corporate ladder, it just feels like all of my hard work and sacrifice wasn’t worth it.

So, in there somewhere, I have done all of those things (get masters, bust ass, save money, be responsible for a friggen decade) and have compromised on things I want (running my own business, getting married, having a family etc.) in order to feel “better than” other people – like my sister and my friend, and in general other people that I meet. For years I felt like it was working, but now as others talk about real estate, I just feel like I’ve wasted my time and that the cost was high.

Am I doing things for the wrong reasons? I’m currently getting another masters so that I can have a credential that will make me feel “good enough”. I don’t know how to get that good enough feeling without accomplishments that categorically allow me to think I am superior – usually in terms of money.

Can somebody help me figure out the thoughts that are causing me so much pain so that I can move through this?

Thank you.