Why is it so hard to let myself win?

This is a question I ask myself day in and out, as I constantly corner myself in a rut I cannot get out of. It’s almost comical, on how I’m both incredibly successful and dinging myself left and right for each failure that I craft for myself. I’ve been through too many therapists to count, have outgrown adolescent angst, and still, here I am, so far ahead, so far behind, all at once.

Financially speaking, I am proud of myself, but feel I don’t deserve to be where I am, and feel deeply guilty for what I do have, yet also terrified of not having enough. My mental disorder(s) may be most easily defined as a cross between neurosis and narcissism, which is so deeply who I am due to my upbringing and fear of taking power over my own free will.

I sat in my bosses’ office the other day, with a goal to discuss my great progress and how I “deserve” a raise. Instead, I found myself being told that I’m viewed as a bit of a mess. People like me (which is progress from where I was as a kid), and people know I work hard (which I do), but ultimately I am unpolished. Instead of asking for a raise, I ended up holding back tears and having a good cry in a bathroom stall once I got through the very accurate and very painful critique.

The painful part comes from how this story has never changed, and it’s my fault. I spent my youth and adolescence assuming as some point I’d magically grow out of it. It’s possible I have a real chemical imbalance in my brain known as ADHD, or maybe it’s the depression, or some form of OCD, or maybe I just need to grow up. Ultimately, there are a few things that I know happen which prevent me from actually being able to win:

1. I feel stupid all the time. I work with a lot of really intelligent people, and I’ve always enjoyed being around intelligent people. I always feel like I need to “prove” my intellect, which never works, since I’m not smart. I feel there are two ways to success — either be really smart, or very talented at socializing.
2. Deep rooted need to “prove” to myself (and others) that I am, despite lacking elegance, able to be a hero and have an epic win. This probably comes from my parents being narcissists themselves, and bragging about my big wins. That’s probably pretty normal for parents, but it was more in how they did it. My victories always felt like nothing more than bragging rights for my parents, not about taking any pride in my ability to succeed.
3. Setting up scenarios where winning was extremely difficult and required a visible fight became an addiction. If something wasn’t hard, it wasn’t worth doing. But I wasn’t smart enough (or focused enough) to accomplish really hard tasks, so I started to make everything difficult. Cleaning my room, for instance — I’d avoid cleaning until everything had piled up and I’d have to spend hours going through piles until finally I might have a spotless room. Chances are, I’d never finish, but I wouldn’t feel bad because it was an impossible task. In the rare case I was able to finish, I’d get such a rush. It’s a true addiction, just like any other drug. Just putting things away on a daily basis, while much more practical, wouldn’t give me that rush. So I let things pile up. Today, I’ve had an epic cleaning day. I may even get through the pile. But then tomorrow, will I just be back to where I started, letting the mess pile up again? Probably. This is a problem. A huge problem.
4. I’m a perfectionist. Maybe even a little OCD. If almost everything is perfect but one thing is off, it drives me nuts. If everything is off, it’s almost calming. Again, like I don’t have any control over it, because it’s so bad, so I can just ignore it.
5. I’m an extrovert but I have no freaking clue how to talk to other people. I can be silly and make people laugh, sure, but, as I’ve written about before, I’m no good at small talk. I’m still much better than my boyfriend at being social, which is laughable, because I’m terrible. I’m bad at conversation. I like deep conversation about the meaning of life, and what makes people tick. Despite not wanting to be a gossip, I find myself only truly able to contribute to conversations when the topic is another person that is a mutual acquaintance. I am lucky that I have opportunities to socialize with my coworkers, who are funny, smart people, and who can talk to each other while I generally listen (or I drink — see my last post — and manage to communicate a bit.) Still, in the end, I feel sad because no matter how much money I have or how good my life is, I want to connect with other people, and it’s a daily struggle.
6. I don’t have any long-term goals that seem meaningful or achievable. When you’re young, life is broken up into years, and the years are long, and each year ahead is something to look forward to. You go to school and do your work so one day you can get into a good college and eventually have a great career and find a wonderful significant other, have two kids, and a house with a white picket fence, where you can have backyard barbecues and invite folks over for dinner. I really don’t know what I want anymore, and I don’t feel like I have a right to want anything. My financial journey is rooted in fear — fear of running out of money, fear of my mental health issues becoming so huge that one day I cannot work, and needing a lot in savings. At least this gets me to save money, and I’m proud I may be able to hit my goal of having $200k in various investments and savings by the time I turn 29 (on track to my major goal of $250k by 30), but this doesn’t make me happy. It helps me not be totally depressed, knowing I have cushion now, but I’m then looking at what happens if I get married and have children, and how I’ll need much more than $250k for cushion then. But, beyond money and savings, I’m not sure what I want. I guess I want a family, I guess I want to be a mother, I guess I want a house. But all the things I maybe want seem like things society tells me I should want, and perhaps things that biologically I crave, but will they really make me happy? I am well aware kids are not an expensive jacket you can return to the store. Do I have any right to bring another human being into this world? And shouldn’t I figure out a life purpose well before having children?
7. If I were to live a much simpler life where I didn’t set myself up for failure time and again, would I actually be happier? I am afraid I’d be bored. Or further depressed. Because the only real meaning I have in life right now is that addiction to making things difficult for myself and setting up situations where if I win it’s almost orgasmic and if I don’t then I can just accept it was impossible to begin with. That’s not a way to live life, however. And it’s certainly not a way to live life once you are in your 30s. It’s time to grow up, and maybe, somehow, just accept simplicity. It may very well be that is the meaning I’m looking for… being able to come home from work at a reasonable hour, and instead of turning on the TV and wasting away the evening watching bad reality shows, open up a book, go for a walk, draw something, do something meaningful with the little free time one has in adult life. Go for a walk in the middle of the day and actually see the sun. The epic meaning of life is in freedom, not being a slave to yourself or anyone else. Work should not be the meaning of life. It’s great if you love it, and it’s great if it provides your life some meaning, but ultimately, it’s a paycheck. Life is much, much more than that. I just want to learn how to live it.

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