Spending time with my friends from high school is always a bit of a reality check. I write about this every time I go home. But the older I get, each trip back home I leave a world where I feel entirely behind in life, without a clear step-by-step process for getting from where I am today to where I want to go next, and, on the verge of 30, wondering both if I’ve waited too long to have children or get an MBA. And if I need either. Or want either.

Whether they’ve had children, have been married, or remain single, most of my high school friends have entered some respectable middle class job at best, or are falling deeper into debt working a few hours a week or, at worst, living off welfare due to their (in denial of) drug and alcohol addictions. Of course, the few that have made it moved somewhere. They got out of New Jersey. Then there are those who I consider stuck in NJ. And I’m sure some of them will have lovely lives. Middle class isn’t that hard to achieve where a nice starter home can be purchased for under $300k. That leaves little to strive for as well professionally. Yet when the cost of raising children, living a life and fixing a house become too much, many are unhappy, with no plans to get them to the next level of financial success. I look at many of my friends and worry about how they’ll be able to afford any sort of retirement.

Yes, there are wealthy areas of New Jersey. Those areas tend to be where people move after they’ve reached success in New York or other major metropolitan areas before being transferred to NY and having a family in the wealthy burbs. That’s not where I grew up. And it amazes me how people tend to stay in their class instead of striving to become better off. Not to judge, surely if this makes them happy then I wish them all the best. But I hear nothing but bitching about how life is hard, diapers are expensive, the mortgage costs a lot, car payments on their mid-class luxury Volvos or Acuras are killing them. Yes, I make $100k per year and drive a Toyota. My friend who is unemployed, complaining she can’t afford to go out because she recently quit her teaching job and she can’t find a better one, drives a luxury car. That’s NJ for you. Appearances are everything.

This certainly is felt in my family. It’s almost ideal that they don’t really understand what I do. All they need to know is that I’m making six figures. That’s a major check of impressive. I’m glad they don’t realize how little $100k is in the Bay Area. Then they’d be asking me why I’m not making $150k. (I ask myself this, and that’s enough questioning.) Because they see I’m set in my job, this gives them plenty of opportunity to whine about how I’m not married or popping out children. I understand my parents want grandchildren, but it’s really unfair for them to put so much pressure on me. And I don’t think they’ll be good grandparents, as judgmental as they are, how can I have children knowing that my parents will just point out everything I’m doing wrong as a mother along the way?

What I love about my boyfriend is that he never will judge me for any choices I make in my life. I wish I could say the same about myself to him. But this man has, for the first time in my life, made me feel pretty ok being myself. I find myself slipping into wanting to date a man who is successful, who can judge me and help guide me to reach the next level of my life. That’s so anti-feminist of me. And it’s also tied directly to being used to being told I’m not good enough. In fact, when my father so kindly drove me to the airport today, the last thing he said to me, in a backhanded compliment that he’s so good at, was “you look good. I want you to look better next time.” I’ve definitely outgrown giving a shit what he thinks, but there’s something to be said about a piece of me, deep down, that wants to be with a man who judges me like that, though I’d actually respect him so I would work hard to prove that I was good enough.

It’s too hard to motivate myself for myself. That’s the problem. I don’t properly reward myself for my success. Director of a up-and-coming software company by 30? Check. Six-figure salary? Check. Seven year anniversary with a man who treats me extremely well? Check. $230k in the bank? Check. And I still feel so empty. I still want someone who has their shit together to look at me and judge my success. I need some comparative measures to judge where I’m at.

My boyfriend doesn’t want me to judge my success. He doesn’t care if I’m CEO or volunteering full time at the local petting zoo. He just wants me to be happy. And as much as I bitch about his inability to obtain a full time job by 31, the real issue is that I’m terrified without being with that external judgment in my life. That sense of constantly being punished for not being good enough. That’s not healthy, but it is what it is. There’s a darkness in me that craves that sort of discipline. Hey, I’m not alone, if I was the 50 shades of grey phenomenon wouldn’t be a phenomenon.

The question I have is if I can separate that desire from reality. It is really good for me to be with a man who is so giving and who isn’t constantly criticizing me. I just worry that my need to be told I’m not good enough will always keep me in this purgatory of self-doubt. Is it possible to have the best of both of these worlds?

Then, I’ve yet-to-determine if my desire to look up to a man I’m with is a bad thing or a good thing. It feels dirty to want to be with a man who shows me new things. Yes, things that cost money. The world. Teaches me things. That’s not really wanting someone to judge me. But inevitably the man who has found his place in the world with a strong suite of opinions is the type of man who will judge by default. Especially if he’s an east coaster. And I feel lost without this. I never thought I’d want to marry a strong man. I didn’t have a type other than someone kind, funny, and who gets my twisted sense of sarcasm tied to the sense of humor of an 11-year-old boy. Well, my bf gets me. I get him. And nothing in the world makes me happier than being embraced in his arms.

But happiness is one part of the equation. I want excitement. For the short term. I want a happy, stable, mellow life to live in one world and a crazy, dramatic, and even angry life in the other. But you can’t have both. You have to choose one or the other. Option A probably results in having a family, buying a house, attending parent-teacher conferences, taking one vacation a year to a place like Disneyworld, and living the life most in this country want. The other, well, the other isn’t clear to me, because it feels like a life I should have lived in my early 20s, when I dived head first into a monogamous relationship, now at its seven year mark. But that other life is one that involves a lot of bad decisions. A lot of heartbreak. And maybe some sort of twisted motivation to get ahead in the world. No kids. Long nights. Growing older and forgetting about it. Thinking I’m still 20 when I’m 40. Being in a constant state of mid-life crisis from now until the nursing home. And loving every minute of it.

I can’t determine which of these lives I want to live. My logical brain is pushing me to number one. And all signs in my life are as well. But my heart is longing for number two. That’s because my heart wants to be beat up. Maybe this is one time when I should avoid the advice of the wise song

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