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Breaking Up With A Rich Guy & Standing Up For Yourself At Work

Ask Chelsea Anything_Graphic_title card_v2

In this week of Ask Chelsea Anything, I’ll be tackling two questions which are about totally different spheres of life, but which come back to the same final notion: defining your own worth. Whether it’s at work or in our relationships, we all have to do it, and it starts by being honest about what’s really going on. So let’s get to it, and don’t forget, if you have a question for me, send it to

I might have a good answer for you, and if nothing else, my robust career in being a hot mess might just provide a cautionary tale!

Hi Chelsea

Today marks my fourth anniversary with a man I love, but whom I do not want to marry. I know that we are going to break up, and I know that he senses it, too (90% of our interactions at home the past few months have been arguments and silence), so I don’t feel guilty or conflicted in my choice. I’m going to be the one to end it, because he’s not the type to actually, formally end things, but it’ll be a pretty smooth breakup, except for one thing: he is rich, and I am (relatively) poor. We live in NYC, and he makes nearly $200k a year, and I make $33k. We live in a big one-bedroom in the East Village where I have a little home office nook and can have as many friends over as I want without crowding the place or bothering roommates. Essentially, it’s the New York City dream, and when I look at the kind of rooms I can get for my soon-to-be $700/month budget, I cringe. My lifestyle is about to take a huge hit, and I admit that it is the major reason I didn’t break up with him six months ago, when it was first clear that we were not headed towards happily ever after.

So, my question is, how can I buffer this transition, and how can I get over my fear of losing out on this lifestyle of travel, nice things, and a big East Village apartment?


A Superficial Bitch, I know

Okay, so there’s a lot to unpack here, but I guess the first thing I should say is that you’ve put a pretty bow on it, but you’ve been spending at least a half a year with a man you do not want to be with because of his money. Now, I’m assuming you would not consider yourself a sex worker (nor would society, probably), but this is a grey area that so many women (and some men, I’m sure) find themselves in, where they justify a behavior that, when analyzed on face value, is pretty morally fucked.

In fact, I’d say it’s amoral in a way that sex work is not, because — at least when consensual on all sides — the person paying for the sex/closeness/attention at least knows what the deal is. For all you know, your boyfriend still thinks he’s in a relatively good relationship with a woman who loves him and intends to move forward with him, but she’s just been sticking around for months on end because of the perks. This is fucked up, and an exchange of romantic attention for money which I’m sure you wouldn’t be comfortable with under most other circumstances, but you have to be brutally honest with yourself about what you’re doing. You are with a guy because of a lifestyle he can provide to you, and exchanging time, attention, and sex for the privilege of having that lifestyle.

Now, do I think this is inherently fucked up? Eh, no, I’m very pro-sex worker/sugar baby/however you make your money. And I know that in the very real market of human life, romantic attention is a powerful commodity that should be compensated if all parties agree. But the bare minimum is that both parties need to know what is what, and your dude, I’m guessing, does not. You’re using him, and disrespecting both of you in the process.

Your life is going to take a hit, yes. But no hit could be harder than the realization that you’re essentially tricking a dude you used to love into funding your glamorous NYC life. And no one can put a price on the self-worth and pride you gain from deciding, hey, I am capable of and willing to support myself, and I’m going to do it on my own, no matter the difficulty. Because you can have all the things you currently have, eventually, you just have to work for them. And I can promise you that those luxuries will be all the sweeter when someone can’t take them away from you, or when you don’t have to carry on a fake relationship to keep them.

In the meantime, get a cheap room in a neighborhood that isn’t the East Village and sign up for Mint or YNAB or some other basic app to help you get in control of your money. Pick up a side job or start really concentrating on your current job to start making some serious moves — enjoy feeling the professional fire under your ass that was dulled for years by someone else’s success. We’ve all had to do it, and from experience, your crappy little room or studio or whatever starts to seem really exciting and kind of luxurious when you realize it is really, truly yours.


Before I get into the question, I’ll give you a little background. Right now I am getting my Master’s degree for Library and Information Science. To pay the bills, I work at a premier retirement community as a receptionist, although my fancy title is Resident Service Specialist. The job is not at all as glorified as it sounds, and is in fact, pretty unorganized. There have been 2 instances where I have been working and things have gone missing. Now, neither of these instances were because of me or caused by me in any way, but because I am working at the front desk, it seems I get blamed and therefore, I can’t help but feel blamed even though I do not think I should feel that way. But essentially it’s a classic case of I’m at the wrong place at the wrong time kind of thing. I feel that this feeling I have is caused by people who are more important than me deciding it is easier to blame me than to handle the problem in a better way.

I am wondering if you have any advice as a woman running her own business, how people who are working as receptionists, or positions similar, can feel empowered and, I guess, guilt free. I don’t like feeling like I should feel guilty just because I happen to be the easiest blame.


Well, Anonymous, I’m not going to lie — your situation sucks. It sucks to be at the bottom of any totem pole, but it especially sucks at work, where you can find yourself taking the blame for any number of things which were not your fault, but which your managers seem content to push on you. (For what it’s worth, in any decent corporate structure — and this is what can sometimes make the service industry feel so crappy — a good manager takes the responsibility for things that aren’t even her fault.) All that said, another reason they could be giving you this specific pile-on is because you are currently a grad student, and therefore not in this for the long haul, which can lead to a (totally unfair) assumption that you aren’t as serious about your job. For more insight, I spoke to my HR friend Dani* again, to get her take on the issue. She said:

The truth is that people just don’t really value you as much as an employee when you’re in a low-impact position and going to school, because they know the chances you’re going to stay at this job and move upwards are pretty low. It’s not like you’re in a corporate managerial position and going for your MBA, which will then be put back into your current career. You’re doing something that’s likely going to take you out of whatever you’re doing.

This means that there’s probably more than a little feeling of “Oh, who cares, it’s not like she’ll be here that long anyway.” This can often mean you’ll be pushed around, tasked with shitty jobs, or, as in this case, blamed for things. You have to let them know, in a way that won’t get you fired, that you’re not here to be their temp. You actually work there. If I were you, I would send a thoughtful email to everyone higher than you who has been blaming you for stuff, simply and concisely asking what you can do in the future to monitor prevent things like this, without accepting blame for it. Let them know you are invested, too, and speak to them as an equal. Not a subordinate.

And on a more philosophical level, Anon, I’d say that when it comes to “feeling blamed” or guilty in some way, simply, don’t. Do what you can to assert yourself within the confines of your job, and don’t think of it as beneath you (even if it’s a falsely-inflated receptionist gig, which I understand can be frustrating). But ultimately remember that if you are not being treated with the respect you deserve, that is not your fault, and it’s not something you should feel guilty over.

If nothing else, allow this time in a low-respect position to teach you how not to be a manager or leader, for when you become one later in your career. Remember what you are good at, and all of the things that define you beyond this job, and that being treated in a less-than-generous way at this job is ultimately a small problem on the scale of life. You have to decide your value, and even as an entrepreneur, I’m faced every day with clients or peers who do not treat me as a businesswoman, or even with respect. I have to remember that my value and meaning exists beyond them, and that all I can do in that individual situation is be honest and have confidence in myself. That’s all you can do, too. It’s all any of us can do.

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