Ask Polly: I Feel Guilty About How Absurdly Rich I Am!

Appearing here Wednesdays, Turning The Screw provides existential crisis counseling for the faint of heart. “Like a really wise friend who doesn’t respect your personal space!”

Dear Polly,

I grew up in a tiny, rural, working-class town in the middle of the country. My family was wealthy — old money. Mom didn’t work, and my dad tinkered at an obscure craft/art in what was mainly a ranching and coal town. In contrast to my peers who had never left the state, my family traveled internationally, did the country-club thing on vacations, and ordered Parisian dog collars for our mutts. When I was a kid it didn’t matter that I was rich because I wasn’t spoiled, so I was just a regular kid. But then I got older. I started noticing that I was different and privileged. When I became aware of all the opportunities and luxuries, I grew so embarrassed. I’m 29 and have spent my life obsessing over hiding how rich I am from my friends. My wealth is my deepest shame. I am cruel and self critical, wondering if I’ve earned anything I’ve ever accomplished in my life. Did I buy my successes? Am I smart or just skating by on the fumes of a fancy education? Do I know what its like to truly struggle for anything? When I am feeling hurt, sick, overworked, underloved, lost, questioning, or tired, I don’t give myself permission to feel these things. I am rich and don’t deserve to feel sorry for myself. My suffering is not real.

I have a fat inheritance and realistically don’t have to work for, like, the next ten years. But I keep a low-paying job because a) I’m afraid of not knowing what its like to suffer at a job and b) to blend in with all my twenty-something, financially fragile friends. My friends and classmates are all poorer than me. I’ve never felt comfortable living the kind of lifestyle that’s expected of people in my tax bracket. Instead, I live simply and I like it. But when friends ask if I’ve gotten my financial aid check for this term yet, I lie and say yes-phew-thank-god-now-I’ll-actually-make-rent-this-month! But I don’t qualify for financial aid. I pay full price and always have: 2 degrees and no college debt. But they don’t know it, because I’m lying to them.

And I actually wish I didn’t have the money. Money has fractured my entire extended family. Because I have it, I’ve never had to ask for help or be humbled that way. My boyfriend tells me he really appreciates how I’m not uptight about money… and that’s because I have too much to care, not because I know what life is all about! I’m not flashy. I work my ass off in medical school right now and plan to work for the rest of my life. But I lie to my friends! I hear how everyone talks about rich people. That’s me they’re talking about. And it’s mean! And totally justified! Rich people suck! I did not participate in Occupy, although I am a progressive young person and had something to say in the movement, because I AM THE FUCKING 1% AND I CAN’T COME OUT ABOUT IT.

So here’s what I need help with. I want to be honest to my friends when they ask me about this part of who I am. And I want to forgive myself for being rich. I wonder if you’ll tell me that we all suffer no matter how much money we have to be nice to yourself. Or if you’ll say what everyone else is thinking: take a look at how lucky you are and shove it.


Ditch The Trust Fund

Dear DTTF,

Yes, yes. You bought all of your successes. You’re not smart, didn’t earn anything you’ve accomplished in life, and are just skating by on the fumes of a fancy education. There’s only one way you’ll prove your worth in this world, conquer your shame, and feel the down-to-earth goodness of poor-folk suffering: By losing all your money. Thankfully, this can be accomplished in an instant. Write me a check for the remaining balance of your trust fund immediately.

Because I was raised by a single mother who made minimum wage as a secretary after my parents’ divorce, with only a pathetically small child support check to help with the bills, I have suffered my way to authenticity. Did I mention that my father was raised among the Eastern European toughs of the sooty working-class neighborhoods of Johnstown, PA? That my grandfather was a coal miner? That, as a kid, my mom repeatedly reminded me that we qualified for food stamps? That I raked leaves and painted walls and cleaned toilets so I could purchase a vaunted Izod shirt and thereby remain viable in the competitive go-go upper-middle-class marketplace of junior high school?

And do you know what this remarkable, hard-working icon of all that is real and good and pure in the world would do with your money? I’d buy fancy tequila and get my hair professionally colored and send my dogs to a groomer and pay someone to clean my filthy house. Oh, but I deserve all of that cash, because I am an incredibly egocentric, myopic asshole who cobbles together a shitty living by writing dyspeptic prose for various newspapers and websites. I do something so self-indulgent and pointless that almost no one wants to pay me for it. And why should they? I don’t contribute meaningfully to society or boost the general welfare in the slightest.

But I deserve your money because I’m genuine and real (unlike you, who are fake and filthy and shameful) and because I also feel like a big loser (like you do) (but unlike you, I deserve to feel my emotions, because I’m not rich). I suspect that I’ll feel much more important and special once I wear beautifully tailored clothing and vacation in Belize.

And won’t you feel much better once you’re poor? Suddenly, all the good things people say about you will feel true, right? You’ll feel more authentic, more worthy! And I’ll feel more worthy, too! I’ll be special and important at last. No need to write or struggle or even wake up in the morning. Other people’s indifference won’t matter anymore, because I’ll be so well-fed and gorgeously dressed and drunk that I won’t give a fuck.

Are you beginning to understand the big, clumsy moral now? Money won’t change a thing for either one of us. For other people, sure. For us, no. We’re both doing fine. We both belong to some well-fed, comfy, advantaged upper tier, even if you’re in the tier that wears cool shoes and eats delicious things created by culinary artistes and I’m in the tier that scrubs the floors on its hands and knees (like Cinderella, only older and uglier). Our shared problem is that we can’t appreciate our own accomplishments. We both imagine that some magical force will change our fate. We’re both dead wrong.

Yours is an emotional problem, a habit of self-abnegation that arises from the sorts of hard-assed parents who dictate that all children should be wholesome and productive and never, ever the slightest bit selfish. Yes, your parents did prevent you from becoming your basic Little Lord Fauntleroy style of fuckwad, and let’s give them a tip of the hat for that. But let’s get real about the load of guilt and shame that they encouraged you to internalize instead. They raised you in a working-class town (on purpose?) so you wouldn’t be spoiled, but when it came to the stuff they wanted — adorable dog collars, international travel — the cash rolled out of the coffers. It reminds me of that scene in the parody “Grizzly Bear Man” where “Werner Herzog” eats a delicious donut in front of Timothy Treadwell’s hungry girlfriend, because sharing it “simply wouldn’t be appropriate.”

And now you’re supposed to be heroic, truly heroic, or nothing at all. You have all the advantages necessary to become a hero. (Which is admirable, really. I mean, I just want to write shit about how I feel, or maybe create some kind of performance art that involves giant vats of chocolate pudding.)

You have an emotional problem, not a money problem. You’re struggling to allow yourself to feel what you feel, for reasons that probably have more to do with the emotional dynamics of your family than your family’s net worth. I’d like to tell you to go ahead, come out of the closet, tell everyone about the money, but I can’t help feeling like it’s none of their business. How do you know how much money they have? Are they submitting budgetary spreadsheets for you to examine? Did I mention that my dad was a professor at Duke? Of course not, because that would’ve made me sound less authentic and gritty-suffering-poor.

Are you prepared to defend every purchase you make? To pick up the check every time you go out? I would hate to see your shame congeal into unfocused resentment (um, like mine has?). If you get serious with someone, I guess you’ll feel like you should tell that person. But be careful! Money is like fame or big tits. People will love you for it without even knowing that they’re doing it. Then one day your guy wakes up and thinks, “How did I get here? Hmm, maybe it was the big tits.” You don’t want that.

And I hate to say this, but you’re going to feel differently about that money as you get older. Life gets a little more brutal as you age. You get tired of working your ass off year after year, and you care more about the miso-marinated black cod than you want to. Certainly don’t give all of your money away now (out of guilt, a real possibility for you actually) or blow it all on some boyfriend (another strong possibility, considering your guilt) just because you’re confused and it doesn’t seem important right now. Save it until you’re older and you’re thinking more clearly about your rights as a human being and your place in the world. By then, everyone you know will be making plenty of money as a doctor — and probably blowing most of it on stupid shit, too.

You don’t need anyone’s permission to have money. You need permission to have feelings. Only a really good, smart therapist will help you with that. (And I bet you can afford a therapist who’s smarter than you. What a luxury that is!) Here’s what a smart therapist is sure to say: You’re a hard-working, good person and you have lots of friends who love you for who you are, right now. I do understand about the shame, and I get that you feel like an ingrate. The world is filled with privileged ingrates. But as far as I can tell, you’re not one of them.

You give that trust fund of yours to 80% of the people out there, rich or poor, and they blow it all on drugs or a giant house or hot cars or whores in a few years, without half a second of guilt over it. 10% of them OD within five years. I’d like to think that I’d start a foundation to help the poor, but chances are I’d also waste an obscene amount on hair treatments made out of pig placentas and enormous flat screen TVs that emerge from the ceiling and heated floors and incredible desert wines and live-in masseuses and master chefs who fix me doughnuts the size of my head every Sunday morning. I would travel the world and feel vaguely disappointed by it. I would buy expensive gifts for my friends, and then I’d be annoyed that they didn’t appreciate my expensive gifts enough. I don’t deserve a cent of your money. But I do deserve to feel a little pride in my measly accomplishments, and so do you.

Lots of people will hate you for who you are, or love you for who you aren’t. Maybe most people will. But some people, a precious few, will love you unconditionally for exactly who you are, warts (and big piles of cash) and all. When you feel sad or out of control or ashamed, pay attention to who draws closer, and who backs away. Stop being so good and pure and tough and start accepting the unconditional love that’s already out there for you, including the love you have for yourself. Some bank account somewhere doesn’t render that love obscene. You have everything you need to be happy already. That should make you feel grateful, and deeply alive. It’s okay that it doesn’t yet. You just need more practice.


Dear Polly,

I have tremendous admiration and respect for you, but I must (sorrowfully) take issue with the advice you gave to your correspondent Red Pen, the editor who wanted to write more. I believe that the kind of job Red Pen has doesn’t allow time for creative thinking/writing; therefore, Red Pen will be unable to obey your instructions and will end up feeling worse than ever, might even conclude that she/he has no creativity, perhaps never had, is unworthy of the humorous boyfriend, might as well get a prefrontal lobotomy so as to be no longer plagued by feelings of longing and concomitant despair, and so on…

I am hereby requesting that you contact Red Pen on my behalf and tell her/him that I am an excellent editor who would be delighted to take over her/his uncool job for a few months to give her/him the opportunity to explore the writing life without the responsibility of a full-time job.

Yours sincerely,

Excellent Editor

Dear EE,

What a generous offer! I bet you’re charitable enough to accept a big check from Ditch The Trust Fund, too.

I disagree, though, that having a vaguely dissatisfying job will prevent Red Pen from doing any writing in her spare time. (Yes, I assume she’s a woman, because she’s read Writing Down the Bones and her boyfriend is a comedy writer [see also: straight, Jewish, loves the Jets, pees in the shower]. So sue me!) Remember how she told us that the stakes were already too high? Every time she couldn’t find anything worthwhile to write about, she felt like a huge loser. Guess how that’s going to feel when the credit-card debt starts piling up? Suddenly, an aspiration, a hope, is transformed into a good reason to toss and turn all night, break out, drink heavily, lash out, spiral downward, etc. Do you think her comedy-loving, J-E-T-S, JetsJetsJets-loving boyfriend is going to tolerate that for a second? He has bongs to load and clever one-liners to tweet! Never underestimate the stress of leaving behind a solid, comfortable job with no promise of a similar job waiting for you in the future, while trying to do something you’re not sure you know how to do.

I’m a huge proponent of taking big leaps, taking risks, in pursuit of your dream. But she needs to accumulate some written work before she takes that leap. With no written work accumulated, you don’t just up and quit your job (unless you have a trust fund, and even then a perilous and insecure emotional journey awaits). Besides, in her case, there’s no reason to quit. You don’t need eight hours a day to become a writer. Sure, it helps to read books, and to exercise. But you should be doing that anyway, right? You need two or three hours to write. Almost anyone can find those two hours. You put down the bong, stop watching “The Daily Show” and go to bed early instead. Then you get up one hour early and write.

But let’s talk about you instead, EE. You believe that there might be some magical solution to your problems. You believe that Red Pen has the one relaxed, high-paying editing job in the world. I’m not accusing you of taking it that seriously, but some small, reptile part of your brain believes in this magic. You have a haunting sensation that a change of fortune might occur through some grand act of destiny.

As modern humans in the throes of late capitalism, many of us think this way in spite of our best efforts to do otherwise. Maybe because every dimension of our lives is thoroughly commodified, we imagine that everything we see can and should be upgraded. Money not only makes anything possible, it transforms us into different sorts of people. Sometimes I sit in my backyard and think: “God, this is nice. I should do this more often.” Then I notice a messy pile of leaves in the corner, and I think, “If I had more money, I would have a gardener, and then there wouldn’t be leaves strewn about. I’d also get some cool lounge chairs, and an umbrella. A red one. No, a blue-green one. No, no…” Next thing you know, I’ve got a Pinterest page with 15 criminally overpriced umbrellas on it. Is that therapeutic (as a close friend of mine recently suggested here) or just deeply fucked?

Maybe I just need to rake up my fucking leaves.

And maybe you also need to get off your ass. You know how you get the right editing job? You work really hard to find it. I’m sure there aren’t that many relaxed, easy editing jobs out there, but there might be a job you’d like better than the one you have now. The Sun is looking for a managing editor, aren’t they? I heard a rumor that Vulture was hiring editors. Go to Mediabistro and look around. Send out a few emails, make a few phone calls. Be bold, and mighty forces will come to your aid.


Who’s to blame for all of your troubles? Write to Polly and find out!

Previously: Ask Polly: I Miss My Maniac Ex

Heather Havrilesky (aka Polly Esther) is The Awl’s existential advice columnist. She’s also a regular contributor to The New York Times Magazine, and is the author of the memoir Disaster Preparedness (Riverhead 2011). She blogs here about scratchy pants, personality disorders, and aged cheeses. Photo by Eric Skiff.