I moved out of my parents’ house a month before my eighteenth birthday. With a combination of personal earnings, grants, scholarships, and student loans I funded the bachelor’s degree in English and women’s studies that I’m still paying for. As of today, I owe $4,876. Over the years I’ve taken to saying—sometimes with astonishment, other times with anger, but mostly with a sense of resigned, distorted glee: “I’ll be paying off my student loans until I’m forty-three!”

  But you know what? I’m waving to you from the shores of forty-three and the months are peeling away. It’s looking extremely likely that I’ll still be paying off my student loans when I’m forty-four.

  Has this ruined my life? Has it kept me from pursuing happiness, my writing career, and ridiculously expensive cowboy boots? Has it compelled me to turn away from fantastically financially unsound expenditures on fancy dinners, travel, “organic” shampoo, and high-end preschools? Has it stopped me from adopting cats who immediately need thousands of dollars in veterinary care or funding dozens of friends’ artistic projects on Kickstarter or putting $20 bottles of wine on my credit card or getting the occasional pedicure?

  It has not.

  I have carried the weight of my student loan debt for about half of my life now, but I have not been “defined by my ‘student loan’ identity.” I do not even know what a student loan identity is. Do you? What is a student loan identity?

  It is, I guess, exactly what you’re stuck with if you can’t get some perspective on this matter, sweet pea. It’s the threadbare cape you’ve wrapped around yourself composed of self-pitying half truth. And it absolutely will not serve you.

  You need to stop feeling sorry for yourself. I don’t say this as a condemnation—I need regular reminders to stop feeling sorry for myself too. I’m going to address you bluntly, but it’s a directness that rises from my compassion for you, not my judgment of you. Nobody’s going to do your life for you. You have to do it yourself, whether you’re rich or poor, out of money or raking it in, the beneficiary of ridiculous fortune or terrible injustice. And you have to do it no matter what is true. No matter what is hard. No matter what unjust, sad, sucky things have befallen you. Self-pity is a dead-end road. You make the choice to drive down it. It’s up to you to decide to stay parked there or to turn around and drive out.

  You have driven out at least once already, Wearing Thin. You found yourself in a “deep, dark hole” a while back and then you courageously crawled out. You have to do it again. Your student loans will only hold you back if you allow them to. Yep, you have to figure out how to pay them. Yep, you can do that. Yep, it’s a pain in the ass. But it’s a pain in the ass that I promise will give you back more than you owe.

  You know the best thing about paying your own bills? No one can tell you what to do with your money. You say your parents are emotionally unsupportive. You say you’re wary of their intentions. You say they don’t see you for the vibrant woman that you are. Well, the moment you sign that paper absolving them of their financial obligation to your debts, you are free. You may love them, you may despise them, you may choose to have whatever sort of relationship you choose to have with them, but you are no longer beholden to them in this one particular and important way. You are financially accountable only to yourself. If they express disdain for the jobs you have or the way you spend your money, you can rightly tell them it’s none of their damn business. They have absolutely no power over you in this regard. No one does. That’s a mighty liberating thing.

  And it’s a hard thing too. I know, honey bun. I really, really, really do.

  Many years ago, I ran into an acquaintance I’ll call Kate a few days after we both graduated college (though, in my case, I’m using the word “graduated” rather liberally—see the chapter “The Future Has an Ancient Heart”). Kate was with her parents, who’d not only paid for her entire education, but also for her junior year abroad in Spain, and her summer “educational opportunities” that included unpaid internships at places like GQ magazine and language immersions in France and fascinating archaeological digs in God knows what fantastically interesting place. As we stood on the sidewalk chatting, I was informed that (a) Kate’s parents had given her a brand-new car for her graduation present, and (b) Kate and her mother had spent the day shopping for the new wardrobe Kate would need for her first-ever job.

  Not that she had one, mind you. She was applying for jobs while living off her parents’ money, of course. She was sending out her glorious résumé that included the names of foreign countries and trendy magazines to places that were no doubt equally glorious and I knew without knowing something simply glorious would be the result.

  It was all I could do not to sock her in the gut.

  Unlike Kate, by then I’d had a job. In fact, I’d had sixteen jobs, not including the years I worked as a babysitter before I could legally be anyone’s employee. They were janitor’s assistant (humiliatingly, at my high school), fast-food restaurant worker, laborer at a wildlife refuge, administrative assistant to a Realtor, English as a Second Language tutor, lemonade cart attendant, small town newspaper reporter, canvasser for a lefty nonprofit, waitress at a Japanese restaurant, volunteer coordinator for a reproductive rights organization, berry picker on a farm, waitress at a vegetarian restaurant, “coffee girl” at an accounting firm, student-faculty conflict mediator, teacher’s assistant for a women’s studies class, and office temp at a half a dozen places that by and large did not resemble offices and did not engage me in work that struck me as remotely “officey,” but rather involved things such as standing on a concrete floor wearing a hairnet, a paper mask and gown, goggles, and plastic gloves and—with a pair of tweezers—placing two pipe cleaners into a sterile box that came to me down a slow conveyor belt for eight excruciating hours a day.

  During those years, I sometimes wept with rage. My dream was to be a writer. I wanted it so badly that it made my insides hurt. And to be a writer—I felt sure—I needed to have a big life. Which at the time meant to me amazing experiences such as the sort Kate had. I needed to experience culture and see the world. I needed to speak French and hang out with people who knew people who worked at GQ.

  Instead I was forced, by accident of birth, to work one job after another in a desperate attempt to pay the bills. It was so damn unfair. Why did Kate get to study in Spain her junior year? Why did she get to write the word “France” on her résumé? Why did she get her bachelor’s degree debt-free and then, on top of that, a new car? Why did she get two parents who would be her financial fallback for years to come and then—decades into a future, which has not yet come to pass—leave her an inheritance upon their deaths?

  I didn’t get an inheritance! My mother died three months before I “graduated” college and all I got was her ancient, rusted-out Toyota that I quickly sold to a guy named Guy for $500.

  Bloody hell.

  So here’s the long and short of it, Wearing Thin: There is no why. You don’t have a right to the cards you believe you should have been dealt. You have an obligation to play the hell out of the ones you’re holding. And, dear one, you and I both were granted a mighty generous hand.

  Your parents helped you pay for your undergraduate education while you were a student and, presuming you didn’t graduate at twenty-five (a presumption which may or may not be correct), they also helped you during the years immediately following your graduation. They’ve declined to continue to assist you not because they wish to punish you, but because doing so would be difficult for them. This strikes me as perfectly reasonable and fair. You are an educated adult of sound mind, able body, and resilient spirit who has absolutely no reason not to be financially self-sufficient, even if doing so requires you to earn money in ways you find unpleasant.

  Your parents’ inability to continue paying your student loans will prevent you from realizing your “dream of attending graduate school” only if you let it. Are you really not going to pursue your dream because you now have one more bill than you
had before? Are you truly so cowed by adversity?

  You don’t mention what you’d like to study, but I assure you there are many ways to fund a graduate education. I know a whole lot of people who did not go broke getting a graduate degree. There is funding for tuition remission at many schools, as well as grants, paid research, and teaching assistantships, and—yes—the offer of more student loans. Perhaps more importantly in your case, there are numerous ways to either cancel portions of your student loan debt or defer payment. Financial difficulty, unemployment, attending school at least half-time (i.e., graduate school!), working in certain professions, and serving in the Peace Corps or other community service jobs are some ways that you would be eligible for debt deferment or cancellation. I encourage you to investigate your options so you can make a plan that brings you peace of mind. There are many websites that will elucidate what I have summarized above.

  What I know for sure is that freaking out about your student loan debt is useless. You’ll be okay. It’s only money. And it was money well spent. Aside from the people I love, there is little I value more than my education. As soon as I pay off my undergraduate debt, Mr. Sugar and I intend to start saving for college for the baby Sugars. My dream is that they’ll have college experiences that resemble Kate’s more than mine. I want them to be able to focus on their studies instead of cramming them in around jobs. I want them to have a junior year abroad wherever they want to go. I want them to have cool internships that they could only take with parental financial support. I want them to go on cultural exchanges and interesting archaeological digs. I want to fund all that stuff I never got to do because no one was able to fund me. I can imagine all they would gain from that.

  But I can also imagine what they won’t get if Mr. Sugar and I manage to give them the college experience of my dreams.

  Turns out, I learned a lot from not being able to go to France. Turns out, those days standing on the concrete floor wearing a hairnet, a paper mask and gown, goggles, and plastic gloves and—with a pair of tweezers—placing two pipe cleaners into a sterile box that came to me down a slow conveyor belt for eight excruciating hours a day taught me something important I couldn’t have learned any other way. That job and the fifteen others I had before I graduated college were my own, personal “educational opportunities.” They changed my life for the better, though it took me a while to understand their worth.

  They gave me faith in my own abilities. They offered me a unique view of worlds that were both exotic and familiar to me. They kept things in perspective. They pissed me off. They opened my mind to realities I didn’t know existed. They forced me to be resilient, to sacrifice, to see how little I knew, and also how much. They put me in close contact with people who could’ve funded the college educations of ten thousand kids and also with people who would’ve rightly fallen on the floor laughing had I complained to them about how unfair it was that after I got my degree I’d have this student loan I’d be paying off until I was forty-three.

  They made my life big. They contributed to an education that money can’t buy.

  Yours,

  Sugar

  THE KNOWN UNKNOWNS

  Dear Sugar,

  I dated this girl for a while only to reach the realization she was a self-absorbed crazy. Last year she and her best friend got into an argument and they stopped being friends. My ex’s friend called me up one night and asked me to hang out with her at her house. One thing led to another and I ended up sleeping with her. A few days later, this former best friend of my ex tells me she’s engaged. She wears this weird short-haired wig while she breaks off our friends-with-benefits relationship. The thing is, I connected better with her in the two weeks we hung out than I did with my ex in months. Please help me figure out if I should never talk to either one of them again. I’m not a smart man but I do know what love is.

  Gump

  Dear Gump,

  I’d rather be sodomized by a plastic lawn flamingo than vote for a Republican, but as I consider your situation, I can’t help but quote the former secretary of defense Donald Rumsfeld, who quite wisely said: “There are known knowns. There are things we know we know. We also know there are known unknowns. That is to say, we know there are some things we do not know. But there are also unknown unknowns, the ones we don’t know we don’t know.”

  Shall we start with the known knowns, when it comes to your little triangular quagmire, Gump?

  a) You found your ex-girlfriend to be crazy and broke up with her.

  b) You fucked your ex-girlfriend’s ex–best friend for a fortnight and felt “connected.”

  c) In spite of such connection, your ex-girlfriend’s ex–best friend donned a wig and announced that she has no interest in continuing to fuck you, claiming to be on the brink of a (presumably) monogamous and eternal connection to someone else.

  Which brings us to the known unknowns:

  a) Why the wig? And if the wig, why the unnervingly short hair?

  b) Is the ex-girlfriend’s ex–best friend actually engaged to be married or is this simply a grandiose ruse to shake you from her disinterested but chickenshit tail?

  c) How can it be that so many people’s ex-girlfriends are crazy? What happens to these women? Do they eventually go on to birth babies and care for their elderly parents and scramble up gigantic pans of eggs on Sunday mornings for oodles of lounge-abouts who later have the nerve to inquire about what’s for dinner, or is there some corporate Rest Home for Crazy Bitches chain in cities across the land that I am unaware of that houses all these women who used to love men who later claim they were actually crazy bitches?

  Lastly, there are the unknown unknowns, the things, Gump, that you don’t know you don’t know.

  a) You have nothing for these women.

  b) These women have nothing for you.

  c) And yet.

  d) And yet!

  e) You are loved.

  Yours,

  Sugar

  ON YOUR ISLAND

  Dear Sugar,

  I’m transgender. Born female twenty-eight years ago, I knew I was meant to be male for as long as I can remember. I had the usual painful childhood and adolescence in a smallish town because I was different—picked on by other kids, misunderstood by my (otherwise loving) family.

  Seven years ago I told my mom and dad I intended to have a sex change. They were furious and disturbed by my news. They said the worst things you can imagine anyone saying to another human being, especially if that human being is your child. In response, I cut off ties with them and moved to the city where I live now and made a new life living as a man. I have friends and romance in my life. I love my job. I’m happy with who I’ve become and the life I’ve made. It’s like I’ve created an island far away and safe from my past. I like it that way.

  A couple weeks ago, after years of no contact, I got an email from my parents that blew my mind. They apologized for how they’d responded when I told them about my plans for a sex change. They said they were sorry they never understood and now they do—or at least enough that we could have a relationship again. They said they miss me and they love me.

  Sugar, they want me back.

  I cried like crazy and that surprised me. I know this might sound odd, but I believed I didn’t love my parents anymore or at least my love had become abstract, since they had rejected me and because we’ve not been in touch. But when I got that email a lot of emotions that I thought were dead came back to life.

  This scares me. I have made it because I’m tough. I’m an orphan, but I was doing great without my parents. Do I cave and forgive them and get back in touch and even go visit them as they have asked me to do? Or do I email them and say thank you, but letting you back into my life is out of the question, given our past?

  Orphan

  Dear Orphan,

  Please forgive your parents. Not for them. For you. You’ve earned the next thing that will happen if you do. You’ve remade yourself already. You and your mom and dad can rem
ake this too—the new era in which they are finally capable of loving the real you. Let them. Love them back. See how that feels.

  What they did to you seven years ago is terrible. They now know that. They’re sorry. They’ve grown and changed and come to understand things that confounded them before. Refusing to accept them for the people they’ve become over these years of your estrangement isn’t all that different from them refusing to accept you for who you are. It’s fear-based and punishing. It’s weak rather than tough.

  You’re tough. You’ve had to ask impossible questions, endure humiliations, suffer internal conflicts, and redefine your life in ways that most people don’t and can’t even imagine. But you know what?

  So have your parents. They had a girl child who became what they didn’t expect. They were cruel and small when you needed them most, but only because they were drowning in their own fear and ignorance.

  They aren’t drowning anymore. It took them seven years, but they swam to shore. They have arrived at last on your island.

  Welcome them.

  Yours,

  Sugar

  PART FOUR

  YOU DON’T HAVE TO BE BROKEN FOR ME

  If love were an animal, what species would it be and could you train it?