The Art of Asking; or, How I Learned to Stop Worrying and Let People Help

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WHO’S GOT A TAMPON? I JUST GOT MY PERIOD, I will announce loudly to nobody in particular in a women’s bathroom in a San Francisco restaurant, or to a co-ed dressing room of a music festival in Prague, or to the unsuspecting gatherers in a kitchen at a party in Sydney, Munich, or Cincinnati.

Invariably, across the world, I have seen and heard the rustling of female hands through backpacks and purses, until the triumphant moment when a stranger fishes one out with a kind smile. No money is ever exchanged. The unspoken universal understanding is:

Today, it is my turn to take the tampon.

Tomorrow, it shall be yours.

There is a constant, karmic tampon circle. It also exists, I’ve found, with Kleenex, cigarettes, and ballpoint pens.

I’ve often wondered: are there women who are just TOO embarrassed to ask? Women who would rather just roll up a huge wad of toilet paper into their underwear rather than dare to ask a room full of strangers for a favor? There must be. But not me. Hell no. I am totally not afraid to ask. For anything.

I am SHAMELESS.

I think.

I’m thirty-eight. I started my first band, The Dresden Dolls, when I was twenty-five, and didn’t put out my first major-label record until I was twenty-eight, which is, in the eyes of the traditional music industry, a geriatric age at which to debut.

For the past thirteen years or so, I’ve toured constantly, rarely sleeping in the same place for more than a few nights, playing music for people nonstop, in almost every situation imaginable. Clubs, bars, theaters, sports arenas, festivals, from CBGB in New York to the Sydney Opera House. I’ve played entire evenings with my own hometown’s world-renowned orchestra at Boston Symphony Hall. I’ve met and sometimes toured with my idols—Cyndi Lauper, Trent Reznor from Nine Inch Nails, David Bowie, “Weird Al” Yankovic, Peter from Peter, Paul and Mary. I’ve written, played, and sung hundreds of songs in recording studios all over the world.

I’m glad I started on the late side. It gave me time to have a real life, and a long span of years in which I had to creatively figure out how to pay my rent every month. I spent my late teens and my twenties juggling dozens of jobs, but I mostly worked as a living statue: a street performer standing in the middle of the sidewalk dressed as a white-faced bride. (You’ve seen us statue folk, yes? You’ve probably wondered who we are in Real Life. Greetings. We’re Real.)

Being a statue was a job in which I embodied the pure, physical manifestation of asking: I spent five years perched motionless on a milk crate with a hat at my feet, waiting for passersby to drop in a dollar in exchange for a moment of human connection.

But I also explored other enlightening forms of employment in my early twenties: I was an ice cream and coffee barista working for $9.50 an hour (plus tips); an unlicensed massage therapist working out of my college dorm room (no happy endings, $35 per hour); a naming and branding consultant for dot-com companies ($2,000 per list of domain-cleared names); a playwright and director (usually unpaid: in fact, I usually lost my own money, buying props); a waitress in a German beer garden (about 75 deutsche marks a night, with tips); a vendor of clothes recycled from thrift shops and resold to my college campus center (I could make $50 a day); an assistant in a picture-framing shop ($14 per hour); an actress in experimental films (paid in joy, wine, and pizza); a nude drawing/painting model for art schools ($12 to $18 per hour); an organizer and hostess of donation-only underground salons (paid enough money to cover the liquor and event space); a clothes-check girl for illegal sex-fetish loft parties ($100 per party), and, through that job, a sewing assistant for a bespoke leather-handcuff manufacturer ($20 per hour); a stripper (about $50 per hour, but it really depended on the night); and—briefly—a dominatrix ($350 per hour—but there were, obviously, very necessary clothing and accessory expenses).

Every single one of these jobs taught me about human vulnerability.

Mostly, I learned a lot about asking.

Almost every important human encounter boils down to the act, and the art, of asking.

Asking is, in itself, the fundamental building block of any relationship. Constantly and usually indirectly, often wordlessly, we ask each other—our bosses, our spouses, our friends, our employees—in order to build and maintain our relationships with one another.

Will you help me?

Can I trust you?

Are you going to screw me over?

Are you suuuure I can trust you?

And so often, underneath it all, these questions originate in our basic, human longing to know:

Do you love me?

In 2012, I was invited to give a talk at the TED conference, which was daunting; I’m not a professional speaker. Having battled my way—very publicly—out of my major-label recording contract a few years earlier, I had decided that I’d look to my fans to make my next album through Kickstarter, a crowdfunding platform that had recently opened up the doors for thousands of other creators to finance their work with the direct backing of their supporters. My Kickstarter backers had spent a collective $1.2 million to preorder and pay for my latest full-band album, Theatre Is Evil, making it the biggest music project in crowdfunding history.

Crowdfunding, for the uninitiated, is a way to raise money for ventures (creative, tech, personal, and otherwise) by asking individuals (the Crowd) to contribute to one large online pool of capital (the Funding). Sites like Kickstarter, Indiegogo, and GoFundMe have cropped up all over the world to ease the transaction between those asking for help and those answering that call, and to make that transaction as practical as possible.

Like any new transactional tool, though, it’s gotten complicated. It’s become an online Wild West as artists and creators of all stripes try to navigate the weird new waters of exchanging money for art. The very existence of crowdfunding has presented us all with a deeper set of underlying questions:

How do we ask each other for help?

When can we ask?

Who’s allowed to ask?

My Kickstarter was dramatically successful: my backers—almost twenty-five thousand of them—had been following my personal story for years. They were thrilled to be able to aid and abet my independence from a label. However, besides the breathless calls from reporters who’d never heard of me (not surprising since I’d never had an inch of ink in Rolling Stone) asking about why all these people helped me, I was surprised by some of the negative reactions to its success. As I launched my campaign, I walked right into a wider cultural debate that was already raging about whether crowdfunding should be allowed at all; some critics were dismissing it out of hand as a crass form of “digital panhandling.”

Apparently, it was distasteful to ask. I was targeted as the worst offender for a lot of reasons: because I’d already been promoted by a major label, because I had a famous husband, because I was a flaming narcissist.

Things went from dark to darker in the months after my Kickstarter as I set off to tour the world with my band and put out my usual call to local volunteer musicians who might want to join us onstage for a few songs. We were a tight community, and I’d been doing things like that for years. I was lambasted in the press.

My crowdfunding success, plus the attention it drew, led TED to invite me, a relatively unknown indie rock musician, to talk for twelve minutes on a stage usually reserved for top scientists, inventors, and educators. Trying to figure out exactly what to say and how to say it was—to put it mildly—scary as shit.

I considered writing a twelve-minute performance-art opera, featuring ukulele and piano, dramatizing my entire life from The Womb to The Kickstarter. Fortunately, I decided against that and opted for a straightforward explanation of my experience as a street performer, my crowdfunding success and the ensuing backlash, and how I saw an undeniable connection between the two.

As I was writing it, I aimed my TED talk at a narrow slice of my social circle: my awkward, embarrassed musician friends. Crowdfunding was getting many of them excited but anxious. I’d been helping a lot of friends out with their own Kickstarter campaigns, and chatting with them about their experiences at local bars, at parties, in backstage dressing rooms before shows. I wanted to address a fundamental topic that had been troubling me: To tell my artist friends that it was okay to ask. It was okay to ask for money, and it was okay to ask for help.

Lots of my friends had already successfully used crowdfunding to make new works possible: albums, film projects, newfangled instruments, art-party barges made of recycled garbage—things that never would have existed without this new way of sharing and exchanging energy. But many of them were also struggling with it. I’d been watching.

Each online crowdfunding pitch features a video in which the creator explains their mission and delivers their appeal. I found myself cringing at the parade of crowdfunding videos in which my friends looked (or avoided looking) into the camera, stammering, Okay, heh heh, it’s AWKWARD TIME! Hi, everybody, um, here we go. Oh my god. We are so, so sorry to be asking, this is so embarrassing, but… please help us fund our album, because…

I wanted to tell my friends it was not only unnecessary to act shame-ridden and apologetic, it was counterproductive.

I wanted to tell them that in truth, many people enthusiastically loved helping artists. That this wasn’t a one-sided game. That working artists and their supportive audiences are two necessary parts in a complex ecosystem. That shame pollutes an environment of asking and giving that thrives on trust and openness. I was hoping I could give them some sort of cosmic, universal permission to stop over-apologizing, stop fretting, stop justifying, and for god’s sake… just ASK.

I prepared for more than a month, pacing in the basement of a rented house and running my TED talk script past dozens of friends and family members, trying to condense everything I had to say into twelve minutes. Then I flew to Long Beach, California, took a deep breath, delivered the talk, and received a standing ovation. A few minutes after I got off the stage, a woman came up to me in the lobby of the conference center and introduced herself.

I was still in a daze. The talk had taken so much brain space to deliver, and I finally had my head back to myself.

I’m the speaker coach here, she began.

I froze. My talk was supposed to have been exactly twelve minutes. I’d paused a few times, and lost my place, and I’d gone well over thirteen. Oh shit, I thought. TED is going to fire me. I mean, they couldn’t really fire me. The deed was done. But still. I shook her hand.

Hi! I’m really, really sorry I went so over the time limit. Really sorry. I got totally thrown. Was it okay, though? Did I TED well? Am I fired?

No, silly, you’re not fired. Not at all. Your talk… And she couldn’t go on. Her eyes welled up.

I stood there, baffled. Why was the TED speaker coach looking as if she was going to cry at me?

Your talk made me realize something I’ve been battling with for years. I’m also an artist, a playwright. I have so many people willing to help me, and all I have to do is… but I can’t… I haven’t been able to…

Ask?

Exactly. To ask. So simple. Your talk unlocked something really profound for me. Why the hell do we find it so hard to ask, especially if others are so willing to give? So, thank you. Thank you so much. Such a gift you gave.

I gave her a hug.

And she was just the first.

Two days later, the talk was posted to the TED site and YouTube. Within a day it had 100,000 views. Then a million. Then, a year later, eight million. It wasn’t the view counts that astounded me: it was the stories that came with them, whether in online comments or from people who would stop me in the street and ask to share a moment, not because they knew my music, but because they recognized me from seeing the talk online.

The nurses, the newspaper editors, the chemical engineers, the yoga teachers, and the truck drivers who felt like I’d been speaking straight to them. The architects and the nonprofit coordinators and the freelance photographers who told me that they’d “always had a hard time asking.” A lot of them held me, hugged me, thanked me, cried.

My talk had resonated way beyond its intended audience of sheepish indie rockers who found it impossible to ask for five bucks on Kickstarter without putting a bag over their heads.

I held everybody’s hands, listened to their stories. The small-business owners, solar-panel designers, school librarians, wedding planners, foreign-aid workers…

One thing was clear: these people weren’t scared musicians. They were just… a bunch of people.

I’d apparently hit a nerve. But WHAT nerve, exactly?

I didn’t have a truly good answer for that until I thought back to Neil’s house, to the night before our wedding party.

A few years before this all happened, I met Neil Gaiman.

Neil’s famous, for a writer. He’s famous for an anyone.

For years, Neil and I had chased each other around the globe in the cracks of our schedules, me on the Endless Road of Rock and Roll, him on the parallel road of Touring Writer, falling in love diagonally and at varying speed, before finally eloping in our friends’ living room because we couldn’t handle the stress of a giant wedding.

We didn’t want to disrespect our families, though, so we promised them that we would throw a big, official family wedding party a few months later. We decided to do it in the UK, where the bulk of them live. (Neil is British, and so are a lot of my cousins.) Furthermore, the setting was magic: Neil owned a house on a teeny island in Scotland, which was coincidentally the birthplace of my maternal grandmother. It is a windswept, breathtaking-but-desolate grassy rock from which my ancestors fled in poverty-stricken terror in the early 1900s, seeking a brighter, less-breathtaking-but-less-desolate future overseas in the promising neighborhoods of the Bronx.

The night before the wedding party, Neil and I bedded down early to get a full night’s sleep, anticipating an epic day of party organizing, eating, drinking, and nervously introducing two hundred family members to one another. Neil’s three grown-up kids were staying in the house with us, along with Neil’s mother and an assortment of Gaiman relatives. They were all snuggled away in their beds across the hall, up the stairs, a few stray young cousins roughing it in tents on the back lawn.

And on the second floor of the house, while Neil slept beside me, I was having a full-blown panic attack.

Somewhere down there I suppose I was freaking out about getting married, full stop. It was feeling very real all of sudden, with all the family around. What was I doing? Who was this guy?

But mostly, I was freaking out about money.

My Kickstarter was about to launch and I was pretty confident it would bring in plenty of cash—I’d crunched the numbers—but I wasn’t on tour, I was in northern Scotland, throwing a wedding party and putting a new band together, earning nothing. I’d just had a talk with my accountant, who had informed me that I wasn’t going to have enough money to cover my office staff, band, road crew, and regular monthly expenses unless I dropped everything and went back on the road immediately—or unless I took out a loan to bridge the gap for a few months before the Kickstarter and new touring checks arrived.

This wasn’t an unfamiliar situation. To the recurring dismay of my managers, I’d already spent most of my adult life putting all of my business profits straight back into the next recording or art project once I had recovered my costs. In the course of my rocking-and-rolling career, I’d been rich, poor, and in-between… and never paid much attention to the running tally as long as I wasn’t flat broke, which occasionally happened due to an unforeseen tax bill or the unexpected tanking of a touring show. And that was never the end of the world: I’d borrow money to get through a tight spot from friends or family and promptly pay it back when the next check came in.

I was an expert at riding that line and asking for help when I needed it, and, far from feeling ashamed of it, I prided myself on my spotless interpersonal credit history. I also took comfort in the fact that a lot of my musician friends (and business friends, for that matter) went through similar cycles of feast and famine. In short, it always worked out.

Only this time, there was a different problem. The problem was that Neil wanted to loan me the money.

And I wouldn’t take the help.

We were married.

And I still couldn’t take it.

Everybody thought I was weird not to take it.

But I still couldn’t take it.

I’d been earning my own salary as a working musician for over a decade, had my own dedicated employees and office, paid my own bills, could get out of any bind on my own, and had always been financially independent from any person I was sleeping with. Not only that, I was celebrated for being an unshaven feminist icon, a DIY queen, the one who loudly left her label and started her own business. The idea of people seeing me taking help from my husband was… cringe-y. But I dealt, using humor. Neil would usually pick up the tab at nice restaurants, and we’d simply make light of it.

Totally fine with me, I’d joke. You’re richer.

Then I’d make sure to pay for breakfast and the cab fare to the airport the next morning. It gave me a deep sense of comfort knowing that even if we shared some expenses here and there, I didn’t need his money.

I knew the current gap I had to cover was a small one, I knew I was about to release my giant new crowdfunded record, I knew I was due to go back on tour, and everything logically dictated that this nice guy—to whom I was married—could loan me the money. And it was no big deal.

But I just. Couldn’t. Do. It.

I’d chatted about this with Alina and Josh over coffee a few weeks before the wedding party. They were true intimates I’d gone to high school with, at whose own wedding I’d been the best man (our mutual friend Eugene had been the maid of honor) and we’d been sharing our personal dramas for years, usually while I was crashing on ever-nicer couches in their apartments as they moved from Hoboken to Brooklyn to Manhattan. We were taking turns bouncing their newborn baby, Zoe, on our laps, I had just told them that I didn’t want to use any of Neil’s money to cover my upcoming cash shortage, and they were looking at me like I was an idiot.

But that’s so weird, Alina said. She’s a songwriter and a published author. My situation wasn’t foreign to her. You guys are married.

So what? I squirmed. I just don’t feel comfortable doing it. I don’t know. Maybe I’m too afraid that my friends will judge me.

But, Amanda… we’re you’re friends, Alina pointed out, and we think you’re crazy.

Josh, the tenured philosophy professor, nodded in agreement, then looked at me with his typically furrowed brow.

How long do you think you’ll keep it this way? Forever? Like, you’ll be married for fifty years but you’ll just never mix your incomes?

I didn’t have an answer for that.

Neil wasn’t the type to attach strings, or play games, but it was my deepest fear that I’d be somehow beholden, indebted to him.

This was a new feeling, this panic, or rather, an old one: I hadn’t felt this freaked out since I was a teenager battling constant existential crises. But now my head was a vortex of questions: How could I possibly take money from Neil? What would people think? Would he hold it over my head? Maybe I should just put this album off another year and tour? What would I do with the band I just hired? What about my staff? How would they deal? Why can’t I just handle this gracefully? Why am I freaking out?

I left the bed after an entire night of tossing and fretting. I went into the bathroom and turned on the light.

What is WRONG with you? I asked the puffy-eyed, snot-leaking, deranged person that was staring back at me from the mirror.

I dunno, she answered. But this is not good. I was scaring myself. What was happening to me? Was I crazy?

It was six a.m., the sun was just beginning to rise, and the sheep were baa-ing mournfully. We had to be awake at eight to drive to the wedding party.

I went back to bed and crawled into Neil’s armpit. He was out cold, and snoring. I looked at him. I loved this man so much. We’d been together for over two years and I’d learned to trust him completely—trust him not to hurt me, not to judge me. But something still felt stuck shut, like a door that should open but just doesn’t budge. I tossed my body to the other side of the bed and tried to sleep, but the cyclone of thoughts didn’t stop. You have to take his help. You can’t take his help. You have to take his help. And then I started to bawl, feeling completely out of control and foolish. I was tired of crying alone, I guess, and ready to talk.

Darling, what’s wrong?

He’s British. He calls me darling.

I… I’m freaking out.

I can see that. Is it the money thing? He put his arms around me.

I don’t know what I’m going to do for these next few months, I snorfled. I think I should put off making the record if I can’t afford to pay everyone right now. I’ll just tour for the next year and forget about the Kickstarter until… I don’t know, I can probably borrow the money from someone else to get through the next few months… maybe I can…

Why someone else? he interrupted quietly. Amanda… we’re married.

So what?

So just get over it and borrow the money from me. Or TAKE the money from me. Why else did we get married? You’d do the same thing for me if I were in an in-between spot. Wouldn’t you?

Of course I would.

So, what is HAPPENING? I’d much rather you let me cover you for a few months than see you in this state, it’s getting disturbing. All you have to do is ASK me. I married you. I love you. I want to HELP. You won’t let me help you.

I’m sorry. This is so weird—I’ve dealt with this shit so many times and it’s never bothered me like this. It’s crazy. I feel crazy. Neil, am I crazy?

You’re not crazy, darling.

He held me. I did feel crazy. I couldn’t rid myself of this one pounding, irritating thought, reverberating through my head like a bitter riddle, an impossible logic puzzle that I just couldn’t shake off or solve.

I was an adult, for Christ’s sake.

Who’d taken money from random people, on the street, for years.

Who openly preached the gospel of crowdfunding, community, help, asking, and random, delightful generosity.

Who could ask any stranger in the world—with a loud, brave laugh—for a tampon.

Why couldn’t I ask my own husband for help?

We ask each other, daily, for little things: A quarter for the parking meter. An empty chair in a café. A lighter. A lift across town. And we must all, at one point or another, ask for the more difficult things: A promotion. An introduction to a friend. An introduction to a book. A loan. An STD test. A kidney.

If I learned anything from the surprising resonance of my TED talk, it was this:

Everybody struggles with asking.

From what I’ve seen, it isn’t so much the act of asking that paralyzes us—it’s what lies beneath: the fear of being vulnerable, the fear of rejection, the fear of looking needy or weak. The fear of being seen as a burdensome member of the community instead of a productive one.

It points, fundamentally, to our separation from one another.

American culture in particular has instilled in us the bizarre notion that to ask for help amounts to an admission of failure. But some of the most powerful, successful, admired people in the world seem, to me, to have something in common: they ask constantly, creatively, compassionately, and gracefully.

And to be sure: when you ask, there’s always the possibility of a no on the other side of the request. If we don’t allow for that no, we’re not actually asking, we’re either begging or demanding. But it is the fear of the no that keeps so many of our mouths sewn tightly shut.

Often it is our own sense that we are undeserving of help that has immobilized us. Whether it’s in the arts, at work, or in our relationships, we often resist asking not only because we’re afraid of rejection but also because we don’t even think we deserve what we’re asking for. We have to truly believe in the validity of what we’re asking for—which can be incredibly hard work and requires a tightrope walk above the doom-valley of arrogance and entitlement. And even after finding that balance, how we ask, and how we receive the answer—allowing, even embracing, the no—is just as important as finding that feeling of valid-ness.

When you examine the genesis of great works of art, successful start-ups, and revolutionary shifts in politics, you can always trace back a history of monetary and nonmonetary exchange, the hidden patrons and underlying favors. We may love the modern myth of Steve Jobs slaving away in his parents’ garage to create the first Apple computer, but the biopic doesn’t tackle the potentially awkward scene in which—probably over a macrobiotic meatloaf dinner—Steve had to ask his parents for the garage. All we know is that his parents said yes. And now we have iPhones. Every artist and entrepreneur I know has a story of a mentor, teacher, or unsung patron who loaned them money, space, or some kind of strange, ass-saving resource. Whatever it took.

I don’t think I’ve perfected the art of asking, not by a long shot, but I can see now that I’ve been an unknowing apprentice of the art for ages—and what a long, strange trip it’s been.

It started in earnest the day I painted myself white, put on a wedding gown, took a deep breath, and, clutching a fistful of flowers, climbed up onto a milk crate in the middle of Harvard Square.