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How Angry is Heather Havrilesky?

When Heather Havrilesky heard about a copy-editing position open at a new San Francisco-based e-zine called, she jumped at the chance to apply, doing what any honest, hardworking young Red Herring intern would have done.

"I lied," the 29-year-old recalls, grinning. "I told them I was a copy editor."

So where is it that lying gets you? If you're Havrilesky, a Duke University graduate with a degree in psychology but a rather short publishing resume, it speeds your way to the sort of life many Web writers only dream of.

After an amended stint copy editing Suck's articles and essays ("We learned very quickly that her copy-editing expertise left something to be desired," recalls Publisher Joey Anuff), Havrilesky was offered a shot at a weekly column.

"Filler," as it's called, took off, and this month, Havrilesky celebrated its four-year "Fillerversary," again proving that the Web offers a limitless array of unique -- and lasting -- opportunities for talented writers who can carve out the right niche.

The genre-bending column, blending stylish cartoons drawn by Terry Colon with Havrilesky's biting, witty dialogue, text and charts, gives the Suck columnist a weekly platform to snicker at, critique and generally comment on any subject that piques her interest.

Her columns -- be they instructional ("Men to Avoid"), self-deprecating ("Cellular Breakdown!"), or simply glimpses at reader mail -- have won her a devoted following. "Filler," which runs Wednesdays, frequently attracts 40,000 visitors, and Polly Esther, the name under which Havrilesky writes, often gets 30 to 40 e-mails a week.

"People just love Heather," says Special Guest Editor Tim Cavanaugh. "They look at her as some sort of therapist figure in their lives. It's like she sort of pierces through the bullshit and illusions in a way that they're unwilling to do themselves. It's a tough job, but somebody's got to do it."

Havrilesky revels in it. In a recent anniversary column, she waxes cynical about changes that may have taken place in readers' lives during the four years she has written "Filler."

"If you started reading Filler when you were a Web content developer enraptured by the community-building possibilities of the Internet, then by now you're an embittered wage slave," she notes in a colorful chart. "If you started reading Filler when you were a well-adjusted, upbeat, positive-thinking person full of inspirational phrases and encouraging words, then by now you're reading Salon instead."

Sound a little gloomy? Try a few of Havrilesky's tips on becoming a writer:

  1. Get angry.
  2. Think you're better than most people.
  3. Try to explain this to others.
  4. Feel alienated by their reactions.
  5. Get angrier.

So exactly how angry and cynical is Havrilesky?

Clad in blue jeans, a T-shirt and a zip-up sweater, the tall, thin writer with long brown hair sits down for lunch in Los Angeles's funky Silver Lake neighborhood, where she now lives, and grins with amusement.

"I'm totally upbeat," she says. "Some people read my work and say, 'Thank God someone thinks the world is as miserable a place as I do.' Sometimes I want to write to them and say, 'Go run around the block a few times and juice some carrots.' "

Which is to say that Havrilesky has her cynical moments, and she often captures them in her column, but she doesn't wallow in them.

"There was a time when I was fine writing about how dating is hell or how most jobs suck or all those things people think about in their early 20s," she says. "As you get older, it's a lot more complicated. You can't hold on to the same disdain and skepticism you used to."

Havrilesky grew up in North Carolina, the daughter of a Duke University economics professor dad. She felt alienated as a kid, she says, but she never wanted to be a writer.

"You think writers are people who sit in a dark closet with a typewriter and concoct descriptions of minute things," she says. "That sounds like torture."

While attending Duke, Havrilesky studied Marxism and feminism, majored in psychology and found time for a few other essential activities.

"I went to school to meet men and drink too much," she says.

She graduated, moved to San Francisco and got a part-time job doing word-processing for a technical writer. In her spare time, she played her Fender Telecaster. Then she enrolled in a nonfiction writing class.

"My teacher said, 'What are you doing? You should quit your job and be a writer,' " she recalls. "I was 24. I was pretty excited. You need someone like that."

The stint at Red Herring followed, and then she applied for the job at Suck.

"I just loved the voice," she recalls. "It was so unabashed and brazen, which was rare at the time. It was obnoxious, but I knew there were smart people behind it."

Anuff,'s co-founder, remembers being impressed by a few writing samples Havrilesky had at the time.

"When somebody comes to you and hands you some stuff, published or unpublished, and it's good material, you're going to be excited," he says. "In a way, you might be even more excited at being the first to publish a new voice."

Of course, Anuff wanted a copy editor.

"The fact that she was a good writer allowed us to believe that we were getting a fantastic two-fer," he recalls. "Being a little green as employers, we were hoping to get it all in one place."

He didn't. While Anuff sought a new copy editor, Havrilesky found herself increasingly enamored of Suck's style. She quickly wrote a few columns that caught Anuff's eye.

"Her early columns were so angry they made me uncomfortable," Anuff says. "I think she thought of herself as writing to style. All that fury was her trying to get the Suck house style down flat, but it basically wound up putting a big pit in my stomach. It was hilarious stuff."

Havrilesky, for her part, recalls unsuccessfully seeking guidance from her editors.

"They left it up to me to decide what the column would be," she says. "For some weird reason, they trusted me."

These days, though, they know exactly what they want.

"I think Heather is a genius," Cavanaugh says. "She always has good things to say, both on news, but more importantly, on affairs of the heart. She has some compassion that makes her interesting. It's not a girly kind of compassion. It's more of a sort of knowing. She knows how people are and it makes it a fun thing to read."

So how does she put "Filler" together week after week?

Each morning, Havrilesky wakes around 9 and goes on a three-mile run. By 10, she sits down in front of her computer in her home office, puts on a little Van Morrison or Elliot Smith, and gets to work.

Sometimes, the ideas come quickly, but not always.

"I have no surefire way of getting a column written," she says. "For one recent column I sat there for four 10-hour days and got nothing. I'm vaguely obsessive. Sometimes I'll decide that I can't start writing until I've had a big glass of water."

Somehow, though, Havrilesky gets the job done, filling "Filler" each week with her own biting, cynical brand of storytelling.

It's a tough job, as Cavanaugh says, but somebody's got to do it, and while Havrilesky is working on some fiction, too, she has no plans to quit "Filler" anytime soon.

"I thought two years ago that I was about to run out of ideas," she says. "I started to write jokes about martians. I know now that I have to just write what I know. As long as I can stick to that, I feel like I'll never run out of ideas."