Karen Karbo will never forget the first time someone referred to her as “difficult.” It was in kindergarten.

“I had a hard time moving from painting time to story time to nap time,” she said. “At that age, if I was in the middle of painting I didn’t want to move on to the next thing if I wasn’t ready to stop.”

So her teacher called in her parents to explain the situation. The teacher described Karbo’s behavior as “insisting on being difficult,” which Karbo didn’t understand.

But now Karbo, of Portland, Oregon, is embracing being a “difficult woman” in her newest book, which celebrates other women who broke the rules.

Karbo, whose other work includes a best-selling book “The Gospel According to Coco Chanel,” wrote 29 personal essays reflecting on heroines who inspire her in a variety of ways. The essays are encapsulated in her newest book “In Praise of Difficult Women: Life Lessons from 29 Heroines Who Dared to Break the Rules.”

The thread connecting the women is the idea of what it means to be a “difficult woman” as defined by Karbo.

“A difficult woman, as I define her, is a person who believes her needs, passions, and goals are at least as important as those of everyone around her,” reads an excerpt of the book’s introduction. “In many cases, she doesn’t even believe they’re more important — many women in this book were devoted, loving wives and mothers — but simply as important.

“A difficult woman is also a woman who doesn’t believe the expectations of the culture in which she lives are more important than what she knows to be true about herself. She is a woman who accepts that sometimes the cost of being fully human is upsetting people.”

Q: What inspired you to write about strong women?

A: It’s interesting because Cheryl Strayed, who is a friend of mine and generously wrote the forward of this book, she’s the one who pointed it out to me. I thought it was just that I love popular culture and movies and art. I thought it was something that was coming from my intellect. ... What Cheryl and I have in common is we both lost our mothers quite young. My mother died when I was 17. I was an only child. I had no living grandmothers. I had no older aunts. I had no older cousins. At 17 I was the oldest woman left in my family. I was a freshman in college and my father remarried quickly.

I was quite alone.

(Back then) I was a huge devour-er — I don’t know if that’s a word — of biographies. I discovered Martha Gellhorn and “Travels With Myself and Another” — the another was Hemingway. Frida Kahlo was being discovered. I love Josephine Baker, Amelia Earhart, Jane Goodall — I kept up with them. They became my family, not to get too corny about it.

They were women who lived full lives. They were true to themselves. They had exciting lives. ... Because my mother died at 46 I had no idea about how to be a woman in the world past that age. I sort of adopted these women who lived into their 90’s and had second acts and third acts.

Early difficult women were my personal saints and icons. I was attached to them.

How did you choose these 29 women?

When I first started writing it we thought there would be large essays about 13 women. Maybe more encyclopedic with 50 women. It fluctuated.

The central point was always that it had to be women who spoke to me in some way. It’s personal in that regard.

If you put together your living list of 29 heroines you’d have a different list. Everyone would have a different list. It would be a great party game.

It had to come back to who I was a big fan of or someone who was inspiring to me. Someone who I was admiring how they were resisting and moving in the world.

I really wanted to speak to diversity. I wanted it to be women from different countries and ethnicities. Women who grew up poor and rich or women with intact families and dysfunctional families. It’s a broad view of woman-ness in the 20th and 21st century.

Is there one that you consider a personal inspiration?

It depends — it’s mood related.

One of the things that I really admire about some of them, for example, like (J.K.) Rowling. Or Elizabeth Taylor who was a global icon when she came out and advocated for AIDS research and awareness.

These women have “made it” and their images are furnished as these great iconic women and they risk that by speaking out. I deeply admire that.

It feels like there are different ways of displaying courage and difficulty. At the beginning of your life you have nothing to lose and you blast forward as you do when you’re young. That’s a different difficult.

One of my favorites is Helen Gurley Brown. “Cosmopolitan” makes me laugh. I’m no reader of “Cosmo,” but when (Brown) was very young she was in a family from the South and had a mom and dad and sister. When the dad died, they were plunged into poverty.

She had to work. College money disappeared. She was a working girl in the late 50s and didn’t want to be treated like she was the saddest person on earth. In the 50s you went from your parents’ house to your husbands’ house or you were a loser.

Her reality was, “Are you kidding me? Being married is a drag.” That became her rallying point when she wrote “Sex and the Single Girl” in 1962.

...But, overall, my beloved Martha Gellhorn. She was a war correspondent and lived a glamorous, swashbuckling life. She was (Ernest) Hemingway’s third wife. She was so distressed that she was best known for that. She was intrepid and fearless and glamorous.

Who was the first “difficult woman” in your life?

Oh — my Polish grandmother.

She died when I was six. But my father and his parents Viktor and Luna came to this country from Poland and settled in Chicago. A year after they arrived, Viktor took off. It was just Luna and my dad and she had no skills.

She was of the Polish Bourgeoisie and was taught to needlepoint and play the viola. She was taught how to entertain people and didn’t really have any skills. But she was a great seamstress. She worked in a sweatshop for a few years and then moved to Hollywood.

She became a dress designer for the wives of directors and producers and studio executives.

... She was ferocious and disciplined and gifted. And even at five years old she put up with nothing from me.

What is your next project?

I’m writing a novel right now. It concerns Gertrude Stein and Alice B. Toklas. That’s all I can tell you right now. It’s in the baby stages.


Amanda Finn is an arts and lifestyle reporter for the Wisconsin State Journal.