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The indescribable Penelope Trunk
Born near Chicago, formerly of New York, now near Willow Springs

Penelope Trunk could be described as living in two different worlds, and not exactly fitting in either.

Trunk grew up in Chicago’s northern suburbs. She played professional beach volleyball as a resident of Los Angeles. She was living and working in New York on Sept. 11, 2001.

Now, she lives on a 125-acre farm in the Town of Willow Springs north of Darlington with her husband, Matthew Walter, and two children, blogging at and being “a serial entrepreneur and writer,” as she later describes herself, “selling ideas.”

“My friends in New York think, wow, I’m really a farm girl,” she said from the living room of a farm house on a farm with, as she put it, “two of everything,” including two alpacas and two goats. “And people think she’s from New York; she’s a wack job.”

On the one hand …

“People here think knowledge work is BS, and they think the number of hours you work is how hard you work,” she said. “The value here is doing hard, physical labor is how you’re valued here. The idea of smart work, of preserving your body, that’s really an insult here. In order to raise an economy you need knowledge workers. The idea that ideas have high value — I can’t convince anybody here that their ideas are worth $1 million.

“This is like another world. For the most part, Matt has to translate for me what is happening — really basic things. I have no idea what to expect from people. New York and Chicago, it’s like a totally different language.”

On the other hand …

“I think it’s a lot more honest down here,” she said. “I really like that. I got an invitation to teach at UW [in Madison], and I think, I’d rather teach in Platteville. They’re just more honest here. They aren’t in delusion that they’re in Chicago.”

Trunk graduated from Brandeis University in New York. After she moved from Los Angeles back to New York, abandoning beach volleyball, she worked two blocks from the World Trade Center.

“When the plane hit, nobody knew what was happening,” she said. “When I got out the subway, there was paper floating in the sky.” A crowd of people were moving toward the World Trade Center to see what had happened, and “I just followed the crowd; it was a couple blocks away.

“When it fell, I thought it was an earthquake, so I duck-and-covered, and everybody else ran away, and I was completely trampled. When I got up, it was completely dark, and I had to climb over bodies, and I had no idea where I was. I assumed I was going to die.

“I was completely traumatized for the next year. I could do very little after that. That was when I got the sense that I didn’t need to start big companies; you think of the people in your life. That’s all you care about — you think about the people in your life; are they OK? And so I thought I need to reorganize my life.”

The companies Trunk has started include, a teaching-tool site for teachers, ECityDeals, which “went under in the dot-com crash”; and Brazen Careerist, “where ambitious young professionals connect and grow.” Brazen Careerist became a book, Brazen Careerist: The New Rules for Success. She also wrote The New American Dream: A Blueprint for a New Path to Success.

“I combined economic development research and positive psychology research,” she said. “I can only do that because I led a different life first. Anybody can come here and do business. But building a network of people that can help you, that’s a barrier here. Something like college — if you live in a farm area and get 600 on the [Scholastic Aptitude Test], you can go to an Eastern college. And people here don’t know that. And you have to understand that to make a significant income, not here.

“There’s huge cash flow in farms, but not huge profits. So unless you leverage that cash flow you’re not going to make a lot of money. … The median income of a reader in San Francisco vs. the median income of a reader in Wisconsin, it’s just night and day. I love that I reach people in Wisconsin. These aren’t people I’m making money from. I’m basically probably one of the businesses that channels the most money locally.

“The thing I’m really good at is pegging trends. I’m not great at getting a lot done, I don’t have great people skills, but I can see trends. Customized education, I think every day what I can do.”

Trunk described her customers as “city people who were raised to be very high performers. To be a high performer you have to go to where the best people are in that arena. It’s so obvious that I can’t believe it’s insulting to people, but people look down at farmers when they’re the only high performers out there.

“I’ll always meet someone because rich kids stick together … really overprivileged people who have unfair advantages. But I see people around here who have opportunities and they don’t take advantage because no one pushes them.”

Trunk seems to never lack for opinions that veer off in different directions from the original thought.

“There are some things that won’t work,” she said. “For example, I work for free when I’m figuring stuff out. People won’t work for free — they’ll help out a friend. They’re on the financial edge, so they don’t work for free, and I understand that.”

About parenting in southwest Wisconsin, she said, “In the city, it’s really important to send your kids on play dates. Nobody does that here; they play with their families. Here, you go to school and you go here and there’s nobody to drive three different people to three different places. Parents are parenting kids as a group. It feels very snooty because it’s extremely expensive to have one kind in the family that only that kid does. It’s another world here.”

Trunk started writing a column for the Boston Globe that now is syndicated to 200 newspapers across the U.S.

“New York and L.A. people think Chicago’s like Milwaukee,” she said. “They don’t see the difference. You live in Chicago because you don’t want to live in New York and L.A. I’ve lived in Jerusalem and I lived in Paris, and they’re like the same as L.A. and New York compared to here.

“The tradeoff here is that people are content. What people want in Wisconsin is they’re surrounded by people who are content with what they have — they have a stable, content life. You’re surrounded by content people, so you’re more likely to be content. This is like home base for contentment. Contentment doesn’t breed risk — taking or trying new things — you don’t try more things if you’re content.

“The most unhappy people are in New York. But people in New York don’t care that they’re unhappy. … Intensity is new, different, difficult. You generally skew one way or the other, and you’re born that way — 75 percent of your personality is determined at birth. But you can influence how you see the world by moving to the opposite.”

In her blog Wednesday, Trunk answered the question of who should start a business:

Yes, it’s true that people who have their own company don’t have to do what they are told. They don’t have to keep regular hours. And they can put CEO on their business card. Yes, it’s job security. But you know what? It’s high risk, it’s financially ruinous, it’s a high-divorce rate, and it’s for people with an insane drive to be right. Research from Berkeley’s Haas School of Business shows that people who do start-ups don’t want to be rich as much as they want to be respected for being right about something. Not very many people are driven by the need to be right. And of those people, not many are willing to risk their personal stability to make sure everyone knows they are right.

So you can be fine climbing the corporate ladder. There is structure and stability in that life, and there is nothing wrong with it. It’s not true that the only smart people are entrepreneurs. It’s true that the smart people look at their core needs and figure out how to address them. Entrepreneurship is not right for everyone. And when you start a company just because you want to be on trend, you look like a misplaced stalk of corn.

Advice: Look at your Myers Briggs score: if you have an S in it, it’s not likely that you should start a company. If you have a history of extreme financial instability you probably shouldn’t create more by starting a company. Look at your core needs, and address those. You do not have a core need to be famous like Mark Zuckerberg.

What about young women who want a family instead of a career?

There is nothing set up for you to do if you know you want to be a stay-at-home mom and you are 23 years old. How do you navigate the work world when you know it is temporary? When people ask what you’ve been doing, it is very uncool to say “I’ve been looking for a breadwinner to marry.” The world is set up for everyone to focus on earning money in their 20s, which obviously does not make sense for people who will have only a short 6-8 years when they will have to support themselves.

The world screams from all angles that it’s important to be able to support yourself. You will have to buck a trend to say, “I don’t want to support people financially. I want to support them emotionally.” Because that’s what a housewife does. Today it’s revolutionary to be a housewife. And I have a feeling that most women who aspire to this have days when they feel like me, sitting at the edge of my garden, thinking that all my time is stupid and wasted. It’s hard to know how to manage yourself when you’re bucking a trend.

Advice: Lie. Tell people you are focusing on work even though you’re not. Because bucking a trend is so difficult, and so disconcerting, that if you can hide it temporarily, until you get your footing, that strikes me as a very good idea. And remember: don’t let people tell you you’re a sponge for having kids and not earning money. It’s just as much a sponge for men to have kids and leave the house every day to do an easier job than taking care of them. The world is full of ways to be a sponge.

Walter is a partner in Jordandal Farms, a Lafayette County sustainable agriculture operation that sells meat from grass-fed livestock in specialty markets and farmers markets and to Madison-area restaurants.

Jordandal Farms received an award in the first Edible Madison Local Hero Awards.

“Now that I live here, it’s totally typical that grown men work for their parents without getting any equity,” she said of more traditional farm operations. “Parents use the farm as a stick and a carrot. In the business world, you get everything in writing.”

Her website includes what she terms five “Big Ideas” — “Don’t do what you love,” “Don’t go to grad school,” “Blueprint for a Woman’s Life,” “Living up to your potential Is BS,” and “Choose sex over money.”

Her meeting, breaking up with, and then marrying Walter takes up an entire section of her blog,

“Matthew sent me fan mail, and I had just gotten a divorce, and my blog because a dating site for me,” said Trunk. “I became great reading between the lines of emails. I was going all across the country; almost no one from this area sent me email. And he sent me email.”

One of Trunk’s causes is school reform. She home-schools her sons.

“It’s not debated anymore — customized education is the best for kids; it’s not scalable,” she said. In “$40,000 or $50,000 schools in San Francisco, they don’t do tests; they customize education. This is not controversial. What’s controversial is middle-class parents taking their kids out of school.

“Wide-spread studies show that any kid who has 100 books in their house, they’ll learn to read on their own. So why do you learn to read in school? It’s for underprivileged kids. In cities a majority of parents homeschooling are not doing it for religious reasons anymore. Here, kids who need it the most, kids who need self-confidence the most that they can learn on their own, are the last kids who should be for No Child Left Behind.”

Trunk sees the farm as a giant classroom for her sons — Yefet, 10, and Zehavi, 7 — who are home-schooled all year.

“There’s no breaking from learning,” she said. “When you’re an adult, you have to learn every day to stay engaged and remain employable, so why do we teach kids they have to learn only part of the year?

“The majority of women who have kids would like to work part-time, and the majority of men who have kids would like to work full-time. And there are no part-time jobs in the corporate world; there just aren’t. It is a throwback to the 1950s. Generation X is not signing up to work full-time and park the kids in daycare.

“Family life is amazing for us. Every day I feel so, so lucky to live on a farm. It’s the things you give up — every day you give up things where you live. It’s peaceful and quiet, and the kids have so much freedom and independence to go off and explore. And it’s like a biology class for me — every day I learn so much about agriculture.”

At some point, she said, “I’ll probably do another startup. I can attract people to do a company here; I have a lot of opportunity.”

And then she said, “I’m raising kids here, and I’ve bought into this. You can say I’m a snob, but I’m a realist.”