Melissa is back. She stayed with us on the farm a little while over the winter, telling me to shut up, and playing with me in the snow.

I think by now you get the picture that Melissa is one of those people who breaks every rule and lands on her feet. One of the things I really admire about her is that she quits a job as soon as she knows it’s not the right fit for her long term.

1. Keep rewriting your story so that it makes sense.

I don’t think I’ve ever told you that Melissa worked at Ogilvy in NYC. Her stint was less than a year, but long enough for her to become an search marketing genius. Not that she’s doing anything with that knowledge.

“It’s interesting to know,” she told me. “And everyone should live in NYC once in their life. For as long as they can stand it.”

She took a finance job in Hong Kong and retooled her resume to tell a new story: Her developer resume showed a child prodigy programmer becoming an Ogilvy SEO queen. But she changed it to a sales resume where she is an Ogilvy account management and moves seamlessly into hedge fund sales. It’s all true. But good storytelling on a resume requires selective shifts in focus for each job description.

2. Do two jobs at once to hide a job that is death to a resume.

Then Melissa quit her private equity job in Hong Kong with tons of tax-free money in her bank account and fled the finance industry to become a nanny in Milan.

It seemed like a great job. There’s one kid in the family. He’s nine years old and he’s in school (the British school) until 3pm. For this, Melissa was earning the equivalent of US0,000 per year. Here’s the area where she was living:

The idea was that she’d hang out in Milan for a year, but she’d also do some sort of official launch of a career coaching business where she helps me put a lot of my individual career coaching online so that I can do more coaching over the phone. And then, I told her, she could drop the nanny job from her resume and say she spent the year building a coaching business. Her resume will look fine.

3. Leave when things get bad. A good resume is not worth a bad year of work.

You’ll notice, though, that we never got to the career coaching part.

It turns out that the family is one of the most wealthy in all of Europe. The boy’s father inherited a luxury brand that I am not going to name because I’m going to tell you that his kid is a monster.

But first, here’s what the job was like. The house has a live-in staff of 35 people, plus security, which was important because the dad has the only complete record of a famous recipe. In his head.

At first Melissa thought her job was to take care of the kid. Then it seemed like maybe Melissa’s job was to speak English at dinner so everyone’s English stayed good. But really, only the dad talked with Melissa. About business. And she found herself researching topics in the day to talk to him about at night.

When the dad was gone on a business trip, it seemed like Melissa’s job was to take care of the mom, who has never worked outside the home and does not appear to have any duties inside the home. So, for example, when the family went to the weekend house in Switzerland, the dad and the boy rode together in one limo and the mom and Melissa rode together in a second limo.

The first problem was that the job was insanely boring. Dinner discussions with the dad were interesting. But in general, the assumption at this house is that the life of the super rich is so interesting that it makes intellectual stimulation unnecessary. People spend their lives on the compound, raising their children there, exchanging their own lives for the glow of the household-palace they serve.

Melissa said, “I had too privileged a childhood to think this life is interesting enough to stay.”

Melissa quit.

The father was horrified. The father told the agency Melissa is the perfect candidate.

I told her forget it. Just leave. But Melissa felt bad quitting. She wants to be someone who sticks with something. So she agreed to stay on.

4. Once your instincts tell you to quit, don’t second-guess yourself.

Melissa’s job was to be on call for the boy, but he had no rules. He has been raised by nannies. His English was impeccable, including a wide range of swear words and personal insults he used on Melissa in front of the parents. Melissa told the nanny agency there were problems. The nanny agency said they had already recommended to the mom that she take a break from nannies and try parenting.

Melissa negotiated a month of extra vacation, which she had to fit in between accompanying the family on vacations to Bermuda, Capri, and the French Alps.

Then the boy, who maybe sensed the idea of a nanny quitting after only three weeks, went on full attack. He clubbed her with a croquet mallet, swore at her in impeccable English, and stole her iPad when his ran out of power.

Melissa told the mom, “He just told me to fuck off.”

The mom said, “Alors!” and shuffled into the boy's bedroom. “Honey," she said, "please don’t use that language. It’s not nice.”

The boy growled at Melissa.

The mom walked away.

Melissa quit again. Probably ten minutes before she was going to fall in love with the dad.

Which would have made for a great story. But fortunately, the story gets good because she had nowhere to go. She called me from the café down the street from the house because she gets no cell phone reception at the palace.

5. Cover up periods in your resume when you are flailing.

I tell her she could come to my house. I loved when she was here last time.

She said it would look bad on her resume.

I told her she could say that she was working for me. She could make it look like she was looking for a job instead of failing at a job in Italy, and I am the job she found.

I told her I was starting a company. She could put it on her resume.

She was concerned. “Goats? You want me to put goats on my resume?”

“Say agri-business. That’s a good city-girl word.”

She’s wasn’t convinced at first. “I don’t know anything about goats.”

“It’s just like any other startup. Startups are formulas. Whatever the product arena is, you go through the same stages of being lost and running out of money and having a marketing plan that doesn’t work.”

6. You have to take so many risks to find out where you fit. Mitigate other risks wherever you can.

Melissa says she can’t work at a company that’s not funded. She can’t run out of money.

I tell her I’m funded.

She says okay.

I tell her I’m not funded enough to pay her a salary. But anyway, there’s nothing to buy on the farm. You don’t need money.

She says, “How about if I fund the company? I can invest the ,000 I saved in Hong Kong. Then it’s okay if I don’t know that much about goats. I’ll still own a portion of the company.”

So great. I have two investors and a company and a good friend living with me.

We decide this on Tuesday. On Wednesday she flies to Madison. It takes her almost 24 hours to get here, which gives me time to ask the Farmer if Melissa can live with us again.

“How is she going to earn money?” he asks.

“She’s working at my new company.”

“What’s she going to do?”

My kids overhear; they scream in glee. “Melissa’s coming. Melissa’s coming!—I get her iPad first—No, it was my turn last time she was here!—Let’s decorate her room—How long will she stay with us?”

“Yeah,” the Farmer says, “How long will she stay?”

Penelope Trunk