Leave the family business to know if you should stay

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For too many people, staying in the family business is the easy way to worm out of difficulties of adult life: finding a place where you fit in, discovering what you love to do, and living with the fear of rejection. Especially today, with a dried-up job market, the family business is a way of avoiding a difficult job hunt.

I worked in a family business — a bookstore. I started when I was eight, selecting titles for the early reader section, and by the end of college I was a walking card catalogue. After so many years, I was the heir apparent to the store. But I wanted to do something else. I just wasn’t sure what.

Fifteen years and three careers later, I am certain that there are three things you should do before you decide to settle down with your family business for the long haul:

1. Figure out your dream job. Don’t worry about being realistic. Rock star, movie producer, politician: everything is fair game. Then decide if you want to go down the path to fulfill that dream. Don’t feel bad if the dream is impossible – many dreams are not realistic, but they contain gems of truth. For example, someone who dreams of being a rock star probably wants to be creative at work. The exercise of dreaming helps you to figure out your core needs. Once you know these needs, take an honest look at the family business. If you cannot fulfill your core needs in the family business, you should leave.

2. Get a job. Even if you are sure you’ll stay in the family business, get a job outside of the business. Job hunting sucks, which is why you should do it. The process is humbling and scary because on one level, you are asking someone to pay you to work so you can eat; at another level, job hunting requires understanding yourself well enough to talk about your dreams, your strengths, and your weaknesses. You need to experience what it is like to ask for a day off from someone who doesn’t love you. Working for someone outside your family helps you to interact effectively with all people outside your family. This process is a rite of passage, and if you don’t go through it, you risk stunted growth.

3. Take a large risk. If the entrepreneur is on the high end of the risk-taking scale, the kid who stays in the family business is on the low end. At the end of life, the thing people most often say they regret is not taking enough risks. Make sure that staying in the family business will not make you wish later that you were a risk taker. If you take a large risk early on, then you can be more certain that you are not staying in the family business because you are scared of taking risks. Risks are different for everyone — a mountain for one person is a molehill for another. Find something that scares you and do it.

Adult life is about learning what matters to you and creating a life that reflects your values. In order to know what’s important, though, you need to see the world. Take time to establish yourself independently from your family — at least for a while — so you can see yourself more clearly. Whether you stay in the family business or go somewhere else, you’ll be a happier person for making the decision honestly.

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The marital dance to figure out who stays home with the kids

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My husband and I always thought he'd be the stay-at-home parent, so I am shocked that I am the one changing diapers all day.

When we were dating, I was making a solid, six-figure salary in the software industry. I had already founded two companies and cashed out of one. He was a video artist and traveled to festivals all over the world showing arcane art on activist topics. He planned off-beat things to do on our dates; I would pay for them.

I was rising so fast in my corporate career that a business magazine paid me to write about my ascent. I ended up making as much money writing as my husband made at his day job. People asked me if I resented having two jobs and subsidizing my husband's career as an artist. Actually, I didn't mind at all; I loved to work, and he agreed to stay home when we had kids. I thought I was one of the lucky women who could blast through the glass ceiling and have kids because I had a husband who would take care of our home life.

We planned to get pregnant at a time when I would not disrupt my career, but in September 2001, our designated family start-date, both my husband and I got laid off. I got pregnant anyway. As my belly grew, I continued my freelance writing career while he volunteered in non-profits, and we lead a bohemian life with corporate savings. But by the seventh month, I missed the structured, team-oriented atmosphere of work. I was editing my resume the morning I went into labor.

When the baby arrived, I planned to get a full-time, office job right away, but after only a few weeks of sleepless nights, my husband got a job offer. He wasn't even looking, really,— he was doing things like soothing diaper rash and assembling the breast pump. But one of the people he met through volunteering got him an interview at a top-notch human rights organization. The job offer was for his dream job, so we decided he should try it.

Now I would be home with the baby, alone. For those of you who haven't had a baby, let's just say that going to an office is about a thousand times easier than dealing with a newborn. With a newborn there is no schedule, no break, and no performance review to let you know if you're screwing up. So naturally, I wanted to be the one with the job. I tried to be happy for my husband. I tried not to hope that he would hate his job and quit.

During my first week as a stay-at-home mom, I couldn't sleep, I couldn't write and I couldn't figure out how any adult can stay home all day with a baby who can't talk. So I hired a babysitter for a few days a week and I went to an office to write and look for a full-time job. But I never got around to the job hunt because I missed the baby while I was away — I missed his smile and the way he stares at his hands like he's not sure if they're his.

People often describe their family life in terms of earning power: The spouse who has the higher earning power is the one who works. This is logical, but it doesn't always work out that way.

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My dad’s career change, and how to know if it’s time for yours

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My dad just called. He said one of his fifteen-year-old students asked, “Why do we need to know this? How will To Kill a Mockingbird help me in life?” My dad loves questions like that because he has asked them himself.

My dad has always loved school. He was the kid who did the extra credit even though he already had an A. So he had a lot of options at the end of college. He applied to two graduate schools: Yale for history and Harvard for law. He got into them both.

Before I tell you what he chose, I have to tell you about my family. Rich. Mob money. My great-grandfather, my dad’s grandpa, was the lawyer for the Chicago mob: solid work during prohibition and a reliable profession during the depression. Money flowed freely during my dad’s college days, but his grandfather threatened the inheritance if my dad chose history over law. The way my dad tells the story, he always knew he wanted to teach, but he was scared to risk his family “?s wrath, to say nothing of their wealth.

So, after Harvard, my dad went to the top law firm in Chicago (without even having to interview.) My dad hated it, but he wasn’t a risk taker, so he hated it for a long time, thinking the money was worth it. Like the BMW: he drove one of the first cars (when the motorcycle company diversified in desperation) and the cars were so rare that the BMWs would flash each other when they passed. (I’d yell from the back seat, “Hey, there’s one! Flash, Dad, flash!)

There came a point, though when my dad asked himself, “Why do I need to know about all these cases? How is this helping me in life?” His grandpa died, his law firm merged, and the bottom of the BMW fell out.

Finally, after years of thinking his career would get better, it didn’t, and he quit. He went to graduate school to teach high school history. He was older than all the professors. His kids were older than all the students. After thirty years of practicing law, he started over.

I asked him about classes and he’s say, “It’s hard to go back to school. It’s hard to no know what I’m dong after so many years of doing the same thing.” He said his favorite class was the history of civil rights, because when they got to the ’60s he could write papers about his college days.

Upon graduation, everyone in his class got interviews and he didn’t. No one even talked about age discrimination because it was so obviously there and so obviously unavoidable. Finally, though, he got a job. Teaching English. He wanted to teach history, but he’s entry level now. It’s like doing HTML when you’ve got a degree in computer science.

But my dad is thrilled. He took a big career risk and he’s happy. He’s happy to be interacting with the students, but also, I have a feeling that he’s happy he took a risk. Changing careers is so scary, but it’s so empowering-it gives you assurance that you can al ways choose to do what you want most — the hard part is to know yourself well enough to know what that is. So think like a fifteen-year-old and ask yourself, “Why am I doing this?” And then think like a risk taker and jump like my dad when you know your time is right.

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How to make graduate school worth the cost

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Whenever I have found myself in financial trouble, the first thing I thought was “Can I solve this problem with school?” I learned this behavior early, when boys were stealing my lunch money on the way to school; I started going to school extra early to do times tables with the teacher until the boys stopped looking for me. I continued this behavior into adulthood, and used grad school as a way to occupy myself during bad economic times.

I am not alone in this technique. But grad school is pricey. Most programs cost more than $8,000 a year, and MBA programs can run $100,000 a year. Unless you can get your parents to pay for school, you risk being stuck with loans that you can't pay. So you should check out predictions for the jobs markets of the future, and get credentials that will prepare you to pay back loans without totally limiting your work options. (Here's a start: Healthcare worker, good. Violinist, bad.)

You should also be honest with yourself about whether or not you can stomach school. A friend of mine wanted to change careers, so he considered getting a degree in the new field. He took one class to test the waters, and the first day, the professor asked students about their political views. Each student defined her views in relation to those of her parents. Not surprising for a bunch of 20 year olds, but untenable for a seminar if you're 35, like my friend. No degree program for him, but here's the good news — he got a job anyway. And you might be able to do that, too. So don't be so quick to sign up for four more years of schooling.

If you are still gung-ho on more schooling, make a plan for what that degree will get you after school, in terms of lifestyle and job satisfaction. For example, polls show that lawyers are typically not happy in their profession and biochemists are very happy. Don't neglect the dreaded grad school essay. If you are having trouble writing about why you want to go to a particular program, you probably trying to solve a problem that school can't solve. My third grade teacher put it to me this way: It doesn't help to come back to school when your brother ate your after-school snack.

A lot of the going-back-to-school game is luck. During the last recession, I went back to school for English. I thought I would be an English professor, but I got sidetracked by the computer science department and wrote my thesis in HTML. I was lucky that while the idea of teaching English was delusional (jobs are scarce), the Web was the new big thing, and no one knew HTML. I turned my generally useless grad school program into a lucrative job in the high-tech industry.

So think carefully before you go back to school, but realize that all the planning in the world does not make you a predictor of the future. Grad school is not a way to play it safe, but it's a way to play the odds by opening new doors for yourself.

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