Sometimes finding a job is a mixed blessing

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Once someone's been unemployed for a while, employment is a mixed blessing. Of course, the jobless are anxious about finances and worried about the growing hole in their resume. But the long, flexible hours of unemployment suck you in and make you think that maybe, just maybe, you do not have the time or the constitution for a full-time job. This situation makes transitioning out of unemployment more difficult than people realize.

After a layoff, my friend Jenny got used to unemployment pretty quickly. She'd job-hunt for a few hours (which is, in fact, a lot to do every day without driving yourself insane). And then she'd have about twelve hours left in the day.

She started using that time to do loathsome tasks that one cannot possibly get done when one has a job: Chase down insurance claims, wait all day for a plumber, hand-write letters to aunts with no email.

Then she started making plans to see friends in the middle of the day. Then, in addition to the band she plays with at night, she joined an all-girl band that practices in the afternoon.

When Jenny finally landed an offer she said to me, “I can't take a job. I don't have time.”

I understood the feeling because I've had it myself. People fill whatever time is open. After all, the alternative to filling time is to stare at the wall, and unless you're clinically depressed, wall starring will not satisfy you.

So, while Jenny was grateful to have a job she was also nervous: Just as being laid off is a huge change in lifestyle, so is going back to work. “If nothing else,” she pointed out, “There will be no one to stay home to wait for the plumber next time the toilet overflows.”

Here are some things that make the transition easier:

Practice waking up. During unemployment, your body clock reverted to its most comfortable pattern, which probably included a late morning and frequent naps. Take a week to get used to working hours so you don't oversleep in the morning or pass out at your desk in the afternoon.

Embrace the commute. After a few days of a new commute, this is the line of thinking that usually happens: “I commute forty minutes each way, five days a week. That's 346 hours a year – 14 full days. Equal to a trip to Hawaii. Hey! I could go to Hawaii if I didn't have a commute!” But you can't do anything with that extra time if you are starving because you don't get yourself to work.

Look, if you really were not meant to commute then when you were job hunting online you'd have answered one of those “Make money working from home” spams. So turn up the radio, or open a good book, and find ways to love your commute.

Stop philosophizing. A common pitfall for those transitioning is to obsessively evaluate the virtue of the workplace. Yes, there are more virtuous things to do than your job. There is stopping war in the Middle East and sex trafficking in the Far East. Did you do any of those things when you were unemployed? Probably not. If you're so worried about saving the world now, you can give part of your new paycheck to charity each month.

Reevaluate your friends. People with jobs cannot party with six different friends every night of the week. You will have to get rid of the ancillary, party-all-the-timers. Keep the friends who understand about budgeting time.

Take solace in the memory of feeling crushed when you got laid off. You had that feeling for a reason. You liked going to work every day. You liked being part of something bigger than you and being valued by your community. Trust that when you go back to work, you will love work again, and that somehow, the toilet will get fixed, even if you can't stay home all day.

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The story of unequal pay: How I came to make more money than my husband

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On my first date with my would-be-husband I said, “You didn't tell me we're getting dinner.”

“I'm hungry,” he said.

So we went to dinner. He ordered a hamburger, fries and a milkshake. I ordered water.

Months later, when it looked like the relationship was serious, I told my would-be-husband, “You were a sociopath for not offering to pay for me that night.”

He said, “You didn't ask.”

“Ask?!?! Are you kidding me? I just left graduate school because I ran out of money and you just got promoted to a video game producer! You should pay!” I was screaming.

He didn't scream back. And he couldn't understand why I didn't ask for what I wanted at dinner. Those were two reasons that I stayed with him. Another reason was that he was doing video art that was shown in New York art museums. I was a grad school dork. He was an art-crowd hipster. I felt like my ship had come in.

I got a job writing for a large company and after watching Tano project manage, I convinced my company that I could do that, too. After a few years together, our finances were on par and we found ourselves applying to similar jobs.

One week, we both applied for the same job at GeoCities. The company was hot at the time, and a little unreasonable given the fact that employees were harder to come by than jobs (ahh, those were the days). In order to get through the interview process, I put up with a lot of corporate bullshit. No only did Tano refuse to put up with it, but he wrote a letter to GeoCities explaining that they asked for so much information from perspective employees that he should get paid to go through the interview process.

That was the turning point in our careers. I started making more money than him. I got funding for my own company. He got laid off and spent his unemployment money funding a new video project.

He became more and more successful as a video artist (read: no money, exciting parties), and I became more successful as an executive (read: lots of money, boring parties). The income disparity became larger and larger until it was clear that I would be supporting us long term.

We started planning our future so that my husband would stay home with our kids and his video editing equipment, and I would continue working as a software executive.

Then Sept. 11 hit us. I was a block away from the World Trade Center when it fell, and weeks later, my company went bankrupt. My husband's way to deal with the trauma was to volunteer at human rights organizations (read: Save the world). My way to deal was to get pregnant (read: Save my eggs).

I never planned to stay home with the baby. It just happened. First there were no jobs in the software industry. Then my husband landed his dream job at a non-profit. And then I fell in love with being a mom.

So we took a huge risk: We decided to give up my large earning potential as corporate climber, cut back our expenses drastically, and live off his entry-level non-profit salary.

My friends said, “He's finally making more than you. Doesn't it feel good?” My mom said, “When will he get a raise?” As usual, I ignored the comments.

But I got bored. I wanted to be in business again. So I took a small freelance writing job I had and got a babysitter for a few hours a day so I could grow my freelance writing. After a few months, I was making more money than my husband, again.

Now I understand that I am inherently good at making money and he is not. When I first met him, I needed money, and he had enough for a hamburger, which made him a good guy for me to date. Now that I have confidence in the workforce, I need the things money can't buy; my husband is interesting, kind and a great dad, and I feel lucky to have him. Sure, we all wish we could marry a millionaire, but you can't have everything in a spouse, so I made sure to get the important things.

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The secrets we keep at work: How I navigate with dyslexia

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Most of us have personal problems we hide from our business associates. In fact, most of us have been hiding problems since we were kids. Often, though, these guarded secrets provide a hidden stash of strength at the workplace.

My problems started at tap dance lessons. As an eight-year-old, I didn't know what to do when the teacher said, “Turn left,” but I pretended to know what I was doing. The teacher said to my mom, “Penelope's always a beat behind.”

In high school, I was in advanced English, advanced history, and advanced French. I waited until no one was looking to slip into my remedial math class. My teacher told me, “When you grow up, don't go into business.”

In college, I took a car trip from Chicago to Detroit and went up the wrong side of Lake Michigan. It's a big lake. And Michigan's a big state. So I shocked even myself when I missed the state completely and ended up in Wisconsin. It was around that time that I realized I was dyslexic.

Once I understood my problem, I was able to keep track of recurring problem situations and find ways to avoid them: For example, I became an ace with Excel so I didn't have to do math in my head. And I quit tap dance and took up swing dancing because the lack of structure in swing means that turning the wrong direction looks creative, not brain-dead.

Contrary to many predictions, I flourished in corporate America. Today I don't worry that the dyslexia will hold me back professionally. Now the dyslexia is just sort of interesting to me. I like watching how my brain works, and I like having a better understanding of why I did what I did when I was younger.

But I hide the dyslexia when it comes up at work. It's easy: Frequently someone says, “The bathroom is at the end of the hall on the right,” and then the person sees me turn left. The person doesn't say, “What the hell is wrong with you?” The person just says, “No, turn right.” And I know what to do. It never occurs to anyone that an adult doesn't know her left and right. So dyslexia is a secret I can keep.

In the perfect world, we would all list our secret disabilities on our resumes. These are the pieces of our lives that make us able to overcome adversity at work. Mental illness, physical limitations, family disasters, these are also secrets people keep from co-workers. Of course, if you bring this stuff up in interviews the hiring manager will think you are insanely needy (or just insane) and you won't get the job.

But keep an active stock of your secret difficulties, because these are what make you strong. In the face of these secrets, a screaming client, incompetent boss, or plummeting stock price all seem manageable.

Admittedly, dyslexia is not as earth shattering a secret as it could be; today dyslexia is fashionable among businesspeople and was the cover story of a recent issue of Fortune magazine. Heck, John Chambers, CEO of Cisco, is dyslexic. Everyone should be so lucky to have a brain so similar to his.

But as CEO secrets start to slip out, take a look at your own secrets. Recognize them for what they are: Huge difficulties that you have overcome to get where you are. And maybe, one day, we will add them to our resumes — in the education section.

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Make a story out of your career

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When someone asks “What do you do?” a one-word answer will put your career on ice. You need to have a story. When you want to establish a connection with someone, a story provides social glue. When you want to impress someone, a story is more memorable and than a list of achievements.

Early in my career, I interviewed for a job as a user interface designer. The hiring manager asked me how I got involved in UI design.

I could have said, “I thought it looked interesting so I gave it a try and I was good at it.” But anyone can answer the very standard how-did-you-find-your-career question with that answer.

So instead, I told this story: An old boyfriend was a programmer, and he worked from home, while I was in school. He plastered designs all over our bedroom wall and our living room floor so that he could think them through. Finally, I told him if he was going to mess up the apartment then he had to be the one to clean it, and I handed him the toilet scrubber. We argued about who had extra time for cleaning and who didn't and finally he said, “Fine. I'll clean, but you do the UI design.” And to his surprise, I did.

I got the job. And every time I have been able to tell stories in interviews, I have gotten the job.

When it comes to your career, have a one-minute story ready. It's the story of you — how you got to where you are and what your achievements are. When someone asks a question like, “How did you get into advertising?” tell your story.

When you interview, tell stories. You know you're going to encounter the question, “What are your strengths?” Don't give a list. It's not persuasive. Tell a story about how you did something amazing by using your strengths. This way you tell the hiring manager something memorable and you get in a bit about your achievements.

Once you get the job, keep telling stories as a way to promote yourself within the company. The first month of your job, no one knows you, so they ask questions like, “Where were you before this?” or “What sort of experience do you have?” These are times to tell your story.

If you are funny, make your story funny. If you are not funny, be vulnerable in your story. For example, when people ask me how I became a writer, sometimes I start my story with how I was working just blocks away from the World Trade Center when it fell and my software company never recovered. This is not essential to my story, but the World Trade Center brings people into my story right away.

Your success at your job will depend on you finding someone to help you navigate the corporate ladder: You need to find a mentor; you need to get on plum projects. You need to show people you are smart and interesting so that they want to help you. Don't assume that your work speaks for itself. It doesn't. Most people will have no idea what you have done, or what you do now. You need to tell them. And the best way to tell them without sounding boring or self-obsessed is to tell stories.

Still feeling queasy about talking yourself up to people? Check out the book Brag! by Peggy Klaus, the master of self-promotion. Worried that you don't know how to tell a story? Give business books a break and take a look at Flash Fiction edited by James Thomas. This is an anthology of two-page stories that have similar pacing as those you'll tell at the office.

Spinning a good story is difficult. But building a career without a story is even more difficult. So you'd better start spinning.

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Hire someone to rewrite your resume: It worked for me

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There came a point in my career when my company went bankrupt, the economy was in the dumps, and my network of friends and acquaintances was getting me nowhere. Like all job hunters, I had good days and bad days. On good days, I brewed coffee for that caffeinated, I-can-overcome-anything feeling. On bad days, I never got out of bed.

Finally, after a string of bad days, I called the phone number in a small ad I had come across in a bunch of business publications. The number was for WSA Resumes.

I told my contact at WSA that I needed a job. I told him I attribute my career success in part to the fact that I have always been able to write a very effective resume, but I have hit a wall.

WSA sold me the executive pack, which was $1000 for someone to rewrite my resume in three days. (They have less expensive packages, but I was in a moment of panic.) I talked to someone for a couple of hours, and she rewrote the resume in a way that smacks of a piece of direct mail: headlines, bullets, italics, and bold lines. The resume did not look like one I had ever seen. My friends said it looked cheesy. They said, “Don't send it.”

But I started to trust the writers at WSA because they noticed patterns and accomplishments in my career that I had not noticed. They phrased achievements in ways that I would not have thought of. They were able to frame my work life in a way that could open new fields to me. But most of all, I wanted to take a risk. I realized that I was getting nowhere and I needed to try something new and this was the only new thing I could think of.

To my surprise, my executive package came with a cover letter. It began, “If you can use my skills on your management team then I'd like to talk to you.” I cringed. I told WSA the letter is not my style.

There are actually a few more things I told WSA. You know how when you're spending a lot of money you get uppity? That's how I was. I argued about file formatting, I argued about hyphens and semi-colons. I'm sure I argued about more, I just can't remember.

Finally, I ran out of things to argue about, and, armed with my new resume, I started my job search again. I found no openings.

So I called WSA, and I was hoping they would not remember me — the person who argued about everything — but they remembered. “Yes, we can help,” my contact said.

They send out resumes cold. Which is, of course, in keeping with their direct mail perspective. So I signed up. It costs $1.50 a resume. My contact recommended sending out 8000 resumes. I wanted 500. He said direct mail is an odds game. I picked 500 companies. Then I changed my mind. Then I picked a new 500. Then I asked for some more lists. I was nervous. The cost worried me, but I took to heart the saying, you have to spend money to make money.

Finally WSA printed all 500 cover letters, stuffed envelopes, and slapped on address labels. Everything was ready to go. Then I sent an email to WSA with the subject head: EMERGENCY. I told them that I have a lot of direct mail experience and they should send the letter out on Tuesday, not Friday.

WSA dumped me. They tore up my letters and my check. They said I should find someone else to help me. So I took WSA's cover letter and the resume they wrote for me, and I spent a week finding email addresses for CEOs and I sent my resume myself – cold – to 500 CEOs. And guess what? I got fifteen responses and two job offers.

So I recommend that you hire a company like WSA. You will get a standout resume, and you will see yourself differently, so you will summarize your career differently, and you have a new chance at landing a job. And this is the other thing: unless your network is coming up roses for you, job hunting is, really, an exercise in direct mail. Once I admitted that I was not above a direct mail campaign for myself, things started happening.

I think WSA hates me, but luckily, I am not proud, so check out their web site: www.wsacorp.com.

(Update: WSA no longer exists. But the woman who oversaw my resume overhaul is Elaine Basham, and she’s still in the resume business today. Send her an email: elaine@theresumegroup.com.)

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Don’t wait until you bottom out to make a big change

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Don’t wait until you bottom out. The worst thing about big change is not that it's so hard to adjust. The worst thing is that we usually have to bottom out before we make a big change; we wait until there is no other choice before we give in.

I bottomed out in the car, during my commute between San Diego and Los Angeles. When I took a position near San Diego, I was so excited to have a paycheck that a two-hour commute back to LA seemed fine. And for about three weeks, the commute was interesting. Then I got bored. I tried listening to books on tape, which only served to ruin the experience of reading. I tried talking on the phone, which caused me to miss exits constantly and nearly double my driving time.

But the job was so good that I persisted with the commute. I started leaving my apartment in LA at 4am. No traffic meant an abridged commute, but also an abridged social life because I had to be in bed at 8pm. After a few weeks, I fell asleep at the wheel and woke up to the blaring horn of a large trucker saving my life before I crashed.

So I went back to my two hours each way. But on rainy days it was 3 hours each way. And finally, on a day of torrential downpour, just a few miles away from Disneyland, I lost it. I pulled to the side of the road and threw pieces of the inside of my car into a ditch. Then I went to Denny's and ate three pieces of pie. Then I called each of my friends to tell them I was quitting.

“Finally!” was what they all said. That's the thing about big change. By the time we are ready to do it, the need for change has been apparent to everyone else for months. Maybe years. It's easy for everyone else to see someone else's need for change — they don't have to make it.

Later, reading the want ads at my kitchen table, I was excited to find another job, and I lamented all the hours I wasted in the car. In my apartment it was clear that the job was not worth the commute. But that's how it always is: I always wish I had made the change sooner.

So here’s what to do with that information: Cut yourself some slack if you’re in a bad situation and not getting out. But get out. Sure, research shows that people have a proclivity to stay in a bad situation, but you can be an overachiever. Get out before you have your own version of tears in front of the Magic Kingdom. Force yourself to change before things get ugly.

It's impossible to see your own life as clearly as others do, but it's a good goal to aim for. As soon as you hear other people say, “Why don't you do [insert change here]?” give the question serious thought. Put that thought on your to do list, so it's right there in front of you.

Still not moving? Close your eyes and imagine what life would be like if you made the big change: Maybe it's giving up some responsibility at work, or quitting, or switching careers. These are the sorts of changes we put off and put off, but once we do them we feel huge relief. These days I try to focus on that relief; I still wait too long to instigate change, but I'm hoping my days of being on the bottom are behind me.

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The Q & A column: Where I (sort of) answer questions you (sort of) asked

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It's the Penelope Trunk Q&A column. I like to think my columns answer the questions that people don't ask but should. But today I'll answer the questions that people really ask.

Most popular question: How can I switch jobs and not take a cut in pay? Of course, the answer is that you can't. But people never ask the question like that. Instead they write six paragraphs about their situation at work, their spouse, their 401K, and then they ask me how they can avoid suffering.

Switching careers is hard. Only rarely do fifteen years in your earlier career count for anything. Usually, you start a new career on the bottom rung because your knowledge is not worth much. So you must weigh the terribleness of eight hours a day in a career you don't like vs. having to tighten your budget strings. Here's an idea, though: In your new job, where you know nothing, spend your time at home learning about the new profession so that you don't have time to go out and spend money you don't have.

Second most popular question: How do I become a freelance writer? It's a riff on the first question, really, but hey, it's a bad economy and lots of people are unemployed in their current field.

Here's how I became a writer. I started writing when I was six and wrote nonstop, about things no one cared about. Then I thought, I like to write, I should get paid for this.

So I went to graduate school for writing and the first day, the teacher said, “If any of you can imagine yourselves doing anything but writing, you should do that. Writing is hard, and lonely and full of rejection and you'll never make any money.”

I stayed in school (I had a fellowship — who can give up free money?) but after school I got a job in marketing at a Fortune 500 company. And I made a lot of money.

But I kept writing. For ten more years. I wrote after work and when my jobs were slow, I wrote at work. I used my vacation time to send writing to publishers who rejected me. But then they stopped rejecting me. And slowly, I realized that I could support my family with my writing. So I took the leap. (And, note, a huge salary cut.)

If you think you want to be a writer, first pay heed to my teacher's advice. If you still want to write, remember that most writers spend years and years writing before they get published. So keep your day job until you're sure you won't starve.

Third most popular question: How can you say that people with messy desks are ineffective at work? (This mail is in response to a column.) The answer to this question is that in the column I reported on a study that showed that co-workers perceive that people with messy desks are unorganized. The point of the column is that you can say you work fine with a messy desk, but studies show that your co-workers will never be convinced.

You'd think people would read this and clean their desks. But instead of cleaning their desks, they write to me, to tell me the study is wrong.

The defensive mail about messiness and the scared mail about career changes all reminds me of how difficult it is to be honest with ourselves. Most people get stuck (under piles of papers, under the weight of a lucrative career) because they are scared of seeing what is really best for them. It's easier to see fear of change in other people than it is to see it in ourselves. But seeing it in readers makes me more determined to face it head on in my own life. So, thanks again for all your mail. Please keep writing, even if you just want to yell at me.

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The way you prepare for the worst reveals a bit of who you are

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Now that the war is official, the workday will change a little bit for everyone. Furtive looks to CNN will be more frequent. Travel will be less frequent. And many people will be nervous for themselves or for loved ones. Depending on where we think danger lies, each of us will do a few quirky things to prepare our work selves for war.

As a New Yorker who was at the World Trade Center on September 11, I probably worry more than most people. I have started working closer to home so that in the event of emergency, I don't have to cross a bridge to get back to my son. (Bridges and tunnels closed in New York City on September 11.) You might think this precaution is extreme, but here in New York, you can feel the tension over terrorism, and most of it focuses on work. After all, that's where most people were the last time terror struck.

My friend who escaped the World Financial Center on September 11 focuses his worrying on the logistics of escape. He warns everyone to know where exits are in your office and to have a good computer backup system. “This way you won't have to think about what you're leaving in the office if you have to run.” (To some this planning might sound extreme, but New Yorkers remember that at least one person died in the last terrorist attack because he took time to finish up his office work before he left the building.)

The war makes my brother Mike worry about money. (Not surprising since he works in finance.) He worries that if his New York office is blown up, he will not have life insurance. He explains that while most companies offer employees life insurance, most companies do not actually hold a large enough policy to cover all employees if their building blows up. Usually the rules of coverage dictate that the highest up in the company receive insurance coverage first. So, to prepare for possible violence, Mike is taking out a separate life insurance policy for himself.

Workplace war preparedness goes beyond New York. My mom's office, in Illinois, now has departure drills. They practice for a crisis where they cannot leave the building, and they practice a plan for evacuating the building. This is not a bad idea; the success of the World Trade Center evacuation is largely attributed to the earlier drills. And, my mom says her co-workers feel more calm in the face of war because their company is thinking about the safety of employees.

My friend Liz, in Los Angeles, has a stash of canned food and a flashlight in her desk drawer. “You never know about terrorism,” she said. “And if I get stuck at work, I don't want to be hungry.” I asked her if her co-workers are taking precautions and she said, “in general, no.” But she lives in LA, and she pointed out that people already have supplies in their offices in case of an earthquake.

At this point, we live in a country that associates terrorism with the workplace. And now that we are officially at war, the threat feels more palpable. You probably won't keep canned food at your desk. But maybe you will take a tour of your office building stairwells. The most important thing is to recognize your own level of anxiety, and take actions to calm yourself down. Whatever action you take will reflect the type of things you worry about, and the type of person you are.

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If you’ve been unemployed for a while, consider a career change

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I know this isn't what you want to hear, but the people who are incredibly good at what they do are not unemployed. So if you are unemployed, you probably are not outstanding in your chosen profession. Sorry. But don't feel too bad, because everyone is great at something — you just need to find that thing. And there's no better time to soul-search than when you aren't making money anyway: No lost opportunity cost.

People who have incredible achievements in their career or show amazing promise have resumes that get snapped up quickly. Hiring managers receive hundreds of resumes for each job opening, and invariably, three or four of these resumes are outstanding. If your resume is not outstanding, you will not rise to the top of one of these piles.

Sure, there are exceptions: your idiot college roommate who is making six figures or the incompetent co-worker who survived the layoff that you did not. But I bet you cannot think of someone who has rocked the world of every boss she's had yet hunts hopelessly for a job.

Still wondering if you're one of the best? Well, if you haven't received some sort of offer in five or six months, that is not a good sign. Doors open when someone incredible knocks — even companies with hiring freezes make exceptions for outstanding candidates. Mike Russiello, CEO of Brainbench, says, “Companies are getting very good at identifying top performers — looking at things like, past roles in projects, certifications, and how someone interviews.” You are not going to fake anyone out with inflated Internet titles or achievements you cannot quantify. If you're not top you're not top.

And do not try to console yourself by saying that you are a rare find who suffers from bad networking. Sure, good networking helps. But the truth is that if you really are a rare find, the network comes to you. If you are amazing at your chosen profession, people call you, people check in with you, people want to be near you. You don't need good networking skills to answer your phone when it rings. You only need good networking skills to compensate for the fact that no one calls.

But instead of banking on good networking skills, how about changing careers to do something at which you are, indeed, outstanding? Unemployment is a great point in life to make use of excess time to figure out where your gifts really lie and what you really love to do.

Most people who are not outstanding in their job are not doing what they really love. The good news is that if you do what you love, you're more likely to end up rich. One survey of 1500 undergraduate business students found that 87% of the students said they wanted to make money quickly and figure out self-fulfillment later. The remaining 13% of the students said gratification was more important than money. Twenty years later 101 of those students were millionaires and all but one of those students were from the group who said gratification was more important than money.

There's nothing like a bad economy to make you more honest with yourself. Less money to go out to dinner, less money to go shopping: Try sitting at home and doing some soul-searching. At least entertain the possibility that you are not that great at your work and your talents lie somewhere else. You can spend another six months sending out mediocre resumes to scarce job leads, or you can recreate yourself as a person who is in love with your career choice and more passionate and competent than any of your competitors.

Change is difficult. And career change is especially scary. But in this economy, some people will find that not changing is more risky than changing.

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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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