Career lessons about grit (and nepotism) from Oscar-nominee Sofia Coppola

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When the Oscars run (probably overtime) on Sunday, I'll be rooting for “Lost in Translation” for best picture. Not that I have seen the other competitors, but I loved this particular movie. In fact, I was so impressed that I read up on Sofia Coppola. In the process, I learned more about career management by how she managed hers.

Of course, Sofia has had more advantages than most fledgling directors. Her dad, Francis Ford Coppola, provided her with a stunning apprenticeship, including giving her a part in “The Godfather: Part III,” screenwriter lessons and producing “Lost in Translation” for her.

But before I launch into a celebration of Sofia Coppola, I need to say that the U.S. is not a meritocracy: Rich people are better connected, so they get better jobs. And rich people who are not well connected tend to get better jobs because they have an easier time envisioning themselves in a successful career than poorer people. An example: My younger brother, now 21, did almost no homework in high school, and he recently landed a job most college graduates would covet — investment banking in Europe.

He used connections and a lofty vision of himself to get it. He started on his career path in high school by getting a management job at a Blockbuster store? This was easy in the wealthy community where we were raised because no adults there wanted (or needed) this type of job. That left the entry-level management jobs to high school students. At my local Blockbuster store in sort-of-rough-and-tumble Brooklyn, the managers are in their thirties. So the first moment of inequality is that rich kids can get great jobs in high school.

Since he had been an actual manager before, I was able to give him a management job in my own company during the summer after his freshman year of college. And I concede he did an outstanding job. But only a sister would give a 18-year-old a management job in a software company.

The next year, my cousin, a high ranking guy at a big ad agency, gave my brother a summer internship even though my brother missed the deadline for applying and wasn’t in business school like all the other interns. And to be honest, my brother did a great job of mending fences with a basically estranged cousin. He also had a stellar resume written by yours truly.

So by the time my brother graduated from college, he had a great experience on his resume that helped him land his new job in Europe. I don’t begrudge him that. And I admit that with a lot of effort and even more luck, a poor kid could land the same positions as my brother. But it’s clear he had a million advantages that poor kids don't have, so he didn’t need as much luck.

Speaking of people who don't need luck, let's get back to Sofia. Tracing the career of a person who had every advantage in the book can make one a little peevish. So how do people act when they have every advantage? That’s the relevant question, because probably we should all act the same way.

People like my brother, who have relatively few advantages compared to someone like Sofia, ask for everything — just to see if they'll get it. He asked my parents to pay for him to attend an expensive college even though he didn’t do a lick of homework in high school. Even though he knew he wasn’t qualified, he asked my cousin for an internship. He could do this because he could envision himself getting it. Poor kids have to stretch to imagine having food on the table every night.

In Sofia’s world, though, you don't just ask for something — you operate as though you’ll definitely get it. The difference is that my brother and others like him still need to make contingency plans, whereas really well connected people don't. Thinking this way is what helps them to succeed.

So Sofia Coppola wrote “Lost in Translation” for Bill Murray before he said he'd make a movie with her. Once she finished the script it took her months to finally get it to him. Then she left messages on his 800-number for five months before he responded to the script.

We should all believe in ourselves so much. How many of us would spend months on a project that might not happen? It's her belief in herself that impresses me. It doesn't matter if your last name is Coppola; if your screenplay is terrible, Bill Murray won’t do it. In that sense, Sofia did, in fact, take a gamble, even though she wasn’t in danger of starving like some screenwriters are. And with the biggest risks come the biggest rewards.

Maybe rich people can afford to take more risks. But my point is that by believing in yourself, as Sofia Coppola did, you may be able to leap career hurdles you once thought were impossible. How can you not root for her on Sunday?

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List of ways to ruin a list

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The goals you have for your life are only as good as your daily to-do list. You can make all the grand plans you want, but if you don’t stay on track each day, you won’t reach those goals. To-do lists are for people who believe in their dreams and their ability to reach them. List makers create daily plans for success. In other words, everyone should have a daily to-do list.

If you aren’t careful, however, your list will become more of a procrastination aid than dream machine. Here are seven typical ways you can undermine your list:

1. Ignore it. This is my pet thing to do. If I can’t handle my life that day, I don’t look at my list. This allows me to think I don’t need to do anything. But then the rest of the week is hell because I’m compensating for stuff I ruined by ignoring it. It would have been easier to review my list, accomplish the most pressing items, and then go back to bed.

2. List vague tasks. Take, for example, “work on presentation”. When is this job finished? How many things need working on? Why would you start this chore if you have no plan for completing it? This item is like poison ivy — you see it and go another direction. Break down the items on your list into manageable parts. Besides crossing items off the list is fun, and the more to cross off the better.. I’ve been known to write “buy envelopes” as one of the tasks needed to send resumes. It’s an easy step in a hard process — makes me feel like I’m getting something done in my big-picture goal of landing a job.

3. Create a wish list. A wish list is not a to-do list. It’s important to have life goals and it’s nice to be lofty, but no point in putting “buy a house” on your to-do list. If you really can buy a house, try listing an easier item like, “call mortgage broker” If you can’t get that far, make a list of things you’d like to have in 10 years. Include “buy a house” and post this list on your fridge. Then get back to your to-do list — every 10-year plan is the culmination of 3,650 daily to do lists.

4. Switching manically between types of tasks. E-mail, phone, errand, e-mail, phone, errand. This is not a productive day. A good day is e-mail,e-mail, e-mail, phone, phone, phone, errand, errand, errand. So organize your to-do list so that you do all your e-mails in one or two sittings.

5. List items you’d like to do but shouldn’t. These are fun things like learn 1000 words in Italian or knit an extra-large sweater. Most working professionals do not have time for these in a typical day. Unproductive adults indulge themselves in doing them anyway because it makes them feel productive. I know I do not have time to make cupcakes for my husband’s birthday and I should buy him a cake from the local bakery. But I put “making cupcakes” on my to-do list anyway, and then, when he comes home, I’m annoyed because making his cupcakes ruined my workday.

6. Lose sight of the big picture. How many people are unemployed but don’t have “get a job” on their list? If you’re among them, good for you — because “get a job” is too vague. But you should include job-search-related tasks, such as “Send out six resumes” or “make two networking calls”. So many people omit chores related to their most important goal because they seem obvious. But if you don’t put them on the list, they won’t happen.

7. Write a novel. A list is not a novel. It is one page.

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A Valentine for my husband

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In honor of Valentine’s Day, this is a love letter to my husband. But apparently, he is too busy to read my column, so he won’t see the letter.

The last time I complained about his disinterest, he said, “Okay, fine, read me your columns.”

So I read a column out loud to him. And in the middle of it, he fall asleep.

To test him, I said, “So, what do you think?”

He jerked his head up, like a college kid in an 8 am class, and he said, “Uh. It got slow after the first couple of paragraphs.”

Fortunately, my affection for my husband isn't based on his listening skills. I love him for other reasons, including his fearlessness when it comes to changing careers. He isn't afraid to reinvent himself professionally so that he always does something he finds interesting. His excitement about his work makes our life together more fun.

My husband's first job was as a composer. When he was ten. For most kids this wouldn't be a job, but his parents couldn't afford a private school in Los Angeles, so my husband got a scholarship to a top-tier school for his musical talents.

In college, he decided that to be a great composer you need to have something very new to say, and he did not have something that new to say about music. So he quit music.

He went to film school and earned spending money by editing soft-core porn: “The Magic Blanket Bikini.” (He says it was very, very, soft because the star announced midway through filming that she wouldn't take her clothes off.) He made video art for his master's thesis, and his work became so well known that it is part of the curricula at UCLA's film school.

But he grew tired of the film industry after one too many Magic Blankets. So when he graduated, he took a job designing video games. He learned to say Ka-pow! and Ouch! in four languages, and he got to wheel and deal with big budgets from major gaming companies.

I married a game designer with a penchant for piano and a portfolio of films that featured ex-girlfriends being constrained. (“The director,” he explained, “always dates the actress.”)

On September 11, my husband found himself looking over me, dust-covered and shaken in a hospital bed. Suddenly, he wanted to save the world. He became an unpaid volunteer for nonprofits until one hired him. Now he helps prisoners establish safe, fulfilling lives when their sentence is up. His job would stretch my patience (admittedly, thin) to its limits.

My husband drives his parents nuts: “We drove to all those music lessons and then you go to film school! We paid for five years of film school and you make video games!” He drives my parents nuts, too: “What is his job? Video is not a job! Volunteering is not a job!” But my husband’s approach to work makes me excited; Members of my family picked a career and stuck with it forever, even when they stopped being fun.

Our careers are not who we are. But what we choose to do with our days reflects our values. I picked a partner who tolerate being bored or uninspired, and his standards for life encourage me to raise my own. His career choices also reveal a bigger heart than I saw when I married him — except when it comes to reading my columns.

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Sometimes work is a welcome distraction

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I am four months pregnant. But the baby is dead, inside me, and must be removed. I am devastated. I always knew this could happen, in the back of my mind. But you are never prepared for something like this to happen.

When I first heard the news, I did nothing. Cancelled every plan I had. Sat in chairs staring at walls, laid in bed hoping for sleep, and cried. And then came the day of the week when I had to either write my column or skip a week. Skipping a week, I thought, would probably be okay. But then I thought. Well, I'm not doing anything. I *could * write a column.

In the face of tragedy work is a weird thing. On the one hand, it becomes unimportant. I think back to the day before the day I knew. My sister-in-law called me and said, “How are you feeling?” I said, “Really rushed. I have two deadlines, and I don't have time to talk.” She said, “No, about the baby.” That day, work was so important.

On the day I found out the baby was dead I had scheduled three interviews. It was a tight schedule but I felt the interviews absolutely had to get done that day. But at the doctor’s office, when I was crying so loudly that I was taken to a room farthest away from the waiting area so as not to scare already jittery expectant mothers, I didn't care if the interviews got done. I know it is a cliche that a job isn’t life or death, but you see that truth very clearly when there is death.

Co-workers who, in the face of death, treat work as more important than death seem crazy. I know because of a boss whose mom died three hours before what was, admittedly, the most important speech of his career. He felt obliged to tell his direct reports the news so they would know why he was crying in his office. Word spread fast. Condolences poured in from co-workers throughout the company. Then he gave the speech. And no one could listen. We all thought, “Why doesn’t he go home? Why isn’t he upset? Why is he standing in front of us now?”

Co-workers who treat less serious events as if they were a death, seem equally crazy. They appear melodramatic and unreliable. For example, when a colleague’s boyfriend of one year walked out on her, she missed a week of work. That’s too much. I’m not sure where the line is for what’s too much, but a week is too much for that.

So where is the line for a dead baby that I never saw, but has been a part of me and is still inside? For two days I did nothing. But today I feel like work might be the best thing for me. For most of us, work isn’t just about getting a paycheck; it’s a way to connect with the world. I don’t want to be alone today, so I’m working.

And although I postponed my interviews, I won’t miss any deadlines. Not because I think the baby’s death is unimportant. In fact, in light of this event, I am sure people would be very sympathetic about my missing deadlines. But I won’t miss any because in the midst of personal tragedy, work is a way for me to maintain structure in my life and find not-so-tragic things to think about.

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Don’t tell me you’re busy

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Let’s abolish the word busy. When you ask someone, “How have you been?” and they say, “Busy,” it doesn’t mean anything. I’m sick of it. We all have the same 24 hours to fill. Everyone’s are filled with something.

The difference is that the “busy” people feel frenetic during those hours. Those of you who walk around telling everyone how busy you are, get a grip. Make some tough choices and calm down. There’s a big difference between a busy day and a full day. The former is so frantic that you aren’t effective.

Don’t tell me you can’t help it. You can. Here are the steps to take:

1. Recognize that a frenetic life is a life half lived. You should aim for “Flow,” a concept from Mihaly Csikszentmihalyi. Flow is a unique state of mind where productivity and creativity are at their highest. Csikszentmihalyi shows, in his wide-ranging study, that Flow generates the grand ideas, phenomenal work, and intense, rewarding experiences that people identify with happiness.

Flow occurs when you are fully present and engaged in what you are doing; the concept of time melts away in a commitment to the goal-oriented activity. This feeling requires being occupied and engaged for uninterrupted chunks of your day without ever once thinking that you’re rushed for time. People who are busy do not get this feeling.

2. Recognize that you are addicted to busy. You like what busy does for you.
Busy gives you an excuse for poor performance. Busy gives you a way to ignore parts of your life that are falling apart and need attention. And when what you do makes you feel inadequate — for example, if you’re a volunteer, taking care of a parent, meditating or doing other things that are not valued by society — busy gives you something to say that society does value.

Many people mistakenly feel that busy means important. But busy really means out of control. A full day means planned and prioritized. A busy day means frenetic and unorganized. Full is fine. It is expected. But important people have full days, not busy days, because important people can’t afford to be out of control.

3. Prioritize. This does not mean making a to-do list. Nor does it mean making a list of career goals. You need to list what you want in life. It should be a short list, because life is short. Don’t make a list of dreams; you need to give up your dreams. Not all, but most.

This is because being an adult means making choices. It means admitting that we cannot do everything and choosing to devote the time we have to what’s most important. By not making choices, you aren’t facing the realities of adulthood. By scheduling your days with more things than you can accomplish, you are not taking control of your life. You’re letting chance take control. Chance will dictate what gets done because you refuse to prioritize.

4. Say no. Whenever someone asks you to do something, be ready to say no. Your priorities at work, home, and during your personal and networking time should be clear.

Do not worry that you’ll hurt someone’s feelings by saying no. To do something well, you must be focused. That takes self-discipline. But when you say yes to please someone, it shows you lack the self discipline to be truly focused. Saying no is a gift to the people and projects that are the priorities in your life.

You do not automatically have to say yes to everything you’re asked to do at work either. Your boss establishes your priorities. If she then gives you work that would compromise those priorities, you can refuse (with an explanation). Sticking to the plan will makes you look smart and committed.

5. Change how you talk. Don’t ever say again that you’re busy. If this is your current response, realize you can’t bear to give up your dreams and being busy veils your fear of underperformance. You need to say something more honest than busy.

When you have done the first four steps, you will no longer be busy. You will have room to be focused and enthralled. Then, when someone says, “How have you been?” you will have something more interesting and engaging to say than “Busy.”

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List of things I hate

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Here is my current list of things I hate. It's an on-going project that simmers week after week until it reaches boiling point and I have to spend a column venting.

1. People who are not coachable. They get good advice and don't take it because they think they know better. Everyone has blind spots that a little advice can shed light on. If you don't know how to take advice, people will stop giving it to you. And then you will stagnate. And the people who tried to help you will think to themselves, “Good. I was pissed that he wasted my time.”

2. Three-page resumes. Two pages are okay. Sometimes. Like, if you've been in the workforce twenty years, or if you don't know how to enlarge the margins in your word processor. But anything more than two pages is someone who has lost all perspective. There is not enough that is important about your career to fill three pages. You give away to all potential employers that you are mired in detail.

3. The high and mighty. The people who say, “I'd never work for someone I don't respect,” or, “I'd never play office politics to get ahead.” Get real. If you want to be able to put food on your table you will need to learn to work for someone else, to do things a way you don't agree with, to do some work that doesn't matter to you. If you can afford to lose your job constantly in order to stay on moral high ground, then you didn't need a job to begin with.

4. The 8pm meeting. I don't care if you don't have kids. I don't care if no one in your whole company has kids. Each of you still needs to get a life. Just because you have no one sitting in bed waiting for a kiss goodnight doesn't mean you should be at work. Go to the gym. Go to a movie. Participate in aspects of life that do not have a P&L. Well roundedness will make you a more interesting person, and even if you don't care if you're interesting, your co-workers will, so you will do better at work if you leave work.

5. The economically alienated. Don't blow off the company party because you have season tickets to the Opera that night. Don't complain about your butler to people who don't even know what a butler does. It's one thing to have a pay scale as if you are god and the people who work for you are morons. It's another thing to shove that in peoples' faces on a daily basis. Act like you're part of the team or you won't have a team to act for.

6. The people who won't change. Each week I get letters from people who say they hate their job but they can't change it because they have so much seniority. Or they want to stay home with their kids but they don't have enough money. Look, unless you are totally impoverished (and almost no one writes to me from this category except maybe recently divorced moms who have never worked) then you can do it. Sell your house. Move to Kansas. Stop sending kids to camp. If you want something enough, you will figure out how to live on less money. If you don't make the change then admit to yourself that you want money more than – a job you love/full days with your kids/you fill in the blank — and stop complaining.

7. People who don't make lists. Usually these are people who can't face everything they want to do. Or they don't know what they want to do. Either way, making lists can change your life. Start small: Distributing a list of items to cover in a meeting makes you look like a leader. Then get big: Maintaining a list of career goals keeps you focused at work. If you love to make lists, try branching out. Like, make a list of lists you could write. Or make a list of things you hate. It's such a big relief.

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Summer reading is serious business

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The flair with which you grow and prune your reading pile directly affects your career trajectory. Sure, you can learn from enlisting mentors and taking on new projects, but you can learn with the most focus and speed by reading on your own.

But don't be swayed by the business book bestseller list. Instead, devise a reading plan for yourself that encourages major shifts in thinking; Leaps in your thinking encourage leaps in your career. Here are some guidelines for your summer reading:

Make summer a time for big questions.
All-day beach trips are great for long books. Blow up rafts promote uninterrupted thinking. Don't waste these precious chunks of time on John Grisham.

Instead, think of a big question, the kind that has no right answer but lots of angles, and dive into the relevant reading. One summer, when I was looking for the meaning of my nine-to-five life, I asked the question: “What makes a career feel satisfying?” Another question that has ruled my summer reading is, “What sort of human-computer interaction is fun?”

Sometimes, the answer to the question isn't nearly as revealing as just discovering what question really piques your interest.

Think like you're studying for a mid-term.
For most of us, rigorous thinking ended in college. But the organized, complex, thinking that gets you through upper-level philosophy courses also makes you sharp at the office. So keep on your toes by reading about Supreme Court decisions: They twist and turn the Constitution in ways that will give anyone an intellectual workout; they're not as dry as Kant and not as brain numbing as Martha Stewart's lawsuit.

(Bonus: reality TV can't hold a flame to some of those cases. For example, a guy kills a cop, and gets shot back — blind in one eye and paralyzed from the neck down. Another cop follows the guy to the hospital, and interrogates him. The injured man screams, “I'm about to die! Leave me alone!” Then he spews self-incriminating information. Legal gathering of evidence, yes or no?)

Read to understand people.
Your career is dependent as much on people skills as it is on how well you do your work. So I recommend An Na's novel, “A Step from Heaven” (Front Street, 2001), which I love. It's a kids book. (For those of you who don't read kids books, you should. They'll remind you of that terrible time of life that is junior high school, and then you'll appreciate where you are in life now, no matter where you are.)

“A Step from Heaven” is about a Korean immigrants, and it does a great job of showing the barriers to success that people of American-born parents do not face. Think of these barriers when you manage someone who didn't have all the advantages in life that you had. Remember that topics like patience and compassion are as important to your reading pile as leadership and finance.

Don't read to stroke your ego.
Just because you have already accumulated a summer reading pile tall enough to last fifteen summers doesn't mean that you have to read those books.

Our tendency is to be attracted to topics we already know a lot about. For a while, I was reading too many books about time management. I am a good time manager, so each book's recommendations would allow me to say, “Great, I'm already doing that. I'm great.” When I forced myself read about sales, because I was uncomfortable in that area, my reading became much more productive.

Force yourself to read in areas that are unfamiliar to you. Read about your weaknesses. Read about people who annoy you and topics that bore you. The best antidote to disdain is a deeper understanding.

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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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Marketing lessons from Esther Williams

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In the early 1990s, when the job market was very bad, I had a college degree that was getting me nowhere. So my friend got me a job signing Esther Williams' autograph for fans.

Esther who? That's what I said. Esther Williams was an Olympic swimmer in the 1940s when the Olympics were cancelled, and she took her bathing-suit-clad body to MGM where she was the star of water musicals. If you've never seen a water musical think Ginger Rodgers with nose plugs. Esther was hot in her day, and believe it or not, she's still hot among nostalgic old people, young girls who like swimming, and gay men who like kitsch.

I worried that the job was illegal, but the person who hired me assured me this is a very common job in Los Angeles. After all, no one would squander life as a movie star by sitting around all day writing autographs for the millions of people who request signed photos.

At the time, I was very upset that the only job I could get wasn't even significant enough to have a title. (Question: “Uh, what do you call this kind of job?” Answer: “I don't know.”) But now I realize that even though I hated the job, I'd have to say that Esther Williams was my first marketing mentor, and I built my own marketing career around rules I learned from her:

Quality control is important.
During my first week, Esther gave me three copies of her signature (different pens, different sizes) and told me to practice. I submitted my best shot to Esther and she said, “Make the E's loopier.” I looped and resubmitted and then she gave me the go-ahead.

Give the customer what they want.
When I started working for Esther, she was well past 60, so when someone requested an autographed picture, you just knew they weren't asking for one she took the week before. So we had a stack of copies of old MGM promotional photos: Esther as Olympic swimmer, Esther as showgirl, there was even one of Esther in a sort of kiddie porn motif. But for the die-hard fans who requested it, I also had a photo of Esther when she was about 50 years old: A head shot.

Cut costs.
We had 8x10s, but I only sent those if the person enclosed postage. Otherwise, Esther instructed me to send a 5×7. Sometimes people would request an 8×10, and even if they didn't send postage, I'd send a big photo. I figured it would make a happy customer and it wouldn't break her bank — after all, she still received residual checks from Million Dollar Mermaid.

Stay out of court.
One guy sent three, pristine Life magazines with Esther on the cover. He wanted each cover signed, and he wrote a note that said, “The last time I asked for an autographed photo I am sure it was not you who signed it. You better not let anyone mess up these magazine covers or I'll sue you.” Esther had warned me to send professional requests to her, so she signed the covers.

As soon as I found another job, I quit working for Esther. But working for Esther Williams taught me that any job can help your career if you let it. Each person, no matter how weird, has something to teach you. And each business has a gem of genius because, hey, they're making enough money to pay you, aren't they? So don't be so upset about the crummy job market; you are about to start your own Esther Williams experience.

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The best way to break rules

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The current business climate encourages rule breakers. Not the kind at Enron — those are law breakers. Rule breakers break with convention. Sallie Krawcheck, for example, was a top stock analyst in the 90s. She could have gone to a big investment firm where the heavy-hitters gave stock advice that, in hindsight, seems to have been garbage. Instead, she stayed at a boutique research company, which she made famous for quality. Last year Krawcheck took an enormous career leap to become the CEO of Smith Barney precisely because she had broken with convention years earlier.

All great business people have had to break some rules on their path to huge success. But be careful: people who break all the rules all the time are not innovators or a breath of fresh air, they are sociopaths. Rules create order and process, and no company can operate in a state of anarchy. The key to breaking rules is to know which rules to break.

Break rules that matter.
You always take a risk when you do things differently, so make sure there's big payoff. Does your company have a dress code? Adhere to it. No one ever made corporate history by wearing torn jeans on casual Friday. If you follow most of the rules, then when you break a rule people will be more willing to let you go with it.

Weigh the risks.
There are a lot of rules that deserve to be ignored, but sometimes breaking rules is more trouble than it's worth. As a marketing executive in a software firm, I was required to have engineering signoff on every word on the front of the box. The process became an opportunity for code-heads to make illiterate proofreading comments. But I still got signoff every time, because while breaking that rule would save me a day in the box production schedule, it would cost me weeks of assuaging engineers' egos.

Know the reason for the rule before you break it.
The best example of this is the renegade barrista at Starbucks (if she has not been fired yet). She keeps changing the composition of standardized drinks. Lattes have a little less milk, Frappuchinos have a little more foam. I overheard her declaring that she gives customers what they want even though they don't know to ask for it. This would be a great idea in another company, but the charm of Starbucks is that wherever you go — Seattle or Milan — the drinks are consistent.

Break rules so that you can be more effective.
Andy Grove broke rules of convention by pioneering the idea of management by walking around. He didn't necessarily set out to break a rule, he just wanted to manage in a way that felt comfortable to him, and walking around talking to people suited him well.

Break rules that other people would be scared to break.
In 2000, when everyone was still running on Internet adrenaline, stock analyst Jon Joseph announced that the chip sector was in for a big fall. At the time, he received so many death threats that his company hired a bodyguard for him. Recently he was rewarded for going against the grain by receiving a top post at Smith Barney.

Good rule breakers spent part of their life as good rule followers. Jeff Bezos is renown for bucking the conventional wisdom that CEOs shouldn't micromanage. He does, and it works well for him. But before he was a rule breaker he spent the beginning of his career in consulting and finance positions where he followed the rules for entry-level employees and did what he was told to do.

If you think you've got a situation where you should definitely break a rule, remember that good rule breakers are good salespeople. You can't just break a rule and think it'll stick. You have to explain to people why your way is better. Get people behind your new way of doing things so that your new direction can have the large impact you hope for. Break a rule and people will gossip; lead down a new path and people will follow.

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