In case you've never noticed, I rarely interview anyone for this column. Most of my sources are family and unsuspecting friends who complain that I make everyone look bad. But it is not true. It is true that they THINK I make them look bad, but in fact, I could rip them apart in my column, and I do not, in the spirit of being invited back for Thanksgiving and Birthdays.

Recently, I have taken up columnist tasks that require me to interview strangers. And, like the courtesy I give to my family, I do not trash the people I interview. But I am at my breaking point. Some people are so incredibly stupid about their career that I actually struggle to make them seem intelligent during the interview.

So here are two interviews from smart people who are career idiots. (But first, a caveat: I am making the people anonymous. Many readers generously send stories from the field. And really, I love to hear from readers. I learn a lot. So you should know that if I think you're an idiot and decide to write about it, I will at least disguise your identity.)

Career idiot number one: The Apprentice. Not all of them. Just the unlucky one I interviewed. He really did not have a career, which was, undoubtedly, the cause of his ridiculous antics on the TV show that eventually got him fired. But he decided to make a career out of getting fired by becoming a public speaker.

Here are things you need to become a public speaker:
1. Something to say. This guy had nothing. Except to tell me that he was available for speaking.
2. You need an ability to answer questions from the press so that your name gets in the paper and people recognize you and hire you as a speaker. He did not answer my questions, which were all softballs. And he even asked to see the notes I was writing so he could edit them. I laughed.

The lesson from this career idiot is that if you must be a poser, pose carefully. When you first start being something new, (for him, a public speaker) you need to pretend you are that person so people hire you as that person. But do some research before you start pretending. At least learn the basics of how to conduct yourself, and what people will ask of you.

Career idiot number two: The painter whose identity I probably don't even need to hide because you don't know him because he's never sold a painting.

He makes a lot of money as VP of Something Big at his tech company and he gave notice six months before his wife quit work to have a baby. He is starting a career as a painter. He has no idea how to get his art to the market, or how many pieces he'll have to sell to support his family. But he says he has to be true to himself, and painting is his dream.

He says he feels trapped at his current job. This is the picture he paints of trapped: He wanted to move across country, so his large and generous company let him set up remote office in his new home. He hates the long hours of his lucrative job, and his company would let him go part time, but he doesn't ask for that because he doesn't want to like his job. He fears that if he liked his job he wouldn't quit to do his art.

Here is the lesson from career idiot number two: Take a big-picture look at what you have. It might be a lot better than you realize. Remember the first time you woke up next to the love of your life, and up close, in the morning, their face looked splotched and scruffy and gross? Well jobs are like people; they never look great up close so you need to pay attention to the big picture. This guy's big picture is that he has a great job for supporting his new family and painting on the side, and if he's really an artistic genius then he can make a bundle painting and quit his job.

I hate to be a buzz kill here. I'm not saying that I don't like dreamers. I do. I like people who reach for careers that are fulfilling but difficult. But just because the odds of success are low doesn't mean you have to make them lower with poor planning.

I got a book deal. So this is, undoubtedly, the first of at least a hundred columns that will plug the book, which is not coming out until spring 2006. Far away, yes, but not too far for you to make a note in your planner: “Buy Penelope’s book.”

I got a big advance for the book. Not big like Bill Clinton, who received four million dollars. But big enough to buy a nice house (if I didn't live in New York City, which I do) and big enough to stop fights with my husband about money (no small feat, believe me).

Yet for all my recent success, someone asked me last night, “So, what do you do?” and I didn't say anything about a book. Lame. That's when red lights went off in my head. Experience tells me that one needs to manage career success as carefully as one manages failure. So I am making a plan to manage the book success.

1. Take time to be happy.
In the past, I have been at points of great success and been too driven toward the top to see how far I had come. For example, when I was a professional beach volleyball player signing autographs and smacking a volleyball in Bud Light commercials, I was always unhappy that I was not in the top twenty players. Now, as someone who makes a living sitting at a desk, I am amazed at my former athletic achievements (and muscle mass). But I never enjoyed them when I had them. I focused too much on what I didn't have.

So I am taking a month to bask in my book success. I am telling myself that my hard work and tenacity with my book proposal paid off. I am patting myself on the back, which I always tell other people to do, but rarely do myself.

2. Tell people about the success.
One of the people I mentor amazes me with his diligence when it comes to telling me about his success. I don't have a very close relationship with him, and sometimes I think to myself, “Why is he telling me this? Why is he sending me links to his stuff?” but I always end up thinking better of him when he tells me his achievements. He has taught me that there is very little harm in letting people know what you're doing that is great.

When it comes time for me to send emails to announce my book deal, my first instinct is to be hesitant — thinking with each email, “Does this person really want to know? Does she care?” But my mentee has taught me that I shouldn't think twice. I should just send the email. If someone is offended by my announcement then they were probably never going to be helpful to me anyway. Being shy about my success will get me nowhere.

3. Draft a strategy to leverage the success.
Too many times in my life I have followed up success with worries — that I would not get to the next level, that the achievement would slip out from under me. My worries about leveraging success undermined my ability to do it.

Take, for example, the time when I was running my own company and hiring all my friends and family and we had tons of money and great press. I spent my days so worried about where to take the company next that my hair started falling out. Really. I never even knew that women could lose their hair from stress until my shower drain clogged.

This book deal has great potential for worries because really, a book deal is all about sales. I have to make sure people buy the book. Also, I can't help thinking about the next book deal. Writing is a business; there's no point in launching one product and calling it a day because a thriving business is a bunch of products.

So this time, I'm going to use my success as a starting point for strategic thinking instead of fearful thinking. And the first thing, in this vein, will be to craft a new answer to the question, “What do you do?” I need to get my book into the answer.

Most of us never had dreams of being a mathematician or economist; we suffered through algebra as a means to get to senior prom. But if you think you’re going to march up the ranks of management with no math, forget it.

So first, the bad news: You absolutely have to manage the math side of business if you are going to get ahead in your career.

The good news is that you don’t need to be good at math in school to be good at math at work. In fact, so much of workplace math is practical that people who are excellent mathematicians are at a disadvantage. Math at work is about spinning the numbers. And mathematicians are focused on finding pure truth. There is no pure truth in workplace numbers.

Job Hunting
Take, for example, your resume. The line that says, “Increased sales 50%.” That could be true. It could also be true that everyone else increased sales 65%, or that the next quarter you got fired for under performing, or that customer returns on those sales were an incredible 45%.

Numbers at work tell a story, and you pick numbers that tell the best story. You never lie, but you cannot tell every piece of information in the whole world, so tell the ones that suit you best.

The best resume is one that lists quantified achievement. So you should evaluate all projects in terms of possible numbers. If there is no way to show project victory in a number, do not take the project. And do not think for one second that you are in a career that does not require quantified success. Even a ballerina can use numbers: “Increased ticket sales 35% when I took over the lead in the Nutcracker,” sounds much more persuasive than “danced beautifully.”

Image Management
Once you land the job, the easiest way to let others quantify your failure is to go over budget; never, never, never go over budget. Always pad each line of your budget, because you can’t control everything and some costs will be higher than anticipated. This budget bloating will force you to cut line items from the start, but better to cut them at the beginning than be over budget at the end.

Before you go blaming your cost overruns on someone else, remember that your boss’s boss never sees your budget line by line and definitely doesn’t care about your finger pointing. She only sees your final number and whether or not you stayed within budget. The best way to manage your image among the higher-ups is to stay in budget no matter what.

Getting a Raise
Use numbers to negotiate your raise, too. When it comes to compensation, do your own research to present a rational, numbers-based explanation for why your salary is not in line with comparable salaries in your field.

If your company won’t budge, figure out which non-financial perks will equal a financial perk. (Finally! A use for high school algebra!) For example, extra vacation time is free to the company and a laptop, after tax deductions, is very cheap for the company.

If you want to get more comfortable with this kind of math, take a look here for help.

Presentations and Reports
This is my favorite book about numbers: How to Lie with Statistics, by Darrell Huff and Irving Geis. This book is a must for everyone. Each of us must use numbers to make our point. So we should all learn to present the numbers in the best light possible. Managing numbers is not about lying (this book title aside), managing numbers is about being smart about what you show people.

Innovative Thinking
Another must for everyone is Excel. It’s quick to learn the basics, and Excel provides endless fun for turning recurring fights with your significant other into statistically revealing graphs. I hate to plug Microsoft, but really, learning to use Excel teaches everyone — even English majors – to think about numbers in new ways. And new ways of thinking always opens up new avenues of achievement.

You don’t have to be a math star to present numbers well. But you do need to give time and thought to numbers on a daily basis so you can leverage statistics to bolster your career.


1. Manage conflict

2. Manage your personal life.

3. Manage hearts and minds

4. Manage diversity'

5. Manage a successor

Those who have mentors are twice as likely to be promoted as those who don’t, says Ellen Fagenson Eland, professor at George Mason University and 2003 Winner of the Mentoring Best Practices Award. So start taking the mentoring process very seriously — it should be a cornerstone of your overall career strategy. Here’s a plan to get you started:

Step 1: Identify a potential mentor. This person can be any age, but the most effective mentor is someone approximately five years ahead of you in your career. A person at this level will know how to navigate your organization at the spot you’re in, and the person will remember what it is like to be where you are. This person should be someone you admire and someone who has good communication skills.

Step 2: Have good questions. Would-be mentors are most receptive to people who ask good questions. What makes a good question? It should reveal that you are both directed and driven. But the question should also demonstrate that you understand the mentor’s expertise and you can use it well. So, a question like, “What should I do with my life?” would be out.

Step 3: Don’t expect miracles. A mentor is not going to rescue your whole career, even if she can. People want to mentor a rising star, so look like you’re on track when you ask for help. Ask, “What skills should I develop to earn an education policy analyst job with a Senator?” rather than, “Can you get me a job with a Senator?” even if the mentor is Caroline Kennedy.

Step 4: Be a good listener. This person is not your therapist. You ask a question, and then listen. If the mentor needs to know more, he’ll ask. Do not tell your life story. It is not interesting. If it were, you’d be writing a book or doing standup, right? If you find yourself talking more than the mentor, then get a therapist before you scare your mentor away.

Step 5: Prove you’re serious. You can demonstrate that you’re hungry for counsel by implementing the advice your mentor gave, showing the result, and then going back for more. So, if your mentor suggests you get on project X, get yourself there, do a good job, and report back to your mentor that you are grateful for the advice because you were able to learn a lot and shine. Your mentor will be much more willing to give you her time and energy after you’ve proven yourself to be a quick and eager study.

Step 6: Always be on the lookout. One is not enough. Each person needs a few mentors, because no mentor lasts forever, and each has a different expertise. Two of my best mentors were very different from each other. One helped me to fit in with the guys so that I could succeed at a company where I was the only woman in management. Another mentor helped me to keep my sanity and my focus when balancing work and children seemed totally impossible.

Step 7: Give back. The best way to learn how to rope in a mentor is to be a mentor yourself. You’ll find out first hand what makes a protégée annoying, which will, in turn, make you a less annoying protégée. You’ll also discover why helping someone else grow is so rewarding, which will give you the courage to ask people to help you.

Handwriting analysis is no longer for freaks and psychics. Multinational companies hire handwriting analysts to understand personality traits of prospective job candidates. Character traits that matter during the hiring process — creativity, self-esteem, leadership, and optimism, for example — are revealed in one's handwriting.

You should learn how to analyze your co-workers' handwriting and your own to give yourself an edge at work. I have found that the basics of analysis are quick and easy to learn. Getting along with other people and knowing yourself are essential pieces to career success, and analyzing peoples' handwriting can help you speed up the process. Here are some examples:

Get along with people better
Knowing someone's personality traits is invaluable for collaborating with and motivating that person. Depending on that person to tell you his or her own traits is risky. Most people don't know themselves well enough; even focus group leaders don't bother to ask people directly what they like anymore.

Fortunately, with very little expertise, you can use handwriting to evaluate someone's dominant traits. For example, someone with a signature that leaves a lot of space between first and last names is not going to be an intimate, emotional person, so you can stop trying to forge that kind of relationship. If the first and last names overlap, that person is relationship-oriented and probably wants more than long-distance management from you.

Make better career choices

For example, you can learn what sort of handwriting is appropriate for the job you aim for, and compare your own handwriting to that standard. Angular is appropriate for a programmer and inappropriate for a sales person. Perfect, schoolteacher writing reveals the need to establish order and would be a bad sign if you aspired to the freethinking required of an inventor.

Handwriting really does reflect your true self. So if you discover your penmanship does not reflect traits necessary for the career you have in mind, ask yourself if you are even in the right field.

Improve your image
Handwriting is like clothing. Your audience cannot help but evaluate your message by what it looks like. You wouldn't wear sweatpants to an important meeting, and you wouldn't wear a ball gown, either. Take the same care with your handwriting.

For example, in a note to your boss, if your letters are rigid and perfect you will project the image of someone who is anal, inflexible, and non-visionary. Fine if you are an accountant, not fine if you want to be CFO. If you scrawl a quick, barely legible note to your boss you seem to be more involved in your own ideas than in the people around you, you might project the image of an eccentric artistic genius, but if you aspire to management, write more legibly.

You also project self-esteem in your signature. I am shocked at how many people have a very tiny signature. You need no training in handwriting analysis to know that this is an expression of low self-esteem. Even if you feel like you want to disappear, force yourself to sign your name like you want people to see it.

To all you doubters, test the theory. Get a handwriting analysis book from the library. You only need to skim a few pages to get an idea of what to look for. Then take handwriting samples from people you know well and evaluate them. I bet you'll find the rules of analysis depict an accurate view of that person.

When you add handwriting analysis to your career arsenal, start out small — look at different loops and slopes and figure out what they mean. After a while, you'll find that handwriting analysis actually feels intuitive; like all good insights, once you have it it'll seem obvious, and acting on results of handwriting analysis will make as much sense to you as it does to those multinational companies.

During the Internet’s go-go days in the late 1990s, I thought the term generalist meant “she's doing two jobs and pays herself double.” Now it seems the word generalist means “good at nothing and unemployed.” In either case, generalist is the label for a career that will die.

Think cars: You never hear an advertiser say, “Buy my car, it's good for everything!” Volvos are safe. BMWs are fun. Saturns are easy to buy. Just as successfully branded products offer specific benefits, successfully branded careerists offer specific talents. You get to the top by being the best, and you can't be the best at everything.

Ezra Zuckerman, a professor at MIT’s Sloan School of Management, agrees — and has the research to prove it. In his study of typecasting in Hollywood entitled “Robust Identities or Nonentities,” Zuckerman found that specialization leads to longer, more productive careers. Contrary to conventional Hollywood wisdom, big bucks come most often to people who become known for a certain type of role. Zuckerman finds that typecasting, as this practice is called, is also a moneymaker in the business world, where the hiring system is set up to reward those who differentiate themselves. “Headhunters are specialized,” he says, “and they look for something they can package and sell.”

Generalist is a good moniker during the first few years of your career. For example, if you're a standout college grad, you may win a place in a general-management rotational training program, such as General Electric Co. and other well-known consumer products companies offer. But the point of such training programs is to figure out what you're good at and then seek an internal role in that department.

So take a gamble. Figure out what you're best at and start making your mark. Then hope for good timing — that someone needs that particular talent when you have become expert at it.

Carly Fiorina, for example, is an outstanding marketer in the technology sector. She got to be chair and chief executive officer of Hewlett-Packard by being the best — and having a little luck: the company badly needed marketing expertise when it was conducting a search for a CEO. If it had needed an engineering genius, Fiorina would not have been considered. By the same token, if a food-products company needed a marketing-oriented CEO, Fiorina would not have been a candidate because her background is in technology. People who define themselves clearly are clearly wrong for certain positions, but super-achievers take that risk.

Many professionals hesitate to define themselves because it limits where you can go. But top players must have clear definition. Most have enough confidence in their abilities to risk specialization. Very simply, they believe that adequate opportunities will be available as they progress up the ladder.

To specialize, think discipline (marketing, sales, operations, etc) and sector (media, technology, fashion, etc.) Become known for your extremes. If you aren’t extremely good at something, you won’t get to the top.

Still not convinced of the benefits of typecasting? Then consider the current job market. Hundreds of applicants vie for most jobs, and many are more than qualified. This means hiring managers can demand a perfect fit — and specialists rather than generalists typically offer a perfect fit.

Figure out what your strengths are and hone them. Sure, take varied positions in the company, and learn a range of skills, but make sure people know where your talents lie. People at the top need to see you as someone who is extremely good at something, and no one is extremely good at everything, so don’t sell yourself that way to upper management.




2. Know what luck looks like




3. Entourages make opportunities for luck


4. Surround yourself with lucky people.


5. Don't tell other people they were lucky



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.


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.


The problem with being nice is that it is not very interesting. It's the people with dirt to dish who are magnets at the water cooler.






Not surprisingly, it is the job of powerful people act as though they don't care what anyone else thinks of them. But everyone likes — and needs — compliments, and one reason for the dearth of them at the top is that men give fewer compliments than women, and we all know who dominates the top ranks.

So start crafting your compliments now.

But don't brownnose. The difference between a genuine compliment and a desperate brownnosing attempt is empathy and insight. If you understand what worries your boss, and what she is trying hardest to achieve personally, then you will easily spot opportunities for praise. Don't just say “good job” for the sake of it. And don't just say “good job” either. Carefully craft a compliment in an area that is particularly important to your boss.

Why? The most effective compliments are very specific. And creative words are more memorable than standard words, according to research by Mark Knapp of the University of Texas. Praise of character is the most rare and most memorable praise of all. For example, “Nice job of being compassionate while you were laying everyone off.”


I also remember when a boss pulled me into her office and said, “Joe (not his real name) is accusing me of leading him on romantically. This is a serious accusation since I am his boss. Do you think other people perceive me as leading him on?”

