Ten Questions With Penelope Trunk: Career Guidance for This Century

Penelope Trunk is the author of Brazen Careerist: The New Rules for Success. She is a career columnist at the Boston Globe and Yahoo Finance. Her syndicated column has run in more than 200 publications. Earlier, she was a software executive, and then she founded two companies. She has been through an IPO, an acquisition and a bankruptcy. Before that she played professional beach volleyball.

My two favorite answers in this interview are #7 and #10. If I had a nickel for every time I had to answer questions regarding getting an MBA and a first job out of college, I would own my own ice rink by now.

1. Question: How much money does it take to be happy?

   Answer: It takes about $40,000. It does not matter how many kids you have or what city you live in—that’s splitting hairs because peoples’ happiness levels are largely based on their level of optimism and the quality of their relationships. So as long as you have enough money for food and shelter, your optimism level kicks in to dictate how happy you are.

2. Question: Is it more important to be competent or likable?

   Answer: People would actually rather work with someone who is incompetent and likeable than competent and unlikable. Most people nod in agreement when they read this. It’s the unlikable people who form arguments in their head.

   But there’s more. At work, if you are unlikable, people start thinking you are less competent. So stop thinking you can skate by on your genius IQ because you can’t. You need emotional intelligence as well. This situation is so pronounced that there are special-education classrooms rife with kids who could read when they were three. Social skills matter as much as intelligence when it comes to long-term success, even for the geniuses.

3. Question: Should I sue a boss who is sexually harassing me?

   Answer: In most cases, you will destroy your career if you report sexual harassment. So unless you are in physical danger, you should not report harassment. The laws governing sexual harassment don’t protect women who report. The law protects companies from being sued by the women who report. Human resource professionals are trained to protect the company, not the woman who reports.

   When you report harassment it is usually the case that you lose your job through retaliation. Retaliation is illegal but nearly impossible to prove in court. And, even if you could prove it in court, you would go through emotional hell, with no salary, and high-profile drama that makes you unable to get another job. All this for a settlement that will almost certainly not enable you to retire.

   This is simply how the legal system works. I am not saying this is okay. But I’m saying that if you care about your career, you’ll do everything possible to not report. Most women are not in the position to sacrifice their career—and their earning power—in the name of trying to bring down one harasser. The legal system needs to step in and take care of this.

4. Question: When should I ask for a promotion?

   Answer: Maybe never. The average salary increase is four percent. Is that going to change your life in any meaningful way? On top of that, someone is promoting you up their ladder, but their ladder is not necessarily your best path. So stay focused on where you want to go instead of the paths other people have created for you.

   Getting a promotion is so last century. Instead of letting last century’s carrots dictate your workplace rewards, figure out what will be really meaningful to you: training, mentoring, flex time, whatever it is that means more than four percent more money. These are all things that can really improve your life and your career.

5. Question: Is being a generalist or a specialist the path to the executive suite?

   Answer: In Hollywood, the best way to get your pick of any role in the industry is to become a specialist—funny guy, tough girl, action hero—get known for being the best at something, and then use that star-power to branch out. The same is true in business.

   Jobs that don’t require a specialty are low level. To move up you need to be great at something, and you have to let people know what you don’t do. No one is great at everything. Even if your goal is not to get to the executive suite, you should specialize. When you want to take five months off to hike in Tibet, if you are easily replaced, you will be. If you have a skill that is hard to duplicate, your job will be there for you when you get back.

6. Question: What do I do about the gaps in my resume when I traveled or couldn’t find a job?

   Answer: Talk about them well. A gap is really bad if you spent your days on your sofa watching cartoons. But if you watched cartoons to prepare for your next career move into children’s programming, then you sound focused and driven. Same TV, same sofa, two different stories.

   People don’t want to hear your life story. This is good news for people with sofa stints. In almost all cases, you learn something during a gap. Tell a great story about what you’ve learned and where you’re going, and your gap won’t get center stage. Leaving out details is not about lying; it’s about telling good stories.

7. Question: Will getting an MBA or any other type of advanced degree be a good use of time and money since I can’t find a job?

   Answer: No. If you can’t find a job, then you should invest in something like better grooming, or a better resume, or a coach for poor social skills. These are the things that keep people from getting jobs. Instead of running back to school, figure out why you can’t get a job, because maybe it’s something that a degree can’t overcome.

   Grad school generally makes you less employable, not more employable. For example, people who get a graduate degree in the humanities would have had a better chance of surviving the Titanic than getting a tenured teaching job.

   Unless you are going to a top business school at the beginning of your career, you should not stop working in order to get the degree. Go to night school because you will not make up for the loss of income with the extra credential.

   Law school is one of the only graduate degrees that makes you more employable. Unfortunately it makes you more employable in the profession where people are more unhappy. Law school rewards perfectionism, and perfectionism is a risk factor for depression. Lawyers have little control over their work and hours, because they are at the beck-and-call of their clients, and many are constantly working with clients who have problems lawyers cannot solve. These two traits in a job—lack of control over workload and compromised ability to reach stated goals—are the two biggest causes for burnout in jobs.

   [May I interject here? I went to law school for two weeks and quit when I was young! Guy]

8. Question: What’s the ideal length of a resume in a world where every resume is electronic and not viewed printed out on paper?

   Answer: A page. Still. Your resume is a marketing document, not a summary of your life, so every line should be about an accomplishment. The more amazing your accomplishments, the fewer you need to list. For example, if you can write “Evangelized Macintosh and made it one of the most beloved brands in the world,” then you don’t need any other sales and marketing bullets on your resume.

   If you have totally lost perspective, and you think you have two page’s worth of incredible and relevant achievements, consider that hiring managers spend ten seconds evaluating a resume, and a scanner looks for ten keywords, which certainly fit on one page.

   So unless you have a great connection with the hiring manager, and you know he’ll look at both pages, don’t bother sending them. And if you do have that great connection then you are probably going to get an interview even if your resume sucks.

9. Question: How should I prepare for an interview?

   Answer: An interview is a test you can study for. So memorize answers to the fifty most common questions. Most interviewers ask standard variations on standard questions, and there are right answers to these questions.

   Whether you are a stripper or a CIA agent, the answer to the question, “What is your weakness?” is a story about how your weakness interfered at work—in a specific situation—and you overcame it. Most of your other answers should be stories, too. This means you need to make them up before you get to the interview. Stories of your life are memorable. Lists of your life are not. Be memorable if you want to be hired.

   Another way to prepare is to go to the gym right before the interview. It doesn’t matter if you never go to the gym—although you should, because people who workout regularly are more successful in their careers. You should go right before an interview because people judge you first on your appearance, and if do heavy lifting with your back and stomach muscles you will stand up much straighter in the interview. This will make you look more confident, which is half the battle in being judged by appearance.

10. Question: What’s the right strategy for the search for a first job out of college?

    Answer: Don’t place too much importance on your first job. You’ll have a lot more. Most people have eight jobs before they turn thirty, and that’s fine. It is nearly impossible to know what career will be a good fit for you until you start trying things. So give yourself the latitude to try a lot. And don’t get hung up on a big soul search. To land a great job, you don’t need to know the meaning of life, just the meaning of hard work.

11. Question: Do only losers live at home after college?

    Answer: On some level it would be insane not to move back home, which is why more than fifty percent of graduating seniors do it. Moving back to your parent’s house is a smart step toward finding a career that’s right for you.

    Entry level jobs typically cannot cover the cost of rent, college loan payments, and insurance premiums—all of which are rising faster than wages. If you don’t have to worry about paying rent, you have more flexibility to wait for the right job and to take a job that feels very right but pays very poorly. The rise of the prestigious but unpaid internship intersects perfectly with trend to move back home.

12. Question: What should I do if I work for a jerk?

    Answer: Leave. I know there are classic Bob Sutton examples of revered jerks like Steve Jobs, but I wonder about the people who put up with him. Can they not find another visionary to work for who is not such a jerk?

    Staying in a job like this makes you look bad. People wonder why you put up with it. And, frankly, you should too. It’s like being an abused wife. The wife who stays always defends the relationship by how much she gets out of it, but to everyone else it is obvious that she should leave. The problem is a loss of personal perspective.