Generation Y has a lot of great traits, but classic, top-down leadership is not one of them. This is not a surprise: Because gen Y is the great teamwork generation. They did book reports in teams, they went to prom in teams, and they are notorious for quitting jobs in teams.

I know this first hand. Because the insult Ryan Healy loves to hurl at me most is that I'm a bad team player. At first I thought this was a joke: Of course I'm a bad team player. I am part of gen x – the most disenfranchised, neglected generation in history.

But as CEO of Brazen Careerist, I work pretty hard to be better at being part of a team. Not only to appease Ryan and his gen-y cohorts, but also because I think effective leadership in today’s workplace is about teamwork and following, not about standing out.

Here are five traits of leadership in the new millennium — traits I try to practice myself:

1. Make yourself a source of information

The key trait in a leader is the bravery to put forth an opinion and maybe be wrong. Jeffrey Kluger, writing in Time magazine, reports research that we value leaders not because they are smarter or right more often, but merely because they speak up. We want to be lead by people who take a shot at the answer — right or wrong. So if you want to be perceived as a leader, speak up. Often. Read more

This is another post about a book. Two days in a row. But before you get all giddy and think you should send your book to me so I’ll write about it, forget it.

First of all, I get five to ten books every week. And I throw most of them away. Second, honestly, for the most part, you have to be my friend for me to write a whole post about your book. Sure, there are exceptions. For example, Tim Ferriss is not my friend but I wrote about his book anyway. But the exceptions are mostly for academic books with research that blew me away.

So stop thinking that I am going to write about your book if you simply send it to me. But really, if you want to promote a book, the best thing to do is make a lot of friends before the book comes out. Just like you don’t want to wait to build a job search network until you need a job, you don’t want to build a book promotion network when you need press.

So, Ramit has put up with a lot from me, including me being an hour late to have coffee with him. More than once. He has earned a post. Read more

One of the best parts about blogging is meeting people I would never meet in real life. Often, this means psychopaths, who use the C word in my comments section. But the best times, the people I meet are like Tony Morgan. He is a pastor and chief strategy officer at NewSpring Church, based in South Carolina.

This is not the kind of guy I usually seek out. But I clicked to his blog, and when I realized that he mixes careers and church like I mix careers and sex, I was hooked.

My conversations with Tony are always about what matters; he approaches this topic from a church perspective, but honestly, careers would not keep me interested if I didn’t talk about it from that what-is-the-meaning-of-life perspective.

Tony combines his religion and his work in a social-media, grassroots, new millennium way. I think that on some level, we’d all like to do what he does: take something with deep meaning to us and add a layer of hipster, what’s-new-and-cool exploration.

In Tony’s new book, Killing Cockroaches, he tells the story of when he was a city manager, and he was in the middle of running a meeting, and he heard a woman down the hall scream about a cockroach. So he got up from the meeting and killed the cockroach. He talks about the dichotomy between wanting to make big-picture impact on the world and being drawn to the smaller, but louder, more immediate issues in front of us. Read more

One of the reasons I moved from New York City to Madison, WI is that I knew I would start another company. I wasn’t sure what it would be, but I had already launched two startups, and I could feel another one coming. It’s a sort of itch I get when I have too many ideas piling up in my head: I think to myself, “One of these must be good for something.”

People ask me how I picked Wisconsin. The bottom line is that I wanted to be able to support my family and take the wild risks that come with having a startup. Supporting a family in NYC or Silicon Valley is insanely expensive especially for someone who has no cushion to fall back on during the months when funding is tight. (Which is a major reason you see lots of Silicon Valley startups from twentysomething men with no expenses and few startups from women with kids, and heated discussion on TechCrunch about salaries for founders who can’t make ends meet.)

So, here are some things to think about when you know you are going to do a startup, and you know you are going to move.

1. The first stage of a startup is constipation, which can happen anywhere.
The beginning of a company is slow and meandering. You have pretty much no idea what the company is or what you are doing with it, or if you even picked the right partner to do it with. You sit in a room and argue for a while. And you throw in the towel ten times. And then go get it and try again. You develop a bunch of revenue models that are either so lackluster that they are not worth your time, or so outstandingly huge that they are not believable.

During this time, it does not matter where you live. You are not hiring. You are not pitching your business because you don’t have a pitch. And you are probably not spending much money because you know the near future does not include a lot of money coming in. Read more

Consistency is an important part of any career. It's not just doing good work all the time. It goes beyond what quality your work is to what quality of person you are. Being consistent is letting people know they can rely on you, and it's following through on what you say you'll do because that's what people do who care.

My problem with consistency is that I am a tornado, and I have found my tornado nature is both wildly inconsistent and difficult to change, which makes me think that co-dependency on a stable (read: low-maintenance) boyfriend might help. So I think I need an ENTP. So, I'm only dating those from now on. (Yes, the 25-year-old is an ENTP. Personality type is ageless.)

But my inconsistency is no small problem. Here's an example. I agree to new photos of me for a publication even though I have done tons of photo sessions already and have a gazillion expensively-lit ten-people-making-it-happen photos of myself.

Not only do I say yes, but I agree to do it the day before I leave for the SXSW conference. And I tell the magazine I'll get a fake tan. Because it's a summer issue. I've never gotten a fake tan and it seemed like maybe it would be fun. Maybe I'd end up looking like I'm in an artsy Versace ad where everyone has big attitudes and big tans. Read more

This is a guest post from Jamie Varon. She’s 23 years old. Her blog is called intersected.

Not too long ago, I started a new job, in which I moved my self from point A (college town) to point B (Bay Area). This was supposed to be my career launch. It took me about two weeks to admit to myself that I was unhappy. So I quit.

I had the security of knowing I could go back to my parents’ house to live. (Which, by the way, is such a good idea that 65% of new grads do it.) Here are five reasons why I am sure it was a smart decision to quit my job after just two weeks:

1. Your job performance will be terrible if you hate your job.

If you hate your job from the beginning, then you will never fully dedicate yourself. In fact, you’ll resent both the company and yourself for staying at a job that you knew you didn’t like early on.

I get it: You have this desire to prove to yourself that you are capable of sticking it out. Or you’re worried that this makes you a complete failure and you have given up. So what? You learn from your failure. You learn from that mistake. You’ll end up quitting at some point soon, so why draw it out? Read more

People always ask me when they can hear me speak. Most of the time the events are closed to the public. Like, the American Bankers Association, or the Public Relations Society of America. But this coming month I happen to be speaking at a lot of places that you can get tickets to. So, here's the schedule:

Austin, TX, SXSW, Sunday, March 15, 10:00 a.m.

I'm on a panel with Robert Scoble (social media stud), Mike Maples (venture capitalist), Kaiser Kuo (China marketing maven), and John Metcalf (community builder). We are talking about how to decide where to have a startup. Well, I think that's what we're talking about. It's an odd panel for that topic. But then, that's what makes SXSW so interesting. Also, if you're going to be there, and I like you, we should meet up. So email me: penelope@penelopetrunk.com. Read more

I told this guy who wrote to me that I do not remember ever actually meeting him, even though he says we had a great conversation.

He wrote back. He was relentless, so I asked him to tell me a bit about himself. He wrote, among other things, “I'm the guy you want to date.”

It was such a direct response. And I like direct. Plus, he was going to be in Madison. That never happens.

Two days before the date, I checked him out on Facebook.

Then I wrote him an email. “You are way too young. I can't go out with you.”

He wrote back, “You should know more than anyone else that online identities are deceiving. And anyway, I'm older than you think.”

That was a good response.

So we agreed to meet at a diner. For coffee. I walk in, and right away I know who he is: The guy with the backpack.

We sit down.

I lean across the table, and in a low voice I ask, “How old are you?”

He says, “I knew you'd ask that.” He says, “Twenty-five.” Read more

Let's sayyou get fired, or laid off, or you quit because after two weeks you know you're at the worst company on the planet. In all of those cases, you will face the interview question: What happened at your last job?

Here's the answer you should always give: “I left to do x.” And you fill in for x.

Which brings me to what you should be really focusing on when you are unemployed: Learning and growing. Because this is what you are going to talk about in job interviews.

Most people require about six months to get another job. This is a big chunk of time that you can piss away sending resumes to Monster and wondering why no one responds. But you cannot job hunt for eight hours a day. Really. You'll go nuts. (Wait. Here's a time-saving job hunt tip from my mom.)

So spend the time creating projects for yourself and executing on them. This is good for you mentally — because you are doing something meaningful with your time and that will keep your spirits up.

But this is also good for you in your job hunt. Because when you talk about why you left the last company, you spin it in a positive light by talking about how you are excited about doing what you are doing. Your interview should include you telling a good story about focused personal growth, and no one will get stuck on why you left your last job. Here are five ways to set that story up:

1. Create a job for yourself. These projects can be wide ranging, but they have to show that you are driven, ambitious and focused. During one stint of unemployment, I worked for free for my boyfriend's company for a couple of hours a day. That way I didn't actually have a gap in my resume; a resume doesn't show part-time or full-time and it doesn't show pay or no pay. So volunteering at my boyfriend's company for a couple of hours a day ended up looking like a full-time job on my resume. Read more

Brian Wiegand is a very low-profile guy who has sold three companies, most recently to Microsoft. He is big enough that TechCrunch writes about him as a good bet for anyone betting. But the bane of Brian's existence is that his exits have all been for under $50 million.

This is enough for him to have a private jet and be King of Madison (Wisconsin), but not enough for him to get a lot of respect in Silicon Valley. A quote from my advisory board member who lives in Silicon Valley: “For big VCs, $50 million is a rounding error.”

So Brian is not looking for people to mentor or boards to sit on because he is consumed with running his fourth company, Alice.com, which will compete with Wal-Mart and Target.

I do not tell Brian that I will have a hard time ever missing a trip to Target to shop at Alice because Target has such great clothes that are so cheap they are almost free.

Well, actually I did tell him that. And I told him a bunch of other stuff, because I decided that I need him as a mentor. Eventually, I got him to agree to be on the board of my company. Here's the process I took to convince him to help me. And these are good steps for anytime you have someone you'd like to ask to be your mentor: Read more