But there is very little advice on HOW to be yourself.

1. Don’t be boring.

On the way to our board meeting today, it was me, and Ryan Paugh, and Ryan Healy, in a car, running late. Ryan Healy told me not to write about him on the blog anymore, but I think only because I used to write about him like he was my little brother or something. At this point, Ryan Healy is COO of the company, so I think I can write about him because really, how can I undermine him when I’m agreeing to report to him?

So I’m riding in the car with Ryan and Ryan and I finished my needlepoint and I didn’t have  anything left to occupy my hands during the board meeting. I know that as a board member, and the majority shareholder in the company, I’m supposed to be enthralled at these meetings, but honestly I find them largely very slow and repetitive. (I know I am not the only one who feels this way because another board member went to the bathroom and when he came back and found out that we waited for him, he was disappointed.)

Anyway, I was in the car with them and I was panicking that I didn’t have anything to do in the board meeting except listen to the board meeting. Then I said, “I think I’ll pop a Xanax.”

And no one said anything. Ryan and Ryan are largely bored with my antics.

But when I’m anxious I’m chatty, and they had already said no to playing the license plate game. So I said, just to make casual conversation, “What do you guys think would go well with Xanax, because I don’t think this is working. And pharmaceuticals have been such a disappointment to me.”

Ryan Healy said, ‘You sure are a late-bloomer to this. By the time you’re going to board meetings you’re supposed to be done with this stuff.”

In fact, I am enthralled with mixing pharmaceuticals off-label. I am also enthralled with trying new things, learning what I’m like with new things so I know who I am.

But it gets old. Not knowing who I am. And anyway, it’s boring for other people when you don’t know who you are. I know that because when I was dating the twenty-five-year-old with the perfect butt and long, thick, curly hair, he had no idea who he was and it got boring, very boring very fast.

(Links about boringness: People do not want to know all of you. Some of you is interesting, some of you is boring. This is why confessional blog posts mostly stink. And it’s why you need to omit most of your life from your resume.)

2. Try a range of tools to express who you are.

I like to think that I know myself well enough to present a consistent and insightful portrait of myself. And when Eva, from Songza, emailed me to see if I’d put together a playlist that they could use on their music streaming site, I said sure. (By the way, if you want to get me to do something, make it fun. People ask for posts all the time, but few people ask for playlists.)

So I start doing my playlist and I think: People judge other people by their playlists. (Which is why Ramones t-shirts outsell Ramones albums ten to one.)  I want people to think I’m fun and edgy and self-confident.

(Ad for my company: It think about this issue a lot because my company, Brazen Careerist, is basically a tool to let people know who you are by showing your ideas and potential. The tools on the site encourage you to display your best self in a professional, online setting. And every time I pitch my company, I end up telling people that you can’t show your true self if the tool you’re using is wrong for who you are.)

3. Understand how people perceive what you put out there.

I picked Moby and TruSkool for edge. I picked Beastie Boys and Arrested Development because I read that people who like hip-hop tend to have high self-esteem. And I picked Fergie for fun. I think when people say she’s for girls, they mean that she makes guys think of girls dancing while they watch.  Then I picked Lilly Allen, Regina Specktor to say that I didn’t feel too much like an old-school Gen X-er. I picked Kings of Leon because Lilly and Regina are both girls.

It turns out that I would have done fine just picking out all Miles Davis, which would have probably been my instinct, but I thought it would be boring and pedantic (which is almost redundant but mildly nuanced instead, I think). It would have been just fine because people have positive impressions of people who like jazz.

This is surprising to me because people do not have positive judgments toward blog posts that are like jazz—complicated and difficult. In fact, my editor will probably slash this whole paragraph because it is off topic and difficult to read and jazz is not writing and so what if my brain runs like an Ornette Coleman composition?

When I sent my song list to Eva I asked her to analyze me. I said, “I bet you read song lists like I read resumes, so can you tell me what you see?”

She said she usually doesn’t see such a wide a range of songs on one list.

On a resume, lack of focus is bad. And in a life, doing many different things at once is bad. And in fact, I’m a stickler for focus because I love knowing one thing well, so it’s counter-intuitive to me that I would have such an eclectic list. In fact, it’s the result of me being scared to just be who I am and accept that I’ll be judged for it.

But P.S. Here's the playlist I made at Songza. And here's my favorite Miles Davis CD.

I do not tell Ryan to shut up because he has taught me a ton about myself since the day I started working with him. And in fact, he makes me feel qualified to tell you how you can fire up your career by paying close attention to the people with the least work experience.

1. Recognize interns are gatekeepers to the good stuff.

When it was time to promote my second book, I went to Keith Ferrazzi, author of one of my favorite career advice books. I needed a quotation from Keith that said something like, “I am The Great Keith Ferazzi and I can tell you for sure that your career will be crap and you will die drowning in the blood of a rabid coyote if you do not buy Penelope Trunk’s book.”

Just so you don’t get confused, I’m going to start calling my first book my first book and my second book my second book. At this point, I have written enough about oral sex and family atrocities that you will not be shocked to hear that my first book is really a memoir that my publisher – out of the University of Colorado — decided was too disturbing to be sold as a memoir, so it was published as a novel.

Anyway, another thing Keith is great at is hiring interns. Keith’s intern, and gatekeeper, at the time of the publication of my second book, was Ian Ybarra. Ian said sure, he could come up with a quote. (It did not have animal references, but still, it was a nice endorsement.) Ian could see that I was a book-promotion novice, so he started giving me tips: Trade email lists, give speeches, pitch bloggers. Note: this was five years ago, when no one pitched bloggers.

Wait, please. Do not send me your book because I get too many. I’m sick of getting copies of business books. (Note to all publishers: I am getting really good at self-promotion and my blog is about to really take off, so could you please start sending me books with literary merit? Here’s my address: 15010 Oak Grove Lane, Darlington, WI 53030.) (And, a note to people who are going to say aren’t I worried that if I publish my address that stalkers will come get me in my sleep. Check me out on Google maps. The farm is so remote that even a stalker would be scared to go there in the dark.) (Finally, a note about using parentheses: Can we talk about style? Can there be more talk about style in blogging? Are links inherently parenthetical? What if each thought in a post is parenthetical, but they all add up to something that is central to our lives? Is that innovative or is it too e e cummings?) It’s so difficult to be original.

2. Don't rush on the phone; interns chat about things that really matter.

Then, one day, Ian wrote to me that he was moving with his girlfriend to Beloit. And then to Saudi Arabia. Or something like that. I can’t remember where he moved, but he grew up in a really really small town in a state that gets joked about just like Wisconsin. And he told me about how MIT courted him because he had high SAT scores in a weird zip code. When I worry about my kids going to a rural school with no orchestra, I hang my hat on hopes painted with broad brush strokes of the tidbits of Ian’s life that I may or may not remember correctly.

The next intern was Ryan Geist. I love him because I met him when he was at a big job at a big firm where I would never have been able to go to when I was his age because I was too busy not doing what the world expected me to do. What I love about Ryan is he gave those expectations a chance, and he was brave enough to say he didn’t like them, and he landed on Keith’s doorstep.

At the same time Ryan was there, so was Sara Grace. She called to get a quote from me. And I started talking to her about what she does. What her aspirations are. And she started telling me all these ways that Keith repurposes content. I was blown away. He is great at turning everything he writes or says into a post. The thing that really struck me was that he records interviews and has them transcribed in India and then edited into a post. That’s a great idea.

3. Let an intern show you your weak spot: you'll love her for it.

That’s a great idea because reporters ask interesting questions. And then I end up talking about topics I hadn’t thought about talking about before. The reporter uses 10% of what I say and the rest is gone. Poof. I do about five interviews a week, so recording them seemed like a good idea. But I realized that I actually like the process of writing. I don’t like the process of reading what I already said. (I wonder, does anyone actually like that process? It seems solipsistic. And shut up to all you people who think everything I do is solipsistic, self-promotion. Here is a list of people who are a thousand times better at self-promotion than I am and I wish I could be any of them for a day:

Guy Kawasaki

Jason Calcanis

Ramit Sethi

And probably all you people who say that I’m in love with myself and never shut up about myself are also people who rant about me into a recorder and then hit replay so you can listen to yourself rant.)

4. Lay groundwork to get a job from the intern one day.

So goal number one is to be better at promoting myself.

And goal number two is to be better at using all the content I generate to create more posts. I am also not good at this because once I generate the content, it bores me. I want to move on. So I’m not sure how I will meet this goal either.

But here’s a start:

Esquire contacted me this week about how to quit. And I decided it might make a good blog post. I see that it’s taken me too many words to get to it. So it’s hard to say that it’s the real subject of this blog post. But maybe you will like it:

Don't do an exit interview. If they wanted to hear your ideas about how to make things better, you wouldn't be quitting, would you? So this is really just a way for you to burn bridges and annoy people. Don't fall into the trap. If they insist on an exit interview, say nothing negative. At all.

Send a thank you note. Anyone you worked closely with should get a hand-written thank you note. Bring up specific times when they surprised you with kindness, made your work better, invigorated you with their own contagious brilliance or creativity. And, if you are thinking that you work with people who merely make you want to hit your head on a brick wall, remember this: Intelligent people can learn from anyone.

Take a vacation. You probably think about work all the time, not because you're a slave but because you like solving problems and learning new things and meeting interesting people. Which is what work really is. This means that the only time you can really take a vacation is in between jobs. So do that. Don't start the new job right away.

Have humility. You are probably not quitting to take a job that sucks, right? So, since you are quitting for a better job, you don't need to shove it in peoples' faces that you are moving up in the world and they are not. The world is not a race to a McMansion, the world is a contest for who can be the most kind-hearted and tolerant. That's what makes a good life—you'll get kindness in return. So be gracious and grateful.

Think of quitting as a networking event. These people are no longer your co-workers, they are the network that will help you get the job after the one you just got. And don't forget the entry-level people who look like they couldn't help anyone. The interns will get big jobs one day, and they will remember each person who saw them for who they are and who they could be.

On the Internet everyone is a celebrity. I think Rebecca Blood was the first person to introduce this concept to me when she said  Generation Y manages itself like celebrities online, so privacy is not necessary for them. I think the proof of this is that gen Y prefers communicating via social media rather than email; news travels faster, via larger groups of people.

Marketers and publicists have made a science out of getting benefits from being a celebrity—sponsors, a fun network, great opportunities that lead to even greater opportunities. In the age of transparency Gen Y can see how to do this and they don’t need permission from MGM or Capitol Records to act like a celebrity.

I am constantly telling people to get a strong career by managing their professional profile online .  The way to a solid career is to be known for what you’re good at. All good workers are celebrities—a far cry from Horatio Alger and the Protestant work ethic, but a much more relevant trope for the new millennium.

Pace University reports that 99 percent of Gen Y is on Facebook, MySpace, or LinkedIn, and Redbook reports that one out of five moms is blogging. In this era, if you’re at all relevant in this day and age, you can google your name, and you will find photos, quotes, and some sort of history of your life, in a few lines or a few million lines.  If you already have everything that being a celebrity can get you, then you can be private.

I am struck by the way Prince William and Kate Middleton handle the media in England.

The paparazzi are all over Kate, who has been dating William for nine years and is pretty much a lock-in to be the next queen of England. (A testament to how in love the media is with William and Kate: The throne will skip William’s father, Charles, because he is so unpopular with the public, and go straight to William.)

William is still livid with the paparazzi because he blames the death of his mom, Princess Diana, on the car chase for photos of her with her date. So after Princess Caroline won a court battle against the paparazzi, William vowed to sue any photographer who violates Kate’s right to privacy. To this end, William is well versed in the laws, and Kate is well-versed in conducting herself in a way that exercises her rights on a regular basis.

This is a great video, for example: Kate is with her sister, both are non-royals at an unofficial event, so it is, by law, considered her private life. On video, Kate asserts (in a relatively kind way) that she is not taking her hand from her face because “this is my private life.”

Once she says that, the photographers leave, because it is true that it’s private, and they have, officially, violated the law. (Still, William pressured Kate to sue, in an effort to keep the paparazzi in line. She won and gave the money to charity.)

William and Kate can do this because they do not need any benefits as celebrities. They will definitely become king and queen, they definitely know enough people for the rest of their lives and do not need to widen their circle of contacts, and they definitely do not need more money. Celebrity is not valuable to them any longer. Privacy is more valuable.

Royal family member Peter Phillips, on the other hand, is eleventh from the throne and almost a commoner. He needs cash, so he sold the rights to his wedding to Hello! Magazine for roughly $1 million.

The problem is that what he really did was sell privacy. Not just his but William’s and Kate’s. There were thirteen photos of Kate in Hello!, which did not violate the law because the publication paid for access.

Now, circle back to the commoners of the Internet. Most people making money from the Internet do, in some way, sell their privacy. I remember, for example, hanging out at SXSW with Guy Kawasaki.

We drove around in a limo to a bunch of parties, and everywhere people swarmed to take photos with Guy. I said, “How can you cope with all this?”

He said, “I don’t mind it, and anyway, it’s my job. And I always remind myself there are way worse jobs than this. At least I’m not a garbage collector.”

He has a point. But still, I ended up sitting in the limo while he went into parties. I needed quiet.

I need quiet, but I am not in a position to guard my privacy like Kate Middleton. I want too much more that mere celebrity status can get me. I want to trade interesting ideas with interesting people. I want to create a constant flow of fun opportunities. I want to write for an audience rather than just for myself. So I have to show myself.

The farmer and I have this conversation all the time: He wants to be with a woman who is intellectual and worldly and who will live on the farm in the boondocks. Very few women would choose this life without being able to make this life better by supporting the family financially. And the way I support myself is writing about myself, and the way I stay engaged in the world is to write about it. Which means I give up my privacy in exchange for being able to live where I want and write about what I want. It seems like a good trade to me.

Did you know that on a farm, dinner is lunch and supper is dinner? The only people who lunch, I guess, are city people. I mix this up all the time and my kids correct me, which is how I imagine it is for immigrants who cannot learn the new language as fast as their children.

Anyway, here is a photo of the farmer and me having dinner on the farm. And it’s telling that I share a private moment, of my own volition, because I’m not next in line for the throne.

But many of you are making lots of social media mistakes. I know because so many people tell me that social media is a waste of their time. They’re wasting their time, and continuing to make mistakes, because there’s a set of common lies that people believe about social media. Here are those lies:

Lie #1: LinkedIn is for networking.

LinkedIn is great. I’m on LinkedIn. I have 650 connections. At first I wondered, why do I need this list of connections published on LinkedIn? What was the purpose of it? But now I get it. With LinkedIn, people can tell that I am a very connected person.

Most of you already know I’m well connected—I’m a print journalist, blogger, and startup founder, which are all very network-intensive jobs. But if you’re someone who doesn’t know how to tell whether someone is connected, LinkedIn is a great scorecard.

Potential employers like LinkedIn because they can glance at your LinkedIn profile and get a sense of how connected you are and how much money you make. (Yes, large networks correlate to large salaries.) That's the utility of the scorecard.

But what you cannot do on LinkedIn is build a network. Networks are built on relationships, which grow from conversation. LinkedIn is not for conversations. So you need to go somewhere else to build your network, and then, when it’s big, display it on LinkedIn so you’ll look great.

Lie #2: Twitter is for conversation.

So if you need conversation to grow relationships into a network, then you look for the social media tools that are for conversation. Right? Twitter seems easy. It’s only 140 characters, so it’s appealing to someone who is weary of spending every waking minute using social media.

The problem with using Twitter for conversation is that we need more than 140 characters to make a genuine connection with someone. So you’re not going to have a whole conversation there; Twitter is great for finding people who have similar ideas, and for keeping track of them in a superficial way.

But you still need to go elsewhere—offline or online—to solidify the relationship to the point where you would actually care about each other in the way a solid network connection does, but Twitter is a good start.

Lie #3: Blogs are personal journals.

Your blog is a record of what you’re thinking, and that record will represent you online, as a high-ranking search result when someone googles your name. So if you care about building a network, you’ll stop using your blog as a diary.

Your blog is intellectual exercise for you—to keep yourself thinking in a disciplined way about things that interest you. And it’s an intellectual exercise for other people—to follow your thought process and decide if they’d like to engage you in conversation. The blogosphere is a cocktail party for the intelligentsia without J Brand jeans or Jimmy Choo shoes. It’s just ideas, bouncing back and forth, and you’re deciding who to talk to.

I know I’m always telling people to stop worrying about what their blog is going to be and to just start blogging. I say this assuming that you understand that a blog is a networking tool. It’s one of the most important ways you can create career stability, by being who you are and connecting with people who like you for who you are. Your blog is a career-management dream-come-true.

Lie #4: Social media is no place for business.

The most common thing idiots say to me about my company is that we are never going to make money. But, we already do. Because companies definitely understand the need to leverage social media to meet their bottom-line goals. And my company helps them do that.

Companies understand they need to participate in conversation, and they are looking a professional places to do it. If you want to be known to companies, you will use social media to allow them to get to know you. (Wait. This just in. Government agencies get it as well! Check out the TSA's stellar use of social media.  A mommy blogger wrote a post accusing airport security of taking her son from her during a security check. TSA disputed her claim by posting video of woman and her son on the TSA blog. The mommy blogger published an apology.)

Which brings me to the seven-second rule. Someone who just met you for the first time, in person, will give you about three seconds to impress them. So you are very careful to show your best first impression in this situation. You already know this.

The same is true online. You probably get ten seconds instead of seven seconds, but the person will google your name, looking for something relevant in the top results, and click. If they are not impressed in the first ten seconds, they won’t keep reading about you.

If they go to Facebook, you have no idea what they’ll find out about you because so many people write on your wall about unprofessional things. If they end up at LinkedIn and you have a relatively shallow level of experience, you will not look good next to the typical LinkedIn user who is 40 years old, earning more than $100K, and has 15 years of experience.

So where do you want people to meet you for the first time online? Somewhere they can hear you talking about ideas. For bloggers, this is often a blog URL. Others could try Brazen Careerist, where your profile is comprised of your thoughts and ideas—you, being you.

1. Pitch yourself as specialized.
Most people are relocating from a city that is in low demand to a city that is high demand. For example: Tucson to San Francisco. There are not a lot of skill sets that someone has to look outside San Francisco to get. If you want to get a job from Tucson, you need to have one of those skill sets that people do not think they can hire for in San Francisco. Usually this means that you're very specialized. So, the first thing about getting a job in a city you don't live in is that you need to be very specialized or in high demand.

The idea behind being a specialist is that you are so good at a very specific thing that people are unlikely to find someone as good as you locally. Sometimes a good career coach can help you rewrite your resume to focus on a specialty. If you don't have one, a good primer for finding a specialty is reading about the funeral industry, where you have to specialize in something (sometimes weird) in order to survive.

2. Pitch yourself as a big-city catch.
Some of you are trying to move the opposite direction: New York City to Tuscaloosa. In that case, you can pitch yourself as having big-city know-how that you can bring to a smaller city. I know from having a company in Madison that when we hear a star performer from a big city is relocating to Madison, we automatically consider interviewing that person. It's a bias that the competition is so much tougher in big cities that people who have risen to the top are probably worth looking at because we don't see a lot of those people.

3. Get a reality check.
If you can't pitch yourself in either of those ways, then you're going to have to relocate before you get a job. Think about it: Why would someone fly you in for an interview when there are plenty of local people who could do the job? It makes no sense.

4. Be amazing at building local networks.
If you are still determined to get a job before you move, you should commit a lot of time to building a network. You know that most jobs come from networking. So you need to have a strong network on the ground where you want to relocate. This does not mean inviting forty people in that city to connect with you on LinkedIn. Those are not the type of connections where the person goes to bat for you. You need a network of people you have real conversations with, and share real ideas with. After awhile, these people will care about you and want to help you. This is one of the reasons that among the professional groups on Brazen Careerist, location-based groups are the most popular.

5. Choose a city since you can't choose a job.
Most of you are simply going to have to relocate before you get the job. And, since you are going to have to move before you have a job, why not make sure you are going to the right place? You can read about the research I used. (For all my complaining about Madison, I have to say that the research I used turned out to be true, and Madison is probably the right place for me.)

Another resource for figuring out where you belong is Richard Florida's book, Who's Your City, which he has conveniently broken up into web-friendly widgets for your relocating pleasure. Try this one, for example.

And, once you decide on a city, you can use Florida's analysis to double check your conclusion. Check out these best places lists. (Note: More than 80% of gen y wants to move to New York City, but, frankly, most of people don't belong there. Here's a test to find out about you.)

6. Consider your friends and family.
Before you relocate for money, consider that the number-one factor for whether or not your next job will improve your happiness is whether you'll be moving closer to friends and family. Because, you already know this, but money does not buy happiness. And, you might not know this, but a job does not make you happy, either. A job can make you unhappy, but once you have the basics of a good job, it's your relationships that make you happy .

Also, Holly Hoffman wanted to meet Guy Kawasaki. And really, it's not like I’m his best friend, but because I know him, I could say to Holly, "Oh, I'll introduce you." And I did that. And Holly was thank-you-thank-you, even though Guy is so nice that you can just walk up to him and introduce yourself and he'll be nice. To everyone.

And I'm standing there with a bunch of 25 year olds, because I'm always hanging out with 25 year olds because that's basically my job—I work with them and my business is for them. But I was not with THE 25 year old because the night before, I woke up to him peeing on the carpet in my hotel room.

When I asked what he was doing, he said, “Oh, sorry” and then he went back to bed. So I woke him up. And yelled at him.

He said he was drunk. He went back to sleep. I woke him up. I said, “I told you you had to go down on me and you didn't. You asked a woman out after she wrote a whole blog post about oral sex and you don't even do oral sex.

I’m pissed.”

He says, "I was too tired.”

“Too tired for ten times? We've had sex ten times.”

The night deteriorated and I told him to leave the next morning, by 8am.

He says, “Can you wake me at 7:30?”

And I say, “No, I'm not your mother.”

So at the party, that night, I was surrounded by 25 year olds, but not that 25 year old, and you can imagine that I was really happy when someone my own age came up to me.

But I really couldn't tell why he was coming up to me. I have said before that I think I have Asperger Syndrome, and I think it's full blown when it comes to dating. So I have to be direct. So when this guy who is clearly in my age bracket comes up to me and says, "Hi, I like your blog," I ask, "Are you trying to date me?"

I know this is not normal. But I had been to a million parties and I had had a glass of wine, and I just wanted to sort people quickly.

He thought for a minute and then he said, “Yes."

Great, right? He showed me that he can cope with my weirdness and still come out okay. So we hung out talked for a while, and then I realized my phone was dead. And the night was early and I needed to text people and so I wanted to go back to my hotel room to get my charger.

The guy said he'd walk there with me.

I tell Ryan Paugh because I think maybe I’m missing something.

Ryan says, “He thinks you're having sex with him.”

“What?”

“Yeah. You can't take a guy to your hotel room and not have sex.”

“Oh. Wait. But I told him I need my charger.”

“No.”

“Okay. Okay.”

So I tell the guy, “No.” Then I walk him over to his friends, who are at the same party, and I tell them our date is over: “I'm getting my charger and he can't come with me because I don't want to have sex with him.”

His friends laugh.

I think this is a good sign.

So the next night we have a date. It is very low pressure because he is from a state that is far away and does not have a direct flight from Madison. And he is not a gazillionaire, so he is not going to buy a house for us to share in Chicago when we meet at O’Hare. So: No future.

I tell him, "Be careful of that wet spot on the floor." And then we have a one-night stand. At least I think it is going to be a one-night stand. But then in bed, I can tell that he’s not thinking one-night stand because he does sweet things that guys never do to me, like stroke my hair. I do that with my kids.

And then things deteriorate quickly. Well, for three weeks, things are good. I like him and I call him. And I see him again. Then things get bad because he twitters about me. And I think, I do not want the world to know I’m dating him because maybe I don’t want to be dating him.

And he tells me I’m out of my mind that I’m worried about who is twittering about me. He says something, which I will summarize as: Get a life.

So I am not with him. Because you can’t be with someone who thinks you’re out of your mind. And I’m not with the 25 year old, who, by the way, is also twittering about me, in an odd sort of way.

So I’m thinking the lesson here is that if work and sex are mixing then it’s a sign the dating isn’t working. But really, there must be a ton of people who think sex and work overlap because, look, my blog has 33,000 subscribers.

So maybe the lesson is I shouldn’t date people I meet through my blog. But then I think, who have I met not through my blog in the last two years? And maybe the answer is no one.

I say, “No.”

He says, “We’re trying to hire her.”

So I check out her blog and dis her and he says, “She was dating Matt Mullenweg.”

I say, “Really.”

He says, “Yeah. I was talking with my business partner and we both thought it must really suck for her that they are not dating anymore but they are still mentioned in the same breath a lot.”

“Really? Like how?”

“Google Glenda Bautista Matt.”

I do that. Their life looks really fun. They do cool stuff, meet cool people, and how can you not think Matt is great? He is. Who knows what he’s like to date, but he’s a great online brand.

That conversation was four weeks ago. And I have talked with this guy I’m sort of dating, D, a lot since then. But I am not saying that he’s my boyfriend because maybe I want my boyfriend to have as big a brand as Matt.

For forever, girls have been looking for guys with a ton of money — even the smart girls. But I married a guy who never earned any money, and honestly, I never really cared. We had problems, but not because I earned all the money.

So now I know that I don’t need to look for a guy with a ton of money. And since my divorce, I've taken time to be sort of a free spirit, just dating people for fun and connection and all the corny things my readers ask me to pay attention to, as they explain how the farmer is not right for me, and how the 25-year-old is not right either, and that the alcoholic private equity guy is an alcoholic.

Then I thought about Glenda. I immediately thought she must be a good hire because she dated Matt. It’s a good reference. You know she’s smart. Because how could Matt be with a moron? He couldn’t. And even before you see her in person, you can know she’s not below average in the looks department, because I don’t think Matt needs to go there. So my point, here is that attaching your own brand to a known, solid brand is very good.

I see Hollywood people doing this. It's not new. But it's new that today each person online is some sort of brand and we are all personal brand managers.

So, D, who is really attentive and normal—two traits I have never had in a boyfriend, ever—is scary to me because I’m giving up the chance to enhance my brand by dating an online star.

So I was sort of keeping D a secret. Because I was worried doors would close. But I could see doors closing because each week I’d spend more time on the phone with him. You might have noticed this. There’s an inverse correlation between how smitten I am with who I’m seeing and how frequent these blog posts arrive.

Last week, for example, there were two posts, and I only wrote one of them. When I was in a terrible marriage and trying to hide in my work, there were four posts a week, sometimes five.

I found myself doing stuff like talking with him all day via IM and text and email and the phone. So that even though he lives very far from me, it felt like he was sort of everywhere, all the time.

I got tired, so tired that I actually sent the kids to school one day and went back to bed and missed all my meetings. When I called Ryan to tell him I overslept I felt like I was the intern calling human resources and hoping not to get fired.

Ryan didn’t care. He knows I work way more than most people and that I would probably be more sane if I worked less.

But I got nervous and went back to working long hours and still talking on the phone late at night, until one night recently.

I saw I missed a call, and I called him back, and I said, “Where are you?” Mostly I asked because it sounded loud and I know his routine now, and it’s never loud at 8pm. He said, “I’m on a plane. Stuck on the tarmac.”

I said, “You didn’t tell me you were flying tonight.”

He said, “You didn’t ask.”

I went ballistic that how could we talk this much and he not tell me his travel schedule.

Then he told me his schedule.

I told him I am planning a trip to the same city. We could be sharing a hotel room. Why is he not telling me ahead of time? I tell him I’m so frustrated that I have to hang up.

He says, “I’m sorry. I’m sorry. I didn’t know you wanted to see me.”

I said, “Are you nuts? I talk with you almost every night. “

Then we both paused.

He said, “You don’t know who this is, do you?”

Then I died as I realized he is my freelance sales guy who lives in the same area code as D.

I tell him,”Oh. God. No. I didn’t know it was you. I have to hang up. I have to call you back. I have to call you back in maybe ten years.”

That was the first thing. Of many things that are the result of me spending way too much time talking and writing to D.

He sent me a quote about how we each vibrate a certain way and we find our vibrational match.

I told him I think that’s true, but I vibrate like an insane person. And I worry that I am attracting my vibrational match for insanity and that if I could just get more sane, I’d attract a different match.

He pointed out the obvious: I will probably not get more sane. “This is just you,” he said.

And then I got happy that he is stable and calm and largely unshakable, when I am often shaking as much as I can.

And then I tell myself that I have to admit that I’m dating him. I’m not sure what that means, but the only reason I’m not doing it is because I’m holding out for some amorphous online brand that will perfectly complement my own.

Do not write to me and tell me that’s shallow, okay? It’s the new millennium version of a gold digger. And I know I’m not the only one. I’m just the only one willing to admit it.

So I guess when someone wants to hire me, I’m not going to be able to get the job based on who I’ve dated.

Personal branding describes a process where individuals differentiate themselves from a crowd by articulating their unique value proposition, whether professional or personal, and then leverage it across platforms with a consistent message to achieve a specific goal. In this way, individuals can enhance their recognition as experts in their field, establish reputation and credibility, advance their careers, and build self-confidence.

Here are five reasons why Generation Y is better at this process than everyone else:

1.   We have the least amount of responsibilities.
Personal branding is a very time consuming exercise that most adults don’t do because of the sheer amount of responsibilities they have, which are priorities to them. However, the more time you invest in your personal marketing efforts, the more successful you’ll be.  For Gen Y, the amount of hours we have left after classes, interships and jobs, is still greater than an older person in the workforce, with twin babies, a pet dog and a list of errands. Millennials can stay up till 2 or 3 a.m. growing our personal brands using social media tools, such as blogs and social networks like Facebook, LinkedIn and Brazen Careerist, to become more well known in our industry.

2.   We're already marketing ourselves intuitively.
We’re all marketing ourselves without thinking much of it, but Gen Y is doing it on steroids. Gen Y is all hyper-connected with mass media, including the fact that their cell phones are an extension of their hands and that we go online more than any other generation. Every time we send out a text message to fifty of our friends or update our status on Facebook to a few thousand friends, we’re marketing ourselves to our world.  Then our network spreads our messages to an even greater audience in just minutes.  The many marketing lists we’re building online, such as Facebook friends, Twitter followers, and YouTube channel subscribers, are assets that will be useful today and in years to come.  Companies that we work for can get the word out for free using our networks.

3.  We are equipped with a bottomless pit of marketing tools.
Every communication channel is a marketing tool, and since Gen Y is the most plugged in generation, there isn’t a tool we don’t touch.  Aside from the phone and in-person meetings, Gen Y has instant messaging, Skype, social networks, blogging, podcast and more.  By using these tools, Gen Y delivers messages faster and in different forms, so we can build our personal brand in a shorter period of time.  Members of Gen Y are very proficient using these tools because we grew up with technology and can easily adapt to the changing technological landscape, whereas other generations have a longer learning curve.

4.  We understand how to build personal connections to build a brand.
Gen Y’ers are the masters of social media, which means we understand that marketing exists through other people. We use social media tools to put us in touch with other people who can help make us more successful.  Since we are young, we can connect with older generations who can share experiences, lessons learned and other career advice.  We are more productive at work by being connected to more people who can help answer questions.  Gen Y-ers can position themselves in their company as the go-to-person for all technology needs, making them an invaluable asset to their work group.

5.  They have no choice but to be marketing mavens.
Standing out among the millions of job seekers is quite hard in this economy and the competition to succeed in any industry isn’t declining anytime soon.  Internship hiring will be cut by 21%, co-op hiring by 11% and 22% less jobs for 2009 graduates, according to NACE.  The amount of pressure on millennials is immense and it forces them to rethink the way they are perceived and how they market themselves to stand out from the pack.  Gen Y can showcase our website, blog and other unique items that can differentiate us, relative to other applicants that are applying for the same jobs.   We spend more time figuring out what makes us unique, compelling and marketable to employers because otherwise we'll be jobless.

This is a guest post from Dan Schawbel. He is 25 years old and already, the New York Times has called him a "personal branding guru." Dan's book is Me 2.0: Build a Powerful Brand to Achieve Career Success, and it just came out today.

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.

Also, he's earned it because he's an incredibly hard worker when it comes to promotion. The other person I know who works this hard is Tim Ferriss, but Tim tells you that he doesn't. Ramit admits to hard work, so I like him better. And Ramit tells me all the stuff he is doing, like convincing people to listen to MP3s where he is selling stuff, which I told him I would never link to on my blog because I'd feel like a used car salesman, but still I admire how many avenues Ramit will travel to sell stuff.

I am not a great seller. Which you can tell on my blog, actually. I mean, I have a company and no one even knows what it does. I could be selling the shit out of it on this blog, but instead, I am writing about requiring my dates to bake cookies with me. Ramit does not have posts about having sex in his apartment. But he does have posts about his friends trying to get laid and I enjoy that.

So I told Ramit that while I am sure that he is the direct-mail genius of Web 2.0, I cannot help without having to go to a mikvah afterward. And since I don't do mikvah, I can't do all his upsell, upsell, upsell stuff.

He replied, “How about a free plane ticket?” But not for me. And that is why I love Ramit.

So Ramit wants you to buy the book. I'm pretty sure he wants you to buy it today. Because Ramit is a Svengali of Amazon ranking and somehow Ramit's book was number one on Amazon yesterday.

And if you buy the book, you can send him the receipt and you might win a plane ticket.

Here’s how: If you order the book and email your receipt to penelope@iwillteachyoutoberich.com within the next 48 hours, you will be entered to win a free plane ticket to anywhere in the US.

If I write a crappy enough post about the book—like this one, where I manage to write about the book but never tell you one little thing about it—then maybe no one but you will send a receipt and then you'll win.

So before you leave a comment complaining that this is just about Ramit and me and Ramit making money, remember that the plane ticket is all about you.

But I do want to say something about his book. I am very bad with finances. I have known this for a while but recently, two things have really bothered me. First, I read that ENTJs are very good with finances, so this makes me think that I am underperforming there. Second, I noticed that every guy I date is amazed at how much money I have coming in (a lot) and how much I have going out (more than a lot) and how crappy a car I drive. (Actually, it’s not just the car, it’s the consistently odd choices, like no living room furniture because it costs too much.)

The first thing I tell those guys is to shut up. And then I tell them that they don’t understand because my financial issues are different than everyone else’s. But you know what? I don’t believe that. I don’t believe peoples’ problems are special. Still, I wasn’t making much headway until Ramit’s book came. The book is geared toward people in their 20s who still have a lot to learn and Ramit is teaching them (hence the title: I Will Teach You to Be Rich), but I am not in my 20s and I learned a lot anyway.

I always have a book in the kitchen that I read to distract myself from two young boys who are always turning harmless stuff into guns and killing each other. So for the past couple of months, while my kids have been shooting each other, I have been reading Ramit’s book, one or two pages at a time. And what it did was make me realize that there are tons of small things I can do to make big improvements. And also, knowing what to do feels empowering, even if I still have a financial mess on my hands.

I actually think this is the way career advice works as well. First, you need to know your problems are not unique. Then you need to know what people do to solve those common problems. The action of actually making change is the last step, but the first two are harder.

1. Be interesting. The questions people ask you are not really what they want to know. It’s what they think will be interesting. They would ask you about the price of tea in China if they thought the answer would be interesting.

So your job in an interview is to give an answer that is entertaining and thought-provoking and all the other things that people like. You don’t need to answer the question as much as you need to answer the need for interestingness.

2. Be short. The world does not have an unlimited attention span to hear how your mind works. So you can’t think out loud in an interview and have everyone wait til you get to your point. Your point has to start right away.

Also, if you are short then you are more likely to be interesting the whole time. The longer you talk about a given topic the harder it is to keep someone’s interest. In the PR world this is called “soundbite”. But really, you can use the sound bite technique everywhere – on radio, in a blog post, on a date.

3. Be conversational. You can’t be chatty in a written interview because there’s no one there. But on the phone, or on TV you can actually make the interview into more of a conversation. In a many cases, the interview becomes more interesting this way.

First of all, it tells the audience that the person interviewing is interesting in their own right, because you are asking questions back to him or her. And a room with two interesting people is better than a room with only one interesting person. The second thing is that the conversation becomes a little less scripted and there is more risk and more space for unbridled passion, on either side of the conversation. And spontaneity makes conversation more engaging.

Be upbeat is also a rule. I think. But why is this a rule? I’m not sure. I think it is like the rule about the first two minutes – or whatever the time frame is that someone forms their judgment of you. You want them to meet someone who is fresh-faced, chirpy and upbeat. But what if you’re feeling grouchy? What if you are not really a chirpy type of person?

Recently I’ve been experimenting with breaking the rule about being upbeat. I did an audio interview with self-confidence coach Steve Errey, on a morning when I was having a confidence crisis. And I decided I was not going to fake it on the phone.

Then a week later, I did a written interview with Gretchen Rubin, who is writing a book about happiness research, and I decided to allow myself to reveal that I feel pissy about the happiness research.

And you know what? I really like both interviews. Maybe you will too. And if you like those, then maybe you will also like the photo that everyone told me I could not put on my blog masthead because the world does not like sulking. But I love a good sulk: