It is harder to know who you are than it is to be who you are. Everyone says, “The important thing is to be yourself!” I say that when I give them career advice. People like you better when you are being authentic. Gay people do better in their careers when they are out of the closet. Women do better at work if they are feminine at work instead of trying to be like the guys.

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.