I'm deciding if I should take a sleeping pill.

I know tons of people who take them. I never understood the need, to be honest. I remember when I was in a mental ward. My group therapy was a bunch of eating disorder girls (which I was part of, but a little old for) and a bunch of grown-ups who were depressed and maybe receiving electroshock therapy. (Does this still happen? I don't know.)

Anyway, the girls' biggest problem was that they hated their family and wanted to live in the mental ward instead. (I definitely fell into that camp.) The adults' problem was that they could not sleep.

At first, I thought, “If this is your biggest problem, do you need to be in a mental ward?”

And this is why I loved the mental ward, by the way. You learn so much about life from people who are unable to live it. Read more

It’s amazing that people admit to being perfectionists. To me, it’s a disorder, not unlike obsessive-compulsive disorder. And like obsessive-compulsive disorder, perfectionism messes you up. It also messes up the people around you, because perfectionists lose perspective as they get more and more mired in details.

We can never achieve perfection — any of us. Yet so many people keep trying to reach this elusive goal and they drive themselves crazy in the process. So cut it out. Accept that it’s okay to do a mediocre job on a certain percentage of your work. If you need convincing, consider this: Perfectionism is a risk factor for depression. No kidding. Sydney Blatt, psychologist at Yale University, finds that perfectionists are more likely to kill themselves than regular, mediocre-performing people.

Here are three steps to take to avoid the perfectionism trap: Read more

For those of you who missed it, Karen Owen, a student at Duke University, sent a summary of her sex life to some friends, via email. The content is not safe for work, but it looks safe because it’s in PowerPoint. She has bullet points, charts, and graphs. How can you not admire a woman who can graph her sex life?

Owen’s sex life is a workplace issue. For one thing, it was the third most searched topic on Google yesterday, which means a large percentage of people were reading her slideshow while at work. But more importantly, Owen’s slides capture the shift in women’s empowerment, which is happening at the workplace and having the ripple effect of empowering women in sex. Owen’s slides make me excited about the new generation of women and how much they take their own power for granted. I’m excited to see what they will do with it.

Here are some things to think about when you read her slides:

1. She used PowerPoint in a revolutionary way.
Is there a more male tool than PowerPoint? First of all, the software is lecture-y and unconversational, which is typical for men at work. Second of all, it's been the tool of choice for the notoriously boys club career: venture capitalists and the people who pitch to them. That Owen used this male tool to talk about what men are really like in bed turns our workplace preconceptions on their head. Read more

This was originally posted on TechCrunch.

My company, Brazen Careerist, is moving from Madison, WI, to Washington, DC, where our new CEO lives.

Running the company has been absolute hell. Not that I didn’t know it would be hell. It’s my third startup. Each has had its own hell before we were solidly funded, but this one was so bad that my electricity was turned off, and I really thought I was going to die from stress.

So while my company moves its center to DC, I’m staying in Wisconsin. I just married a farmer and my two young sons and I are learning to live among the wonders of pigs and cattle and corn.

I thought I would be sad that the company is moving. It’s weird to be the founder of a company and not be where all the action of the company is. But honestly, I’m relieved.

There is good evidence that you have to be crazy to do a startup. Jeff Stibel, writing in the Harvard Business Review, calls entrepreneurship a disease. Because you are not likely to make money — you are likely to die broke. And you work insane hours — longer than any other job — and you do it over and over and over again. This is not sane.

In fact, David Segal reports in the New York Times that there is a mania that entrepreneurs exhibit that is very attractive to investors. The trick is to make sure you’re investing in someone who is on the border of insane, but not insane.

So I had a going away party. To say goodbye, but also to acknowledge that I am officially not crazy enough to spend another year missing out on being with my kids. There is still an office in Madison, but the company is running well enough that I don’t have to be the center of it.

It’s hard to not be the center, but I want to be the center of my family. There are enough articles in the last year alone to fill a book (not to mention conference panels) about why women don’t get funding for startups. But really, you could tell that story on one page: Startups move at a break-neck pace, under a lot of pressure to succeed bigger and faster than any normal company. And women don’t want to give up their personal life in exchange for the chance to be the next Google. Or even the next Feedburner. Which is why the number of women who pitch is so small, and, therefore, the number of women who get funding is small.

Did you know that in Farmville, women make colorful, fun farms, and men make big, sprawling farms? And I don’t think it’s a social pressure sort of thing. My sons are under no pressure from me to beat each other up with anything that they can turn into a sword, which is everything. And the girls who visit are under no social pressure to sit quietly and watch. Boys and girls are fundamentally different even before they get to Farmville.

Women are under real pressure to have kids, though. They have a biological clock. So women who are the typical age of entrepreneurs, 25, need to be looking for someone to mate with. Think about it. If you want to have kids before you’re 35 when your biological clock explodes then you need to start when you’re 30, allowing for one miscarriage, which is more probable than most young people think. If you need to start having kids when you’re 30, you probably need to meet the guy you’re going to marry by the time you’re 27, so you can date for a year, get married, and live together for a year before kids. If you need to meet that guy by 27, you are very distracted during your prime startup time. (I have done years of research to come to this conclusion. Here’s the post.)

And I’m not even going to go into the idea of women having a startup with young kids. It is absolutely untenable. The women I know who do this have lost their companies or their marriages or both. And there is no woman running a startup with young kids, who, behind closed doors, would recommend this life to anyone.

For men it’s different. We all know that men do not search all over town finding the perfect ballet teacher. Men are more likely to settle when it comes to raising kids. The kids are fine. Men are more likely than women to think they themselves are doing a good job parenting. This makes sense from an evolutionary perspective. Men have to trust that the kids will be okay so that they can leave and go get food or make more kids.

Before you tell me there are exceptions, I’m going to let you in on a secret: I’m a magnet for high-powered women with stay-at-home husbands. And when the men aren’t listening, the women always tell me that their men don’t pay enough attention and they (the women) are really running the household. They would never say this to the men. It would de-motivate them. So even the most child-oriented men are not as child-oriented as their wives.

And this is why women don’t have startups: children. It’s not a complicated answer. It’s a sort of throw-back-to-the-50’s answer. You could argue the merits of this, but you could not argue the merits of this with any woman who has kids and has a startup.

There’s a reason that women start more businesses than men, but women only get 3% of the funding that men do. The reason is that women want a lifestyle business. Women want to control their time, control their work, to be flexible for their kids. This seems reasonable: Women start more lifestyle businesses and men start more venture-funded businesses. This does not, on face value, seem inherently problematic.

But wait, let’s ask why so many men with kids are doing startups? Why aren’t they with their kids? A startup is like six full-time jobs. Where does that leave the kids? We use social service funding to tell impoverished families that it’s important for dads to spend time with their kids. But what about startup founders? Is it okay for them to leave their kids in favor of 100-hour weeks? For many founders, their startup is their child.

My startup is me and a bunch of twenty-something guys. And if you’re a woman launching a startup, my advice is to stick with this crowd. They never stop working because it’s so exciting to them: the learning curve is high, they can move anywhere, they can live on nothing, and they can keep wacky hours.

The problem with that mix is that someone who is not a guy in his 20’s has different priorities. And that’s something we saw really clearly at Brazen Careerist. The more I became focused on my personal life, the more annoyed everyone got with me. Sure, they understood, but they were pissed also.

I think our new setup will alleviate much of that stress. I’m on the farm, Ryan Paugh is in Madison, and Ryan Healy is in DC. It’s not how I imagined the company evolving when we started it, but that’s part of the fun of entrepreneurship: you never get what you imagined, ever.

 

One of the hardest things about being unemployed is worrying that you will not end up in a good job. People want to be picky, but that’s a mistake. You should take any job. It really doesn’t matter. You’re better off taking any job and then start trading up.

Here’s why: Read more

Here’s an idea for what women should do if they’re unemployed: Have a baby. Your first reaction is probably that this is a throwback to the 1950s. But it’s not. This is the most up-to-date career advice you’re going to get for dealing with a down-in-the-dumps job market.

Here’s why a stint of unemployment is a great time to have a baby: Read more

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. Read more

I am going to be a better person at self-promotion because I don't brag enough. Ryan Paugh, who was basically my intern when I met him, and now he’s almost my boss and definitely my social-skills mentor, tells me that I am popular because I’m interesting but that I suck at self-promotion. (He uses, as an example, the day I promoted an event on my blog a few hours after it actually happened.)

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. Read more

Hi there. You are probably here because you read the article about me having Asperger’s syndrome. I have never seen the Mail on Sunday, but it must be a big publication because thousands of readers are coming to the blog from London today.

(For readers who did not see the article, I like it. Here’s a link. And, sidenote, the author, Louette Harding, was so good at interviewing – so patient and so insightful and I wish I could talk with her every day. But maybe that’s just because we talked about me and this is just evidence that I am really hard to be friends with.)

If you are here for the first time, here are some shortcuts to posts I’ve written about having Asperger’s syndrome:

Why I need a sick day to register my car

Five ways to be less annoying

5 Ways to make telecommuting better

Why I’m difficult at meetings

How I deal with sensory integration dysfunction

Really, though, almost all of this blog is about having Asperger’s syndrome because most of my writing is me trying to figure out the rules for succeeding in the workplace. I know that people say I have an odd take on the rules, but I think I’m usually right, I’m just more literal and more blunt than most people.

Here are some examples: Read more

You don’t need to be a basketball fan to know that LeBron James has been deciding if he should stay with his current team, the Cleveland Cavaliers, or move to another, more winning team. ESPN set aside an hour-long special episode for James to announce that he’s going to the Miami Heat.

James is extremely talented and has been called the next Michael Jordan. He is a free agent this year which is the genesis of the hoop-la surrounding his decision, and he has been madly courted by multiple teams.

Many sportswriters have said that the widespread obsession with James’ decision is totally over the top. The New York Times called the ESPN segment an ego-a-thon, which it may well be. But there’s more to our fascination with the decision than just our natural tendency to be drawn to celebrities. James encapsulates the issues each of us faces when we decide if we should relocate.

It’s friends and family vs. opportunity. James grew up in Akron, OH without a father. His basketball coaches played father figure roles to him. The Cavaliers picked him up when he was only 18, and he’s been there for the last seven years. This is his home, his support system, and his roots. Read more