I think each person struggles with one, singular thing. I learned this when I was a graduate student in English. Each writer we studied actually wrote the same book over and over again. We each have a primary question in our lives.

Rob Toomey, a friend who is an expert in personality type, coaches executives. He sees that it’s always the same problem that holds each given personality type back. ISTPs, for example, (which is the farmer's type) have trouble planning anything in the future. They lack commitment to anything long-term. ENTJs (what I am) have trouble with tact. They lack a sensitivity that many people require in order to listen.

So, anyway, I notice that the farmer and I have the same argument over and over again. And like writers and executives, the farmer has one problem: he cannot separate from X.

A problem we have, which I don't think has actually been a problem until this post, is that I'm not allowed to mention the thing he cannot separate from. So it will just be X. Anyone who has read this post or this post can figure out what X is. And after just a little while with him, I knew that the farmer did not actually need an adult relationship with a woman until he separated from X.

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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

So, I am lost. But I need to be useful more than I need to confess feeling lost. So, here I am, telling you what I’m doing to get through this, because I think you and I have an agreement that you’ll put up with me being lost and not posting very often, as long as I’m useful. Read more

Feeling lost is part of being great. If you are forging your own path then you are often lost. Because you have not seen this route before. I wrote my book because I did not have a road map and I am wanted other people to have a road map to do a career like I did.

I have been thinking about this because I am really lost right now. I’m going to show you something. Here is stuff that’s going well. The farmer is totally hot, and he tries so hard to get along with me, and his singing voice is the kind that allowed him to hook up with any girl after his band played a gig. And he matches my wall:

Another good thing is that he lets me do whatever I want with the house. See? In the background? We definitely needed a hutch in the dining room. It’s exactly what fit with the decor. But I thought if I bought a hutch I’d just start buying stuff to fill it with. So instead, I drew a hutch on the wall. I showed it to the farmer and he said, “I really like the undulating lines. They have confidence.” Read more

It's the fifth annual Penelope Trunk Q&A. It's not that I don't answer questions. I actually answer almost every question I receive. But only rarely in a blog post. The problem is that most questions suck. Look, here are posts about how to ask good questions.

In fact, I’ve been getting so ornery about questions sucking that I did a webinar about how to write a good blog post and I got pissed off in the middle because the questions were so bad that I walked off camera and half the video is Ryan Paugh telling me not to be a brat.

So, in the spirit of not being a brat, I am answering questions that I think are interesting. Read more

This is not an exhaustive list on the topic. In fact, it may be an inexhaustible topic. There are older lists of what I hate. So today’s post is merely my most recent list.

Which is notable because hatred is a process. Neurologists have proven that love and hate are closely related, and I have found it’s hard to hate a person unless I am also close to that person, and the same is true for a topic. In that vein, life is the process of expanding our love and our knowledge, and I suppose, our hate.

So here are some things that I have recently reached the point of thinking so much about that I feel qualified to hate them:

1. Sarcasm
The use of sarcasm is always inappropriate. Sarcasm reveals insecurity and cynicism — both things that make a person unlikable. Sarcasm is always negative in meaning, and the tone is always disparaging. On top of that, people who use sarcasm think they are being funny, but this is a poor man's humor; because comedy is about timing. You say it, then there's a beat, and then people laugh. With sarcasm, you say it, there's a beat when someone realizes you've said something you don't mean, and a beat to process what you did mean. The timing is off.

So comedians rarely use sarcasm because it's not funny. And top performers don't use sarcasm because it's mean. Read more

I think I'm over the happiness thing. I think I am thinking that the pursuit of happiness is, well, vacuous. I don't think people are happy or unhappy. Because I think knowing if we are happy would require knowing the meaning of life, or the ultimate goal, or the key to the world, or something that, which really, we are not going to find outside of blind religious fanaticism.

The first thing I have to grapple with, besides having spent the last three years of my life completely enthralled and ensconced in the happiness research from positive psychologists, is if I don't want a happy life, what sort of life do I want?

I think I want an interesting life. Not that I want to be interesting, but I want to be interested. I’m talking about what I think is interesting to me. I want to choose things that are interesting to me over things that would make me happy. For example, this post. I am not sure if I’m right on this, and I’m sure there’s going to be a lot of telling me I’m an idiot in the comments. But it’s going to be interesting.

I think choosing a life that is interesting to us and choosing a life that makes us feel happy are probably very different choices.

For one thing, people who are happy do not look for a lot of choices, according to Barry Schwartz, in his book, The Paradox of Choice. People who want to have an interesting life are always looking for more choices and better choices, and they make decisions for their life based on maximizing choices. Read more

I am back with the farmer.

This probably is not surprising to you, because admittedly, it is absurd to be engaged one day and not engaged the next day. But there are exacerbating factors, and basically, the way I got him back was to be more likable.

I have spent most of my career overcoming my lack of social skills by studying research about what makes people likable. And I think the research I’ve applied so systematically in my career is finally helping me in my personal life.

Here’s what we know about being likable:

1. Don’t give ultimatums. It’s disrespectful. Instead, be a negotiator.
The farmer does not want to be in this blog. As you might imagine, we have this discussion a lot.

First it was like this:

Him: I don’t want to be in the blog.

Me: You have to be. I can’t live without writing my life.

Then the conversation was like this:

Him: I don’t want to be in the blog.

Me: How about if you can edit whatever you want? Read more

I am lost. I have been lost before in my career. It's just that I did not write about it while it was happening. I wrote about it after the fact. That's much easier. But in the past, during the time I was lost, I simply stopped writing.

For example, I quit playing volleyball and went to graduate school for English. And, at the same time that I realized that English professors make no money and have no job security, I also got dumped by the guy I had been living with for five years. So this is what I did in graduate school: Nothing. I had already written two full novels, so I turned in a little bit of them each week. And I had to take literature courses, which I passed by reading New York Times book reviews (you'd be surprised how far back those go.) And then, after burning every bridge possible at Boston University, I left, one credit short of a graduate degree.

There were other times I fell apart. And stopped writing. For example, when I had a baby, I stayed home with it, every hour of every day, while I had an identity crisis. I still needed to support the family, but I couldn't write anything because I couldn't imagine giving career advice when I was having a total career meltdown. So I took columns from five years earlier and turned them in as new columns. And, after about three months of that, I got fired.

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The first step to growing a good career in the face of Asperger’s Syndrome is to recognize that this is a social skills deficit, by definition, and work, by definition, is a social skills decathlon.

I have written before that for me, the biggest problem at work stems from my own sensory integration dysfunction — something that typically tags along with an Asperger’s diagnosis. But for someone with Asperger’s, it’s not enough to deal with sensory integration dysfunction; in order to succeed at the workplace, you need some guidelines for bridging the gap between other peoples’ social skills and your own.

So, based on my own experience, here are some concrete rules for doing better at work if you have Asperger’s, and maybe if you don’t.

1. Spend limited amounts of time with people.
One of the things that is alarming to non-Asperger’s people is how few friends and relationships people with Asperger’s have. But I have never heard anyone with Asperger’s lament this. (Temple Grandin is a good example.) It’s not something we feel a loss about. We only need a small amount of closeness in our life. What I do hear Asperger’s people sad about all the time is a lack of employment opportunity. Read more