Penelope Trunk’s Brazen Careerist. Advice at the intersection of work and life.
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This is what it looks like to have a hard time making a change

Posted to: Fulfillment |  Knowing yourself
November 20th, 2009
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Some days I look through old posts, reminding myself of posts that I've written that I like and that I should link to. Often, this process serves to let me procrastinate writing while pretending to be engaged in writing. If I were a body builder, this would be me looking in the mirror instead of lifting weights.

Yesterday I was trolling for posts, and I remembered this one, about hiring a babysitter. I never link to it because I can't read it. I get physically ill. It was a short, stinging moment during an absolutely terrible time in my life. But a part of me likes that sting. I'm the kind of girl that picks scabs off just to feel like I'm alive.

So you can imagine that a blog post about how to sell is not rocking my world. It's true that I've been thinking a lot about creating more stability in my life. But it's also true that in the recent post about what I learned from sales guys, I should have told you that when I met one of those sales guys on a plane, I went to a hotel and had sex with him. I had never had a one-night stand and I thought I should know what it's like. And it was terrible. I like picking scabs, but it's very controlled. It's hard to control a one-night stand, and it was, actually, very scary and not fun at all.

I want this blog to be somewhere in between a one-night stand with a sales guy and a five-point list of sales tips. In fact, I want my life to be that way as well.

A few days ago I flew to LA to get my haircut. I know that sounds crazy, but remember that I live in the middle of Wisconsin. Also, my best friend, Sharon, is in LA, and she owns a hair salon, and she's been cutting my hair for 15 years. Before I was her free-haircut-friend, a cut and color with her was about $300. So I feel like the plane ticket, together with the free haircut, is somehow still a bargain.

I go there on a day the salon is closed, and we do my hair and then spend the day hanging out in Santa Monica talking.

At lunch, outside, with cars driving by, I tell Sharon I need a break. I need a vacation. I have been working absolutely insane hours for the last five years. I traveled so much that when I get on a plane now, I have panic attacks.

She said, "What would you do on vacation?"

Me: "I'd probably wake up, take the kids to school, go to the gym, write a blog post, and then work on whatever company I was percolating. And then pick the kids up at school."

So I don't really want a vacation. I want breathing room. But not a vacation. To be honest, I still work at night. I am not sure why. I think because I'm interested in what people are doing. In what I'm doing. I don't want to miss anything because everything is still fun.

I think working at night is like picking scabs. It feels lively to solve some problems before I go to bed. Or create some. (Same way with pulling a scab, right?)

After lunch, Sharon and I drove to Culver City, to get my eyebrows done. I usually go to NYC for eyebrows. But I don't want to travel anymore, so I don't want to have a hair person in LA and an eyebrow person in NY. So, as a step toward simplifying my life, I did my eyebrows in LA.

I liked the place immediately because there was a whole display of gray nail polish and I know gray is the it-color for fall, and I know no one is wearing it yet in Madison, so I had high hopes for my eyebrows.

But they are uneven. Sharon tried to tell me they were okay, but good friends, really, don't do that. So in the end, she didn't. And I'm going back to NY next time.

I know you'll say, "Just find someone else in LA." It's not bad advice. In fact, this is what Sharon said.

But I'm upset about the eyebrows, about how it turned out. It's hard to make changes, even if the changes could make my life more calm. It's so easy to convince ourselves that the change is too difficult to make. For eyebrows, for a blog, for a career.

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How to know if you'll be good at sales

November 19th, 2009
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It’s clear to me that emotional intelligence is the most important skill for success in adult life. And the consummate career application of emotional intelligence is the sales department. So I’m fascinated by sales.

I used to think I’m not that good at sales. For example, I’m an open book—I have very little ability to bluff or play my hand close to my—actually, what is that expression? I don’t even know the expression.

But then, when I told one of my mentors that I’m not good at sales, he said, “Of course you’re good at sales. You’ve gotten three companies funded.” He’s right. I wanted to take back all the times I said I’m not good at sales. The thing is, I have a specific talent in this department: selling ideas.

I have gotten companies funded when they were still just philosophies about how a market will move, what the trends are, and what ideas will work. I have yet to raise a later round of funding, where the company is selling actual products or services with me raising money to sell them faster.

I’m also great at the consultative sale. I’m great at meeting someone who wants to think in new ways, and tossing some ideas back and forth and then going to lunch, or yoga, or commenting on each others’ blogs. I connect easily on ideas, and can close a sale there because the idea exchange is so rewarding. (more…)

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What makes a blog successful?

Posted to: Goal setting |  How to blog
November 17th, 2009
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I have always thought that blogging is a way to reach your career goals. It’s hard to write a blog if you don’t have a goal. You need to know what blogging success looks like to you, so you know what you're aiming for.

Like most goals in life, my definition of blogging success has shifted as the circumstances of my life have shifted.

1. Post regularly without messing anything up.
My first goal was simply to understand how to get my writing onto the Internet. All the buzzwords overwhelmed me: feeds, trackbacks, SEO. I understood none of it, and it took weeks to get up the nerve to blog before I actually started. My first goal was to post regularly and avoid basic publishing mistakes like posting a draft before it was ready. (Reality check: There are much easier ways to start a blog than the method I chose.)

2. Create traffic.
I started measuring my success by traffic. But after a few months, I was totally overwhelmed and had to rethink what I was doing. Suddenly I couldn’t answer all the comments, I couldn’t even answer all my email at the beginning—it started coming in faster than I ever imagined. (Reality check: Traffic metrics are addictive.) (more…)

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Don't be a snob about career advice

November 16th, 2009
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I have found that the best way to manage myself is by asking for a lot of help. The question is, how do you know who to take advice from?

The answer is not always intuitive. For example, you'd think that if Bill Gates wants to give you career advice, you should take it, right? I mean, the guy’s had a pretty decent career. The problem is that if he doesn’t care about your career, he’s going to give you generic advice.

Here are five other counter-intuitive principles I have used to figure out who to listen to when it comes to my own career:

Listen to people who hate you. People ask me all the time how I put up with the level of criticism this blog draws. The interesting thing about taking advice from people who don't like me is that sometimes, they'll say things that other people wouldn't say because it would hurt me. I rely on my gut in terms of whose criticism comes from caring and understanding and whose criticism comes from an obsessive need to take me down, but after I figure that out, I still pay attention to my critics. (more…)

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How to make business travel manageable

Posted to: Productivity |  Self-management
November 11th, 2009
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Last year I traveled almost every week. Some weeks I traveled to three different cities.

If you are excited about business travel, thinking it’s a free ticket to see the world, you should stop reading now. But if you are having trouble maintaining your personal life in the face of tons of travel, these tips from a cynical traveler will make life easier for you.

1. Stick with your priorities. When people travel to another city, why do they throw out their to do list for sightseeing in random museums? If you have on your top three things you want in life: go to the gym, stay in touch with friends, read a book a week, then sightseeing is not on the list. You don’t need to do it when you travel. You need to stick to your priorities. If sightseeing is on your priority list, then get a new job, because you have no control over where you sightsee if you have a job with a lot of travel.

2. Eat really well. First of all, you’re not paying for your own food, so you should eat really good, healthy food, which is always more expensive than junk food. Second, if you have a rule for yourself that you always eat well when you travel, then you will actually be healthier from traveling. Most people eat crap when they travel because they are tired and they feel like the calories don’t count because they are across state lines. That attitude will make you burn out faster. I can’t find a link but I’m sure there’s a study to support the hypothesis that you deal with the stress of travel more effectively without McDonald’s. (more…)

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Shifting the balance of power. (Mainstream media stinks.)

Posted to: Journalism |  Parenting
November 6th, 2009
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I wake up Wednesday at 4am to a phone call: The Guardian, in London, asking for an interview about my miscarriage twitter. Then a half-hour later, an Irish radio station. And then the phone kept ringing.

I tell Now Magazine (I think it’s basically People magazine for the UK audience) to call back after I got the kids off to school. I ask my housemanager to come early because I can't handle the sleep deprivation and the early-morning interviews and school lunches all in one morning.

I block out the morning to write a thousand-word essay for the Guardian to justify tweeting about my miscarriage. Which the Guardian wants done in the next 20 hours.

Now magazine wants to know if they can send a photographer to take a photo of my kids.

No.

Or the Farmer?

No.

What about if their faces are blurred?

No. (But this at least makes the Farmer laugh.) (more…)

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First, be honest about what you want

Posted to: Goal setting |  Knowing yourself
November 2nd, 2009
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Someone once asked me to think of a moment in my childhood that was really nice. I thought of one.

Wait. You think of one, now. Quick. Just any one…

So I thought of a time:  it was in my grandparents’ huge yard with fruit trees and flower gardens and grass for running. And it was so peaceful.

What you remember as really nice tells you something about where you belong. Whatever you thought of, learn something from that.

Where I belong is in nature. And in quiet. When I lived in New York City, I spent most of my time in Central Park and the Brooklyn Botanical Garden. Most people who live in New York City say they spend a lot of time in Central Park. I almost lived there. I thought I would die if I didn’t go there each day. (Wait. Here's a test to see if you belong in New York City. I definitely don't.)

When I drove up to the farm, the first time, I knew I belonged there. I think I fell in love with the farmer that second. And I saw my whole life as the process of coming to grips with the fact that I am not as fast and cool and cutting edge as I wish I were. I do not belong in a city. (more…)

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We overestimate the gap between nonprofit and for-profit jobs

Posted to: Finding a career |  Fulfillment
October 30th, 2009
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My ex-husband worked in the nonprofit sector for a while. And you know what? He rarely got health insurance. At one point, we were completely stressed out about not being insured, and he asked his boss what everyone else was doing, and she said, “Can’t you get insurance from your spouse? That’s what we do.”

That’s appalling. Being a non-profit is no excuse for treating people poorly. And it’s not just benefits—It’s pay, too. Paying way below a living wage is elitist—as if working in a nonprofit is a rich kids’ playground that your parents fund.

Luckily, the non-profit world is changing. The difference between not-for-profit and for profit is becoming more and more artificial.

When a business is deciding whether to be for-profit or not-for-profit, they are thinking about what is the most efficient way to meet their goals. For example, the Gates Foundation was established to get the money out of the hands of one family and give it to people who can change the world with the money. They do not want to make a profit, so they put all the money they make back into the Foundation.

Merck, on the other hand, is changing the world by curing diseases, but they need to create a profit in order to keep their stock price up and pass money on to shareholders.

Both companies are solving huge health problems. Both companies have equal capacity to get you, an employee, very close or relatively far from the act of saving a life. The only difference between the organizations is the financial structure.

So, here is a new way to think about careers in the non-profit sector: (more…)

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Asperger's at work: Why I'm difficult in meetings

Posted to: Diversity |  Knowing yourself
October 29th, 2009
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Eighty percent of adults with Asperger Syndrome do not have full-time work. This not because they can’t do the work. It’s that they can’t manage to be socially acceptable while they get the work done. ‘

Countless studies show people would rather have pleasant and personable co-workers than a co-worker who is always right. I try to keep this in mind each day, and consequently, I spend a lot of time planning my interactions.

But sometimes my plans fail. To give you an idea of what I’m talking about, I’m going to walk you through my most recent parent-teacher conference. Which was a disaster.  And while it was a meeting in a second-grade classroom, it could have been a meeting with anyone, anywhere.

1. I can’t tell the difference between social niceties and reality.
I think I'm late.  I am bad with transitions — I space out from the stress of change so I drive around the school a few times without noticing before I go in. I am bad with time, because I don’t totally understand how to predict what the next number will be. So sometimes I forget where I am in the hour.

But then I get to the school and I think I am early to the conference, and I go to the bathroom, because the school halls are bustling and I want calm.

I get to the room and the teacher is sitting at her desk. Doing nothing. I think this means she is waiting. So I ask if I’m late. She says no, but I am pretty sure she means yes. I know some people say the answer they think would be good manners instead of the right answer. I stare at her body language for a clue. (more…)

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Why men should give women flowers

October 28th, 2009
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Here’s the deal with giving flowers. Women like receiving flowers. Men think flowers are stupid.

Men think: Flowers die, they don’t do anything when they are alive, they are expensive, and they are a cliché. Men know that women in general like flowers, but men also believe that women they know personally do not like flowers. The women they know are the exception to the rule.

I think it’s safe to say that mostly women are reading this post. Women are reading to figure out how to get the men in their lives to send flowers.

Here’s what it’s going to take: Bottom line impact. Yes, the guys want to get laid, but dinner seems better: it's like money well spent to them – you still get the sex, but you also get good food. What do you get with flowers? This is how men think, for the most part.

So, here’s what you get: (more…)

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How to deal with doubt: Take a leap

Posted to: Fulfillment |  Parenting
October 22nd, 2009
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The farmer broke up with me five times the first five months we were together, last year. So I learned that he had huge commitment issues.

I tried to do the advisable thing to do when you’re with someone who has commitment issues. I tried to fall in love with someone else. But I didn’t. I only missed the farmer more.

So I told myself that it’s okay to be with someone who has commitment issues, as long as I am having fun.

But my kids grew to love the farm, and the farmer, almost as quickly as I did. This makes sense. My oldest son was with me on my first visit to the farm,  and if you have ever been on a working farm you know that to kids, it’s like Disney World.

So my kids were constantly asking to go to the farm, and constantly trying to figure out, what is the farmer? A friend? An uncle? And why did I kiss him if he’s not in my family?

This is not a good path for kids if the relationship isn’t going toward marriage. So I waited until a day when the farmer and I were holding hands, walking between rows of corn higher than our heads. And I told him that I can’t keep bringing the kids to the farm because we’re not getting married and I’m scared the kids will get hurt.

The farmer didn’t say anything for five minutes. And then he said, “Okay. Let’s get married.” (more…)

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4 Lies about social media

Posted to: Job Hunt |  Networking |  Promoting Yourself
October 21st, 2009
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Everyone knows that the best way to get a job is to leverage your network. And almost everyone knows that social media is a great way to build your network.

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. (more…)

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The Internet has created a generation of great writers

Posted to: College students |  Diversity |  Journalism
October 19th, 2009
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The best writers in the history of the world are graduating from college, right now. So everyone can just shut up about how no one can write anymore.

Newsflash: No one could write in the Middle Ages, when the good writers wrote in Latin and everyone else spoke colloquial languages like French and English, which priests told them were too lame for real writing.

It’s the same situation today in that the best way to have a population of good writers is for people to write constantly, in the language that is theirs, so that they are great at expressing themselves.

People do good writing every day, in social media—when they write a note on someone’s Facebook wall, when they post a caption to a photo on flickr, or when they post a comment in a group on Brazen Careerist.

The people who are complaining that no one can write anymore are the same ones who are stressed about information overload. This is not a coincidence. Information is changing, the flow of ideas is changing, and written communication is changing with it. Information overload is the feeling of not being able to deal with this change. Young people do not feel information overload, which is another sign that they are excellent writers for the new millennium: They can process and communicate new ideas at the new pace. (more…)

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4 Types of questions get us in trouble

October 12th, 2009
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How far you get, in almost anything, is limited mainly by your ability to ask good questions.

The problem is that we are not taught to ask good questions. We’re trained to answer questions. But only answering questions doesn’t make an interesting life. After all, if you have all the answers, and you’re spewing them all the time, then you are not learning anything new.

Asking questions is how we get smarter. One of the earliest signs of a child with Asperger syndrome is that they fall behind in their learning because they do not understand how to ask a question. It doesn’t occur to them that someone would have information.

And maybe all my blog posts are actually about my obsession with a good question. For example, my recent rant about how blogs need topics is really about how a good blog is based on a good question. (My question is: how can we make the the intersection of work and life better?)

Today I’m going to focus on the kinds of questions that back us into a corner.

1) The question that asks: What is the meaning of life?

I think a lot about how people ask questions because I get them all the time. Often, the questions are so vague and poorly framed that I can’t believe the person actually sent an email. Here’s an example of one: (more…)

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Obama. Wow. And one thing about work.

Posted to: Career fulfillment
October 9th, 2009
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I was in the process of setting up Dora the Explorer for my four-year-old so that I could make breakfast. But when Yahoo popped up on the screen, I paused. Then I said, "Look. There's President Obama. He won a big award."

My son said, "For what?" Then he pointed to an advertisement for Target — a boxing glove that punches images of the flu. He said, "Did Obama win for killing that stuff?"

I saw a teaching moment. I tried to think of something good. I said, "He won for being nice to people and reminding us all to be nice every day."

The Nobel Prize Committee said something interesting about Obama's award:  "Only very rarely has a person to the same extent as Obama captured the world's attention and given its people hope for a better future."

And this, I think, is what good leaders do. They help us a see a future that we like, that we're a part of, and that we can help create. In the case of Obama, his combination of strong values and intellect and charisma are mesmorizing to watch. And to me, his lack of BS in politics is almost as revolutionary as his skin color in politics. I love the whole package, and he makes me proud to be a US citizen. (more…)

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Blogs without topics are a waste of time

Posted to: Finding a career |  How to blog
October 6th, 2009
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Stop thinking that you are such an incredibly wide-ranging thinker with so many interests and insights that you cannot be pinned down to just one topic. The top bloggers are all wide-ranging thinkers. That’s why they are interesting. The more information and angles you can draw from, the more interesting your insights are.

I challenge you to think of a popular blogger who lacks focus on their blog.

In the history of writing, everything has a focus. It's a contract you have with the reader. You stay within the bounds of the reader's expectations, and if you do that, you can write surprises that seem to stray from your topic, and the reader stays with you. Because surprises are fun. But if there's no contract because there is no focus, then there are no surprises. Every great piece of writing works this way.

Think about it: Canterbury Tales. The topic is getting to the end of the trip.  Or Moby Dick. Melville can write about everything—God, the American dream, fishing boats, marriage, mental illness—and he gets away with it because his topic is totally solid: Nailing the whale.

I challenge you to find a great piece of writing with no topic.

Even columnists stick to their focus. It’s part of the fun. When you audition for a print-based column, you submit ten sample columns to show that you can be interesting in a variety of ways while still sticking to the main topic. Because it’s hard to do. (more…)

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My miscarriage — on CNN, ABC and AOL

Posted to: Women
October 1st, 2009
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I don't usually post clips of myself when I go on TV. But I'm posting this one, where I talk about trying to get an abortion in Wisconsin and end up with a miscarriage at work instead. It was a difficult interview, which is why I like it. And, remarkably, I have good hair without trying, which is another reason I like watching the clip.

For those of you who have no idea what I'm talking about. Here's my twitter that caused uproar. And here's my post about it.  To give you an idea of the recent coverage, here's the link that is, right now, on the front page of AOL, and here's a link to an article by Lara Salahi at ABC News — I really like that one.

If you are new to my blog, and you've gotten this far, maybe you'll like staying here for a while. Here's a good page to begin on: About this blog.

I know I said that that this week is Asperger's at work week on my blog. Maybe me talking about my miscarriage to newscasters is part of this series. I'm not sure. But I've been learning a lot about women from the comments about the miscarriage twitter — on my blog and on other sites. So I'm sure that other people are learning a lot about the lives of women — at work and at home. And that has to be good.

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Asperger syndrome in the office: How I deal with sensory integration dysfunction

September 30th, 2009
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A lot of people ask me how I manage to keep a job when I have Asperger syndrome. So I'm doing a series this week on the topic, because it’s true that most people with Asperger’s are not doing well at work. The work place rewards social skills, and people with Asperger’s have a social skill disorder.

I will never have great social skills, but I make them better by ensuring that I’m in my best social environment for work. For most people with Asperger’s, inadequate social skills are exacerbated by sensory integration disorder, which is a tendency to be overwhelmed by outside stimuli. This frequently overwhelmed feeling makes one unable to concentrate on social skills.

Here are the ways I compensate for sensory integration disorder so that I can focus on having social skills that will make people want to work with me.

1. Establish routines to limit input.
Food is a problem for me. I hate variety. I hate that I don’t know what is coming. My effort to control food got so extreme that I landed in a mental ward with an eating disorder. Today, I try to never go out for a meal. If I have to, I order salmon. Everywhere. And just looking for the salmon I get overwhelmed reading the menu. Too many details about food.

Given a choice, I eat a Power Bar for every meal and snack, (two= a meal, one= a snack,) and I hate if the store is out of both peanut butter and vanilla. I don’t like variety, even in Power Bars. (more…)

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This week's series: How to deal with Asperger Syndrome at work

September 29th, 2009
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People often tell me that I should write career advice for people with Asperger Syndrome. This is because I am surrounded by people who have Asperger’s, and I have it myself.  Please, do not tell me I don’t have it. First of all, it looks very different in men and women, and most of you have experience with men. Second, I’m way more weird in person than I am on the blog. And surely you thought it was the other way around.

So, anyway, the reason I’m good at giving career advice is because I had to learn things systematically, which helps me break it down for everyone else.

For example, I had to learn that a candy dish on someone’s desk means “I like to talk with people.” Other people read this cue instinctively. It makes for a good blog post but an annoying co-worker if I don’t teach myself stuff quickly.

I don’t really do career coaching. I don’t have patience. But often career coaches send people with Asperger’s to me, because mostly, these people are extremely difficult to coach.

They are difficult to coach because the biggest problem is that non-verbal cues that are obvious to everyone else are totally lost on people with Asperger’s. For example, you can tell when you are boring someone, but someone with Asperger’s cannot—we just keep talking. (more…)

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All career issues are religious issues. Maybe.

September 28th, 2009
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I starting to think that the most effective preparation for a good career is religion.

I am writing this post on the eve of Yom Kippur. I am constantly trying to figure out how religion fits in my life. Sometimes I think it doesn’t fit. I mean, I’m a Jew dating a pig farmer. And I can’t figure out what to do with my kids on Yom Kippur, so I’m sending them to school. I never, once in eighteen years, went to school on Yom Kippur. So I know it’s going to feel crappy. I hope my family is not reading this.

Well, of course they are not, because they are in synagogue today.

I wish I could make my religion problems go away. I wish I could not care about religion because I’m an intellectual. Or I wish I could not care about religion because I am fine doing it however I do it.

One thing that nags at me is that I know for sure is that religion is great preparation for being able to get what you want out of your work life. And, if you read this blog regularly, you know that I think the purpose of work is to get you what you want out of your whole life, not just the work part. (more…)

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