I had a breakdown at the Charlotte airport

This post is the third in a series. Here are the first and second posts. I’ll be talking about these posts and answering your questions live on Monday at 5pm Eastern. Become a paid Substack member to receive a link to the session.

I get off the plane in Charlotte and all my money’s gone. I think: How will I get home once I land in Boston? But then I remember the last time the money was gone my kids showed me you can sneak on the train without paying.

So I call the Wisconsin Department of Revenue to see if they are the ones who took my money. I say a little prayer about being able to get my money back: Please god make it the DOR and not the oil guy who sued me. Read more

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WNBA is totally annoying, here’s how to fix it for Caitlin Clark’s arrival

Professional women’s basketball is a cesspool of mediocrity full of women gatekeeping so the sport can’t change. Fortunately, incoming rookie Caitlin Clark is worth more than the entire WNBA due to her sponsorships. This means that unlike other players, Clark doesn’t work for the WNBA she works for her sponsors and her fans. Read more

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Guest post: How I manage up, working for Penelope

This is a guest post by Cassie Boorn. She works with me at Quistic. That’s a photo of Cassie and her son. And here’s another guest post she wrote, before we started working together. 

A few years ago I targeted Penelope as someone I want to work with. Then I spent a lot of time and energy getting her to hire me. You can probably tell from reading this blog that Penelope would be a difficult boss. I work hard figuring out how to make her like working with me. This is called managing up. And these are rules for managing up that I’ve learned from working with Penelope: Read more

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Why problem employees don’t get fired

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We finally got a dog. Sparky. His original name was Prince. But I decided you can’t have a prince on a farm. So we changed the name. Sparky is five years old, so he was probably pretty used to the name Prince, but name changing, is of course, normal in our family. (After all, I’m on my fourth name.)

We picked Sparky at the pound because my son wanted a lap dog. I am not a fan of lap dogs. They scream Paris Hilton to me. A study at the University of California at San Diego confirms our hunches that people pick dogs that resemble them, and sure enough, the rat terrier is like my son in that they are both delicate and jumpy. I think I am more labrador—strong and fun—so I thought I was being an extra good mom getting a dog I would never choose myself.

Rat Terrier

At the dog pound, Sparky sat in my son’s lap, but as soon as we got him home, he looked for larger laps. It turns out, Sparky prefers adults. At first we thought it was my son’s jumpiness. We told the kids to be calm around the dog.

But the dog got snappier as the week went on. And growly. Read more

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Don’t give your boss a gift

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It's the time of year when there are a bazillion articles about what gift you should give your boss. The implication is that of course you'll give a gift. But I think you're better off skipping it. Here's why:

1. Gift recommendations are not really recommendations.
When a journalist or blogger (is there a difference?) writes about gift items, they get to review the gift items. Which means each gift was already a gift to the writer. I know about this because I'm terrible at it. For example, I would like Bose noise canceling headphones. They are too extravagant for me to buy for myself, so I should ask Bose for a trial pair and then tell you to buy them for your boss.

2. Christmas at work is bad for your boss. Really.
First of all, it's bad for your company to have everyone give end-of-the-year gifts, or holiday gifts, or whatever companies are calling Christmas gifts lately. It's bad because Christmas in the office is bad for diversity. I write about this every year, and every year it is the most controversial post. So you don't need to write to me about how I am a Grinch and a cultural moron and Jews should move back to Israel, okay? Because I get those comments—about 300 of them—each year. So all I'm going to tell you now is that you are not helping your boss reach his or her performance goals for your team by undermining diversity by celebrating Christmas at work. Read more

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List of social skills a solid career requires

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I’m always shocked to hear that people don't like brown-nosing. If I could do it, I definitely would. But as someone who has Asperger’s, brown-nosing always looks very difficult. So I have been looking for someone to teach me how to be better at brown-nosing, and finally, I found it.

First, here is research from James Westphal and Ithai Stern at Kellogg School of Management. They found that being adept at ingratiating behavior was the number-one factor for getting positions at the top of the corporate ladder.

This is not surprising to me. What is surprising is that the research comes with a how-to provided (perhaps inadvertently) by the American Bar Association Journal.

According to the study, here are the traits that are most likely to be rewarded.

1) Frame flattery as advice-seeking. For example, you can ask, “How were you able to close that deal so successfully?”

2) Argue before accepting a manager's opinion. Read more

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The nuts and bolts of building a brand

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I am switching up the blog a bit. It’s time to take the Brazen Careerist part off of my blog. It’s time for the blog to just be Penelope Trunk, and only my company should use the name Brazen Careerist.

We have been saying this in Brazen Careerist board meetings for about five months. The conversation goes something like this:

Board member: How is the blog redesign going?

Me: Um. I’m thinking.

Board member: That’s what you said two months ago.

Me: Yeah. That’s true. I’ll get some bids.

Board member: It’s important the we differentiate the Brazen Careerist brand of the company from the brand of you.

Me: Yeah. I get it.

Then we have a pause in the meeting while everyone is silently frustrated with my inability to make changes. Read more

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Underrated career skill: Asking questions

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It might be that the only useful thing you ever learned in school (besides how to make small talk at a party) is how to ask a good question.

Most of us didn’t learn that, though. Because it’s so hard to teach. I know it’s really hard to teach because people with Asperger Syndrome don’t understand how to ask a question, and I watched speech therapists (pragmatics specialists) try to teach my son, while I took notes for myself.

Children with Asperger’s often have to learn when to use Why, What, and Where because they don’t know how to ask questions, even though they often have through-the-roof IQs. They actually seem mentally slow because they cannot learn as fast as other children due to the lack of good questions – which is a great illustration of how important asking questions is.

I will answer almost any question someone asks, which makes me better at asking questions myself, but I am also very conscious of the fact that most questions people ask me are terrible.

So here are tips on how to ask good questions. Read more

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Workplace situations we don’t talk about

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There are some things about work that are difficult for even me to write about. These are the issues that I have not quite worked out for myself. I wonder if I am normal in these areas? Maybe no one is talking about them, but they are thinking still. And if no one else is thinking about this stuff, why do I think about it?

One thing I've learned on this blog, though, is that most of my personal qualities that feel weird to me are actually pretty common traits among thinking people who desire self-knowledge. So to those people, I hope this blog gives you a sense of fitting in.

And, here are three workplace issues that I wonder if you think about as much as I do.

1. Having a huge crush on your boss.

Seriously, I have never worked for a guy for more than three months without developing a huge crush. This is, in part, because I have been fired so often that any guy I did not last three months with probably fired me and probably had no synergy with me. Read more

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Maybe there will be a recession. Here’s what to do just in case

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The debate continues about whether and when a recession is coming, and what the markers would be. Most of us are in no position to do the analysis ourselves, but you don’t need to be an economist to know that if people are talking about recession, you should do some thinking about what you would do if one occurs.

As a gen-Xer, I am a master of recessionary times: I graduated into one of the worst job markets since the depression and then lived through the dot-com bust.

But since we’re not actually in bad times right now, the question really is, what do you do in a job you have if you want to get ready for a downswing in the economy? Here are four ways to prepare for a job market that might turn sour:

1. Specialize
People think that if there are fewer jobs, a wide range of skills makes someone more employable. It’s not the case, though. In a tight job market, employers can hold out for the perfect fit. And if you are not clearly defined as a specialist, then you are not going to be a perfect fit for anything.

Researchers have found that you get the most benefits from specializing after you have three to five years of experience under your belt. So don’t specialize too early – because you won’t have learned enough about what you want. But if you have a few years of experience, and you see layoffs looming, try to get on some focused, short-term projects that will allow you to market yourself as a specialist in something when you have to get your next job.

2. Do something great – right now
Most people have been participants in the last decade of manic job hopping. Which means most people have followed a pattern of performing well at a company, writing those achievements on their resume, and then making the next hop. This works in a job market where you can control when you leave.

But if you get laid off before you accomplish something significant, you will end up with a dark spot on your resume – a place where you did not do anything particularly notable.

So do something now, fast, that you will be able to quantify as an achievement on your resume – as in completed X project in X percent less time than anticipated, or saved X dollars by working twice as fast as normal.

3. Consider graduate school
There’s a reason why so many Generation Xers went to graduate school: There were no jobs in the early ’90s. In a down job market, grad school is a way to enhance your skills when there are no available jobs that will do that.

One of the most popular choices is law school because a law firm provides a clear path (and an A in organic chemistry is not a pre-requisite). I have never been a fan of law school as a fall-back plan, because 44% of practicing lawyers recommend that you do not go into the field.

That said, law firms have become much more accepting of people’s personal lives since the last recession. Many law firms have retooled how they operate to give people more time to have a life outside work, and they have changed their policies to accommodate different stages of life.

Grad school is a treacherous route, though: Be careful about spending money for a degree with no career path to follow it. But also, be careful of investing in a career path you wouldn’t want to follow.

(Hat tip: Elise)

4. Focus on the quality of work and quality of mentoring
The hardest thing to do in a bad job market is to keep your learning curve high. If the market goes sour, instead of focusing on the perfect industry or the perfect company, focus on developing new skills. And then refocus your career into a more suitable industry or location when the job market gets better.

By cultivating a great mentor in your current job, you can make your job a spot where you can wait out an economic slump should one come. So instead of focusing on the negative predictions of economic doom, focus on the positive conversations that build a solid mentoring relationship, and you will weather the storm better because you won’t weather it alone.

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