The most fun I ever had interviewing someone was when I talked to Daniel Gilbert, a psychology professor at Harvard University. It was about a year ago, and I thought I would just ask him a fast question about how much money someone needs to be happy. (Answer, about $40,000 a year. That’s enough to be happy. Money you get after that doesn’t affect your happiness.)

But Gilbert went on and on about how we have no idea what is going to make us happy so we should stop trying so hard to figure it out. His book just came out. It’s called Stumbling on Happiness, and I recommend it. Gilbert has a lot to say about the flawed ways we look for happiness.

Here are things he told me:

1. You can’t predict what will make you happy. People are, in fact, hard-wired to do a poor job of imagining what will make them happy. (This is why we think more money will help, for example.)

2. The best way to figure out happiness is to look at other people. Find people who look happy to you and do what they are doing.

3. You are not special. We are all basically the same. So you don’t need to look for any special code for happiness. Just find people who look happy to you.

To get a sense of Gilbert’s research, here’s an excerpt from his recent op-ed in the New York Times that describes why we are biased when we examine the evidence:

“When our bathroom scale delivers bad news, we hop off and then on again, just to make sure we didn’t misread the display or put too much pressure on one foot. When our scale delivers good news, we smile and head for the shower. By uncritically accepting evidence when it pleases us, and insisting on more when it doesn’t, we subtly tip the scales in our favor. Research suggests that the way we weigh ourselves in the bathroom is the way we weigh evidence outside of it.”

When it comes to picking a career, Gilbert says you should personally try out a lot of different jobs. This is great news for young people today who generally have nine jobs before the age of thirty-two.

I spent two hours this week writing an article about autism. My son was diagnosed with autism and I could write five hundred pages about dealing with the diagnosis. But then I reminded myself about specializing. About focus. Specialists get a lot of good things in this world, and people who dabble in everything get nothing.

Dabbling is fine, to a point. I mean, you have to dabble to figure out what you want to be a specialist in. But let’s be real. I write a career column. I have a book about careers coming out. I speak at universities about careers. I am not an autism writer.

So I trashed the autism article. Because it’s not going to help my career in a focused way. Sure, it might help in a haphazard way, the way playing basketball at the park helps your career because you never know what will come of anything. But the only way to reach focused career goals is to have focused efforts.

I stick to writing about careers because specialization is the ticket to freedom from boring and inflexible work. Let’s say you want to have every other Wednesday off to go to a yoga class. If you are a specialist who would be hard to replace, your boss will be more likely to say yes than if five hundred entry-level people can do what you do.

The more you need, the more this rule applies. Moving in and out of the workforce is easier once you’ve established that you’re great at a specific thing. And entrepreneurship is easier as specialist, too, because one of best ways to gauge aptitude is if that person has a strong knowledge base and network in the field of the proposed business.

You don’t have to specialize right away, but you should see your work path as a quest for specialization. View random corporate jobs as possible apprenticeships. You don't need to know what you’ll specialize in, but you need to be open to it when it comes. Specialization often creeps up on you, like a friend who you never expected to turn out to be a friend.

When I first started writing columns, I had no idea that I would write about careers. I was hired to “write about what it’s like to be a female executive.” I tried lots of different types of columns. I wrote about software development (my specialty at the time). I wrote about consumer products (definitely not my specialty). Those columns flopped, and so did most of my columns that were not, in some way, about careers. I learned by trial and error that I was a career writer.

It is always scary to specialize because there are so many jobs that become out of your focus. But there is good research to show that you will have an easier time staying employed if you specialize.

Specialization is also scary because we think we need to address all aspects of our personality with our work. But no work can do that. Autism, for example, is important to me right now, but it doesn’t need to be important in my work. In fact, work is sometimes a nice break from that aspect of my life.

My son was diagnosed with Asperger’s Syndrome, which is a type of autism that occurs when someone has a very high IQ but a large deficit in social skills. His teachers taught him a way to leverage his specialty — memorizing — to learn rules for socializing that other people know intuitively.

I learned many lessons from watching him do that. One is that once you have a specialty, you can leverage it to add things that are not necessarily your specialty, but you still want to have them in your life. In that way, a specialized path is one of the most diverse and rewarding paths you can choose.

Most jobs turn out to be very different than what you were told about in the interview. So your first task in your new job is to figure out what the job really is. Most people don’t do this which is why there is a whole cottage industry of people who coach for the first ninety days of a job (here’s a book and a web site for starters).

You must realize that each new hire has political motivations. It’s your job to uncover the politics behind your position so you can figure out what you should really be doing instead of relying on your official job description.

A good example of this situation came up in Fortune magazine this week. Garry Betty, CEO of EarthLink said, “Google only has three engineers working on Wi-Fi. [CEO] Eric Schmidt laughingly told me in a meeting that the best hires they ever did was when they hired those three Wi-Fi engineers and put out a press release. The market cap went up $10 billion.”

In fact it was never Google’s intention to be a huge Wi-Fi provider. But Wall St. Analysts loved the idea that Google hired some top Wi-Fi engineers. By hiring three people, the stock price went up significantly. Certainly enough to justify the three salaries. So in fact, these three engineers didn’t need to do anything. For these engineers to thrive at Google, they needed to understand this situation, and decide where to go from there.

So before you get giddy about your new job, don’t get too attached to the job you think you got. Spent the first ninety days figuring out what people really want from you but couldn’t tell you in the interview.

And then, instead of complaining about bait-and-switch, recognize that it’s part of corporate life – it is, in fact, very hard to predict exactly what someone might do once they get to an office. So just do the job that needs doing. If you do it well, you should be able to finesse your position into something you like in no time at all.

Movie mogul Mark Gill, the guy who produced blockbusters on a shoestring like “March of the Penguins” ($77 million at the box office) and “Good Night, and Good Luck” (six Oscar nominations) has been fired. Well, officially resigned, but really he was pushed out because he can’t get along with his boss.

The New York Times reports that, “Mr. Gill’s personal style continually clashed with that of Jeff Robinov, Warner’s president of production and Mr. Gill’s boss.”

About a year ago, Gill knew there was a problem and said, “I definitely had to make some adjustments to fit into this culture.” But he obviously did not make the necessary changes. No surprise. The more you feel like a star, the more you feel like you don’t need to change.

But don’t kid yourself that doing great work for your company means you don’t have to adjust your attitude and behavior to fit in. Even a guy who produces the most popular documentaries of the year has to get along with his boss in order to keep his job.

This is not revolutionary management. In fact there’s a Harvard Business Review case study (that you have to pay for) called “What a Star – What a Jerk” that discusses the need to fire people who perform well but don’t mesh with the organization.

But, like most case studies about interpersonal skills, you don’t need to read twenty pages to know the truth: If you don’t like someone, nothing else about them matters.

My husband and I both want to be home with our kids while they are young, and we downsized our standard of living enormously to do that.

I made a career change from software company executive to writer. This has been great for me. It’s a career that can grow big, but there is lots of flexibility for working around my personal life.

My husband ended his entertainment industry career and downshifted, slowly, first to the nonprofit world, which we found surprisingly inflexible for parenting, then to stay-at-home dad.

You know how you hear about the dads in the 50s who folded under the pressure of having to support a family with no financial help from a partner? I am sorry to say that I felt like that — especially living in New York City.

But, like most people who want jobs with flexible hours, my husband was not able to find one. And a standard job would mean leaving at 8 a.m. and getting home at 7 p.m. which are pretty much the hours our kids are awake. So, he had to choose between working nights or not seeing the kids. He chose working nights.

There are not a lot of options for working nights. Especially if you don’t have the talents to work at a nightclub. So my husband is answering phones at a car service. He takes down the time the person wants the car and some other information and a computerized system dispatches the car. My husband does the same thing, over and over again, for eight hours a day.

To give you a sense of his co-workers, the woman next to him slammed down the phone the other day and said, “The customers are so outrageous! This guy wants a car in a quarter hour. How am I supposed to know what a quarter hour is?”

In between calls, his coworkers play brand-name Internet-based games that my husband produced in his former career. He doesn’t tell anyone. He tries to fly under the radar.

But the customers, investment bankers at the most chic-chic firms in the city, notice something is different about my husband. Two or three times a week, someone will say to him over the phone, “What are you doing at this place?” One guy said, “Is this your real job?” My husband said yes and the guy pushed until my husband explained our situation. The guy said, “That would have never happened when I was your age. Men couldn’t do that.”

The hardest part about this life is that very few people understand what we’re doing. You can imagine what a conversation killer it is when someone asks my husband the great American question: “So, what do you do?”

Although I overheard one woman say to him, “Your kids are so lucky,” the best support system I’ve found is learning from other people who are thinking seriously about this topic.

I particularly liked The Bullshit Observer’s rant this week about how difficult it is to manage career aspirations and be a hands-on parent. He has some interesting statistics as well as insights like this one:

“American parents have two very fundamental responsibilities at war with each other every single day. Those who’ve chosen the path that goes up the ladder appear to have chosen not to be parents. Those who’ve chosen the path that leads to the diaper bin have chosen not to move up.”

One organization that publishes a lot of information on changing the situation is the Third Path. This organization helps couples move beyond the idea that one parent is the primary caretaker and toward a mindset of “shared care”.

Third Path offers mentoring to couples who are trying to implement a shared care arrangement in their home. Though this path is not easy for anyone, the stories of what people have gone through to make shared care work are inspiring.

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The reason you need to take breaks from your work is that if you don’t pick your head out of the trees you’ll never see the forest. Great ideas do not come to those continually mired in details. Your brain needs a moment to relax. Most of us know this intuitively. The problem is that most of the ways we relax at during work are destructive: candy break, smoking break, online shopping.

I thought of this because today Chad’s Reviews, which is totally over-the-top workplace commentary, pokes fun of the idea of taking a break to do something destructive: “If You Get A Smoke Break, Then I Can Punch The Wall For 15 Minutes.” (If you like Chad, you must read his blog raison d’etre: “Why I’m Frickin’ Doing This“)

I find that I usually degenerate from doing something hard to surfing to eating to biting my nails. It’s a frustrating path and I always wish that I took a true break at the surfing and saved my nails.

I have actually taught myself how to meditate, and it works every time. But sitting on the floor next to my computer, which takes no energy and less than two seconds to do, somehow has become as difficult for me to do as going to the gym.

Being with yourself is hard. Turning off the input is hard. Believe me, it is so much easier for me to read Chad’s Reviews than it is to clear my head and think of nothing. But when I meditate, even for a minute, which is acceptable but on the too-short side, I see huge improvement in my ability to do good work. And I am not crazy. Researchers have found that meditation improves work performance.

I have to be honest, though. Training myself to meditate took a lot of practice, and I learned it in order to perfect my jump serve in volleyball, not to be better in an office. (Visualization is a proven technique among Olympic athletes.) But you know what? I really don’t think I’d have reached the professional ranks of volleyball without having added meditation to my training. (The book I used: Peak Performance: Mental Training Techniques of the World’s Greatest Athletes.)

Just typing the name of the book reminds me of what a big impact it made on my life in terms of my ability to focus and think big. I really believe meditation will improve my office work, too, if I’d just sit on the floor and do it. I thought maybe if I blogged about how important it is, then I’d be more likely to do it next time I find myself going to the fridge when the only thing I’m hungry for is a break.

The best companies to work for are those that understand that priorities among workers are changing. In fact, Laura Shelton and Charlotte Shelton conducted a nation-wide survey about worker priorities, published in Generation NeXt. The survey showed that for Generation X, “Recognition scored very low, and power and prestige ranked dead last. Salary, a major preoccupation for boomers, came in third from the bottom.”

The companies that do the best job of keeping Gen Xers happy are companies accommodate life outside of work and that downplay hierarchy, since “rank and seniority mean nothing to Generation Xers.”

The book is full of fascinating statistics which you would never know by looking at the dowdy cover. But anyway, when I interviewed Laura Shelton, who is an Xer herself, we talked about the difference between what women did twenty years ago (her mom and co-author, Charlotte Shelton) and what they do now. When Katrina hit, Laura, who is a newscaster in Louisiana, left with a few of her friends to take a break and regroup. Her mother said that when she was Laura’s age the women would have been too nervous about getting ahead in their careers to think about leaving for a break during such an important time.

Laura’s final message: Forget about being nervous. “Don’t sit in a job with a baby boomer boss who doesn’t get it. Vote with your feet.”

The new workplace currency is training. Title is not important if you’re not staying long term. Salary increases of 3 or 4 percent are ceremonial. So use the clout you earn to get training; it will make a difference in a way salary and title cannot because training can fundamentally change how you operate and what you have to offer.

This column shows you how.

The book I’m reading right now is by twenty-five-year-old Ryan Heath: “Please Just F* Off, It’s Our Turn Now: Holding Baby Boomers to Account.” The book is great and offers incredible insight into what young people have to offer and why baby boomers need to get out of their way.

It’s published in Australia so you can’t buy it in the U.S. in stores. So it’ll cost you $40 to buy the book from the Australian publisher and have it shipped, but it’s worth it. In any case, I will tell you some of my favorite parts here.

The premise of the book is that baby boomers refuse to retire, refuse to admit that their ideas are outdated, and they are making their institutions irrelevant to young people, who are basically refusing to take part in baby boomer institutions. Heath focuses a lot in Australia, because young people are leaving in droves. But a lot of his points resonate in the U.S. also, where young people have little interest the all-consuming corporate life that baby boomers have institutionalized.

Heath describes his generation with great one-liners like, “We’ve been to IKEA more than we’ve been to church.” And he does a great job of describing how totally different his generation is from the baby boomers. Of young people’s energy he says, “It’s not a counter-culture or a mass protest. It’s not even a movement — it’s a view on hundreds of little movements, technologies, communications, social networks and practical philosophies.”

His ability to describe his generation is reason enough to buy the book. Young people will cheer at his ability to frame them in an extremely positive light and his ability to inspire excitement. The U.S. supports a large industry of baby boomers selling themselves as experts on generation Y to other baby boomers who want to retain gen-Y employees (who usually leave after less than two years). This book also makes you wonder about the ability of baby boomers to train other baby boomers on how to handle gen-Y employees.

Heath also does a great service when he tells boomers to change how they are dealing with young people. He warns boomers that, “We lead a much grander lifestyle than our incomes suggest, we solve problems in a flash and we’ve read about the latest dumb thing George Bush said before most of you have even turned up to the office.” He describes the power of blogging and being part of a networked community and says, “We want conversations not lectures.”

Heath shows that the impact of a networked community and a generation that refuses to receive lectures is that hierarchy is dead. “You are playing the wrong game if you thin power and influence and even fun is about being in control anymore,” warns Heath. “Hierarchies can’t cope with the new complex world we live in unless they are rigidly enforced as in the case with armed forces. But they aren’t needed for most things in our lives. Networks are designed to negate hierarchy — their members collaborate rather than compete.”

He has great insight, and he’s brave to dis the boomers when they still control almost all media outlets. Generation X might bristle at the unbridled self-confidence and optimism of Generation Y. But the Xers will be relieved to see that finally young people have the demographic force to take the boomers to task. Ryan Heath is the beginning of a tidal wave.

You have to specialize. Not right away, but figure out how to own some sort of niche. It is the key to your freedom. A specialist in a large company can demand flexibility, but a specialist also has an ability to leave corporate life and succeed on her own, which is something generalists can’t easily do.

There is good research to show that you will have an easier time staying employed if you specialize. This research comes, in part, from Hollywood, where people say they don’t want to be typecast, but the reality is that being typecast is a great way to get steady work.

In the corporate world, headhunters always have a job description they are trying to fill exactly. If you are a square peg, you can go in a square hole. If you do not define exactly what kind of peg you are, a recruiter can’t put you in a hole: No calls from headhunters.

But most people who are strategizing their career right now are not thinking long-term employment, they are thinking entrepreneurship. (Industry pundit Paul Saffo said in the EETimes, “I think the unintended consequence of the dot-com bust is that we have created the largest generation of entrepreneurs this country has ever seen.”)

For this generation, specialization is key to getting OUT of corporate life and into a more flexible work situation. You can’t market yourself to clients if you don’t offer any specific, unique service. And you can’t start your own company by selling to everyone all at once. Specialization is what will make you stand out enough to make it on your own.

When you are wondering why anyone would go work for a big company, the answer is to learn a specialty. Think of corporate life as an apprenticeship so that you can start your own company. Big companies are crawling with mentors and training programs that will help you narrow your focus effectively.

If you’re looking for a road map, there’s a nice story this week about how Christopher Burge became a specialist in running snooty auctions.

And when you get a little further down the specializing road, check out the book Slightly Famous, which, of course, has a web site in an effort to dominate the how-to-be-slightly-famous niche.

© 2023 Penelope Trunk