In this age of transparency and authenticity it seems absurd to not tell you my real name. My real name is not Penelope Trunk. Well, in fact, it is Penelope Trunk. Sort of. At any rate, my name is definitely a lesson in personal branding.

My name started out Adrienne Roston. It’s fun to write that because if you Google that name, you will find only professional beach volleyball statistics. But running this post means that finally all my unrequited high school crushes, who surely are desperate to contact me, can find my email via Google.

So, anyway, I was Adrienne Roston, and then I started reading Adrienne Rich’s poetry in college. This lead me to believe that the key to undermining the patriarchy was through words, and I didn’t want my last name to be a definition of the men I was associated with.

So I went to court to change my name to Adrienne Greenheart. As a foreshadow of my complicated relationship with feminism, I was careful to pick a last name that my current boyfriend would take as well, should we get married (we didn’t). So in fact I have a name he picked. (My first choice was Breedlove. Thank god he voted that down.)

It was in the heart of the start of the Internet: GeoCities, EarthLink, CompuServe. So I spelled my name GreenHeart. I policed my family assiduously — they could barely remember to stop using Roston, let alone add a capital H in the middle of GreenHeart.

In court, the judge asked me why I was changing my name (they have to look out for felons, you know?) I said, “I’m changing my name because I don’t want to be associated with patriarchal naming conventions.”

She said, “That’s a great reason,” and banged her gavel.

Changing my name was amazingly easy. I had just quit playing volleyball and I moved to Boston for graduate school. I got there and introduced myself as Adrienne GreenHeart. Done. I couldn’t believe how well it worked.

Of course, there is a thousand-year history of women doing this – changing their last name overnight. So the world is set up for it, in a way.

When I got my first major job, at a software company, I dropped the capital in the middle and kept my name origins to myself. Then, lo and behold, my master’s thesis won a big award in the software industry. I found out because my boss told me. He shook my hand. He said he’s honored to have me on staff.

Then he called me into his office where and said, “Did you write this?” he pointed to the screen where my thesis was unfolding. He said he thought it was pornography.

I didn’t say to him, “you are an ignoramus and Philip Roth won a National Book Award and he wrote about a boy who masturbates with meat.” I did not say that because my boss had been very supportive of my career.

And this time was no different. He said, “You will go very far in corporate America, but not with your name tied to this. If you had your name on this when our board investigated you we probably wouldn’t have hired you.”

So I made up a new name and slapped it on my master’s thesis. I sent news of my award to my mom. I told her to go read my stories online. And she said, “Oh my god, did you change your name again?”

Then, I got my first columnist job from Time Warner. I approached the contract like any other business contract, and I started negotiating. I said, “Do I really need a new pen name? I already have a pen name.”

My editor said, “Time, Inc. does not negotiate with a no-name like you.” So I didn’t say anything when the magazine assigned me the name Penelope Trunk.

The day my column launched, I had my mom go to the magazine site, and she couldn’t find my column, because of course, she did not know my name.

For a long time, I wrote the column in cognito. I actually had no idea how widely read my column was until I wrote about my company’s office party at the beach. I was too specific about details, and I blew my cover. I nearly got fired, but instead agreed to delete from the online archive a small group of columns including the one about diagnosing my CEO with manic depression.

Soon after that, I became a full-time writer, I thought of writing under Adrienne Greenheart, but I already had too much invested in Penelope Trunk. That’s who people had been reading for three years. It was too late to change. So I posted my photo by my column and I became the name officially.

I used to change my email settings when I had to send something from Penelope. But I ended up having so much email for Penelope that I created two, separate email addresses. One for Penelope and one for Adrienne. I was always forgetting which email client I was in, and I sent email with the wrong name on it all the time. And surely you know that people delete email from names they’ve never heard of.

By this point, I also had a lot of people calling me on the phone and hanging up when they heard Adrienne Greenheart on my voicemail. So I took my name off my voicemail.

Before I started writing for the Boston Globe, I seldom interviewed people. I usually just wrote about me and my friends. But the Globe demanded interviews. It took very little time before I was spending more of my day talking on the phone as Penelope than as Adrienne.

Then I started becoming friends with people I interviewed. And I could never decide when to tell people that my real name is Adrienne. If I told people too late in the friendship they would get insulted. So I started telling people earlier, and then I couldn’t remember who knew what name. And then I found myself signing my Penelope emails as Adrienne.

Things were getting complicated. So I took a drastic step and got rid of my Adrienne email. One email account would be much easier. And by this time, almost everyone who knew me as Adrienne Greenheart also knew that I wrote as Penelope. So I thought it might work.

Things just got more and more complicated, and then I moved to Madison. And I remembered, on the plane ride to Madison, how easy it was to change my name in grad school. You just tell people a different name.

So when I signed up for my son’s preschool, I told them my name was Penelope Trunk. My husband had a fit. He told me I was starting our new life in Madison as an insane person and I cannot change my name now.

But I explained to him that it would be insane not to change my name now. I am way better known as Penelope than Adrienne. And my career is so closely tied with the brand Penelope Trunk, that I actually became the brand. So calling myself Penelope Trunk instead of Adrienne Greenheart is actually a way to match my personal life with my professional life and to make things more sane.

At first it was a little weird. For example, we were driving in the car one day and my son said, “Mom, who’s Penelope Trunk?”

But now it feels good to be Penelope Trunk. No more having to figure out what name to give where. No more pretending to be someone, sometimes. No more long explanations and short memories of who calls me what.

Now, even my husband calls me Penelope. He has to. Because if he called me Adrienne in Madison, no one would know who he’s talking about. So, my real name really is Penelope. Now. And you know what? It’s not that big a deal, since, after all, it is the fourth time I’ve changed my name.

The old paths through adult life don’t work anymore. Graduate school is no longer a ticket to a stable career, and in some cases, it’s not even a ticket to a job. Student debt weighs so heavy today that people should not expect to have what their parents have. Technology opens up many types of new types of unstable careers, but slams the door on many stable ones.

Workers today will have no fewer than three careers in their lives, and they will change jobs frequently when young. After that, they will cut back when they have kids, ramp up when they need money, and switch when their learning curve flattens.

The good news is that a large consensus of experts say in today’s world, this kind of living will not necessarily hurt your career. And in fact, changing positions frequently makes you a better candidate in many circumstances. Jason Davis, blogger at Recruiting.com says, “If a candidate has been at the same company for 10 years or more, you should take a red marker [to the resume], draw a big x through it, and throw it in the garbage.”

Today’s worker focuses on finding positions–all the time–that are fulfilling, engaging, and accommodating of personal time. It’s a nice picture, but it’s hard to imagine it’s a stable life.

And, for the most part, people do not like instability. Even the people who you’d think would be risk takers, entrepreneurs, are not, really. Most people are thinking of ways to mitigate the risks they are taking, according to Saras Sarasvathy, of the University of Virginia Darden School of Business.

So what can people do today to mitigate risk in the face of an inherently high-risk workplace? Get good at dealing with transition, because today’s workplace is full of it. The people who are most adept at dealing with transition are the people who will do best in their career and in their life.

1. Have two jobs at the same time.
The easiest way to make a transition is to do it slowly. The old way to change careers is to quit one, leave everything behind, and start everything over new. This is extremely difficult, and extremely risky. An easier transition is to start a new career while you’re doing the old one.

In some cases, you will end up doing the new career most of the time, in some cases, you will find out you don’t like the new idea and you’ll try something else. Recently, though, some people find they like doing both. Two careers makes sense to a lot of people, especially if one is fulfilling and the other pays the bills. Or one is very unstable and one is stable.

Marci Alboher describes the nuts and bolts of having two careers in a way that works in her new book, One Person/Multiple Careers: A New Model for Work/Life Success. She moves between her own set of careers as author/lecturer/writing coach as she tells a wide variety of stories of how people maintain multiple careers successfully.

“It used to be that the only way to transition was to leave your prior career behind. Today’s strivers are learning how to take what comes before and overlay new experiences on top of that. Today a career can be a mosaic.”

Alboher shows this is a path people can use to not only create more stability as they change, but also to follow their dreams as they’re going.

2. Be comfortable with uncertainty.
Eve Ensler, author of the play The Vagina Monologues and also, more recently, the book Insecure at Last:Losing It in Our Security-Obsessed World, thinks one cause of insecurity in our lives is the expectation of being secure. “If you think you’ll get to the point that you’ll be secure, then you’ll be chronically depressed,” says Ensler.

Since we can never really be secure, we should instead learn to be comfortable with that. Getting good at dealing with a world that does not provide security is actually a more healthy way to live than trying to find that one, perfect path through life that leads to a mythical security.

Ensler’s ideas suggest that today’s career paths, that wind and stop and turn and surprise us along the way, may be better for us once we get used to not knowing what’s ahead. “When you start working with ambiguity and living with it initially, it’s scary because there are no signposts. But eventually it seems to be a much more interesting way of living.”

3. Take time to explore.
It used to be people started exploring when they turned 40, and we called it a mid-life crisis. It seems clear, now, that exploration and self-discovery is something to do throughout life, not just when you get sick of your mortgage or your marriage.

But this process requires we take time to check in with ourselves during transition times. Jumping quickly from one thing to another is not as effective as taking time to figure out how you’re feeling, and what you enjoy, each step of the way.

Mike Marriner was planning to go to medical school but realized he wasn’t passionate about biology. He decided to take time to figure out what he should do next.

During this process, he started Roadtrip Nation, which sends teams of students around the country to interview people about their lives and careers. The idea is to provide inspiration or cautions for people as they consider making a transition. “Today there is no transition period,” says Marriner. “Everything is very quick and we are trying to put the spirit of exploration back into American culture.”

Roadtrip Nation has become a book, a summer program for college students, and a PBS Series, all addressing the idea that transition is serious business, and part of moving into adult life is getting good at figuring out where to go next.

To many people, the continuously shifting workplace is disorienting and discouraging, but really, you just need to reorient yourself and develop personal tools for a new workplace. Transition is an opportunity, and today life is full of more opportunity than ever before.

Today is the first of a weekly event where someone gets free coaching. The coaches will be different each week, and they will address a variety of aspects of work and life.

I’m calling this feature Coachology because I think we all are going to learn a lot about the wide range of coaching that is available, and which types can help each of us the most.

I’m a big fan of coaching. I have learned something from every coach I’ve had, and coaching has been a great way for me to get out of a rut, get up to speed on something faster, and know myself better.

Also, it’s an important skill in life to learn to be coachable. You need to learn how to take advice, incorporate new input into your old plans, and make changes in yourself. You’ll be a better person if you are coachable — you’ll be more of the person you want to be.

So the first coach is Debra Feldman of JobWhiz.

The person who first told me about Debra said, “She cold calls and gets you a great job.”

Fantastic, right? So I called her up, and not only interviewed her, but asked her to role play how she does a call so I could figure out if I thought I could do what she does.

In fact, I probably could, if she trained me. That’s why I thought she’d be good for Coachology.

What Debra is great at is understanding the groundwork you have to lay in order to call someone and get the job. She knows which person to find, how you have to pitch yourself, what research you need to do before you call, and how to show that you bring significant, immediate value to an organization.

I have recommended in many columns that people hire Debra. But her expertise is not inexpensive. So someone will be lucky to get to work with her a little for free.

But listen, the people who will work well with Debra will already have great communication skills. This is not for underperformers. This is for if you are good at what you do, and you know what job you want, but you’re not sure how to get it.

So how do you get ninety minutes with Debra? Email me three sentences about why you think this sort of coaching would be good for you. Put “Coachology” in the subject line. I will look through the emails and pick the person who will benefit the most from working with Debra.

Please note, though, that I’m sure there is a better way to pick the person who gets the coaching. So if you can think of a better process, let me know before next Friday, when we do this all over again with a new coach.

Update: Email submisssions close Sunday, March 4.

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It’s tax time, and every year I think to myself that I should be deducting everything. Really. All my income comes from freelance writing, and since there’s almost nothing in my life that I don’t write about, maybe I can deduct everything.

After years of thinking I should do this but not really doing it, I finally took action. I talked about my deduction plan with Anne-Marie Fisher, director of tax services for CBIZ.

Here’s a transcript of our conversation:

Me: “I spent a lot of money on expensive eye cream so that I looked good for my Yahoo! photo. Can I deduct that?”

Anne: “They don’t like cosmetics or clothing that they say you could use outside of your article.”

Me: “But I wouldn’t have had to look that good if I didn’t take the photo.”

Anne: “But you looked good after the photo. The IRS is really tough on things that help your appearance.”

Me: “What if the cream made me look bad?”

Anne: “That’s a very aggressive position.” (This is tax-preparer speak for “No! Don’t do it!”)

Me: “OK. Forget the cream. What about moving. I wrote a lot about how I moved from New York City to Madison, Wisconsin.”

Anne: “That’s a fine deduction. Just document that you did if for a job.”

Me: “But I didn’t. I can work anywhere. I did it because I was going to die if I had to live in a 500-square-foot apartment for one more minute.”

Anne: “Do you have more business opportunities in Madison?”

Me: “Well, there are a lot of writers in New York City and very few in Madison, so I’m more unique being from Madison and editors like unique.”

Anne: “That’s good.”

Me: “I write a lot about how you’ll have more career opportunities if you keep your rent low. The new American Dream is about having a lot of time, not owning a house. Can I deduct my rent?”

Anne: “That’s very creative.” (That’s CPA-speak for “You’re out of your mind.”)

Me: “Here’s something I did. I went through all my expenses last year looking for some that are big and don’t seem to be deductible. I saw that my son’s violin lessons are really expensive. And you know, violin teaches self-discipline, and self-discipline is important for workplace success. I could write that. Then could I deduct the lessons?”

Anne: “He’s still getting a lot of benefit from the lessons, though.”

Me: “What if I write that he hates them?”

Anne: “Well, if he hates violin and you put him in the classes specifically to write your column, maybe you could prove that he was really upset by you taking pictures of him.”

Me: [Silence. Obvious disappointment.]

Anne [in a perky, helpful voice]: “How about meals. Do you deduct those?”

Me: “Of course. But what about my brother? He guest blogs on my blog. Can I deduct meals with him?”

Anne: “Sure. As a way to thank him.”

Me: “What about the plane flight?”

Anne: “To go see him? Well, things like this are always worth asking about. It’s like gambling. Some people just never want the IRS to talk to them.”

A Roll of the Dice

At this point I decide I’m a gambler, so I call another CPA. Larry Rice, director of strategic consulting at Rodman & Rodman. I cut right to the chase:

Me: “What can I write in my column about toys so that I can deduct the toys I buy for my kids?”

Larry: “Maybe if you had a regular feature where you review toys. But you’d have to throw them out. If you kept them, the IRS would assume your kids got personal enjoyment from them.”

Me: “Could I throw them out later?”

Larry: “No, that wouldn’t work because there was personal enjoyment. The IRS lets you deduct only 50 percent of meals, for example, because while they’re for business, you still get personal enjoyment.”

Me: “Can I deduct 100 percent of the meals I had with people I hate?”

Larry: [Pause.] “When you deal with your taxes, you’re presumed guilty until proven innocent. You need to prove why you have the right to take the deduction.”

Me: “OK. How about the coffee shop I write in. I’m there every day and I don’t have a home office. Can I deduct my lattes?”

Larry: “The IRS has a term — ‘ordinary and necessary.’ You have to show that what you’re doing is ordinary and necessary for your business.”

Me: “OK, there’s an article about how my generation loves to work out of coffee shops and many of us don’t have home offices. We just have a backpack. So how about I send this to the IRS and tell them it’s a new day and they have to get with the program and large latte bills are ordinary and necessary for writers?”

Larry: “Maybe you could do it if you met with people related to your business regularly. The IRS publishes a 30-page book to help people determine if their home office deduction is legal, and it has very tight requirements.”

Me: [Long, dejected silence.]

A New Hope

Larry gives me a good idea. He says that IRS agents receive audit guides that tell them what deductions they should expect from a person in a given field, such as 10 percent of a writer’s income is spent on travel.

So I can get one of those guides, and at least make sure I hit the top levels in all those areas. It’s a new approach, and I have new hope.

Finally, a note to my mom: Please don’t call me to say the IRS is going to read this column and come after me. I know you’re going to worry. But you don’t need to. In fact, now that I’ve written about you worrying, the next time I have lunch with you and you worry about me, I think I’ll deduct it.

 

A couple of months ago, two people sent me the same thing: A womens’ magazine was looking to interview a woman who was doing a good job balancing kids and a freelance career.

“You should respond to this!” said one of the emailers. “This will be great publicity for your book!” said the other emailer.

Articles that talk about women doing a good job balancing work and kids make me sick.

Annoying articles like this are everywhere. Here’s one. It’s about a woman in the military who is also a mom. Right away my radar goes up — lives of miliatary families are not exactly stable for the kids. The title of the article is “Admirable Mom”. I find this title despicable because who is the arbiter of “admirable” when it comes to this?

And why do we need to admire the moms we write about? Why do the women who are successful in work also have to be successful in the kid department? You know what? Most women who have a full-time job and a partner with a full-time job are having a really hard time holding things together. And the longer the hours, the worse it is.

But the bigger issue is why do we have to rate the job people are doing in their parenting? It’s an impossible job. Most people are making errors every day, and no one has any idea which of the infitinite amount of errors we can make are the really bad ones.

There is no rating system for parenting. The parents of kids at Harvard might like to believe that this means success, but it doesn’t. There is no measure. The parents of the kids saving starving kids in Africa also do not get to go to the top of the parenting chart. Becuase there is no chart.

So everyone should please shut up about the articles about women who “do a good job balancing work and family”. What does that mean? Good job? And what about that it’s all self-reported? What sane woman is going to speak on record about her career and say that she is not doing a good job with her kids?

Do your kids love you? Do you love your kids? That’s all there is. It’s very frustrating, in light of intricate and predictable quantified system of rating ourselves and others in the workplace. A study by Stanford DeVoe and Jeffrey Pfeffer at Stanford Business School shows that people think about work while they watch their kids soccer game. No surprises there. The study says that people are computing their billable hours and time lost for the day. This makes sense to me becuase math problems about work are easier than interpersonal problems about family.

Work is measurable and parenting is not. Bob Sutton, also a Stanford professor, quotes a study that shows people like things that are measurable. We like to know how we’re doing. We like to have a goal and meet it and know we’ve done a good job. We like acknowlegement. There is none of this during an afternoon hanging out with your kids.

The parents whose minds are not wandering to work are parents who don’t have engaging work. Because any type of engaging work is easier than being with kids. I’m not saying don’t spend time with your kids. I spend every day from 1 – 8pm with my kids. And even later than that if I don’t do a good job during bedtime negotiations. I choose that. But it’s hard.

And I would never hold myself up as a role model for parenting becuase the idea of ranking parents is absurd. Besides, I’m like that dad who can’t keep his mind from work. When my kids are really difficult, sometimes I’ll escape to my web metrics report. There are not official kudos for getting through another round of superhero wars. But there’s no arguing with the graph that shows a good day for blog traffic.

You know what? It’s stressful to have a career and kids, but also it’s stressful to have just kids. So the best you can do is try to not bring the workplace stress home with you. becuase that’s really realy bad for kids. They notice. But sometimes, let’s just all be honest, work is a way to alleviate some of the stress at home.

So here’s my advice: Don’t have too much stress at work, don’t have too much stress at home. And don’t have the hubris that makes you want to respond to one of those journalists looking for an admirable mom. If you want to be ranked, go to work. There are not rankings for parents. That’s what makes parenting so hard.