“If you don’t want to, then don’t,” my mother replies.

But it’s more complicated than that, and I tell her why. I tell her that I really do what to be with him - a lot - but I don’t know how. I tell her that I’ve been sabotaging the relationship, and I don’t know how to stop. I confess everything, and feel the weight dissipate.

“You do look for problems,” she says. “You push things too far. You test people too much. That’s not good. So now you need to figure out if you’re going to mature and grow up or not.”

I’m silent because normally my mother tells me how great I am, how I can do no wrong, and how all men suck. It is the Gen Y parenting creed. But tonight, I am not so lucky.

“Why do you think you’re picking fights?” my mother presses. “You must be doing it for a reason – a lack of confidence in yourself, or in him?”

I concede that I don’t feel like my life is together enough to be in a relationship. And that I’m worried Zeus will sell his company, get rich and dump me. Or we’ll get married, live happily and divorce at the age of 40. Or that he won’t remember to suggest we eat something when I’m moody. Because I get cranky when I’m hungry.

These are the things I worry about. I am a woman. And this is what we do.

Women need constant reassurance, and the only way we know how to get it is to fight, and push buttons, and push past the buttons all the way to the brink of breaking up, so we can see – will he be there then?

My mother argues men can deal with this at first, but it adds up and is like a brick falling from the sky each time. It builds and it is cumulative and eventually they have a wall, and they think I don’t need this. I don’t need to be unhappy, nothing I do ever works or helps, and I can’t make her happy. This isn’t the way I want to live, men think.
 
And there’s a limit to what a man can take, my mother says.

“And you - ” she continues, “you need to live for today and for you. You can’t know the future. And nothing about your past relationships is pertinent for today. You have to resist the urge to fight. Resist the urge to be angry in an instant over nothing, resist pushing to the breaking point constantly.”

Careers are like this. Maybe you have an idea, or you really want something, or all of your dreams are suddenly within reach. But you make up excuses of why you can’t get there. You prove every hypothesis on why it won’t work. You extrapolate the worst. You don’t call people when you should. You think less of yourself than you used to. You ask others to comfort your decisions. You trip over your own accomplishments just to see – are you on the right path?

Lucky for you, careers are often just as forgiving and patient as men in the beginning, but you have to grow up for continued success. You have to mature before the wall seems insurmountable.

“It is work,” my mother concludes. “It’s a lot of work. But if it’s truly in your heart, you have to do that. You have to work to make it happen.”

Motherly advice.

Such a small thing years ago, but I think about it constantly because it’s one of the few times I haven’t spoken up.

More recently, Maria Antonia and I had planned to go to a local political fundraiser, and she cancelled at the last minute. Her boss thought it was a bad idea since we are both semi-public figures and should remain neutral.

And then at my family reunion just this past weekend, we weren’t allowed to discuss politics or religion. Out on the patio, I secretly tried to goad one of my uncles into telling me who he was voting for, but silent he remained. Instead, we talked about the weather.

Business Week’s Bruce Weinsten argues in his ethics column that mum should be the word on politics, especially at work. Apparently, speaking up can bring you down career-wise.

“Along with sex, money, and religion, politics is one of the most controversial topics of conversation that exists,” he states. “We talk about sex with our closest friends (with whom we probably would not even discuss our income), but this kind of conversation is wisely held after business hours. Neither your salary nor your sex life is anyone’s business at the office.”

Except that Generation Y’s rituals fly in the face of Weinsten’s fearsome foursome.

As products of the Sex and the City generation, Belle and I openly discuss sex, but we also openly discuss income. I know what both she and her fiancé make, and they both know what I make. We know how much each of us paid for our condos, and how much debt or lack thereof, we both have.

This isn’t a trend relegated to personal relationships either. Nonprofits have routinely disclosed executive salaries as part of a law for increased accountability, and now transparent salaries are being implemented in forward-thinking companies like Brazen Careerist.

Taboo topics are quickly becoming acceptable as part of Generation Y’s demand for authenticity and transparency. Except, maybe, for politics.

Despite projections that we will define one of the most influential elections in history, in part due to online discussions facilitated by people like Tim Weaver and Milena Thomas in the Gen Y blogosphere, we still seem to be weary of expressing our opinions openly in the workplace.

 “Ultimately I’m at work to work, and I wasn’t hired to discuss my personal political opinions,” one commenter argues. Which is like saying you weren’t hired to talk about the Red Sox, the back problem you have, or the Kooks concert you went to on Thursday night. Because I’m sure people are dying to hear how you made tacos with hot sauce AND sour cream more than your informed opinion on the most important issues of today.

What we believe in and have faith in informs our work and personal lives intimately, and to say that we shouldn’t discuss them anywhere is dangerous.

“The idea that practicing any profession somehow obliges or even encourages a vow of silence on any subject, politics or otherwise, that might offend someone somewhere, is odious,” argues author John Scalzi. “Everyone should be encouraged to say what they wish to say about the important matters of the day. Everyone should feel that participation in the life of their community and their state and nation is a critical act. To do less invites ignorance and ultimately tyranny.”

And to argue otherwise is to say that the whole idea of America – a democracy where people aren’t persecuted for speaking their minds – is based on a fallacy. But it isn’t. Generation Y is just entirely too quiet and conservative.

And while voicing your opinion may invite all sorts of opinions and criticism and the chance that you might – gasp! – have to defend your beliefs, we cannot have as our legacy a production that mindlessly follows the corporate establishment.

As one of the largest generations born into idealism, we are now facing the first true test of whether we will rise or recoil in the face of adversity. It doesn’t matter if you’re a librarian or are in the most public of professions, you have enormous political power.

Years from now, when I look back and reflect, I will know that I never, ever regretted opening my mouth, only keeping it shut.

Open wide.

Indeed, when I started my current job, there was much disruption. In the beginning, it was the challenge of transitioning from being an employee to running an organization. Of being lonely. Of complete work/life distortion.

And when I say challenge, I am being polite, because what I really mean is not all unlike the walk of shame after a particularly rowdy and untoward night of college drinking. That is, what exactly did I get myself in to?

Lately, it’s been an entirely different type of challenge - that of being in limbo because the responsibility and possibility of it all paralyzes me more than I’m willing to admit.

Because, really, given the opportunity to change the world, would you take it? We all think we would, but it is so very hard to look in the face of what you truly want and take it. It is so very hard to fight the war of what really matters.

So Generation Y isn’t always stepping up. And those that do, often think about stepping right back down. Because unless you’re in the fight to make change, it’s difficult to know how ridiculously hard it is. I thought that this might have just been me, that maybe I’m just not cut out for all this leadership change stuff. But I recently met with a thirty-one year old vice-president. She told me no, we’re all neurotic. Really. Neurotic was her word.

“This next year will probably be one of your hardest,” she said. “But you know and I know, once you’ve tasted this, you can’t turn back.”

I think about her words on the days that I don’t want to strategize, or build encampments, or be so obsessed with seeing a CEO or colleague or client on the street that I spend fifteen minutes trying to look vaguely presentable before going to Walgreens just to buy some toilet paper. Really. Some days, I just want to buy toilet paper in peace. Some days, I just want to be normal.

“Being normal,” Hercules replied, “gets you a middle-class life in the suburbs. It’s fifth place, and you know you want to be in first.” All successful people then are understandably eccentric. They take risks that normal people wouldn’t.

There’s this thing about risks though. It’s easy to sign up, but it’s the follow-through that’s hard, the follow-through that decides your character.

Like when I went skydiving two weeks ago (here and here). I wasn’t nervous. Honestly. They tell you to get nervous because if you’re not, you’ll freak out when the door opens at twelve thousand feet. So I was trying to be nervous, but I just wasn’t.

But in skydiving, eventually the plane does fly up to twelve thousand feet, and the door does open. When that happened, my tandem instructor put my hand out into the wind. “That’s not so bad, is it?” he asked. No, I nodded; it wasn’t so bad. I was a rockstar, invincible to anything and everything. I was a rockstar, that is, until we moved to the edge of the plane and I had to put one foot out into the air. It was then that I thought oh, holy crap, I can’t do this. What have I gotten myself into?

That’s the moment, see. Where you have to muster strength from somewhere you didn’t know you had. The moment where you face all your fears. It’s only a split-second in skydiving. Literally. A split-second where you decide if you’re going to smile or cry. Move forward or turn back. Jump or freak out.

When you’re pushing adulthood, however, it can last months. It’s easy to say you’re going to do something. It’s easy to be eager with words. Actions are much harder. That pesky day in and day out stuff.

Like putting down the potato chips and going to the gym. Or not taking things personally when it would be so easy to join the fray. Or putting down your guard, opening yourself up, and then – and this may be even more difficult – letting someone else in.

“It’s the hardest thing in the world, to do what we want,” this character says. “And it takes the greatest kind of courage. I mean, what we really want. Because it’s such a big responsibility – really to want something.”

Oh, and in case you were wondering… I jumped. With a smile on my face.

Risk normalcy.

See, I was supposed to figure out who the man of my dreams was this past week. Stop laughing. This is serious business. Last year, I felt overwhelmingly that this would happen in March or April, and as time went on, I began to believe that it would happen in the last week of March.

I told a couple people about this craziness – my mother, Belle, Hercules. They all humored me while explaining in a good-natured way that I shouldn’t count on it.

You can’t plan for things like this, they said. You can’t plan for love.

Fine, I told them. But I went ahead and had drinks with every eligible bachelor I knew. Just in case. Then I waited for fireworks.

Nothing.

Okay, so you can’t plan love. And you can’t plan for your career any better.

When you stick to a plan, you miss out on opportunities. Besides, you’re only in control of yourself. You may have goals, but unless you’re ruthless with yourself and who you are - your abilities, your strengths, your weaknesses - you’re not going to get anywhere.

For instance, I had drinks with Johannes last week. He’s been planning one particular career path for a number of years now and found out recently that he didn’t get the job he really wanted. He got another great job, but it wasn’t the one he had put on the map he carried around and relied upon. Understandably, he was pretty despondent.

This was probably you when you realized that you would never use your degree. Or when you found out you couldn’t have children. Or when you started your dream job, the one that paid you large sums of money, and you looked outside your corner office with a view and realized you’d rather be a musician.

That’s the thing about life. It doesn’t really care about your plans. So you can chart all the courses you want, but it’s much better to just be prepared and flexible for the opportunities that come your way.

Like Sunday, when I shot a gun. Um, yeah.

If you know me at all, you know how ridiculous this is. And my mother is probably having a heart attack right now. But mom, it’s okay. I was very safe.

I’ve never believed that people should own guns. In England, they don’t allow people to own guns, and there’s virtually no gun-related crime. Seems easy enough to me. So I’ve always thought that owning a gun was downright stupid. Or I did. Until my friend drove us to a shooting ground, taught me the rules of gun safety, and I pulled the trigger. I actually even hit the target several times.

Do you know how exhilarating it is to try new things? To take risks and do something you never thought you would?

That’s why it’s so necessary not to hold onto your plans, opinions, and beliefs with such strictness that you can’t change and adapt, and with such fear that you don’t live your life.

You know, I was never going to be the person I am today. I was going to be the next William McDonough. I was going to be the next Samuel Mockbee. And well, I’ve always wanted to be Oprah. And maybe someday I will be. But I’m pretty glad life got in the way of my plans.

In summary, to rock your life and your career:

1) Focus on the now.
2) Like plans, love change.
3) Take risks.
4) Repeat.

In the meantime, I’m accepting that maybe I’m just not ready for a relationship. Or maybe the person that I like isn’t ready. Or maybe we’re not meant to be together. Whatever. The point is, I’m done worrying about it. And I’m ready for today.

Love it like you mean it.

And guess what? I could care less.

Sort of. Because not immediately, but always eventually I notice there are fewer women than men in my life. And then, inevitably, I feel that it’s necessary to say something like, “Where are my women at?” I don’t know why such words fly out of my mouth because I feel comfortable around these men. They’re good guys. But there’s this undercurrent that just doesn’t feel right.

Monica O’Brien calls this casual sexism, and basically tells us to shut up about it, play by the rules and move on. Which is good advice. It’s the path that’s gotten me where I am today.

Indeed, this month’s issue of Portfolio observes that nobody wants to talk about it because most people think there’s nothing to discuss.

Generation Y women in particular are growing up believing they don’t have to worry about sexism. In college I certainly didn’t feel there were inequalities.

It was only a few months after graduation that I learned otherwise. Somehow I had finagled my way onto the Board of a local nonprofit, and the rest of the Board was comprised of men. Older men who didn’t listen to me. There was one woman who joined our meetings by teleconference; she was pregnant and bed-ridden. And those meetings always made me a little indignant.

Like when I read advice that tells me I have to get married and have babies before I’m thirty. I guess it’s smart advice, but it doesn’t resonate with me. I don’t feel that my entire life needs to be managed around having a baby, because I don’t feel that my sole purpose in life is to have a baby.

But it seems that because women are different, being built to have babies and all, that our success isn’t the same as the success of men.

For example, when one of the top alpha females in my area personally called me last week to congratulate me on a recent success, I was ecstatic. I told Hercules all about it, and he said to me, “That’s great. But you know, she’s really not all that smart.”

And I took what he fed me, because I respect Hercules and I like him a lot. But then, do you know what I did after that? Each time I told the story, I added that clause to the end. That this wonderful, well-respected woman who personally called me might not be that smart in reality. What?!

That belittles her success and it belittles mine. It’s casual sexism at its best.

This is what Gen Y women are dealing with. And it may be entirely more dangerous than outright discrimination since it seeps quietly into our minds and then out of our mouths. That sucks.

Because while we may not be marching for our rights any longer, we’re still debating whether pantsuits are unfeminine and men like Jun Loayza now think it’s charming to ask if we were “a little crazy as an undergrad.”

We’re not out of the woods yet.

Gen Y women will have to breed an entirely different form of feminism to deal with this. I don’t have the answer here, because I often feel conflicted. I genuinely enjoy being a woman. In my view, I want to wear the dresses and have the power. Only time will tell if I can have it all.

Working girl.

After talking about Gen Y leadership, in which I blatantly quoted my blog to close the deal, she asked me what I would do if I witnessed unethical behavior.

“I would investigate to see if it was really unethical behavior,” I said, “or if I was misunderstanding the situation.”

It was the perfect answer for a business that loves gossip, but doesn’t like to make waves.

Then out of nowhere I felt compelled to add, “And I would probably call my mom and ask her advice.”

My interviewer smiled. Turned out my answer was right on all counts.

We ended up spending a large part of the remaining time talking about her relationship with her mom. She described how her mother had come to interviews with her, and how she continued to count on her mom in her high-profile position.

Gen Y isn’t the only one counting on parents for advice. This is behavior magnified and built upon from previous generations.

I call my mom all the time. Not as much as she’d like me to - a constant source of debate - but I value her thoughts and respect her advice more than anyone else.

She’s usually right too. Men, career, friends, she just knows. Everything. Annoying, that.

“Most Gen Y’s have strong, positive relationships with their Boomer parents,” Tammy Erickson argues at the Harvard Business Review. “They speak with Mom or Dad when they have a problem, and most feel that their parents understand them.”

I’m not saying that you should always listen to your parents, or that they’re always right. My own mother, who I referenced in my interview to get the job, and who praised me for my smart answers, was hesitant that I should even take it.

She didn’t really understand what I would be doing. I still don’t think she fully understands. But I took the job anyway.

I also listened to my mother at the same time.

Listening to my mom is recognition that I am becoming an adult. See, asking for help is one of the most adult things you can do.

There’s no one better to ask for help than your parents, because despite the fact that sometimes they might annoy or guilt-trip you, they really, in their heart of hearts, want the best for you. And they’re always proud of you. They always love you. That’s what parents do. And they know you better than anyone else.

I find it funny to read that some experts believe that Gen Y “may well shatter,” as the result of intense Boomer parental involvement. Do you know what I do when life isn’t going my way? I call my mom. And do you know what she tells me? “This is your life,” she says. “Stop crying and deal with it.”

Okay, it may not be those exact words, but today’s parents are not ignorant. They know that despite their coddling, Gen Y will need to become independent in order for us to succeed.

So we might as well stop getting up in arms that parents are helping their children. Because in the game called life, we really need as much as help as we can get.

“Use your parents’ insight to gain experience when you have none,” Rosie Reilman argues. “But don’t let them live your lives for you. This is your life. Take ownership of it.”

I agree. I’m not saying don’t grow up. We should grow up and take responsibility. I don’t believe, for instance, that you should move back home after college. Because of how I was raised, I think that’s irresponsible.

But I think we all feel, especially in our twenties – and maybe it never ends – that we’re doing a good job of just acting like adults. And maybe if we’re good enough actors, we’ll actually become adults someday. With the help of our parents, of course.

While Erickson believes we should accept all this as “a changing cultural norm,” Scott Williamson argues that “accepting this sort of behavior just enables more of it.”

But I believe we want to enable a workforce that asks for help, that respects their parents, and who aren’t afraid to admit that we don’t have all the answers. Certainly, there are instances when it can go overboard, but why must we continually let a few bad apples set the tone?

We shouldn’t sensationalize what is generally a good trend.

Motherly advice.

As a twenty-something in the workforce, you will be questioned time after time. Here are three ways to build credibility:

1. Develop skills that travel.

Most likely, you’ll change jobs 6-8 times before your thirty. You need to develop a set of talents that will travel with you from job to job. Career coaches call these transferable skill sets (e.g. communication, interpersonal, and management skills).  Essentially, the skills you’ve been developing since grade school. Consistently developing these abilities will not only open the door to any job you want, but will make you successful wherever you go.

2. Hug thy naysayer.

Generation Y wants to be liked. We grew up being coddled by our parents, and frankly think we’re the best thing on earth and like to be told so. Not everyone agrees with us however, and a lot more don’t even like us.

While it’s important not to get wrapped up in what others think, you need to build relationships, even with the people bringing you down. Learning to deal with criticism effectively is about knowing yourself, who you are, and what your motivations are for working.

The next step is to develop mutual respect. When comments get heated on my blog, I often email the person and talk to them individually. I say thank you a lot, even when their thoughts make me want to scream. I appreciate that they’ve taken the time to respond to what I had to say. It’s best to engage in conversation when all the players are at the table. That’s how you learn.

3.  Don’t work harder, work smarter.

When a twenty-something doesn’t show up to the office at 9 AM, the rest of the world worries.  But our generation works differently. Make sure it’s in your contract that your performance isn’t based on when you show up to work, but if you get the job done. And if you want to wear jeans to work every day, say so. Be upfront about how you can add the most value.  You’ll work better if you’re able to choose how you are productive, and your results will speak for themselves.

I walked in and almost everyone was sitting down, and the speakers were close, shoulder to shoulder. It was so hot and sticky outside, I went to the bathroom to freshen before sitting down near the door, lest the presentation be boring and I should want to leave in the middle.

Big Brother was the moderator of the panel, and I had seen him in the press, but never in person. After the event, we somehow managed to walk out at the same time. He said hello to me, in that special way he has, gleaming with charisma.

Much later we sat at a coffee shop, and I saw him repeat this behavior with other people who stared at him, as people often do. And I must have been staring too, because I remember the way that I felt was that my future was intrinsically and inexplicably linked to this man.

I couldn’t have known then that we would eventually sit in a car together as he expertly handled a disastrous situation. Or that we would have flurries of text conversations at nine o’clock at night. Or that he would be the one of the few people who could simultaneously inject fear and ambition into my dreams, that he would be one of the few to infuriate and inspire me all at once.

At the time, I was confused and unhappy. What I thought was supposed to be my dream job wasn’t working out and I felt claustrophobic in an invisible box, like a mime putting on a bad show.

I had a ridiculous time getting up in the morning, often rising out of bed just fifteen minutes before I was supposed to be sitting in my office chair. A three minute walk from where I lived. I didn’t really tell anyone at the time, not my boyfriend, or even my mother.

And little did I know things were only going to get worse, much worse, before they got better.

Eventually, it was mutually agreed upon that it would be best if I left my job, which sounds better than being fired, and it was just two or three days before Thanksgiving.

I felt a huge sense of relief, and full from a big plate of humble pie, I applied for and started my next job a short two weeks later. And then, a short two months after that, my body decided to send me to the emergency room. The day that I got out of the hospital, my boyfriend broke up with me.

It’s a strange feeling, hitting bottoms you never knew existed. But what’s even stranger is the wherewithal you find in yourself to keep going. That night, I cried on the shoulders of two of my friends, but in part of my head – the part that was growing an antidote to my flair for drama – I also thought that it was no big deal.

I needed to get healthy. I needed to get a paycheck to eat. I needed to figure things out.

So, I did that. With no other choice, it was remarkably easy.

I won’t describe much more about my second job because, in short, I loved it, and it’s difficult to write about such happiness without sounding absurdly corny. Suffice to say, the job was like a retreat for my career, and the organization I worked for was tremendously good to me.

So it was a surprise to everyone, most of all myself, when I started to feel restless later that year, and into the next. Seemingly losing it all made me remember I wanted much more.

That’s when I started this blog. Actually, I started a different one where I posted bad prose that I had written, and told around three people to go read it. Then I started this blog. And I told everyone in my address book to read it.

See, here’s the thing. When you put yourself out there for all to see, when you make yourself vulnerable, and you’re taking a big risk, and you’re doing all this because you can’t think of doing anything else, people will rally behind you. They will support you. Because people like to see others succeed. The universe will conspire in your favor.

The rush of this risk was so big, and the potential payoff so great, that I started to take more risks. I acted in a play where I learned the lines just eight hours earlier. I went skiing for the first time, fell on my butt, and got back up again. I learned sushi was the best food ever.

Oh, and I applied for my dream job and got it.

I don’t want to make it seem that I went through this big transformation over a short period and I know everything now. I didn’t and I don’t.

Let me be clear. It was really the years before this one, and those before that, which set me up to succeed. But eventually, you reach a tipping point and things begin to flow in your favor.

The pace since that’s happened has been like a water slide at a water park. The ride down is fast, scary, and exhilarating, and once you’ve reached the bottom, you can’t wait to make the long, hot and sticky crowded climb back to the top and do it all over again.

Because now I have an entirely new set of challenges and struggles that I face. I work hard, but also strategically and intelligently. And Big Brother, who seemed untouchable to me a couple years ago, is now one of my many mentors.

Dreams = Reality

This is good for those people, most people. Most people either don’t have the balls or are not well-equipped to do what they want.

The can cross off the “career-equivalent of winning the lottery,” because that dream was making them feel anxious anyway. And while they love to write, they can see that it gives them some sort of peace to admit that they may not really love it if they never make time for it. They’re good to go with the cubicle.

This is all okay. It’s called settling. And it’s a viable option. A good one that will make you happy.

Some others, well, they’re not settling. They are different from most people. This is the group that seems to find the prize in the cereal box every time. They’re leaning into the wind and winning, and the book industry is making a good deal off the fact that most people want to be just like them.

Along with the crowd that is Oprah, I’m currently reading, A New Earth by Eckhart Tolle, in which the author predictably states that the book, “can only awaken those who are ready.”

It is both a shame and a triumph that the most banal statements are always the most obvious, the most difficult, and the most necessary.

The only way you can be ready is if you’re ruthlessly transparent, authentic and honest. In the book The Fifth Discipline, Peter Senge argues that a commitment to truth is a “restless willingness to root out the ways we limit or deceive ourselves from seeing what is, and to continually challenge our theories of why things are the way they are.”

This is much different than knowing that you’re afraid to talk to your crush because you have unrealistic expectations of the happy movie ending.

Rather, it’s an advocacy and inquiry that rivals trying to find the pot of gold at the end of the rainbow. Or if you’d prefer, finding the one good-looking guy at the bar on a Friday night.

There is a shortcut, the sound of settling. It’s comfortable like a blanket over your shoulders, spaghetti in your stomach, sex in the dark.

Settling leads to mediocrity. It’s the acceptance of the “good enough” status quo.

Successful people know that the gap between our vision and current reality “can make us feel hopeless. But the gap is also a source of energy,” Senge argues. “Truly creative people use the gap between vision and current reality to generate energy for change.”

In encouraging yourself to rely more on your concepts of reality, rather than your observations, and in discarding your dreams and goals in order to be realistic, to settle, you lose this creative tension.

That’s why Generation Y is uniquely positioned to create real change in our next career move. We’re idealistic and yet keenly aware of the world’s scorecard. We understand, as Senge argues, that “the juxtaposition of the two, the dream and the present reality, [is] the real force for change.”

Fall into the gap.

A big thank you to Joan Gillman of the University of Wisconsin School of Business, and Jody Glynn Patrick, Publisher of In Business Magazine for inviting me to be on the show!

You can listen to the free podcast here. (A direct link to the free download, where you can listen in your browser or download the audio. A full list of available podcasts from the program is available here.)

Check it out… you can tell when I stop being nervous when I stop talking so fast.

Let me know what you think!