Find people who compensate for your weakness

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The update on my company is that Ryan Healy and I are not talking to each other. Well, he is talking to me, but I am giving him the silent treatment.

Still, I am confident that things are going well. First, because I am bad at the silent treatment—I have too much to say all the time. Second, there is very good research about what makes a good entrepreneur. And the answer is that there is no single personality, but rather it is the type of person who can see their weaknesses and get a partner to compensate for that.

Ryan and I have done that with each other. And during my short stint of silence, I thought about how in fact, we are doing a lot of things right. Here are six things that entrepreneurs must do in order to have successful partnerships, and I think Ryan and I are doing them:

1. Make time for arguments because they are inevitable. You must consider this part of your job, in order to have constructive conflict.
We fight like we are married. Which says a lot, since I am in the middle of a divorce and he has never had a girlfriend for more than fifteen seconds.

So I call him from my kids’ soccer practice to tell him I am not calling him for a week. And I am the parent at soccer who is on my phone instead of cheering every good kick. This is my way of bringing diversity to Madison: if it were not for me, only men would do this at soccer.

To be annoying, Ryan calls me at 5pm, which is death hour to all parents who have hungry kids who are a half-hour from food, and he says he can’t manage cash flow because any question he has must wait 24 hours if it comes up at 2pm, which is when I stop working.

I want to be like, Duh! If I stopped working at 2pm then I would not have any time to fight with you from the soccer field. But I stay quiet because I am trying to be a more reasonable person to work with.

2. Remind yourself why you picked that person. You probably still need him for that reason.
I remember when Ryan and I were first thinking of going into business together. And we spent two months arguing over equity. There was the day I got so angry that I had to pull the car over to fight with him. And neither of us walked away from negotiations. Someone who really hates fighting would have called off the partnership right there. It was a sign that this is what our partnership would be, and we both signed on the dotted line.

In that fight, Ryan was more mature than I was. I was definitely right on the business issue we were arguing about, but he handled himself better. He was very calm. And that only made me more hysterical. (I hesitate to use the word hysterical, by the way, because I know that it validates Ryan’s propensity to call all women he ever comes into contact with “crazy” but whatever. Now he and his friends can have a four-syllable word they can use for variety.)

So, anyway, that’s how it is now. I envy Ryan’s ability to be even-keeled. I am not an even-keeled person.

3. Give each other feedback on strengths and weaknesses.
I’m also going to tell you the worst thing he said. He has no idea that this even bothered me. So right now is the part in the paragraph where he will jump ahead, amazed that I didn’t tell him something that was offensive. Because believe me, he hears about it every single time he is rude to me.

So, anyway, it was a day when we both got dumped. We had each had about four dates with people from Madison, which is, in itself, a miracle, because we are both fish out of water here, and neither of us really expects to find a long-term relationship.

But miracles happen. And we were both smitten. And then we were both dumped. Ryan is the great analyzer of our social lives because he thinks I am a social mutant and only know how to talk if CNN is interviewing me.

So, he says that he was dumped because she was a college girl and didn’t want the structured dating life that a recent grad wants. Then he tells me that I got dumped because I don’t dress like a girl. “You don’t even try!” he says, with his patented combination of exasperation and incredulity.

I’ve been around Ryan long enough to know what this means. He thinks I look like those moms who throw on designer jeans and a Calvin Klein T-shirt and think they have stepped up their game. And they have, for a going to a preschool play date.

So I wore that and I thought I was dressing up, and Ryan thinks I look like I’m in preschool-play-date mode.

4. Use the other person's expertise to improve yourself.
Really, Ryan gave good information about my wardrobe because there have been many times that I have not dressed quite right for television appearances and people have been largely unimpressed.

Also, I am good at taking criticism (lucky, since Ryan is good at dishing it out). So I implemented his recommendation to be girly in Austin, while everyone was Twittering at SXSW about how Mark Zuckerburg's interview sucked. I was down the street at Nordstrom buying accessories.

(There is no Nordstrom in Madison. I plan all my shopping trips at the intersection of the Nordstrom store finder and my speaking engagement itineraries. And, by the way, the next time I use scientific data to choose where to live I will never move farther than 15 miles from a Nordstrom. Nordstrom customers have good taste and Nordstrom opens stores near their customers. )

5. Be aware of generational differences, and don't assume you're above them.
We know we are a shining example of the generational train wreck in corporate America. And it’s not for nothing that Ryan just wrote a post about how the biggest problem in work life for Gen Y is not the Baby boomers but Gen X.

Sometimes we find ourselves laughing about what a stereotype we are. For example, Ryan always wants to collaborate and I want to be alone and answer emails.

He wants to socialize with everyone at work, and I am all about picking up my kids at school.

I asked him to fax something to a client, and he said, “Fax? Do I look like I’m forty years old? I don’t even know how to use a fax. Can’t they take a PDF?”

Ryan and I have parents who are roughly the same age, yet his parents call all the time because they think the company is so cool, and I don’t even think my parents could tell you the name of my company.

6. Startups are difficult for everyone. So don't get hung up on hierarchy. Or anything else.
I was going to tell Ryan today that his problem is that he doesn’t manage up. I was going to say, “Look at the sidebar on my blog. I write about managing up all the time. How about brown-nosing once in a while?”

But he would not take that criticism well. And anyway, he’d tell me he managed up the only night maybe in my whole life that I was drunk: at TechCocktail in Chicago, which I promised I would blog about, so thank goodness I’m getting it in now.

Ryan took off my nametag in an attempt to gain some anonymity while I was totally drunk and probably inappropriate. For us, that qualifies as managing up, probably. But then again, that was the night he told me I am the most socially eccentric person he has ever met, and I’ll never get a date.

I told him that men like socially eccentric because in bed it’s not about being social, so there’s just eccentric left, and men think that means a likely possibility of anal sex.

Ryan was silent. He was driving. But I don’t think he was silent because he was driving.

I said, “See. I told you I’ll get dates.”

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Announcing the launch of BrazenCareerist.com!

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It’s the big moment where I tell you to go check out BrazenCareerist.com. It’s the first stage of our company, and it’s a network of fifty young bloggers who I love, all blogging about their professional interests.

This would be a great time to tell you the grand story of the birth of my grand company.

When people tell you about their company they always tell you the mythology. You know Pierre Omidyar deciding to sell his girlfriend’s Pez containers and then making eBay, James Hong talking about sorting through photos of girls with his dad in the early days of hotornot. But those stories are really the ones you create after the fact.

During the very early days of a startup, there is no mythology. There is only doubt, Ramen, and fighting. For the lucky few founders, there is probably some smooth-things-over sex, but mostly early startup life is suffering. Suffering with a twist.

The twist is that entrepreneurs are generally very optimistic, so we can spin suffering into fun. I never thought of myself as optimistic until I took a test in Oprah’s magazine and found that I was so optimistic that I’m maybe borderline delusional.

But without the optimism, here’s what a startup really looks like: nothing.

For a while, my startup was my column. I always knew it was the basis for something bigger, but I couldn’t tell people that. People think you’re crazy if you tell them you’re doing a business when it doesn’t look like a business. So I kept building my column and the audience and then my blog and its audience until I could think of a company to launch with it.

What I’ve learned by now is that when you start doing your company, there is nothing really to do, and everything to think about. In fact, researchers know that there is no single entrepreneurial trait that predicts success except the propensity to mitigate risk. That’s right. Entrepreneurs are not crazy risk takers but rather people who are trying to decrease the risk as much as they can.

So successful entrepreneurs decide to start a company and then think about it. They play with it in their mind. Maybe they talk about it, just a little. And then they make a commitment to the company, and you know what? Nothing changes. It still looks like a lot of nothing, because it’s mostly just thinking.

And there’s no one to talk to because you’ve been fighting with your partner for weeks because you’re so angry that there’s nothing to do. And you can’t talk to your friends or business associates because they’ll say “When are you going to start your company?” and you’ll snap, “I told you ten times that I already have started the company.”

If people knew what they were doing at the beginning of the startup then early investments would be much less risky. But the truth is that business plans are so apt to change that no angel investor has even asked us for one.

Here’s our business plan: Leverage our established brand to build a big community of young professionals. Here’s what we have: a network of fifty bloggers who have agreed to participate in a community of people helping each other with careers.

And this is also happening: we have a slew of companies asking us to consult with them to tell them how to deal with Generation Y. But that is not in our business plan. We are so excited to take in money that we’re doing it anyway.

Our mythology will not be about how we spent months not knowing for sure what to do, and sort of launching and then pulling back to rejigger things and then going at it again. That is not typical startup mythology; that is typical startup constipation.

Our mythology is going to be something like: we knew we were experts in Generation Y, and we did a lot of consulting to fund a community of young professionals. Or, maybe our mythology will be that crazy startup that Penelope couldn’t stop blogging about.

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How to decide if you should start a company

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Do you want to know how to tell if you have a business idea that will succeed? You know what? I don’t know how you know that. And if I did, I’d be a venture capitalist, right? But I do know how you can tell if you have a business idea that is worth reorganizing your life to try.

Who knows if you have a good idea?? No one. Actually, in some cases some people can tell you for sure that your idea definitely sucks, but no one can tell you for sure that your idea is good. And, if nothing else, any for-sure good idea is already being pursued by ten people, or ten million, depending on how big the market is. Which makes it, again, not a for-sure good idea because maybe you won’t do it best.

So if you want to know if your idea is one that you should actually try, don’t spend time figuring out if your company will be the next Web 2.0 darling. Instead, figure out if it’s going to give you a life you want. The best way to figure this out is to look at how other entrepreneurs are living their life.

I did not do this. I purposely ignored what the lives of other entrepreneurs look like, because a gazillion studies show that entrepreneurs work longer hours than everyone else. And they are under more stress than other people.

I ignored this research because I told myself that a startup would be a good thing for my kids. I told myself that my blog was growing too fast and I couldn’t keep up, and if I spun part of it off into a startup then I would have people helping me. I am a great delegator. I imagined the list of things I could delegate to the slew of people who would go into business with me.

It is not uncommon for people founding startups to lie to themselves about how much work it will be. It’s similar to having a baby. Everyone tells you the baby will take over your whole life. Daniel Gilbert even tells you that kids will not make you any happier than you already are. You go ahead with it anyway. You tell yourself that the kid-time-crunch will not happen to you. You are the exception. Other people are incompetent time manager and you ‘re not. But if we didn’t lie to ourselves, who would have kids?

So, anyway, denial goes very far in both the birth of a child and the birth of a company. Which means it is should not be surprising to you that I have done things like let my son dump boxes of cereal all over the house so that I could be on a conference call, or that I hid in the broom closet at swimming lessons so I could do a radio interview with no background noise. (Please, don’t send me emails telling me I am a negligent parent. Negligent is relative. And why are you reading this column instead of playing Candy Land, huh? )

When you imagine your life doing your startup, do you imagine laying in bed at night worrying about money? Because no matter how great your idea is, you will worry about money at the beginning, in that terrible time between when you quit what you had been doing and you start drawing a salary form the startup. And you know what is worse than one person stressing about money? The two or three people who do the startup with you, all stressing about money together. At some point during the early time, it’s not even about the idea any more; it’s about just getting through the early, tough part.

Now, go back to your idea. Go back to the question of is it a good enough idea to try? Entrepreneurship is not about one, static idea that you implement. It’s about an idea that you go with, and mutate, and act on because you want to do a company so much that you are willing to delude yourself into thinking that maybe it won’t be so hard.

Are you there, to that point? Then you have an idea that’s good enough for starting a company.

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Use the entrepreneurship boom to improve your corporate job

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The new wave of entrepreneurship is changing the startup landscape for sure. It’s nearly free to start a company online, even teens are having wild success, and young people are flipping web sites like boomers flip houses.

Life as an entrepreneur has never been so fun, but that is very annoying to hear if you are in a corporate job. Fortunately, this trend is so big at this point, that it’s affecting corporate life as well. Here are five ways to use entrepreneurship to make your corporate job better.

1. Think of entrepreneurship as a safety net that allows you to demand more from your job. If you don’t like the job offers you have, you can leave. Start your own company. The history of the organization man is someone who is defined by whatever track the company puts him on. You don’t want to be that.

Today, you have the freedom to figure out who you are and what you want, even in the context of the company, because if you find out that you are not compatible, you can leave.

The freedom to leave gives you the freedom to truly examine who you are.

Chris Britt is chief executive of accounting firm Priviley. He founded the firm after a quick stint doing finance in the hotel industry and finding that he was not well suited for the environment. Britt is an example of the massive wave of young people who are testing big-company waters and then striking out on their own.

2. Think of intrapreneurship as a launching pad for who are waiting for the right idea. Seventy percent of young people say they eventually want to work for themselves. The problem is that only a fraction of those people have an idea for a company—or a friend with an idea for a company. So there are a lot of people in corporate America waiting for their moment, but thinking of themselves as entrepreneurs at heart.

These people are great at taking a project and making it their own. They create a project arena for themselves that have the feel of a small company within a large company, and then take ownership like it’s a start-up. Of course this is incredibly annoying to some old-school managers, but to a young person hellbent on entrepreneurship, starting something small within something big—which is what intrapreneurship is—often is the only way to make big company life palatable.

3. Get in a rotational program to learn a broad range of skills that many entrepreneurs learn as they go. Some of the most popular post-college routes today are management training programs at companies such as General Electric or Procter & Gamble, where superstar candidates get to test out the work in lots of departments in a company. Candidates often see these programs as stepping stones to running their own business, when the time is right, because as an entrepreneur you wear so many different hats.

4. Recognize that with no clear ladder to climb, you’re an entrepreneur even if you never leave corporate life. Even if you don’t want to launch a start-up, you still end up functioning like an entrepreneur in today’s new workplace. There is no long-term stability, so the way you create stability is with your skill set and your connections. You are the product, and you are the sales and marketing team for your product. On average, people today are changing jobs every two to five years, which means you must function like an entrepreneur nearly all of the time if you are going to bring in a steady paycheck.

5. Think of corporate jobs as a way to fund entrepreneurship. It used to be that you were either corporate or an entrepreneur. Today, people move in and out of big companies and start-ups, using the steady paycheck to fund the risky venture. This is what Britt did, using the money he earned from the hotel industry as the seed funding for Priviley. This model gives founders the benefit of not having to divert their attention to raising angel funding.

The self-funding model has spawned a generation of scrappy founders who use virtual tools and low-budget marketing. Priviley, for example, provides services to a wide range of other start-ups, creating a community of entrepreneurs that model these larger trends.

And, of course, the self-funding model also allows founders to reap benefits more quickly because they don’t have to share large pieces of their pie.

Priviley is doing so well, for example, that at this point Britt is able to take an afternoon off to go flying.

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Obama's victory in Iowa sheds light on today’s workplace

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My brother just started school at the University of Iowa, and this was his first caucus. He describes a room totally crammed full of young people: “It was basically all the students caucusing for Obama and the adults dispersing among the other candidates.”

In the end, in his Iowa City precinct, the students sat victorious at the Obama camp with 70% of the votes, while the caucuses for Edwards and Clinton were shouting over to the Kucinich supporters to abandon camp and come to them.

This is a metaphor for the workplace. The young people have, effectively, shifted the balance of power to themselves, and the older people squabble between each other, as if their power structures still matter.

Millennials are fundamentally conservative

The victories of Generation Y will not look like the Boston Tea Party or Kent State. They will look like this Iowa caucus: Gen Y, playing by the rules, and winning.

When Gen-Xers were this age, we were so overwhelmed with trying to earn a living that voting was the last thing on our minds. And when baby boomers were this age, they were protesting, and dodging the draft, and disrupting the establishment. So in a way, it’s remarkable how engaged, optimistic, and rule-abiding Millennials are during their twenties.

But as a group, Gen Y is fundamentally conservative, so it’s not surprising that they come out and vote in droves. Voting is a way for people who color-within-the-lines to instigate change. Voting is a fundamentally conservative way to tell the establishment to get out of the way.

Baby boomers are being forced out, in a non-disruptive way

And this is the exact same way that generation Y is telling baby boomers to get out of their way at work. Gen Y plays by the rules, meets expectations, and in the same step, pulls the rug out from under the people with power. How? By refusing to pay dues, by customizing their own career paths instead of lusting after a promotion, and by job hopping when learning curves get flat.

When USA Today wrote “Gen Y has already made its mark” the story was about entrepreneurship – Gen Y is ambitious, driven, and success-oriented, and since hierarchical structures of corporate life allow for so little mobility, young people are turning to entrepreneurship and are starting businesses at a blistering rate not seen among young people earlier.

This is not exactly the Civil Rights movement or grunge music. But Gen Y doesn’t need to rebel because, as I wrote in Time magazine, young people are already in the driver’s seat at the workplace. They can work within the established lines of business to get what they want, but they get it faster than we expect.

The gender divide is an antiquated view of the world

So many times I give a speech and explain to the room why women should not report sexual harassment. Invariably, the room divides. The millennials think the advice makes sense, the baby boomers are outraged.

Baby boomers perceive that there is a gender war going on at work, and women are fighting for equality: “The glass ceiling still exists!” But millennials are entering a workforce where women are making more than men in major cities, and the salary gap is essentially gone in most fields of business for this demographic. Nearly 50% of millennial girls were sexually harassed in their summer job, and by the time they are of voting age, sexual harassment is old news– it doesn’t scare them because they have plenty of power at work.

Early pundit posts declare that the results in Iowa hinged on the votes of young women. The Clinton campaign assumed women would vote for women. But young people did not make this election about gender, they made it about age. They want change. They want a chance to do things differently, within the established structures of power.

And this is true of the workplace as well. There are not women fighting for women in Generation Y. The gender divide ended when Gen X dads started giving up promotions to stay at home with their kids. Today there is a generational divide, and it’s happening at work and in politics and the balance of power has shifted to Generation Y.

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4 Ways to sidestep corporate hierarchy

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Most people stay at a company less than seven years. Most young people stay at a company less than two. So why are companies still set up for people who stay 40 years and climb the ladder? It makes no sense, and frustrates nearly all workers.

Well, all workers who aren’t at the top of the ladder, anyway. Those at the top surely think keeping the ladder there is a good idea, because what was the point of their climb if no one is climbing up after them?

Fortunately, there are ways to circumvent this way of thinking. You can’t change corporate structures and procedures, but you can sidestep them in a way that gets you more interesting work and higher pay without having to trudge up an anachronistic ladder. Here are four:

1. Get on a team.

“Teamwork” is one of the big corporate buzzwords of the last two decades. This is because companies with effective teams do better than companies without them.

The problem is that baby boomers never learned to play on teams. They’re the consummate competitors, born into a demographic in which there were always too many candidates for every position. Boomers are thus keen competitors, measuring each other up for everything. So the data that showed the importance of teams was followed quickly by a round of consulting companies specializing in teaching people how to be in multidisciplinary, non-hierarchical teams.

Then came Generation Y, the best team players in history. They did book reports in teams, went shopping in groups — they’re so team-oriented they even went to the prom in packs.

Put these two groups in a room and tell them to be a team, and you know what happens? The young people run circles around the older ones. The older workers try to establish a hierarchy while the younger ones are oblivious because they’re busy tossing out ideas.

A messy scene, for sure, but this is the way to get heard, and this is the way to shine outside the hierarchy: Get on a team, speak your mind, and implement your ideas — all while the baby boomers are worrying about hierarchy.

2. Job hop.

The rules for when you can be promoted, when your salary can increase, and when you’re eligible for training are all strict and senseless and essentially a waste of your time. Why should you wait for these things when you’re not staying with the company more than a few years anyway?

If your learning curve is flattening because your company can’t promote you to another level, take things into your own hands and go to another company. That is a fast way to give yourself a promotion without having to endure the duress of a corporate structure.

Job-hopping used to be the sign of a disloyal employee, but today we know better. In today’s workplace, frequent job change is a way to stay engaged in your work, and job-hopping among positions you’re good at actually builds your skill set and network much faster than if you stay in one job for a long time. This is why job hopping is a great tool — it can actually provide your career path with a stable, upward slope.

3. Start your own business.

You don’t need a lot of money to start your own company, because most of the tools to open up shop online are free. And in most cases, marketing is cheap and easy if you can establish a viral networking effect among your friends. This is why, in the short time that Generation Y has been in the workforce, they’ve already made a mark as a generation of entrepreneurs.

In addition to being fast and easy to do, starting a company lets you do interesting work you can control without having to wait to get to the top of a corporate ladder. Some people quit their jobs to start a company while others run theirs on the weekend. Increasingly, however, people are running a company from their corporate cubicle.

4. Be nice.

You know who gets promoted the fastest? The person your boss likes the most. So why not spend your time making sure you’re that person? Don’t dish out any excuses about how you won’t kiss up — a kiss-up is someone who tries to be nice but is instead insipid. I’m not recommending that you be insipid.

What I am recommending is that you genuinely try to figure out what your boss needs from you and how to give it to him. Determine how to make extra time in your day to help your boss out, and figure out what she needs help with before she realizes it. And then be there.

Office politics is often a way to sidestep corporate hierarchy, and the great news is that if you’re nice this will be right up your alley. Because office politics is about being nice. And how can you resist training yourself to be nice at work?


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How to recognize the good and the bad of team diversity

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Ryan and Ryan P found this great test by JT O’Donnell to find out personality type. Of course, we have each taken tons of personality tests, but what I really liked about JT’s test is that it was only twenty questions, and it revealed each of the three of us perfectly.

The test immediately explained why Ryan P is writing posts about how crazy it is to work with me, and I’m writing posts like the one about a rash on his upper thigh. Because really the test lays bare each of our very different ways of operating: Ryan P is an empathizer, I am an energizer and Ryan is a commander. Basically, Ryan P and I are sick of Ryan being a dictator, and now I know why. And Ryan is sick of Ryan P doing nothing, and now I see why – because a commander would never even notice the work of an empathizer.

Also, I have meetings with each of them every day trying to help everyone to get along, and now I know why: I am someone who is always optimistic and I want everyone else to be happy too. Great for blogging, difficult for corralling two ornery twentysomethings who keep calling their parents to get a second opinion on what I say.

When I was in grad school, let me just say right now that I never read a complete book for any class, but that didn’t stop me from having some favorites. And one of them was Between Men: English Literature and Male Homosexual Desire. I read this book for a course about.. um. I can’t actually remember. But each week in this course we watched a Hitchcock movie and then talked about deconstructionism and homosexuality.

So, anyway, this book I loved was about how in the history of English literature, men related to each other through women. Even if the men were not gay, they were often mediated by a woman. I remember thinking to myself that this is such a lame way to function and that only lame women would put up with this position in life. But look, here I am. And actually, it does not feel lame so much as useful.

I can see that I have had this position at work a lot. Men who are getting along at work can talk about football and go to strip clubs together. But men who are not getting along at work do well to put a woman in between them. Women seem to be natural mediators.

Right now is the time when people will start gearing up to write a comment to me about how gender is complicated, and the lines are not so clearly drawn anymore, and I am peddling stereotypes. This might all be true, but I get the temerity to talk about gender lines from danah boyd, a fellow at the Berkman Center for Internet and Society at Harvard, and my hero when it comes to philosophizing about identity. She found that in the blogosphere, in general, men link to men and women link to women. This is because gender stereotypes are generally right, and men and women are very different.

Okay. So back to my idea that I am the mediator. I don’t mind, because I’m good at it. And I don’t mind that Ryan P doesn’t churn out work really quickly, because he does a lot of things that Ryan and I are not great at, like having the patience to meet with people day after day for long and languishing lunches.

Each of us has strengths. But let’s talk a minute about weaknesses. We each have weaknesses, too. So why don’t we stop trying to work with them? Why not admit the stuff we are not great at and move on? I think a lot of people take a test like JT’s and then ignore the fact that the test reveals what we should NOT be doing as much as what we should be doing.

For example, I should not be making labored decisions where I gather tons of information. I’m not like that. I make fast, gut-level decisions. This is why I was terrible as an account manager in an ad agency: I had to justify every decision to my client and I kept thinking, “Whatever. It’s just my instinct. Please just shut up and trust me.”

You need to recognize what you are not great at, and stop doing it. It will help the people around you to get more work done, and it will help you to perform more like a star.

And for now, I have stopped asking Ryan to have empathy for anyone. And I have stopped asking Ryan P to analyze business models. The act of letting someone work in the area they are strong is such a gift, and of course I want to give that – I’m an energizer.

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Confidence boosters that work for me

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I woke up today with crust all over my left eye: Pinkeye. And on the way to the bathroom I stepped on edible gold-leaf dust for decorating cupcakes. And apparently sometime in the night the cat ate my son’s map of Wisconsin. And threw it up.

At times like this, I wish there was a morning-after type anti-depressant that you could take as sort of an immediate pick me up. I remembered my agent once told me that Advil works that way, once in a while. So I popped a couple.

They did not work. I put antibiotics in my eye and tossed on an old sweatshirt and jeans that are so big they fit like sweat pants. And I headed out the door to go work.

Then I turned around, and went back in the house.

I think people do startups for a variety of reasons. Sometimes we are not even sure what the reasons are until after we get started.

I moved to Wisconsin from New York City a year ago. It was a traumatic move, where we had to leave almost everything we own behind. And there was big culture shock in Madison when we got here.

The way I dealt with the trauma was blogging every day (therapeutic structure to a crazy life) in my pajamas (a nod to the fact that I was working alone and in fundamental disarray).

For the most part, when I had to show up to meet someone somewhere, I would pull things together a bit. Although when Ben Casnocha met me in Madison for breakfast his first comment was, “You don’t look like your photo.” And when I met Rebecca Thorman, she blogged about my ratty shoes.

So it was clear that I wasn’t holding things together that well. And when I convinced Ryan and Ryan to move to Madison to start a new business with me, I decided I had to go back to dressing up for work. Not suit and skirt or anything like that. But not pajamas. Not ratty sneakers.

And something happened – immediately I felt differently because I was back to getting dressed to go to work, because there were people I had to see every day. This moment converged nicely with the blossoming of my speaking career, which is one of the most lucrative career moves I’ve ever made, so I spent a lot of time at Bloomingdales, buying Joe’s Jeans and DKNY tops, to replace the expensive jeans and black tops that I bought six years ago, which was the last time I had to get dressed to go to work.

Then I started wearing makeup. Not a lot, but enough so that I could mark the difference between cleaning up cat puke and writing a blog post. And I felt a little more organized, a little more focused.

So today, I walked out of my house in ratty clothes and no makeup and I turned around. Because now I know that one way to feel better – maybe the most noninvasive anti-depressant of all – is to get dressed up to do work. The best days of work are those when I have the self-confidence to attack the hardest things on my to-do list with the most vigor. And one way to bolster self-confidence is to dress like someone who is self-confident.

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Underreported hazards in early-stage startups

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It’s Tuesday, which is usually the day for the Twentysomething column. But Ryan announced last week that he’s quitting as a columnist. I’m not surprised. He’s gone through a huge transition – quit his job in Washington, DC, started a company (with me), and moved to Madison, WI – two blocks from me.

It’s a small town, so it’s not like he was ever going to move ten miles from me – I mean, ten miles from me in almost any direction is a corn field. But it’s funny to me to have him so close.

I ended up going over to his house a lot in the first few days, to check in on him and Ryan P without saying so. Almost immediately my kids saw the situation as new neighbors. They refer to “The Ryans” and when we went apple picking, the kids thought of the Ryans immediately.

So we brought over a bag of apples. The kids did not really understand the concept of red all over, so the apples were not ripe. And I couldn’t tell if the Ryans noticed, but they were very grateful, because it was when the Ryans first got here. When they were grateful in general.

Now it’s been six weeks. And Ryan is thinking that maybe his new blog will be about how crazy life is working with me.

I asked for examples. He gave the one about how I invited the Ryans over for dinner. I picked a night when my husband wasn’t home because there is too much tension between us to put the Ryans through it as well. I also picked the night my kids wanted an impromptu Halloween party.

So there was our nanny, who is actually a guy who is a college sophomore taking a year off to establish residency so his University of Wisconsin tuition goes down. And there were fake eyeballs and pumpkin glitter. And it was like a frat party with toddlers instead of girls. To me, that is the weird part. To Ryan, it’s weird that I didn’t cook.

“You ordered burritos!” he says.

I tell him it was better than Batman spaghetti O’s.

He shakes his head in disbelief. He thinks I’m eccentric, which I probably am, but I think this is not the best example.

Other mentioned eccentricities: I have been working out of a coffee shop for a year. Ryan can’t believe it.

The women who own the shop are probably my best friends in Madison – I see them every day. In the summer they noticed me showing up in my obsessive long sleeves and long pants so the sun doesn’t get me, and in the winter they saw me fighting with my husband at the curb when he drops me off. I always imagined I’d have some great post about how the owners let me do radio interviews from their land line (radio producers hate cell phones) and they buy Lean Cuisines especially for me so I don’t have to eat their muffins for lunch. It was a great setup.

Til the Ryans came.

They said everyone in the coffee shop is annoyed by my talking on the phone, which is probably true. So we went to their apartment. Like it’s not eccentric for me to be spending my days in the apartment of two twentysomething guys.

But as we were leaving the coffee shop for good, new art was going up on the wall: Phil Porter. I loved the art. Ryan hated it. So I gave a lecture right before we left, about why good art forces you to see things differently and the Ryans only like art with naked women on it because it doesn’t challenge anything that’s already in their mind. (Yes, they have a painting of a naked woman in the apartment. And yes, it sucks.) Ryan called me a snob.

He is a snob, too. For example, Ryan does not wear black shoes with khaki pants. I have never heard of this rule, but I confess to immediately putting my khakis aside until I got brown shoes, just in case he’s right.

Maybe we get along because we’re both snobs. Or maybe our excessive judgementalism, which probably makes for good blog posts, gives us a sort of detente.

I went out to dinner with Ryan P’s parents. I can’t ever recall going out to dinner with a co-worker’s parent. But here’s a tip. You know how when you go out to dinner with a boyfriend and his parents, you end up liking him even more? I am not sure why, but this always happens. And I have to say that the same thing happened in this situation: I liked him better. He has the same odd speech cadence as his dad, the same bright smile as his mom. It was nice to see.

Nice as long as I could squash my jealously; I don’t recall a time when my parents drove across state lines to dote on me.

Now I wake the Ryans in the morning. They are not morning people. I know you expected this post to be about starting a company, and this sort of is, because the first part of starting a company is learning boundaries.

A startup is inherently intense. Founders are so dependent on each other, and there are almost always only two or three people involved. I have two close friends who have startups: The woman’s company is three women and the man’s company is three men. I think that most startups with a both genders involve sex, and/or marriage, and those that don’t require navigation of a difficult and dicey new language of boundaries, (which I have touched on before).

There is a lot written about work spouses. That is, people who feel like they spend so much time together that they’re married. But they are not. The context for these relationships is usually a big company, where there is safety in numbers, and there are office conventions to keep boundaries in place.

A startup usually has none of these safeguards, and a startup usually entails longer hours at the office. Maybe this is why so many startup teams are all men or all women, but not mixed. And maybe this is why my friend, who has a startup team of three guys and will not consider hiring a woman as the fourth, is making a smart decision.

Meanwhile, we continue to draw boundaries at our own startup. For example:

Ryan P comes to the dining room table that is also our office and says, I have a rash.

I start thinking about my kids.

Where is it?

On my leg.

Can I see?

No.

Why not?

It’s too early. Ask in twenty minutes.

Tyeptyeptyep type

Can I see it ?

No.

While Ryan P is typing a blog post about how he would rather work for man than a woman (yes really: he says men bond better with men) I look under the table. I don’t see the rash, but the light is not that good.

What are you doing?

I need to see it.

It’s not on my leg. It’s on my groin.

And this is the moment. The boundary moment. I look away because some boundaries are clear. But I also think of my kids – some boundaries are murky — and I navigate the best way I know how as CEO of a startup:

Does it itch?

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Twentysomething: Preparing for life without health insurance

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By Ryan Healy – About a month ago, my brother, Dan, was in the hospital. Originally, the doctors told him he had a small cut, and he should use some Neosporin to prevent infection. A couple of days later, they told him he had a staph infection. Staph infections are bad, but for my brother they are especially bad.

Dan was born with congenital heart disease, and any type of infection could be life-threatening. My parents hopped in the car and made the 10-hour drive from Connecticut to Columbus, OH. According to my parents, the three days in the Columbus hospital were like a bad episode of House. Nobody knew exactly what was wrong. The infectious disease doctors were in and out of his room every day.

Eventually, Dan was released from the hospital. The antibiotics killed the infection before it could spread. Regardless, the whole experience was incredibly scary for all of us. And it really made me nervous to ditch my corporate job with benefits to work at a startup with no health insurance.

But my mind was made up and sticking with my job was not an option. So the first thing I did was schedule a physical. I crossed my fingers and went into the doctors office, hoping there was nothing wrong. At first glance I was fine.

The doctor than asked if I wanted to have some blood tests done to test for HIV, hepatitis and whatever else they test. It sounded like a good idea at the time, so I strapped in and gave some blood. I regretted the decision immediately. If I tested positive for anything, private health insurance would go from expensive to completely unaffordable.

Luckily, everything turned out fine. But you know there is something wrong with the health care system when putting off being tested for a life-threatening disease for a few months is a “smart” financial option.

After the blood tests, the doctor asked if I wanted to have my cholesterol checked. Despite my mother constantly reminding me of my family’s high cholesterol, I declined for fear of an unusually high test and in turn, higher future health care costs. Finally, before leaving, I requested a tetanus shot even though I was 99 percent positive that it wasn’t necessary.

Buying fitted running shoes was next on my list. I try to run four to five times per week and my legs were beginning to bother me. It was definitely time for a new pair of shoes. But a week before you quit your job to pursue something with no immediate stream of income is not a great time to drop $100 on shoes.

After some thought, I realized that $100 now could be the only thing saving me from a stress fracture or another common running injury, which could end up saving me thousands in future uninsured medical costs.

After doing everything I could think of to prepare for life without insurance, a buddy of mine told me about a program that covers 80 percent of all medical expenses after a $500 deductible for “healthy” 23-year-old guys. It’s certainly not free, but all things considered, it’s a really good deal. (I plan to actually purchase the plan this week, so if anyone knows of a better deal, please let me know!)

Still, I’m lucky that I don’t have any preexisting medical conditions. I’m lucky I am not on any prescription drugs and I’m lucky to have tested negative for any diseases. Not everyone will be able to get such a good deal, and that’s a big problem.

My brother has full intentions of continuing his own business and starting companies for years to come, but he is going to have to take some major risks once he is off of my parents’ insurance policy.

Whether this means purchasing a catastrophic plan, borrowing money or completely going off of insurance, he will figure it out and I will help however I can. Because dropping everything to chase a dream might sound risky, but in my book, working a dead-end job for fear of not having health coverage is much riskier.

Ryan Healy’s blog is Employee Evolution.

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