How to be more interesting to other people

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For a while, I was a visual artist. Well, sort of. I mean, I made money from it. But as you may know, I am a big advocate of specializing, and I realized that I had a better chance of being outstanding in my field by focusing on writing instead of visual art.

But I did learn some lessons from my visual art mentors, and one really cool thing someone taught me is that the color I choose is most interesting where it intersects with another color. Just knowing the right color to use is not the clever, interesting thing. Rather, interesting is when I am unsure what the two colors will do when they interact. (Here’s a great set of paintings that illustrate this idea.)

The same is true for writing. The interesting part of writing is not the part of the piece where you know exactly where it’s going. The interesting part is when you get to an unplanned moment in a paragraph and you surprise yourself by what you write next. It’s the moment of uncertainty, when you have to look inside yourself to keep going, and pull out something you didn’t know you had before.

When I taught writing at Boston University, it took most of the semester to get students to get to that moment. Most people are scared to get there.

That’s why most people do not appear to be as interesting as they really are.

We each have spots in our lives where two colors are coming together and we’re not sure what will happen. That’s the part we should talk about when we talk about ourselves. If you limit the conversation, discussing only what you are certain about, then there’s no chance to stand on equal footing with your conversation partner. You stand on equal footing when you both reveal your struggles with what you don’t know yet, and the conversation can contribute to the answer.

A while back I wrote about Moira Gunn, and how she is good at interviewing people because she can find what’s interesting about them. She interviews scientists, and she is a pro at finding the quirky, unexpected moment within the topic of their science.

You can do this with any subject. I do it with careers. Every week, for my column in the Boston Globe, I interview someone about their career. The beginning of the conversation is always the part they expect—where they tell me what they know about themselves and their career. There is not room for a real conversation. I just take notes.

And then I don’t use them. Because then I try to ask questions to get to what they don’t know. What are they trying to figure out? And we have a conversation about how people do that. And that is the part I use. Because that is the part that is interesting.

So look, interesting does not come from greatness. Interesting comes from conflict. Tolstoy opens Anna Karenina with the line, “Happy families are all alike; every unhappy family is unhappy in its own way.” This is true of everything—not just families. So talk with people about the issues and problems you’re struggling with. That is how to be interesting. You don’t have to describe your life as if it were all struggle, with all the drama of Russian literature. But find that small moment when two of your own colors collide, and point it out to make interesting conversation.

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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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Barack Obama, the female vote, and why this matters at work

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Did you see the rally for Obama in Los Angeles last Sunday? It rocked my world: Michelle Obama, Oprah Winfrey, and California First Lady Maria Shriver talking to a packed stadium at UCLA. (Watch the video here.)

For one thing, Michelle Obama is a great speaker in her own right and she is teaching us how to talk about race and women in new ways that only a non-candidate could do. But also, Maria Shriver made an unscheduled appearance to endorse Barack Obama even though her husband, Governor Schwarzenegger, had just endorsed John McCain.

It’s a great picture of how much power women have—women who are so confident in their power that they know they can throw it behind a man to get what they want out of the world.

Some of my harshest critics say that I’m “bad for feminism.” They say I give bad advice to women because I don’t see work as a place for women to fight against men to get equality.

Indeed, I generally see work as a place where women have equal footing with men. And personally, I see work as a place where men have mentored me the whole way. I would be nowhere without all the men who have helped me.

Sure, I know I’m still at a disadvantage because I’m a woman in the workplace. I was reminded of it just the other day when my business partner Ryan and I met with a potential investor. The guy passed on girl-related small-talk and spent twenty minutes with Ryan talking football.

And the same is true for black people in this country. Obama’s success doesn’t mean that things are suddenly great for black people everywhere. But Obama’s success suggests that we can stop requiring everyone to divide everything by black and white.

And that makes me also think we can stop dividing things by men and women. I don’t need to vote for Hilary Clinton to show that I support women. I support women by looking ahead to the next generation. My generation—which is Obama’s generation—does not need to fight the women’s fight anymore. Other people did it for us.

So thank you, feminists, but we’re moving on. And to see all those women in California—those women who got their power on their own, using it to support a man—that sends chills up my spine, because I relate to that. I want to stand with the men and be on their team, and the only way to do that is to earn power myself and share it, with whoever deserves it, man or woman.

Watch for this in politics, and do it yourself at work. You can get stronger at work by breaking free of the divide that some people assume is there. We don’t owe it to the last generation to keep fighting their fights. We owe it to the last generation to thank them, and then move on.

We have our own, more relevant fights today. Like how to work to live instead of live to work, how to stop being a slave to money, and how to make time for our families. These are issues for men as much as women. We are in those fights together.

And that’s what I saw happening in Los Angeles on Sunday. I saw a centerpiece of the new fight: For change. Whoo hooo!

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