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There’s still a part of me that remains from my days of living beyond the law, and that’s my desire to just mess with things. Life is unwritten, like a great big experiment. Why not see how long the red string of my imaginary kite can get? And why not let it whisk me up into the sky with it when my dreams start to become reality? For that, I think it’s worth putting up with making some compromises, and even playing by (some of) the rules.

PORTRAIT OF A #GIRLBOSS:

Alexi Wasser, IMBOYCRAZY.com (@imboycrazy)

I started my blog, I’m Boy Crazy, in 2008. It’s a mix of funny self-help stuff and hyper-personal accounts of my love, life, sex, dating, and relationship experiences—all different things that convey the voice and plight of the modern single girl who wants a great life, thinks too much, and feels a lot of feelings. As a result of starting my site, I’ve sold several shows to Showtime, E!, and Amazon. I sell merchandise on my site, have a weekly call-in advice show, contribute to magazines, speak at schools, and basically serve as the big sis you’ve always wanted but never had.

I had no idea I’d end up doing what I’m doing now. I always knew I loved writing and making people laugh. But I went from saying “I want to be a writer” to “I wanna be a model” (I’m not super-ugly and I’m very tall, I swear!) or “I wanna be an actress.” I did all those things, but writing continues to be what makes me happiest. Whether it’s a book, movie, blog entry, or TV show, I have creative control and it’s way cooler to be a writer than to be an actor saying the writer’s words.

I learned at a young age that people were happy when I asked them about themselves, and I listened and retained the things they told me. I found that by sharing my personal experiences, like through my blog, we’re not alone—that the most shameful, personal, specific things you’re going through are actually universal. You can laugh about it. I want to make a contribution that matters, and I want to be as vulnerable and raw as possible so other people feel less alone. I want to make people happy or make them laugh—even if it’s at my own expense.

I’m still trying to figure out how to balance work and a personal life. When you’re freelance like I am, if you don’t build structure for yourself, you feel like you always have to be working and it’s exhausting. I think this is a constant struggle for every freelance career girl. Make a schedule for yourself that incorporates time for phone calls to catch up with your annoying family and friends, sex with your boyfriend, exercise, dinners, therapy, parties, texting, social networking, mani-pedis, shopping, and the work that’s gonna get you paid to maintain the lifestyle you so desire! Create boundaries and structure! You have to be your own parent!

As for finding a guy who will support you on your #GIRLBOSS quest, I’ve accidentally dated variations of boneheads, such as the guy who appears secure and confident at the beginning of our relationship, but ends up being completely threatened by and uncomfortable with my personality, career, and how flirty or open my persona is. Another guy blatantly ignored what I do. He took no interest in it at all. I can only date a man I respect, am fascinated by, and consider interesting. If he can’t do the same for me, we have a problem.

Figure out what you love doing and don’t suck at, then try to figure out how to make a living doing that! Don’t be scared. We’re all going to die, it’s just a question of when and how—so be brave! You will never regret trying to fulfill your dream! Don’t get caught up in hanging out and drinking or partying. Celebrate when there’s something to celebrate. Take pride in what you do. Don’t do sloppy work. Be the best. Have something original and special to offer that makes people’s lives better. Don’t have sex with everyone in the world you work in. It’s a small world. Good luck.

“When you treat your possesions as emblems of your hard work, they inherit a meaning that transcends the objects themselves.”

5

Money Looks Better in the Bank Than on Your Feet

There is no dignity quite so impressive, and no independence quite so important, as living within your means.

—Calvin Coolidge

I never set out to be rich. I had no idea my company was worth anything until venture capitalists started knocking on my door. “Your company is worth hundreds of millions of dollars and you own this much of it, and so now you yourself are worth this much.” It was shocking how fast it all happened. Nasty Gal went from doing $150,000 a year to doing $150,000 a day, and now we do $150,000 over lunch. I think that part of the reason Nasty Gal has been so successful is because my goals were never financial ones. I believed in what I was doing, and fortunately other people believed in it as well. I cared as much about the process as I did about the results. No decision was too small. Whether it was the word choice in a product description or the expression on a model’s face, I treated everything with the utmost care. At the time this was just because, like I said before, I’m the kind of person who pays attention to something as small as a crooked shipping label. In hindsight, I see that it’s those small things that can make or break a business.

My adopted political ideals had let me approach money with an elevated level of distaste. I saw it as a materialistic pursuit for materialistic people, but what I have realized over time is that in many ways, money spells freedom. If you learn to control your finances, you won’t find yourself stuck in jobs, places, or relationships that you hate just because you can’t afford to go elsewhere. Learning how to manage your money is one of the most important things you’ll ever do. Being in a good spot financially can open up so many doors. Being in a bad spot can slam them in your face. And being broke gets old, so start making smart decisions now to avoid paying for stupid ones later.

Credit Cards Blow

I wasn’t always stealing stuff. Sometimes I went the conventional route when I wanted something; I went into a store and, you know, paid for it. And it was on one of these crazy such occasions that I managed to make a legitimate purchase and ruin my credit in one fell swoop.

I was nineteen and at the mall buying a bra at Victoria’s Secret because while it’s possible to dumpster-dive for food and trawl the Salvation Army for clothes, even a freegan knows to invest in new underwear. At the register, the salesperson asked me if I wanted to sign up for a Victoria’s Secret card and I said yes. I thought I was signing up for a rewards program, where I’d earn points toward a free bra or something. What I failed to realize at that moment was that I had unknowingly been bestowed my very first credit card. Because I moved so much, I rarely had a steady address, causing bills to miss me as I jumped from state to state. By the time my $28 lingerie charge caught up with me, my credit was wrecked, and I had learned the hard way that you can ruin your credit in one seemingly responsible afternoon, but rebuilding it takes years.

When people write about Nasty Gal, the articles almost always note how I built the company with no debt, because that’s a pretty unusual feat in the business world. And yes, once I finally got a job and started working for my money, I was extremely responsible with it. But what these stories usually leave out is that it wasn’t by choice that I built the company debt-free. It simply wasn’t an option, because no one would even give me a credit card, never mind a business loan. This was frustrating; however, it was also a blessing in disguise. As I had no financial cushion to support me while the business ramped up, I had to bust my ass and make it profitable from day one. In the end, this meant that I grew Nasty Gal to $28 million in revenue without borrowing a dime.