Bullish: How To Go To There (Your First Steps To Making It Big)

Welcome to Bullish! This column previously appeared weekly on our sister site The Gloss (here’s an archive). The column will focus on helping women get and make the most of their careers.

In response to last week’s post, Bullish: Are You Thinking Too Small?, a reader commented:

“Reading this is like watching a movie where the character is initially struggling and then they get to success through a swift montage of blurred clips, when all you want the movie to do is slow down to show e x a c t l y how they got from A to B. I am so ready to think big but how do I go from graduate to successful business woman! What is the first step??”

So, here is a column, titled of course “Why We Want To Go To There” in honor of Tina Fey.

Obviously, there are a lot of ways to get from A to B, if I am correct in understanding that “A” is a young adult in a less than ideal situation, and “B” is a successful business woman, the journey between which is now sort of sounding like an SAT problem that would require you to use the distance formula, which most people have understandably forgotten but that, if employed here, would undoubtedly yield an answer that most of us would regard as “too fucking long.” I totally get that.

In any case, an exhaustive treatment of “how to be a successful business woman” is not possible in lady-blog format, but I can talk about the way I did it — and what would’ve been easier than that.

The way I did things, I think, has been greatly a function of a massive knowledge gap between growing up being told “You can do anything you set your mind to!” and actually knowing how to build competence doing practical things. (“Girls can do anything boys can do!” “Okay, how?” “I don’t know! But BELIEVE IN YOURSELF!”)

I work in education — when I’m not giving business advice, I write educational books and help people get into college and business school, and incidentally, I don’t think you should take business advice from anyone whose only business is giving business advice, because that is a big pointy pyramid scheme — and I am constantly confronted with the fact that Americans are obsessed with the idea of “teaching students how to think”. We really hate the idea that anyone should just be taught to memorize and “spit back” facts. As though facts are somehow not useful, true, or important in critical thinking (it’s kind of hard to think critically when you don’t have much to think about, and incidentally it’s also hard to learn about many topics in math if you didn’t memorize your times tables twenty years ago).

In a graduate level education class, I was the only person to speak up when a teaching technique we were learning about didn’t actually seem like it would help anyone learn anything. I said, “Isn’t that a lot of classroom time to spend on something that doesn’t really involve any knowledge?” One of my classmates said, “But it really helps their self-esteem!” I said, “Self-esteem isn’t the same as learning.” And … crickets chirping. I think this might now be my main professional philosophy: Self-esteem isn’t the same as learning.

It’s this gap between self-esteem and learning that led, for me, to so much stabbing in the dark. I was the “CEO” of my own internet marketing company, and then tried to be a model. In that order. Which makes no sense. A partial list of other things I tried: standup comedy, being a monologue artist, producing comedy shows, fiction writing, selling sex toys online, podcasting, running a newspaper syndication service for LGBT newspapers, renting out rooms for cash, selling my eggs, taking donations for blogging, editing manuscripts for educational publishers, being a Director of Marketing for a startup, founding an internet marketing conference and selling sponsorships, selling “I Love Jet Noise” bumper stickers to people in my hometown who support the local military base, pitching a reality TV show about nerds, and offering spelling bees for corporate events.

I think the bizarre size and variety of that list is more interesting than the individual things on it. (See Bullish: How To Do Many Different Things At Once) I don’t mind letting nine out of 10 of my projects fail so I can find the one good one. Many things work this way — venture capital, book publishing. Let your babies die. I am very skeptical of advice to “do what you love.” Sometimes what you love doesn’t make money, and then you are poor and what you love is kind of ruined by the whole experience. You can love (or learn to love) hundreds of ideas in your lifetime. You only need a few of them to work.

Also, I think it’s important to realize that failing usually doesn’t make you look bad in front of other people because 1) most people, if they notice, are impressed that you did something in the first place, 2) but if you have a lot going on, no one will notice, and 3) other people don’t think about you that much anyway.

I wrote about some of my failures in Bullish: Three Career F*ckups I Made So You Don’t Have To. So let me talk about some things that were turning points for me and which worked very well. Obviously, not everything applies to everyone. But maybe this will help!

Pitching constantly

In Bullish: Personality Qualities More Important Than Anything on Your Resume, I talked about the very important skill of pitching. Here I’m talking mostly about pitching freelance projects, but this could also apply to pitching yourself as an intern (even when no internship is advertised) or as a volunteer to build skills in a field you’d like to break into.

Having grown up socially awkward, I relish the fact that I can now basically pitch things entirely over email. Things I have recently pitched: A series of funny commercials for the classic philosophy texts sold by an educational publisher. A revenue sharing arrangement for an SAT book I would write. Blog sponsorship from online dictionary companies. Oh, and I got an email from a national magazine asking me for a funny story about learning to do standup. I don’t really have a story about that, and I’m not trying to promote myself as a standup comedian these days. I wrote back and said, “Thanks for thinking of me! You may not know this, but I actually do [all this other stuff]. Would you be interested in a brain training column?”

What’s the worst that could happen? 1) No response, 2) An email that says “No thanks.” I suppose someone could email you back and say “You are an idiot,” but that’s really never happened to me. Most people are pretty polite when responding from their work email addresses.

I’m really not a fan of the Glengarry Glen Ross school of sales, wherein you persuade people to buy things they don’t want. I prefer to cast a wider net and work with people who are actually enthusiastic about doing business with me.

If I had a big-time business idea I wanted to pursue full-time, I’d get my business plan straight and contact Ashton Kutcher on Twitter. According to the New York Times, he’s a savvy investor in startups. I’m pretty sure you wouldn’t get Punk’d.

Pitching is free and easy. You can do it multiple times per day. If you pitch more things than you could possibly ever do if everyone said yes, then it won’t bother you at all when not everyone says yes.

Never competing directly

I don’t apply to things. If there’s already an application process and an organized competition, then too many other unimaginative people will be competing against you. Do things that don’t have applications.

I mentioned earlier the idea of pitching yourself as an intern to a company that isn’t even offering an internship. (Don’t make the email about you. Make it about the company and exactly what you’ve noticed and intend to do for them during your brief but productive tenure.) Amazingly, you have a better chance of winning an internship that doesn’t actually exist than you have of getting a position that’s already made its way to Monster.com.

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