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

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.

Assuming that anything could be learned, and then going into The Cave to do it

In 2007, I learned that the top company in my field paid the world’s best GMAT teachers very, very well. I had many important qualifications (classroom experience, public speaking skills), and I’ve previously written (Bullish: How To Do Many Different Things At Once) about how my standup comedy experience has been far more valuable to me as an add-on to other services than it ever was for its own sake, which was also the case here — everyone loves the idea of being taught otherwise dry material by a comedian. But then there was the GMAT itself. In short, I spent about seven months of unpaid study and training time teaching myself to ace the GMAT, and weeping bitterly when, after the first five months, I took the test and scored 20 points below the goal. I probably lost $10,000 in income that year, taking time to teach myself a skill that I knew would pay off. I have since made back that investment many times over.

While there are many paths from A to B, as it were, I often note that extroverts have some serious disadvantages. Surely, extroverts find networking much easier! But I feel as though it must be a very shallow networking. Someone who likes everybody flatters no one with his attention. People who always need to be around people lack the ability to “go into the cave” and build the skills needed to leap ahead. Be comfortable with solitude. Blithe, lazy friends you lose along the way will later be replaced with new friends who have also catapulted themselves ahead through clever and focused effort.

Cultivating multiple income streams

I am a broken record about multiple income streams. You need to have your money coming from more than one place so that no one can exploit you, so you have security, and so you don’t need your employers more than they need you. Having multiple income streams creates a healthy balance of power.

I’m not suggesting that you have to run three totally separate careers at once or anything of the sort. I believe in exploiting efficiencies. If you already sell something to a group of people, is there something else you can sell to those same people? Or if you’ve already set yourself up with a web designer and a telephone answering service for one business, isn’t it now fantastically easier and cheaper to do it again for a second business?

I also believe in the principle of low-hanging fruit. A small business might bring in $10,000 a year without having to advertise, and $50,000 a year if you really work it. Or … you could run five of those $10,000 a year businesses that dont require much effort. At the simplest level, I discovered when I first started SAT tutoring that I didn’t have enough business to do it full-time, but that doing it about half-time was pretty easy. I also discovered that I would never be a full-time model, but doing it half-time was pretty easy. Once I stopped hustling on both fronts and just took the work that came in, I was able to direct my mojo to the next income stream.

Selling Services to Rich People

This is just the easiest way to get started making money. Obviously, there are many other ways to make money. But I think this is the easiest one.

Rich people pay other people to do everything for them. Not just things like personal training and getting their kids into college. Everything. Including many normal, human activities that anyone could do. Rich people just don’t feel like it, or else they are so busy making all that money that it makes sense to outsource the basic tasks of life. Here are some positions held by people I know, serving the rich:

Personal trainer for kids (takes kids to the park, where they toss a ball around).

Overqualified handyman paid to hang pictures on walls.

Guitar teacher to three year olds (um, their hands are too small to play the guitar).

Stretcher. A person who helps people stretch. I am not joking.

Rich people also order meal delivery services, hire carpet cleaning services even for small Oriental rugs, pay extra for babysitters who teach their kids foreign languages, and teach their babies yoga.

Here are some more ideas, just off the top of my head:

Babysitter who specializes in self-expression through music (or French, or vocabulary)

Personal coach for girls and sports (offer to help get people’s daughters into sports, which is an excellent way to prevent future eating disorders and self-esteem issues)

Auto detailing for ladies, by ladies (spritz people’s cars with essential oils when you’re done!)

Errand running service (if you went to a prestigious college, advertise this)

Memoir ghostwriter (lots of people want to write their memoirs but are lazy)

Cat hair removal service (clean furniture and floors and never indicate that what you are doing is ridiculous)

Of course, to get started, you’ll have to meet some rich people. So, never turn down an opportunity to meet rich people. Taking a low-paying job that puts you in contact with many wealthy people might be worthwhile. Volunteering or reconnecting with family friends might also do the trick. Once you meet the first few clients, do a good job and they’ll pass your name around. Many wealthy people have much more money than time. They may or may not be price sensitive, but they are always very concerned about trustworthiness. If you seem professional, friendly, and normal — and as though you understand them — you’ve just started a business.

That said, it always helps to get the basics out of the way first; being able to pay your bills is helpful in creating the mental space to think big. This might mean pursuing particularly cheap rent, taking a temp job, or otherwise sucking it up with some line of work you don’t really want to do but which (hopefully) isn’t too exhausting. (You might enjoy Bullish: How to Make an Extra $100 a Month).

Financial basics are important. I’ve never pursued nor even been particularly attracted to wealthy guys, but once I started making a real income, I dated completely differently. I stopped trying to get men to like me and instead scrutinized whether I liked them. I realized that my precarious finances had been making me feel vulnerable without my realizing that that was the reason. Making money is deeply feminist.

I do talk a lot about entrepreneurship, and I want to emphasize — everyone needs to be an entrepreneur, even if just a little. Even for employees, having a side business or serious interest can create novel opportunities — you could end up doing business with your company as a peer rather than as an employee, or you insinuate yourself into leading a new project at your company due to your diverse experiences. You could pitch something within your company — starting a new division, or marketing the company’s product to a new group of people you know something about. Doing two things at once for five years is in some ways equivalent to having had a ten-year career.

So, whatever your goals, I hope you’ve found something here that will give you your next move from A to B. You can get started now. You don’t have to play three moves ahead. Just take one step, and then the next.

originally published on TheGrindstone