Bullish: Three Tips for Pitching Your Dream Gig (And Why You Need To Pitch)


When I was a kid, I remember being outraged at the introduction of Double-Stuf Oreos (yes, that’s really how the product name is spelled).

Why was I full of rage? Because I was sure I had invented Double-Stuf Oreos myself. I mean, I had been disassembling Oreos, halfheartedly eating the excess black cookie parts, and gloriously reassembling one massive dual-creme Oreo for YEARS. Why had the Oreo cookie company not called me about this?!

One reason is probably that I was five. Another reason is that, according to the Internet, Double-Stuf Oreos came out in 1975, before I was born; I guess we just didn’t get them in our local grocery store until years later.

Another reason is that no one ever comes to your house to prompt you for your excellent ideas. You have to find the right people and pitch them.

Here’s a reader question:

First I must thank you for your wonderful articles (all the way from little old New Zealand). I understand you are a very busy gentlewoman, but I desperately need a few pointers about pitching.

The basic run down: I have a friend who runs a handful of successful fashion and beauty websites. I already do regular freelance work for him, but I would love a permanent position in the company. He has spoken in the past of the possibility of this, so I feel it’s just about broaching the topic properly and pitching myself in such a way that he can’t possibly say no.

I’m bright and extremely knowledgeable in my field (beauty). I write great content and I am willing to contribute in any way possible (helping with advertising sales etc.). We already have a great business relationship, I just need to figure out how to sell my talents to him in the most Bullish way possible. Do I suggest a business meeting over lunch to pitch? Or send him a fabulous email?


In Bullish: Personality Qualities That Are Way More Important Than Anything on Your Resume — nearly two years ago — I first started nagging lady readers to pitch ballsily and often:

In the freelance world, the value of pitching is obvious. You pitch an idea, you get the gig, you deliver on schedule, you pitch again. You should be great at pitching. You should have enough good ideas that you can pitch several things to different people in a single day and not get hung up waiting for replies, because you know you’ll have more good ideas where those came from.



However, pitching is extremely important even in traditional jobs. Here’s what I mean: individuals move faster than companies. Or, at least, they should. If you’re waiting for a job opening to be posted on a job site, that company’s need has gotten so acute that the company has already gone through a dozen or more slow, bureaucratic moves to try to fix their problem. At that point, it’s resume versus resume. You want to get in there first. Even a shitty entry-level job gives you that opportunity. If you answer the phone at the front desk, you will learn enough to be able to spot problems and suggest ways to fix them — ideally, ways that involve a new, expanded role for you. If you don’t already have a foot in the door, plenty of people have made jobs for themselves by tracking down the president of a small company and saying (tactfully), “I know how to market your product better,” or “I can rewrite your web copy so you’ll sell more of your product,” or “This is great — I can help you take it to the Spanish-speaking market.”

Whether you are a student, an employee, an unemployed person, or an entrepreneur, you are fortunate enough to live in the age of the internet: pitching can be as easy as sending an email to someone whose email address is on the internet. You can pitch 10 good ideas in a day. You can pitch in the middle of the night. Try getting something published somewhere — if you’re not expecting to get paid (yet), this should be easy. If you’ve never been published anywhere, that can actually give you more credibility, provided that you are writing about something you do know: even professional science writers are trumped by actual scientists who stop doing science long enough to pen an op-ed. If the guy who cuts my hair wanted to comment on celebs’ new looks, I’d be way into it. When people who aren’t writers bother to get something published, it’s usually because they really have something to say. (Of course, not all pitching is about writing. Pitch yourself as a hitting coach for the local Little League team, I don’t care. But it’s easy to open doors when you’re creating those doors yourself).

(See also Bullish: Be A Badass, Not An Intern.)

In the question writer’s case, she’s got all the “in” she needs. She already does great freelance work, and the boss-man has already spoken about the possibility of a full-time position for her.

Is a lunch better than an email? Probably, since it provides the opportunity for more back-and-forth (important to tips #1 and #3 below). But we’ll talk a bit about emails as well, since a lot of us need to pitch complete strangers from time to time.

Here are three pitching tips that apply to the question writer’s situation, but also to the pitching needs of freelancers and employees alike.

1. Get the person you’re pitching to craft your pitch for you.

You clever devil, you!

No, seriously.

When I ran a dotcom (see Bullish: Three Career F*ckups I Made So You Don’t Have To and Bullish: To Give Up or Not to Give Up), I had a really dysfunctional method of selling.

I would have a meeting. I usually do really well in those! I would wow everyone with my technical knowledge, or else I would at least intrigue the decisionmaker (What does this tiny young person have to offer me? Maybe she’s a magical child prodigy!) I would take notes on what the client wanted. I would assure him or her that we could totally do all those things. I would promise a proposal. Like some snivelling little bitch-coward. And then I would go back to my office and procrastinate over the proposal until the client thought I’d forgotten about it. And then I’d send the proposal and procrastinate about following up, because, hey, that’s a really tense situation.

Why not just close the deal on the spot? I didn’t even try. Why? Because someone might say no to my face. That’s a stupid fucking reason.

For some reason, women are rarely called “cowards.” I’m starting, with myself. And anyone who acts like 23-year-old me. Don’t be a fucking coward.

Ideally, I would have tried to close the deal on the spot. As in, “What you’re talking about is a $6,000 job. We do stuff like this all the time, and we’ve got the bandwidth to start this on Monday. Does that sound right to you?”

If so, I’d have pulled out my laptop, made some quick bullet points of what we just talked about, written “$6,000” on the document (half upfront or whatever), and printed it out or emailed it ASAP. If he needed to talk it over with someone else, I’d have him look it over before I emailed or printed it: “Did I get everything you wanted? This is the proposal you want?” Get him to own it.

If not, I’d have asked some questions, and — if the dude was reasonable (not, “I thought you could do this for the publicity while paying your rent with fairy dust and butterfly breaths”) — I’d get to the point of pulling out my laptop and getting him to work out the bullet points together with me.

Instead, I had a typical effete, overeducated response to proposal-writing: I turned them into term papers. No need. If the rapport and relationship are there, the proposal is a formality. A wedding ring for people who’ve already decided to get married.


For the question-writer: I’d ask boss-man what, ideally, he would like from you in a full-time position, and offer to write your own job description and send it to him for approval. If he agrees to that, it’ll be hard for him to say no to hiring you. Since you’ll basically just be writing up everything he said, with maybe a bonus or two for him thrown in there (see this Bullish about tech skills helping young employees differentiate themselves), it’ll be hard for him to say no, unless your price is too high.

Of course, if you’ve set your initial salary requirements high enough to begin with, you’ll have some negotiating room. (See Bullish: How to Ask for More Money, Part I and Part II.)

2. Make the pitch about them, not about you.

That should be obvious. But seriously: You know how I hired my current virtual assistant? She had read basically all of my columns and we’d corresponded briefly, and then I mentioned on Facebook that I could use an assistant, so she sent me an email about all the things she could do for me. Since she had been following my online activities, she was pretty specific. She offered to send a resume. Since I had just written Bullish: How Basing Your Career on a Resume Is Like Competing in a Brothel Lineup, I responded, “No, that’s okay!” What would a resume have told me that wasn’t apparent from an email that spoke exactly to what I needed?

If I were in the lucky position of writing a proposal for someone who was pretty sure he already wanted to hire me, I’d probably say, “Do you need to show this to someone else where you might want me to attach a resume and references?” This sort of thing should be a formality. If I’m hiring someone to do my PR, I first want to hear what they can do for me. Then, once I’m mostly sold, I want to verify that the person has done similar work for other clients. But that’s not what you should lead with. In other words, I want a doctor who says, “I can cure that,” not a doctor who says, “I got a 4.0 at Harvard.”

If I were pitching a stranger over email, I’d probably write a short, snappy email about what I’m offering, and leave most of the “about me” available via links in my signature.

People are more interested in you anyway when they feel like they’re digging up your goods on their own, even if their “detective work” is pretty much finding your LinkedIn page and blog (ooh, and a photo of you drinking out of a plastic cup at a conference!)

3. Have a backup pitch.

Some things can’t be saved. I wrote about this in last week’s Bullish: How Negotiating a Raise is Like Dating:

Imagine this were some article on “How to Get Your Boyfriend to Marry You,” and so you try some magical technique, but the guy responds, “Actually, I can get a woman hotter than you to marry me and work a full-time job while also doing all the cooking and cleaning and giving me blowjobs while I play video games.”

You wouldn’t blame the negotiation techniques, or yourself, for not turning that around. Instead, you would conclude that that guy was a douchebag.

Some jobs are just like that. You can’t fix the job, you can’t turn it around. You can’t get someone (a guy, a boss) who never respected you to suddenly start respecting you. You just have to move on.


But plenty of things are negotiable. Also, if you are out to lunch with someone and you ask for a full-time job and he’s like, “I really wish I could but we have zero dollars and are letting people go,” it’s kind of awkward to have to finish lunch with nothing else to talk about.

So, come prepared with something else in your back pocket. Like, “Oh, well, maybe when the economy picks up! As long as I have you here, I have another idea for you. I am working on a book and thinking that it might work out for both of us to run some excerpts in the magazine — you get free content and I get publicity.” Or, you pitch more and higher-paying freelance work. Or try to wrangle a job title (Editor-at-large?) Or maybe there’s something in-between freelance and full-time — maybe you could work in the office for the summer, to manage and coach the interns, and then you two could revisit the full-time idea in the fall.

In closing…

Finally — and this is for everyone — get in the habit of pitching so often that rejections don’t faze you.

Many sleazy books about seduction encourage men to inure themselves to rejection by going out and hitting on, say, 20 women per night. There are lots of other women out there. Ask 200 women, there’s a good chance you’ll find one who just broke up with someone and is looking for an easy rebound. (That’s kind of a gross example, but it’s true.)

I wrote in a column about asking for more money about working with rich people and capitalists. (“The best way to get paid is to work for people who really believe in capitalism, and to make a bunch of money for them. And then they give you a bunch of it, or else you’ll go elsewhere and they’ll stop making money off of you.”)

Even so, it’s important to spread the pitches around. Employers and clients are in no way involved in fairly evaluating your skills and services and making fair offers to you. They are involved in their own complicated soap operas, which you are entering somewhere around episode #812, and while you can and should do some research, you’ll never know all the factors that go into making a hiring or buying decision.

Pitching abundantly and regularly is a good way to put yourself in front of someone who has money and a problem that needs solved now. It’s also a good way to become the kind of person who responds to rejection — in your head, at least — with, “That’s cool, I have more awesome opportunities to pick from than I could ever take advantage of anyway.”

Originally published on The Grindstone

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