Not comfortable asking for more money?

Trevor “Toe Cracker” Crook was at the front of the room, finishing his presentation, and was about to launch into the pitch for his offer.

“How many of you regularly close 5-figure copywriting contracts?” he asked.

You’re supposed to participate if you’re in the audience at a conference, and give the speaker some signs of life. So I raised my hand.

I was sitting in the front row. I glanced over my shoulder. I realized that, out of 25+ other copywriters in the room, maybe two or three also had their hand up.

I felt sheepish. I put my hand down.

The fact is, I’m not overwhelmingly confident. I’m certainly not assertive or demanding.

And yet, a couple years ago, back when I was still regularly taking on client work, I was closing 5-figure deals matter-of-factly. And if I were taking on a big project now, I wouldn’t have any trouble asking for — and probably getting — $15k or $20k, upfront, depending on what needs to be done.

In my experience, asking for more money is not a matter of confidence, in the sense of some unshakeable self-belief. Nor is it a matter of assertiveness.

It’s really about systematically putting yourself into a situation where neither of those is needed. As negotiation coach Jim Camp, who guided Fortune 100 CEOs and revamped the FBI’s hostage negotiation process, had to say:

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I’ve got wonderful non-assertive people that just do magnificent jobs in negotiation. But that’s because they have the tools. They don’t need to be assertive. Assertive is not a trait that is to be desired in negotiation by any means.

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I’m thinking about putting on a training in June about how to be comfortable charging more. This isn’t only about copywriting work. I’ve been selling courses, live presentations, and consulting to make up for the fact I rarely work with copywriting clients any more. I’ve found the same principles apply whenever money changes hands.

If such a training is something that would interest you, hit reply and let me know. In case there’s enough interest, I will put it on.