3283 4:41 Q&A

Q&A: “How can I keep from negotiating against myself?”

Today’s caller undercuts her own price before the client even speaks. Let’s help her overcome this pattern of self-sabotage!

4:41

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Episode 3283

Self-discounting usually isn’t about money—it’s about nerves. The fix is less willpower and more structure: a set price sheet, a one-sentence response, and a two-second pause you practice until silence feels normal. Let’s give the photographer a quick system she can deploy on the very next inquiry.

"Whenever someone inquires, I panic and say things like ‘My rate is $600, but I can do $500 if that helps.’ They hadn’t even objected yet. It’s costing me revenue and reinforcing insecurity. How do I break this habit of negotiating against myself? Are there scripts, confidence exercises, or pricing structures that prevent me from rushing to a discount out of fear?"

Listen to today's episode to learn more...

Yours in the revolution,

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How to Price Your Side Hustle (Without Underselling Yourself)

Real pricing strategies from side hustlers who figured it out. Stop guessing, stop underselling, and start charging what your work is worth.

Read the full transcript

This transcript was generated from the episode audio and may contain minor errors.

All right, as I mentioned yesterday, getting more and more questions about the emotional side of increasing prices or selling or dealing with obstacles that come up in your side hustle that are not about technical or logistical problems, but are more emotional difficulties being burned out, having a partner who doesn't support your business, worried about failure, sometimes worried about success and what that involves and how that might change your life in some ways. So today, we've got a caller just to continue this theme. Today's caller undercuts her own price before the client even speaks. So yesterday, it was a bookkeeper who was trying to raise his prices. Today, we've got a photographer who just has a hard time kind of saying their prices in the first place. And we've talked about this, I think, maybe 10 or 15 days ago in a

different way about somebody who grew up in a culture in which you just don't talk about money. And so they also had a difficulty in doing that. So I'll try to give some different advice here to hopefully help this person and others out there increase confidence and be able to charge, again, what they're worth, just like we talked about yesterday. I think it's an important theme because people keep asking about it. I'll do my best to give a helpful answer. How do you keep from

negotiating against yourself? Detailed question and my answer coming right up. Hi, Chris. I'm a freelance photographer. Whenever someone inquires, I panic and say things like my rate is $600. But I

can do 500 if that helps. They hadn't even objected yet. It's costing me revenue and reinforcing insecurity. How do I break this habit of negotiating against myself? Are there scripts, confidence exercises or pricing structures that prevent me from rushing to a discount out of fear?

Well, just like we talked about yesterday, with a related issue, I understand that, you know, it feels a little bit intimidating to increase your prices or to quote the price in the first place. But like we talked about, I think maybe a couple weeks ago with the other caller, a simple thing you can do is to publish your prices, publish that menu essentially. And so that PDF or the website is already available. People know what to expect. So you don't actually have to kind of go into a sales process. Or your sales process is basically like which one do you want? Maybe you

have two packages, right? You've got the half day shoot, you've got a full day shoot. Perhaps there are some add ons. I think that's helpful to have as well. Not too many. You don't want people to

feel nickeled and dimed, but maybe a couple things. And so that way, you're just like, do you want A or B, right? And if you do actually need to state the prices, use a short, like 10 word script, let's say, and then stop talking. Okay, so that those 10 words, I'm not sure if this is exactly 10 words, but the half day package is $600. And it includes editing. And you just pause, you just

wait, right? Wait for the buyer to respond. Most likely, they're going to say okay. And I think you reserve any discounts for a reason, not a reflex. So maybe a discount could be like if it's a weekday shoot, or some other time when you're not busy, and it's booked two weeks in advance, that could earn a 10% discount. And if somebody says, Oh, I really want this, but I can't afford it. Well, here's a

way to get a 10% discount. But this way, it's like, there's some accommodation for that, it makes it easier for you as well. And you're not automatically offering discounts. I want you to just kind of practice saying this script. Most of all, get that menu of prices ready. So you don't actually have

to say it too often. And then discount only when it suits your needs as well. Okay, like I said, I know it's hard, but it's worth it. Like you're providing a great service and you deserve to be paid. Listeners, I believe you deserve to get paid as well. I believe you deserve to create

something for yourself so that you can do more of what is important to you, whether that is to quit your job or pay off debt or just have more security in general. Those are all good things. And you shouldn't doubt them. Don't doubt those values. And don't doubt yourself as well. We're coming to

the end of a year. New year's coming up. Hope you set some goals. Let's do something exciting together just around the corner. But for now, I wish you well. My name is Chris Guillebeau. This

is Side Hustle School. From the Onward Project.

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