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Side Hustle School

Ep. 3283 - Q&A: “How can I keep from negotiating against myself?”

Side Hustle School

Chris Guillebeau / Onward Project

Business, Careers, Entrepreneurship

4.83.3K Ratings

🗓️ 27 December 2025

⏱️ 5 minutes

🧾️ Download transcript

Summary

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

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

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Transcript

Click on a timestamp to play from that location

0:00.0

Lemonada.

0:02.7

All right. As I mentioned yesterday, getting more and more questions about the emotional side of

0:15.8

increasing prices or selling or dealing with obstacles that come up in your side hustle

0:20.6

that are not about

0:21.7

technical or logistical problems, but are more emotional difficulties being burned out,

0:26.4

having a partner who doesn't support your business, worried about failure, sometimes worried

0:31.5

about success and what that involves and how that might change your life in some ways.

0:36.2

So today, we've got a caller, just to

0:38.2

continue this theme, today's caller undercuts her own price before the client even speaks.

0:43.6

So yesterday it was a bookkeeper who was trying to raise his prices. Today we've got a photographer

0:48.4

who just has a hard time kind of saying their prices in the first place. And we've talked about this, I think,

0:55.9

maybe 10 or 15 days ago in a different way about somebody who grew up in a culture in which

1:01.6

you just don't talk about money. And so they also had a difficulty in doing that. So I'll try to

1:06.6

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

1:14.8

about yesterday. I think it's an important theme because people keep asking about it.

1:18.4

I'll do my best to give a helpful answer. How do you keep from negotiating against yourself?

1:23.4

Detailed question and my answer coming right up.

1:32.7

Thank you. detailed question and my answer coming right up. Hi, Chris. I'm a freelance photographer. Whenever someone inquires, I panic and say things like,

1:40.0

my rate is $600, but I can do $500 if that helps.

1:44.7

They hadn't even objected yet.

1:46.5

It's costing me revenue and reinforcing insecurity.

1:50.0

How do I break this habit of negotiating against myself?

...

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