4.8 • 3.3K Ratings
🗓️ 27 December 2025
⏱️ 5 minutes
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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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| 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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