4.8 • 3.3K Ratings
🗓️ 19 December 2025
⏱️ 5 minutes
🧾️ Download transcript
Today’s caller feels guilty just naming a price. We’ll reframe selling from “asking for money” to “offering a structured service,” and use a script to make the conversation automatic.
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.
Show notes: SideHustleSchool.com
Email: [email protected]
Be on the show: SideHustleSchool.com/questions
Connect on Instagram: @193countries
Visit Chris's main site: ChrisGuillebeau.com
Read A Year of Mental Health: yearofmentalhealth.com
If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼
See omnystudio.com/listener for privacy information.
Click on a timestamp to play from that location
| 0:00.0 | Lemonada. How do you talk about pricing when it feels impolite or awkward? Some people inherit the |
| 0:16.4 | belief that discussing money is just kind of difficult or can be greedy or it signals disrespect. |
| 0:24.1 | And so when you start a service business, you're going to have to talk about pricing one way or |
| 0:27.7 | another. And that conditioning collides with reality. Because if you can't quote a price confidently, |
| 0:33.0 | then the client assumes the value is uncertain or they're just not sure what to do. |
| 0:41.1 | And you never want your client or customer to be confused. You always want them to know exactly what they need to do, you know, what the price is, what they're going to get, what the process is, |
| 0:46.1 | and so on. So what do you do in this situation? The solution, I think, isn't to change your personality. |
| 0:51.2 | It is to move pricing out of improvisation mode where you just kind of |
| 0:56.1 | have to like think about it each time and into a system to where you never really ask, |
| 1:01.1 | you simply present. So let's talk about that as it applies to our caller and perhaps some other |
| 1:05.7 | folks out there as well. I always want to present questions that represent our broad community, |
| 1:17.4 | people out there trying to start a side hustle, trying to make extra money without quitting their job, or just build something for themselves. |
| 1:19.5 | So that's our topic of the day. |
| 1:24.2 | How do you talk about pricing when it's a little bit awkward or it seems impolite, detailed question? |
| 1:26.4 | And my answer coming right up. |
| 1:36.8 | Hello, I'm Zakira from Toronto, Canada. |
| 1:41.6 | I grew up in a culture where discussing prices or negotiating feels rude. |
| 1:43.9 | Money talk is something you keep private. Now I'm offering one-on-one |
| 1:46.0 | language tutoring sessions online, and I freeze when it's time to quote my rates. I either |
| 1:51.9 | underprice or I mumble through the pitch. How do you get comfortable asking for fair payment |
| 1:57.9 | when every instinct says it's impolite. |
| 2:06.3 | I really appreciate you bringing up this question. I imagine this is something that a lot of other people have thought about or experience, or maybe they don't think about it until they're |
... |
Transcript will be available on the free plan in 4 days. Upgrade to see the full transcript now.
Disclaimer: The podcast and artwork embedded on this page are from Chris Guillebeau / Onward Project, and are the property of its owner and not affiliated with or endorsed by Tapesearch.
Generated transcripts are the property of Chris Guillebeau / Onward Project and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.
Copyright © Tapesearch 2026.