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Side Hustle School

Ep. 3282 - Q&A: “I’m ready to raise prices … but how?”

Side Hustle School

Chris Guillebeau / Onward Project

Business, Careers, Entrepreneurship

4.83.3K Ratings

🗓️ 26 December 2025

⏱️ 5 minutes

🧾️ Download transcript

Summary

Inflation climbs and workload grows, but rates stay frozen—sound familiar? Today we’ll run a quick value check, set a price-rise timeline, and craft a client email that keeps loyalty high.

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

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Transcript

Click on a timestamp to play from that location

0:00.0

Lemonada.

0:10.7

I've noticed over the past year I've been getting more and more questions that are not so much about logistics or technical things like which platform is best and such, but much more about overcoming self-doubt,

0:23.7

which we're going to look at tomorrow, and other like emotional issues related to running your

0:28.8

side hustle, being burned out. We recently had a skeptical spouse, you know, somebody whose partner

0:34.6

didn't really support them. And I think this is so important to look at because running your side hustle or small business is not all about just how do you set up your website and so on. And today we're going to talk about raising prices, which is one of those things that is both strategic, but it is also emotional in the sense that people are afraid to do it. They worry they're going to lose their clients or clients are going to be upset with them. They just kind of see it as a conflict as opposed to an

0:58.2

opportunity. And we can't just flip that entirely. But maybe there are some things we can do to

1:02.9

help somebody feel more comfortable in raising their prices, which would then allow them to,

1:06.8

of course, make more money and be more sustainable. So today we've got a caller, a bookkeeper

1:11.9

who hasn't raised prices in, I think, three or four years, and they understand that they need to do it,

1:17.4

but they are terrified, in their words. This is John. So let's see what we can do to help John

1:22.2

and hopefully other folks out there too. You need to price what you're worth, but I know it's not easy.

1:26.8

So I'm going to try to give you some specific tips. Stay tuned.

1:32.6

Hello, it's John calling in. I run a small bookkeeping practice. I've charged the same monthly retainer since 2022 because I'm terrified of a price

1:46.1

increase will send clients running. Inflation's up. My workload has grown. And new prospects still say

1:53.0

yes immediately, which probably means I'm underpriced. How do I analyze current value to decide on a new rate and communicate the change without triggering a mass exodus?

2:08.5

I think this is the thing where after you do it, you're going to wish you had done it sooner, and you're going to say, well, it wasn't as hard as I thought it was going to be.

2:15.7

So don't worry about the first thing. Don't worry about wishing you had done it sooner. But do get to that point of relief.

2:21.7

So to do that, I think you want to think about the value that you provide for your clients.

2:26.6

What are the outcomes you provide? Presumably on-time tax filings, maybe some clarity, maybe avoiding

2:32.5

penalties, and make sure the client knows about this value

2:35.9

that you provide. For example, if the client avoids a $500 late fee each year, well,

2:41.8

that's worth what, $500, right? And the next, pick a database new rate. Make sure you check the

...

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