Should You Trust AI to Help You Price Your Freelance Services?
No. And I learned that the hard way.
I lost a deal recently because I let ChatGPT talk me into changing my price the night before a proposal was due. I'm putting that out there upfront because I recorded a podcast episode six months ago about exactly this. About how to not trust AI with pricing. So yes, this is embarrassing. But it's too useful a lesson to keep to myself.
Here's what happened. I was working on a proposal for a potential client referred to me through my Speaker's Agency. She needed two things: a commission structure for booking speaking engagements, and a strategy intensive where I'd help her figure out who to target and how to grow. The commission piece was straightforward. The strategy session was new territory for me. I'd never priced something like that before and I sat on it for three days.
At 9pm the night before the proposal was due, tired and already insecure about the number, I finally wrote it out. I pasted the scope into ChatGPT to clean it up, and accidentally included my proposed fee in the paste. ChatGPT came back telling me I was underselling, that my expertise was worth significantly more, and suggested a price that moved me from the hundreds into the thousands.
And I listened to it.
I ignored my gut, which was clearly telling me this client pays hourly, isn't familiar with packages, and this is a first-time offer. I deleted one number and typed in another.
Here's what I want you to understand about why that happened. I've been using ChatGPT since 2023. As a coach for freelancers, pricing and underselling come up constantly in my content. AI learns your patterns and reflects them back to you. It told me what I had essentially been teaching it to say. Add in the fact that I was exhausted, insecure, and a little flattered that even a bot was telling me I was worth more, and my guard was completely down.
I. Should. Not. Have. Listened. To. A. Bot.
AI is a brilliant tool for copy, for editing, for making things more concise. I use it that way constantly. But brainstorming and pricing decisions? That's where it gets dangerous. It doesn't know your client. It doesn't know the context. It doesn't know that your gut is telling you something important. It knows what you've fed it and it will reflect that back at you, dressed up as advice.
If you're tired, pay attention to that. If you're feeling insecure about a number, that's worth sitting with before you change it. If your gut is saying something different than the chatbot, stop and listen to your gut. You have years of experience and real client knowledge that no AI has access to.
Use it for what it's good at. Don't hand it decisions that require judgment.
Common Questions You Might Have After Reading
Q: What should freelancers actually use AI for when it comes to proposals? A: Copy, editing, and making things more concise. AI is genuinely helpful for cleaning up your writing, tightening a scope of work, or improving the flow of a proposal. Where it falls short is anything that requires knowing your specific client, your gut read on a situation, or real pricing judgment based on context.
Q: Why is AI unreliable for freelance pricing advice? A: Because it pulls from patterns in your own history and from general web content, not from the specific context of your client relationship. It doesn't know what a client is used to paying, what the market looks like in your niche right now, or what your gut is telling you. It will often reflect back what you want to hear, which feels validating but isn't always right.
Q: How should freelancers handle pricing a service they've never offered before? A: Slow down. Don't price something new at 9pm the night before a deadline. Think about what the outcome is worth to the client, what your time and expertise actually cost, and what you know about how this particular client operates. If you can, talk it through with a coach or peer before you send anything.
Q: Is it bad to use AI as a sounding board for business decisions? A: It can be useful as a starting point, but treat it like a first draft, not a final answer. AI will often tell you what you want to hear, especially if you've been feeding it content around a particular theme for months. Always run it through your own judgment before acting on it.
If you want help building a pricing strategy you can actually trust, connect with me here.