There's a conversation you've been avoiding…

You know the one…

The "Hey, I need to raise my rates" talk with your current clients.

You've been thinking about it for weeks (maybe even months).

You know you're undercharging and this needs to happen.

But every time you think about actually saying it...

You imagine them getting annoyed and saying no, or dropping you.

So you keep putting it off…

And in the meantime, you're leaving thousands of dollars on the table.

Here's how to stop avoiding it and actually have THE TALK →

The problem with having the “rate rise” convo:

It can feel awkward asking for more money from someone you already have a relationship with and already have an agreed-upon price. You don’t want to seem like an ungrateful opportunist.

The benefit of solving it:

You get paid your worth and start earning more in your business.

You also have more time to develop new business and future leads (because you now need fewer clients, or you can now afford to subcontract more help, or both).

Why what you’ve tried has failed:

You are hesitant to have the money talk and are going into the convo half expecting them to say “no” or be annoyed with the request and walk away.   

Here’s how to solve it:

A successful rate-rise conversation comes down to 2 core things: preparation and communication

Just like you would prepare for a meeting with a prospective client, you want to prepare for a rate rise conversation as well. 

Rehearsing what you will say is a great way to get you warmed up and ready (especially if you haven’t had many of these conversations before).

Think about what you will say to the client, how you will start the conversation, and what data supports your position.

Be prepared to reminisce about the “big wins” that you’ve helped the client accomplish so far as a strategic partner.

But more importantly, prepare yourself to resist the urge to justify the rate increase.

This is what’s best for your business, no explanation really needed beyond that.

You can prepare even more by thinking about what objections your client might have, and how you will address them.

Have a few different package options in mind that you can present as alternatives as well.

With a couple of different plans in mind, you know what to say depending on how the conversation goes.

If they can’t come to the new rate, you can have a scaled down package available in order to keep the budget where they need it (still less work for you).

All of this preparation directly benefits your ability to effectively communicate throughout the call. 

We talk about clear and effective communication a lot in this newsletter because it’s SO important.

It’s the difference between being a successful freelancer and one who is constantly struggling to make ends meet. 

So when it comes time for the actual conversation, stay cool and professional.

Begin with a heartfelt thank you for their ongoing partnership and let them know that this conversation is all about ensuring the growth and sustainability of your freelancing business (which ultimately benefits them too).

Your goal is to demonstrate your commitment to a collaborative partnership.

So be an attentive listener and encourage them to share their thoughts and concerns.

When addressing their concerns/objections, use the preparation you've done to provide thoughtful responses.

Remember, this is business, it’s not personal.

It can be hard to separate the personal from business, especially after working with a client for a while.

But don’t let that hold you back or settle for less than out of fear. 

Whether they agree to the rate rise, or you decide to part ways, it’s a win. 

If they say yes, you are that much closer to your monthly revenue goal. 

If they say no, you have the time and space to look for clients who will value what you bring to the table, and the higher pay you are getting from the clients who do stick around subsidize the ones who walk away. 

Best, 
Jamie

Here's how I can help accelerate your freelance success in 2026:

  • Not sure how to price your services? → My FREE pricing mini-course reveals the exact framework that gets you premium rates.

  • Ready to escape the feast-or-famine cycle? → Join The Freelancing Program and master the Client Domino System that turns chaos into consistent $10K+ months (1,000+ freelancers and counting). 

  • Serious about scaling? → Let's build your custom $100K+ roadmap in a focused 1:1 coaching session.