How to Charge More for Your Services (What a $3,000 Client Taught Me About Pricing)

Most people who run a service business or sell their skills online undercharge for their work. Not by a little. By 50 to 200 percent. And the reason is almost never lack of skill, lack of value, or lack of demand. The reason is that saying the higher number out loud feels uncomfortable, and comfort is what most people optimize for by default.

I learned this the hard way years ago on a single call that changed how I’ve priced everything since. Here’s the full story, the lesson underneath it, and the exact protocol to start charging what your work is actually worth.

Why Most People Undercharge for Their Services

Before the story, the honest diagnosis. Most people who undercharge do it for one or more of these reasons:

1. They price against their own bank account. They pick numbers that feel reasonable to them, not numbers that reflect the value they create for the buyer.
2. They confuse cheap pricing with kindness. They think lower prices help clients say yes. In reality, low prices signal low confidence.
3. They test the ceiling once and stop. They quote a slightly higher number, get one no, and revert to safe pricing forever.
4. They never test the ceiling at all. They stay at whatever number felt comfortable when they started and never re-evaluate.

The fix for all four is the same. You have to be willing to say the number that makes your stomach turn slightly, out loud, to a real person, and see what actually happens. Most people never do this. The ones who do end up building the businesses that make the rest of the industry wonder how they got there so fast.

Here’s the story of the exact call that made me understand this.

The $3,000 Call That Changed My Pricing Forever

There was a stretch early on where I was living abroad, didn’t know anybody, and I really needed the money. Not “it would be nice” money. Actual “I need this to work” money.

Around that time a guy I’d reached out to over a year earlier came back around.

I’d messaged him once, way back, when he wasn’t a client yet. He said no. Then a year, year and a half later, out of nowhere, he reaches out to me. He’d found out the results I was getting. He knew some mutual connections. And now he wanted to work together.

Here’s the part I’m not proud of but it taught me everything.

By the time he came back, I didn’t need the money the way I used to. So I was feeling a little petty about the original no. And I decided I was going to quote him a price higher than anything I was charging anyone else at that time.

My normal rate for that exact offer was fifteen hundred dollars. I quoted him three thousand.

The Half Second That Changed Everything

Quoting that number made me sick to my stomach.

I want you to understand that, because if you’ve ever tried to raise your rates you know exactly the feeling. That voice in your head going “this is too much, who do you think you are, he’s going to laugh at you.” I had all of that. Same as you.

I said 3,000

Half a second later he said, “Great. How can I pay?”

Half a second. No negotiation. No pushback. No “let me think about it.” He was ready to pay double before the words were fully out of my mouth.

I sent him the payment link. He paid it while we were still on the call.

And then I had the epiphany that changed how I’ve priced everything since.

This guy was paying me almost double what my other clients were paying. For the exact same work. The exact same offer. Nothing about what I delivered was different. The only thing that changed was the number I had the courage to say out loud.

From that point forward I only charged three thousand. Then eventually ten thousand. And on from there.

The Core Lesson: Expensive to You Isn’t Expensive to Them

Here’s what I need you to actually take from this.

Just because something sounds expensive to you does not mean it’s expensive to the other person.

That’s the whole thing. The price felt enormous to me because I was measuring it against my own bank account, my own fears, my own story about what I was worth. He wasn’t measuring it against any of that. He was measuring it against the results he was going to get.

You are not pricing your work. You are pricing the value you create. That’s what people pay for. Whether you’re flipping items, running a service, closing deals, it’s always the same. You get paid for the value, not the hours, and definitely not for how comfortable the number feels to you.

The fifteen hundred dollar price wasn’t humble. It was fear with a decimal point. I was charging what felt safe to me instead of what the work was actually worth to them.

Why Cheap Pricing Is a Signal, Not a Kindness

When you undercharge, you think you’re making it easy for people to say yes. You’re not. You’re telling them something.

A low price signals low confidence. If you don’t believe your work is worth more, why would they. The number you say out loud is a piece of information about how much you trust your own results. People read it instantly, even if they never say so.

The guy who paid me three thousand didn’t respect me less for the higher number. He respected me more. Real buyers, people who actually have money and actually have a problem worth solving, are not looking for the cheapest option. They’re looking for the person who clearly knows what they’re doing. And nothing signals “I don’t know what I’m doing” faster than a scared price.

How to Actually Raise Your Rates: The Protocol

I’m not going to pretend the feeling disappears because you read an article. It doesn’t. The only way through it is the same way I got through it. You have to expose yourself to it.

Here’s the exact protocol.

Step 1: Don’t Raise Rates on Existing Clients First

Raising the rate on longtime clients all at once just annoys them and can push them elsewhere. Do it with the next new client instead. Give yourself an easier first rep.

Step 2: Pick a Number Higher Than the One That Feels Safe

Quote the number that scares you a little. The one that makes your stomach turn slightly. If your comfortable price is $1,500, quote $2,500 or $3,000. If your comfortable price is $5,000, quote $8,000 or $10,000.

The number should not feel comfortable. That’s the point. Comfort is what has been keeping you at the wrong price.

Step 3: Say It Clearly. Do Not Backpedal.

Say the number out loud, clearly, without flinching or immediately backpedaling into “but I can be flexible.” No hedging. No qualifying. Just the number.

Then be quiet. Let it sit.

The silence is the hardest part and the most important part. Most people fill the silence by softening the number the second they see any hesitation on the other side. Don’t. Let them respond first.

Step 4: Accept the Outcome and Move On

Worst case, they say no, and you work out a deal a little cheaper. That’s fine. Nobody died. You learned the ceiling for this specific type of client.

Best case, they say “how can I pay” half a second later, and you realize you’ve been leaving money on the table this entire time out of nothing but fear.

You only find the ceiling by testing it. The only way to test it is to say a number bigger than the one you’re comfortable with, to a real person, and see what happens.

The Real Shift Is an Identity Shift

The transition from charging what feels safe to charging what the work is worth isn’t a pricing change. It’s an identity change.

At the lower number, you are the business begging to be chosen. At the right number, you are the expert deciding who’s worth your time. Same work. Same offer. Completely different man saying it.

I found that out in a half second, on a call, with a client I almost didn’t want. He paid me double for feeling a little petty.

The number was never the problem. My willingness to say it was.

Say the bigger number. Then get quiet and watch what happens.

Frequently Asked Questions

How do I know if I’m charging too little for my services?

You are almost certainly charging too little if any of these are true. Your prospects rarely negotiate or push back on your quotes. Your close rate on qualified prospects is above 70 percent. Your clients frequently tell you the results were worth much more than what you charged. You feel a knot of unease when quoting your current rate because it feels either too low to be respected or too safe to be exciting. Any one of these signals is enough to justify testing a higher number on your next new client.

How much should I raise my rates by?

There is no universal percentage. A useful rule for a first test: quote a number that feels roughly 50 to 100 percent higher than your current rate to a new prospect. That range is high enough to matter, low enough to not seem outlandish for the work you deliver. If it lands, adjust your standard rate upward and continue testing from there. Real pricing power is discovered incrementally, not calculated in advance.

Will I lose clients if I raise my prices?

Some, yes. That’s part of the process. The clients you lose are typically the price-sensitive ones who wouldn’t have driven your business forward anyway. The clients you keep and gain at the higher rate are usually more serious, easier to work with, and generate more referrals. Most people who raise their rates report a smaller but significantly more profitable and less draining client base within 6 to 12 months.

How do I handle it when a prospect pushes back on price?

Silence is the most powerful response to price pushback. Do not immediately drop the number or offer discounts. Ask them what specifically is causing the hesitation. Often the concern is not the price but a lack of clarity about the value or the deliverables. If, after clarification, they still push back, you have two options: hold the price and let them walk, or offer a smaller scope of work at the lower price. Never offer the same scope at a lower price. That trains prospects that your pricing is negotiable and undermines all future pricing conversations.

Is it better to charge hourly or by project?

Charge by project or by outcome whenever possible, not by the hour. Hourly pricing caps your earnings at your time and rewards you for being slow. Project or outcome pricing rewards you for being efficient and effective, and it aligns you with the client’s actual goal (the result), not the process (the hours). Clients also respond better to a fixed number than to open-ended hourly billing that could balloon unpredictably.

How do I raise rates on existing clients without losing them?

Raise rates on existing clients gradually and with notice. Give at least 60 to 90 days of warning before the new rate takes effect. Frame the change in terms of the results you’ve delivered and the increased demand for your work. Some clients will accept, some will negotiate, and some will leave. The ones who accept typically respect you more for the move, not less, because it signals that you take your business seriously.

The Bigger Frame

I work with clients across the world building service businesses, personal brands, and product companies. The single most consistent pattern I see in the ones who break through to real income versus the ones who stay stuck is this: the successful ones learn early that pricing is not about the work. Pricing is about the identity of the person doing the work.

The scared price and the confident price often deliver identical outcomes. The difference is not in what gets built. The difference is in who is doing the building, and how they see themselves at the moment they say the number out loud.

You don’t need to be better before you charge more. You need to charge more before you’ll become better. The higher price forces the higher standard. The lower price permits the lower standard.

Say the bigger number. Get quiet. See what happens.

Always the best,

Dylan Madden

If this was useful and you want more real-world breakdowns like this one, from someone actually doing the work instead of just talking about it, subscribe to my Substack. New essays go out weekly, written for men building service businesses, personal brands, and companies that actually pay them what they’re worth.