You quote someone $500.

They hesitate.

And suddenly, without being asked, your mouth does this:

“But I could probably do it for $400.”

WHY?

They didn't negotiate.

They didn't say no.

They barely had time to inhale.

And yet somehow you've just negotiated against yourself.

Welcome to one of the strangest things small-business owners do:

We work very hard to make money and then feel guilty asking people to give it to us.

There is absolutely nothing wrong with being generous.

Give a loyal customer a break.

Help somebody who's going through a rough patch.

Throw in something extra because you feel like it.

Do something for free because you genuinely want to.

But make it a decision.

Because there's a big difference between:

“I'm choosing not to charge for this.”

and:

“I'm scared they'll think I'm expensive.”

One is generosity.

The other is fear wearing a little business hat.

Generosity should be a decision. Not a pricing model.

This one sneaks up on you.

You started doing X.

Then X became X + Y.

Somehow Z wandered in.

Then came:

“While you're in there, could you just...”

Of course.

It's just one little thing.

Until there are seventeen little things.

Meanwhile, your original $300 price is sitting there exactly where you left it three years ago.

The customer is thrilled.

You are increasingly irritated every time their name appears in your inbox.

And here's the uncomfortable part:

The customer may not be the problem.

You might just be undercharging them.

If the work has doubled and you've never changed the price, your customer hasn't necessarily done anything wrong.

They've been paying the invoices you've been sending them.

Ouch.

Of course they do.

Maybe they can't afford $1,000.

That's useful information.

It doesn't automatically mean your $1,000 service should now cost $600.

Your customer's budget is information. It is not your pricing strategy.

Maybe you reduce the scope.

Maybe you offer a different service.

Maybe you decide they're not the right customer.

Maybe you deliberately give them a break.

All perfectly reasonable options.

But quietly chopping hundreds of dollars off your price because you're worried about how somebody might react?

That's how you end up very busy and strangely broke.

Oh boy.

You know you're undercharging.

You know your costs have gone up.

You know the work has grown.

You know you haven't raised your prices since dinosaurs roamed the earth.

So you finally send the email.

“Effective September 1, my monthly fee will increase from $550 to $600.”

And then you stare at your inbox like you've just issued a declaration of war.

😂

Maybe they'll be angry.

Maybe they'll leave.

Maybe they'll tell everyone you're a terrible person who enjoys both puppies AND price increases.

Or...

Maybe they'll reply:

“Sounds good. Thanks for letting me know.”

And carry on with their day.

Because sometimes the person most upset about your price increase...

is you.

Put your prices on the calendar.

Pick a regular schedule — once or twice a year, annually, whatever makes sense for your business — and review what you're charging.

Has the scope changed?

Have your costs increased?

Are you doing considerably more than when you originally set the price?

Is the customer still profitable?

You don't have to raise every price every time.

You just have to look.

Because “I haven't thought about that price since 2022” is not a pricing strategy either.

This is another trap.

Business owners sometimes think:

“That only took me an hour. I can't charge THAT much.”

Why not?

Maybe it only took an hour because you've spent 15 years learning how to do it in an hour.

Your customer isn't only paying for sixty minutes of your life.

They're paying for the experience, equipment, software, overhead, insurance, training, mistakes you've already learned from — and the fact that they don't have to figure it out themselves.

Your price doesn't have to make everybody happy.

It needs to make sense for the value you're providing and for the business you're trying to build.

A woman took on contract work at a hotel a couple of hours from home.

It seemed like a pretty good arrangement.

The drive was long, so when she didn't want to make the trip home, she could stay overnight at the hotel.

At a discount.

She could eat there too.

Also at a discount.

Great deal, right?

Well...

Eventually, she brought me her income and expenses.

I added everything up.

Then I looked at it again.

Because this couldn't possibly be right.

It was.

Between the driving, hotel stays, meals and other costs of working that far from home...

She had spent more money doing the work than she'd earned from it.

She wasn't making money from the job.

She was paying to have a job.

😬

And those discounts?

They hadn't saved her money.

They'd just helped her lose it more cheaply. 😂

Looking at what she was saving instead of looking at what she was spending.

A 30% discount doesn't save you 30%.

It still costs you the other 70%.

And business owners fall into the same trap all the time.

A discounted piece of equipment you don't need.

Software that's “only $40 a month.”

A customer who generates lots of revenue but costs even more to service.

A sale isn't profitable just because money came in.

Don't ask only:

“How much am I making?”

Ask:

“What is it costing me to make it?”

Because revenue can look fantastic right up until you calculate what's left.

And sometimes the best deal...

is the one you don't take.

Pick one customer, product or service you haven't repriced in a while.

Don't raise the price yet.

Just look at it.

What are you charging?

What are you actually providing now?

What does it cost you?

How much time does it take?

Has the scope changed?

And most importantly:

If this customer walked through the door today, would you quote them the same price?

If the answer is no...

Well.

You may have just found your next price review.

See you next week.

Revenue & Regrets

Real business. Real money. Questionable decisions.