Why I Stopped Raising My Prices And Put Them On A Calendar Instead
Why I Stopped Raising My Prices And Put Them On A Calendar Instead
The advice everyone gives treats your price like a courage problem. Here is the scheduled review I run instead, and what it catches.

Everyone tells you to charge more. Almost nobody tells you when.
Search "raise your rates" and you'll get the same article forty times. Charge what you're worth. Know your value. Stop leaving money on the table. Most of it is written by someone with a call to action at the bottom of the page, which tells you who the advice is really for.
The diagnosis isn't wrong. On Hacker News, a thread asking consultants what mistakes they made starting out drew more than 260 replies, and the highest-rated answer was blunt about it: "Setting my rates too low. Whatever you're charging now, without even knowing what it is, I'm certain it's too low." A second thread, on lessons from six years of solo consulting, drew 460 points and 149 comments, and one reply cut closer: "The more $ you charge, the better you get treated by customers. The less $ you charge, the more abuse you take."
So the whole internet agrees your number is too low. What almost none of it addresses is how the number got low and stayed there.
All of that advice treats your price as a confidence problem. If price is confidence, then the fix is a single act of nerve. Work up your courage, write the email, hold the line when they push back. It's a satisfying story with one flaw baked in. It only works once. You do the brave thing, you set a new number, and then that number does exactly what the last one did, which is sit perfectly still while your costs, your skill, your delivery, and your capacity all move around it.
Telly Arnold described this on the podcast from inside the trucking industry: new owners taking contracts that don't cover what the work actually costs, because brokers won't touch a new authority, then holding onto those contracts because the note is due every month regardless. Nobody in that story has a confidence problem. What they're missing is a moment, on purpose, where the number gets held up against what the work costs today.
A price is usually right on the day you set it and slowly wrong after that. Nothing in a small business forces you to notice the drift, because the drift doesn't announce itself. It shows up as being busier than ever and no better off.
What I do instead
Back when this was a lunch-hour business, built on two fifteen-minute breaks and whatever I could steal from a lunch hour, I set my rates as a much newer version of myself. Then I never went back to them. They carried forward, year over year, like they'd been handed down by somebody with more information than I had.
And when a prospect hesitated on a number, I discounted. Every single time. Then, because the discount bothered me, I'd over-deliver against it. I'd hand over more than the engagement called for so the price I'd just cut would feel earned. I was paying, in hours, for the right to charge less.
Here's what let that run for years without consequences. When I still had a paycheck coming in, the revenue looked fine, because my salary was quietly absorbing the difference. The business never had to pass a real test. A business that's being subsidized will happily tell you your pricing is working right up until the subsidy stops.
So the practice now is simple and it isn't about courage at all. My prices sit on the calendar.
It's a standing block, and it's a review rather than a raise. Nothing is required to change. The only requirement is that the number gets looked at on a date I chose in advance, instead of on a day when I'm annoyed or a day when a client pushes. Here's what I bring to it:
- Every active offer and every active client, in one list. Not the ones I'm proud of. All of them, including the ones I set long ago and stopped thinking about.
- What the work costs now. Hours in delivery, hours in support, the tools it takes, the people it takes. Not what it cost when I priced it.
- Cash collected against active clients. That's the number I check on a normal week anyway. Not revenue booked, not pipeline, not what's promised. Cash collected, measured against how many people I'm actively serving. When the client count climbs and the cash doesn't move with it, the pricing is the thing that's broken, and no amount of working harder is going to fix it.
Two rules come out of that review and they hold for the rest of the year. The first: no price moves in a live conversation. If someone hesitates, they can have a smaller scope at a smaller price, and they cannot have the same scope at a smaller price. That one sentence retired the entire discount-then-over-deliver habit, because there's nothing left to make up for.
The second: nothing gets bought unless it can answer what it replaces or what it produces. I learned that one the expensive way and I've written about the receipts. The same test applies to tools, which is most of why I tell people to stop starting with the CRM. Anything that can't name its job is a cost dressed up as an investment, and it comes out of the same margin your pricing was supposed to protect.
In the Serve to Scale 5-Point Growth Method, pricing lives in Target and Multiply. You can't multiply anything that loses money quietly, and a scheduled review is the cheapest way I know to find out whether it does.
When this is the wrong thing to fix
A pricing review only works on something repeatable, so there's a real line here.
If you haven't delivered the same offer to a few different people, you don't have a price yet. You have an estimate, and putting an estimate on a recurring review formalizes a guess and gives it the authority of a system. Deliver it a few times, watch where the hours actually go, and price it after you know.
The bigger disqualifier is this one. If your real problem is that not enough people know you exist, a pricing review will make things worse before it makes them better. It'll look at your numbers, tell you the price is defensible, and hand you back the same quiet calendar you walked in with. Pricing is the wrong lever when the pipeline is what's empty, and the review will happily let you spend an afternoon avoiding that.
And one more, because it's the one people trip on. A real review sometimes tells you to lower a price, kill a tier, or retire an offer entirely. I've retired offers that looked fine on paper. If you're only willing to hear "charge more," you want permission rather than a review, and you can get permission anywhere for less effort than this takes.
The Offer Ladder Audit
Before you review your prices, you need your offers laid out as one ladder instead of a pile. The Offer Ladder Audit walks you through what you're actually selling, where the gaps and overlaps are, and which rung is quietly carrying the others. It's $27, and it's the thing I'd do first, because a price review on a tangled offer set will just tell you everything is fine.
Take the auditThe number that outlived the reason
Every price you set has a shelf life, and it will keep collecting long after the conditions that made it right are gone. Give it a review date the way you'd give a launch a launch date. A number you look at on purpose can't quietly outlive its own reason.
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You Are the Bottleneck: Why the Chaos Isn't Happening To You, It's Happening Through You (published Tuesday, September 8). This one opens the Chaos to Freedom arc, and it's a solo episode. If every decision, approval, and task in your business has to pass through you, what you have is a structure problem wearing a time problem's clothes. Karena walks through how to tell what genuinely requires you, how to stop being the default for everything, and how to move from doer to guide, starting with one task you take off your plate this week.
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