ISSUE № 10 · TUESDAY, July 7, 2026
I got on a call with a firm owner last week, and the whole hour was really about one email she'd been avoiding for six months.
❝ "He was one of my very first clients, going on eight years now. Back when I started, he ran a small event production company and the books were simple, so I charged him $500 a month and it was fair. He's grown a ton since. Revenue went from under half a million to north of one and a half million, and now I run his payroll, his bill pay, his invoicing, and his whole books. He opens new credit cards and bank accounts and tells me months later, usually after I've already found one myself as a mystery payment sitting in his checking account. He even signs my name on emails to his clients, which I hate. I bumped him to $850 at some point, then to $1,550 two years ago, and that time I told him I'd revisit it in six months. The six months came. I chickened out. I know it needs to be closer to $3,500. He's a genuinely kind person and I don't want to blindside him. Honestly, if he decided to walk, I think I'd be relieved. But I can't stand the thought of leaving him stranded, because without me he'd be in real trouble."
Here’s what I told her.
You didn't forget to raise his price. You scheduled it, watched the date come, and let it slide right past. I have done this EXACT thing, so I'm not going to pretend it's a mystery… it's scary to hand someone you like a number that's nearly double what they're used to.
Start with the math, because the math is firmly on your side. His current fee, annualized, is about $18,600 a year. On a business pulling in north of one and a half million, that's a little over one percent. Even at $3,500 a month, you're talking $42,000 a year… still under three percent of what he brings in. So let's be clear about one thing right away: affordability is not what's standing between him and staying.
And look at what that money is actually buying him. You stopped being a vendor he pays an invoice to a long time ago. You're his part-time employee now, on retainer, running his payroll, his bill pay, his invoicing, and his full books, plus chasing down a dozen credit cards he keeps forgetting to mention. All for part-time-employee money.
Time for the reframe: we fight this with facts, not fear. The fear says "this is going to blow up and he's going to leave." So let's actually look at the worst case. You ask for $3,500 and he says no. You're out $1,550 a month, which you've already told me you're making up by raising a few other clients anyway, and you're rid of the single biggest headache on your whole roster. That's the entire downside!
Not even sure $3,500 is the right number, or whether you should pad it to cover all his chaos? That's exactly what The Pricing Decision is for. Walk through the scope and the buffer and land on a number you won't second-guess the moment he pushes back.
Now here's the part I really want you to believe. You did not fail to raise this price for eight years. You SUBSIDIZED him. You kept his fee low on purpose, because you care about him and you've got history together. That was a gift… and gifts end. This raise isn't a punishment, and it isn't you finally catching some mistake. It's just the price the work has become.
Two things have to be right, or none of this holds.
First, price the chaos in. He is going to keep opening airline cards and sending invoices behind your back. He just is! So build a buffer into the fee for exactly that, so the next surprise costs him, not you. When you're getting paid for the curveballs, the curveballs stop making you resentful… and that resentment is the real thing eating you, way more than the dollars are.
Second, and this is the one almost everyone gets wrong. Do NOT hand him the new price and your list of "please stop doing these things" in the same breath. The second you do, he negotiates the behaviors instead of the fee. "So if I stop signing your name and fill out the tracker, can it stay at $1,550?" Now your price reads like a reaction to him being annoying, which makes it negotiable the moment he behaves. It is not. The price reflects what the work IS now. The behavior stuff is a separate, much smaller conversation. Keep them apart.
So here's the move, and lucky you, he's already on your calendar tomorrow!
Lead with the human, because you are one. Something like: "I've been chickening out on this for six months, so I'm just going to say it. We've worked together eight years, your business has grown a ton, and my fee has crept up slowly the whole time. I told you the next bump was coming, and here it is. Starting [date], it's $3,500 a month. It's a big jump and I'm owning that. This is what I need to keep supporting you the way your business actually requires now. I can't negotiate the number this time, but I'm glad to walk you through exactly how I got there."
Then, separately, the housekeeping. Not as the reason for the price… just while you've got him. "One other thing. I need you to stop signing my name on emails to your clients. I'm a real person out here, and it tangles me into threads I shouldn't be in. Let's set up a generic accounting team identity instead. Nothing changes for your clients, and I'd love to have it done by Friday."
And while you're at it, fix the thing that's creating half the chaos in the first place. He doesn't loop you in, so make the path so easy he has no excuse: a once-a-week automated email, same time every week, asking for the three things you need to know, with the examples baked right in so he doesn't even have to think. Any staffing changes coming? Any new cards or accounts? Any invoices you sent without me? He replies within 48 hours and that's the whole job. No tracker to go hunt down, no new tool to learn. That one little habit turns your monthly archaeology dig back into bookkeeping.
And keep one rebuttal in your back pocket, because he WILL reach for the scope. "Well, I do some of the invoicing myself, so take that off." Your answer: "Honestly, when you do it yourself and I have to reverse-engineer what happened, it costs more, not less. If anything, pulling the invoicing would push the fee up, not down." Said kindly, of course. It's just true.
That's the whole move. One email, or fifteen minutes of a call you're already having. One number, one date. And you've done a version of this before, so you already know the only two ways it goes. He says yes, maybe with a little flailing, and you're finally paid right tomorrow. Or he says no, you pour a glass of wine, raise two other clients, and get your biggest headache off your plate for good. Either way? You wake up lighter! There's no version of this where you lose.
And that stranded thing, the "he'd be in real trouble without me" thing… letting him choose to leave at a fair price is not abandoning him. If he goes, you help him land somewhere good. That's re-homing, not abandoning. You are not on the hook to charge yourself half price forever so that a grown man running a seven-figure company never has to feel a change.
One more thing… When you told me how you'd feel if he walked, the word you used was "relieved." Not panicked. Relieved. Don’t ignore that! That's how you know it's time.
Send it. You have nothing to lose!
The boundary is the service.
— Rebecca
Got a boundary you wish you could hold?
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