⚡ Today's level-up ⚡
Last week I told you the human has to create the event and check the work. Then I turned that on my own business and found a hole I had never once looked at. Here is what fell through it.
On Wednesday, I looked under the hood at my own operations. Not the writing or the lessons, but the billing—the boring part I've never enjoyed, and therefore never examined.
Here's what I found.
When a member's card was declined at renewal, my system attempted a single charge. It failed. Then nothing happened. No second attempt. No email telling them. A couple of weeks later, the membership was quietly marked unpaid, and that person stopped being a member.
They never knew. I never knew.
Those were not members that churned. They were ones removed by a broken communication process.
Then I checked the next setting, and the next. Every customer notification in my billing system was switched off. Every single one. Not one of them had ever been turned on.
This means a member could be charged for another year without hearing from me first.
I wasn't caught off guard, exactly. What I felt was frustration, and not at anyone else. At myself for not getting ahead of something I suspected could happen. But I never checked, so I assumed I would hear about it directly if anyone was disappointed.
My first thought was: how would I react if that happened to me? Sure, it says annual membership on the page when you sign up, but it's still not good service.
What I told you last week
The human must create the event and check the work. The evidence has to come from outside the system.
I was mostly writing about AI systems. Then I went and looked at my own business.
The part I'm least proud of
When someone did notice, and wrote to me about it, I handled it personally. One at a time. Apologizing.
I'd been calling that customer service. It isn't. It's a missing system with me standing in the hole.
And standing in the hole doesn't scale well, or, more importantly, deliver the type of experience I know is possible.
The ladder isn't (really) about AI
Last week I drew a ladder that included prompt → context → loop → graph and called it a map of how sellers evolve in working effectively with AI.
I had it slightly wrong.
The four eras aren't really about AI. Instead, they describe which events have a human checking them.
I'm at the top of that ladder on the part of my work that gives me energy. All of my writing—whether for my book, the weekly essays and lessons, or posts on LinkedIn—runs through a graph. Instead of a blank page, I start with raw voice notes and ideas as inputs; then I set up separate workers to absorb my old content, draft, and cut; then a dedicated detector grades the result; and finally, I decide what survives, where I then do most of my actual writing.
It’s not just a modern way to write; it’s a different form of work altogether. It’s orchestrating.
However, I'm at the bottom of this ladder on the parts that drain my energy. Things like renewals and billing—you know, all the unglamorous stuff that you don’t want to do, but still has to get done.
Nobody was checking those events, and when I finally did, I could see things were broken.
Your version of this
This isn't just a simple billing problem. It's the same shape everywhere you look in a sales role:
The deal you keep in commit this month because it was committed last quarter, but still has no definitive next step agreed to by the customer’s Mobilizer (if one has even been identified at all).
The comp plan you signed in January and have never modeled against your actual pipeline.
The account you inherited with a renewal date you've never once looked up.
The role you've been in for three years without asking whether you’re still growing.
Every one of those is running on autopilot with nobody checking. Not one of them is an AI problem. Putting a model on top of an unchecked event just gets you to the wrong answer faster, and with more confidence.
Pick the one you've been avoiding. Go look at it this week—it'll take about ten minutes, same as it took me. Then hit reply and tell me what you found.
Here’s what one subscriber wrote in after last week's essay:
For me, as an enterprise seller in the AI space, it's about breaking through the noise to get the initial conversation, even with people I know or have worked with in the past. Even with an on-trend, differentiated product, it is hard to get that initial conversation. I'm good once I get that discovery call going.
The answer isn't a better cold email.
It's building the point of view underneath the email, so what you send is something only you could have written. That's a system, not a message. I've been walking two members through building exactly that over the past two weeks, and it's the heart of what I'm putting together next.
What I'm doing about it
Two changes. Both made this week.
1.) Nobody gets charged by me without hearing from me first—a real email, thirty days ahead, every time, from now on. And if a payment fails, the system now retries properly and tells you it happened, so nobody gets dropped in silence again. All of it took about ten minutes to turn on. It should’ve been enabled two years ago.
2.) I'm not going to auto-renew anyone into something I haven't finished.
I'm in the middle of editing my upcoming book, and it deserves a lot of my attention. So, Learning Path 6 isn't built yet. I've been quiet on LinkedIn on purpose, and this newsletter has slipped from Wednesday morning to Friday to whenever I surface. Charging a full year for that and hoping you don't notice is exactly the kind of unchecked event I just spent 800 words complaining about.
Why now, and not later
I could wait until Learning Path 6 is finished and do this from a position of artificial strength. I'd rather just own it and do it now.
Here's why.
I came up in an industry where I watched “influencers” who never earned serious money while they were actually selling turn around and try to teach others how to do it once they had left. I won't name names, but it never sat right with me.
I gave myself a long financial runway inside strategic corporate sales. I don't need to squeeze more income out of this year. So I'd rather take the income off the table, build the thing properly, and charge for it when it's real—at the standard I’d appreciate as an active seller.
To be clear about what that means for you: the knowledge stays free. The essays, the frameworks, the breakdowns—same as always. What I'll charge for is the practice. You can get a framework from the same AI I use. What's scarce is having someone who's actually done it look at yours and tell you the part you got wrong.
Whether you’re a free subscriber or a paid member, you’re going to see some changes from now and through the rest of the year, which feels to me, for the better.
Why I’m the one saying this
I'm still in the early stage of running everything myself, and I'll be the first to say I don't know what I don't know. But I've tried it once. Before I took my first Account Manager role, I tried to get a DJ business off the ground with little entrepreneurial skills, no financial runway, no assets, a makeshift plan, and a ton of personal debt. Maybe I could’ve figured it out back then. Honestly, I just wasn't ready. A career in sales gave me what I needed this time around.
What's different now isn't confidence. It's that I finally have the four things I keep writing about: a real financial runway, actual options, ownership of my own calendar, and a craft I'm still working at. That's what lets me make a decision like this one rather than chase the money.
Mind you, the chase for “more” never stops. I have to work purposefully to keep my priorities in check. Nearly everything I see in my LinkedIn feed is just someone selling a shortcut and trying to get rich off it. I think of those as “sugary snacks.” You can live on them for a while, but you can’t live on them forever.
Here’s to choosing a different path.
Stay human, friends.
