Hi Reader,

A few years ago I saw a functional medicine doctor for the first time.

I came in with one complaint, expecting a quick answer and a prescription. Instead she spent the first hour asking about everything else. Sleep, stress, what I ate, what my life looked like ten years ago. She wasn't treating the thing I walked in with. She was trying to figure out what was behind it.

I've thought about that visit a lot since. It's close to how I try to work with a business.

What I'm noticing

Most business help is urgent care. Something hurts, a metric drops, a launch slips, a team keeps missing its dates, and the instinct is to treat whatever's in front of you. Reach for a tool. Add a process. Ship a fix. It feels good, fast. Then the same problem shows up again a quarter later, somewhere else.

I saw this recently with a team that was sure they had a reporting problem. Their dashboards were a mess, so they wanted help choosing a better tool. But the mess turned out to be downstream of something else entirely: nobody had agreed on what the numbers were for. Three teams, three definitions of the same metric. A shiny new tool would have just made cleaner-looking versions of the same confusion.

AI makes this even harder to resist. When you can generate a fix in thirty seconds, why would you slow down to diagnose? But if you've aimed at the wrong problem, the fast fix doesn't help. You just end up back in the same spot a few months later.

This is a rhythm I learned as a Site Reliability Engineer. When a system goes down, sure, you restart the server to stop the bleeding, you have to. But you don't stop there. You run the postmortem afterward and trace the failure back to what caused it, because the restart only bought you time before the same thing takes you down again. Functional medicine does that for a body. SRE does it for software. I try to do it for a business.

Your next move

"Automate yourself" has never meant automate the thinking. Automate the busywork all you want, the reporting, the formatting, the follow-ups. The diagnosis is the part to do yourself: figuring out what problem you're solving before you build anything to solve it.

(I hand clients a magnet with one question on it: "What is the problem we are trying to solve?" It has saved more projects than any tool I've recommended.)

So this week, pick one problem you keep re-fixing, and run a tiny workup before you touch it again:

1. Name the symptom precisely. What hurts, and how would you know it got better?
2. Ask what changed upstream. When did this start, and what moved right before it?
3. Keep asking why. Engineers call it the five whys: the first cause you find is usually still a symptom, so ask what's behind that one, and the one after it. You'll feel when you hit the bottom.

Then fix the thing you find at the bottom, not the thing you walked in with. If the workup turns up more than you expected, hit reply and tell me what you found. That's usually where the real work is.

Life beyond the screen

The funny part is that my visit worked. Not because of any one prescription, but because someone finally looked at the whole picture instead of the loudest complaint.

I catch myself needing the same reminder at home. The loudest thing in a hard week is usually not the thing that needs attention. The kid melting down isn't really upset about the shoes. The tension at dinner isn't really about the dishes. When I slow down enough to ask what's underneath, the real thing is usually quieter, and a lot more workable.

A question for this week: What's one problem you keep treating that never quite goes away, and what might be sitting upstream of it?

Work with me directly. If you want a thinking partner on your product strategy, AI rollout, or building your fractional practice, here's how I work with people: https://gamma.app/docs/Chill-Labs-Coaching-Information-ifjuyb0hjgw9xtb​

Come to the next Water Cooler 🚰 I host a free monthly gathering for people building fractional and independent practices - honest conversations on positioning, pricing, and pipeline, plus recaps when you can't make it. Come to the next Water Cooler 🚰 On Thursday, September 24 (9am PT), I'm hosting Sara Royf, a LinkedIn coach who's helped 200+ consultants build predictable pipelines. She's walking us through how to start conversations that lead to booked calls, warm or cold, with word-for-word scripts and a live "hit send" exercise. It's free. Save your spot: https://luma.com/w53o3qmx​

Let's Chillaborate,

Dina

Founder, Chill Labs

PS: New to the Automate Yourself podcast? There are plenty of episodes worth digging into - start anywhere: https://chillaborate.com/podcast 💙