WHERE IT'S BREAKING

Nothing Was Technically Broken. The Business Was Just Hard to Run.

There’s no fire. No disaster. The business is doing fine. Customers are happy, mostly. The team is good. Revenue is okay, maybe growing.

But every week feels heavy. The owner approves a dozen small things. Somebody double-checks a report because they don’t fully trust it. Information gets typed into two places. A new hire asks the same question for the third time. A spreadsheet gets rebuilt every month. The owner gets texted on a day off. Two people do the same task two different ways. Something falls through the cracks, gets caught, gets fixed, and nobody changes anything so it doesn’t happen again.

None of these is a crisis. Each one takes a few minutes. Together, they’re the reason the owner is tired.

What the owner thinks

“This is just what running a business feels like.” And for a long time, it is. Every business has friction.

But there’s a point where the business has simply outgrown the way it used to work. It’s not broken. It’s just harder to run than it should be. And because nothing is technically broken, it’s easy to keep living with it.

What I’d investigate

I’d look for the clusters. Not every annoyance, just where they pile up:

  • Owner approvals. How many decisions still need the owner?
  • Manual checks. What gets double-checked because people don’t trust it?
  • Double entry. What gets typed in more than one place?
  • Inconsistent ways. Where do people do the same thing differently?
  • Unclear ownership. What has several people involved and nobody responsible?
  • Knowledge stuck in heads. What can only one person answer?
  • Workarounds. What spreadsheet, side channel or habit exists because a tool or process doesn’t fit?

Then I’d look for connections. Because here’s the thing that makes this kind of business interesting: the symptoms are usually connected.

The time entry habit, the billing delay, the owner double-checking invoices, and the report nobody trusts might all be one problem. The approval bottleneck, the new hire’s questions and the dropped follow-ups might all be one problem: nobody decided who owns what.

What’s underneath it

Accumulation. Every fix-around made sense when it happened. Somebody built a spreadsheet because the tool didn’t do something. The owner kept approving things because it was faster than explaining. A process stayed in someone’s head because there was never time to write it down.

None of those were bad decisions. They just added up. And at some point, the pile of reasonable workarounds became the way the business runs.

What I’d change

Not everything. That’s the trap. When everything is a little annoying, the temptation is to fix it all at once, and that’s how you end up with a big project nobody finishes.

I’d map the friction, find the two or three root causes behind the most symptoms, and pick one. The one that would make the biggest difference, the soonest. Fix it properly. Then the next.

One active priority. Everything else goes in a queue.

What I’d leave alone

Anything that’s fine. Not every workaround needs fixing, and not every manual step is a problem. And everything except the current priority, until it’s done.

The tradeoff

Fixing one thing at a time feels slow when everything is annoying. But fixing one root cause often clears up several symptoms at once, and it actually gets finished.

Why this matters

This is the kind of problem that’s hardest to ask for help with, because it’s hard to name. It’s not “our software is broken” or “our numbers are wrong.” It’s “everything is a little harder than it should be,” which doesn’t sound like a reason to call anyone.

But it is. Sometimes the problem isn’t one thing. It’s the pile.

And you don’t need to know what to call it before you ask. That’s the whole point of a Systems Fit Call. Fifteen minutes. Bring me the messy version. I’ll ask questions, tell you what I think is actually going on, and tell you what I’d look at first. If I don’t think you need me, I’ll tell you that too.

If you want to start on your own: write down every small annoyance from one week. Don’t filter. At the end of the week, look for the ones that are connected. That’s usually where it’s breaking.

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I write Quit Winging It, a free newsletter about running a business, leadership, ADHD and figuring things out as you go. It's not about having everything figured out. It's about not winging the same thing forever.

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