Most operational pain isn’t the work itself. It’s everything around it. AI is supposed to help, but we’re stuck in the awkward middle where implementation is just another thing on the pile.

Most operational pain isn’t about the actual tasks. It’s the stuff around the tasks.
The request sitting in an inbox that should’ve been routed somewhere. The follow-up you’re tracking in your head because you’ve been burned before. The fifteen minutes lost every time you switch between apps just to find where something lives.
The work itself is usually fine. Sometimes you even enjoy it. When you can actually do it.
But you can’t. Because you’re managing the chaos that was supposed to manage the chaos.
And it probably will. Eventually.
But right now? We’re in the awkward middle. The promise is real. The implementation is another thing on the list.
Another system to evaluate. Another tool to learn. Another integration that needs babysitting. And the day-to-day doesn’t stop to let you figure it out.
Nobody really talks about this part. The gap between “AI can automate that” and “AI is actually automating that for us” is real. It’s full of migration headaches, training hours, weird edge cases, and the slow realization that “plug and play” assumed your data was clean and your processes were normal.
So the boulder stays. Not because something better doesn’t exist. But because “better” takes time you don’t have while you’re still buried.
Every new tool costs more than the subscription.
There’s the learning curve. People reading documentation instead of doing their jobs. There’s the opportunity cost. What didn’t get built? There’s maintenance. Who picks up the phone when it breaks?
And then there’s the quiet one: the mental overhead of another login, another system, another place where the thing you need might be hiding.
Sometimes the fix just adds more weight.
That doesn’t mean new tools are bad. It means you have to be honest about what you’re actually solving. And whether now is the time.
The teams that seem to have this figured out aren’t running the most tools. They’re running fewer. And they’re brutal about what earns a spot.
They ask uncomfortable questions. Does this remove a step or add one? Does this save time or just report on where time went? Does this match how we actually work or how a product manager somewhere imagined we might?
They go deeper on fewer things. They accept that good enough beats perfect. They stop waiting for the ideal solution and start making small changes that stack.
And they build systems that work without someone watching them.
The point isn’t to automate everything. It’s to stop carrying stuff that doesn’t need to be carried.
Some things need a human. Some decisions need context that no tool has. Some work is just better when a person who gets the nuance handles it.
The goal is to protect that. Let the human stuff stay human. Let everything else run without you hovering.
That’s not a tech problem. It’s a design problem. Most teams haven’t thought about it that way yet.
If you’re stuck in the awkward middle, you’re not behind. You’re normal.
This stuff takes time. One process. One integration that actually works. One tool that finally earns its keep.
The boulder doesn’t go away overnight. But it gets lighter.
11 years of "can you make these things talk to each other?" - turned into a career.
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