Back when I was practicing law, I created an automation that used the terminal, AppleScript, and chewing gum to make a weekly status report for the staff.

It was formatted beautifully. It went out like clockwork, and I spent too much time building it. Then one day in a meeting I asked about something from that week’s report. Nobody had read it. Not once, not ever.

I want to tell you the lesson there was about automation. It wasn’t. The report ran perfectly. It just should never have existed.

I’ve spent twenty years teaching people how to make their technology do their work for them, and the question I get most is some version of “how do I make this faster”. While that’s a fine question, it shouldn’t be the first question. The first one is whether the thing should exist at all.

We reach for optimization because it’s progress you can see. You learn a tool, you wire two apps together, the system looks sharper today than it did yesterday. It scratches the same itch as tidying the shop. But speed is only a virtue when you’re pointed the right way. Going faster down the wrong road just puts more distance between you and where you actually needed to be.

AI has poured gasoline on this. The models are eager to please, and they express that eagerness in prose. Ask one for help and it will happily hand you a report, a summary, and a plan, all beautifully formatted, all about something that only glances off what you care about. Tokens are sacrificed. Nothing gets read. It’s my weekly report again, except now it runs every morning.

Optimization can also be an excellent procrastination tool. When I’m avoiding hard work, I don’t go watch television. I go tune my system.

It feels virtuous, like I’m investing in some more efficient future. When really I’m running out the clock on something difficult. Interestingly, and almost always, the system I’ve suddenly decided to improve is the one attached to the work I don’t want to do.

So the question I try to ask now isn’t how to do a thing faster. It’s whether the thing deserves my hours at all. Relevance before speed.

And to know whether something is relevant, you first need to know what relevance means to you. That’s a tough question, but everything else runs downstream of it.

That is why the Productivity Field Guide is so important to me. It’s the result of my own journey of figuring out what actually matters.

So the next time you catch yourself reaching for a clever fix, pause long enough to ask whether the thing is worth doing at all. Sometimes the answer is yes, and then go build something great. Often the answer is no, and that’s the better result. Cross it off and get back to the work that matters.