Hi Friend,
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.
Your pal,
David
P.S. I'm trying something new. I made a video based on this newsletter, and you can watch it here. I'd appreciate you checking it out. That'll help me get this message to more people.
Read this post on macsparky.com
This Week in the MacSparky-Verse
One app update and three podcast episodes went out on the public side this week.
- On Focused 261, Mike and I take apart our complicated relationship with measurement. Goodhart’s Law, law school rankings, and the bathroom scale all make the same case, that a number stays useful only as long as you still remember what it stands for.
- MacWhisper 14 adds a new Editor View, so you can fix a transcript, reassign speakers, and flag the parts you want to keep without leaving the main screen. I also passed along a warning about scam .org sites impersonating MacWhisper and shipping malware in the download.
- On Intentional AI 5, Chris Bailey and I get into where the dragons actually live with AI. It’s good at planning and it’s great at logic. The trouble starts in execution, when you let it think for you.
- Mac Power Users 859 is the one to lock your wallet for. Stephen and I go through the bags, chargers, batteries, and fitness trackers we normally only mention in passing, and there’s a home theater confession I’ve been avoiding for years.
In the MacSparky Labs, we covered a lot:
- The Q3 planning session recording shipped, including where AI belongs in a reflective practice and where it doesn’t
- I made a video on Siri’s new speed and drama dials in iOS 27, which I thought were a dumb idea until I spent time with them
- I made another video sharing a shell script that ejects every external drive with one keystroke, and checks Time Machine first so a running backup doesn’t get corrupted
- We had the Book club meetup on Rick Rubin’s The Creative Act, and how you make room for creative work when the day is already full
- I published The Lab Report podcast current apple news and rumors, including Apple retiring the iPhone Upgrade Program and replacing it with a lease
That was a single week, and the Labs run like this every week. If that sounds like your kind of place, come join us.
This newsletter is sponsored by iPhone Life. With iOS 27 arriving this fall — featuring the greatly anticipated Siri AI — now is the best time to tune into a trustworthy source of Apple tips.
The Tip of the Day Newsletter by iPhone Life goes after the stuff that doesn’t get written about as much — the buried settings, the shortcuts you never thought to look for, the features that have been sitting there for years.
It’s free, and over 700,000 people subscribe because it delivers exactly what it promises, every single morning.
Subscribe for free and get your first tip today →