How to Stop Overthinking Something (Before You Make Another Spreadsheet)
There comes a point when you have thought about something so much that you are no longer making progress.
You are conducting surveillance.
You check on it, revisit your notes, Google one more thing, and reopen the tab you closed yesterday because apparently Past You knew something Current You does not.
Maybe you make a spreadsheet.
This feels productive because spreadsheets have columns.
But three days later, you still haven’t made the decision, sent the email, fixed the paragraph, picked the thing, started the project, or figured out why something that seemed like a perfectly good idea last Tuesday now has seventeen known complications and a small advisory board.
At this point, I have a suggestion:
Ask another human.
I know.
After all that research.
We Have So Many Ways to Avoid Doing This
To be fair, we live in an extraordinary time for people who would prefer to investigate something privately until we have achieved absolute certainty.
Google will give you approximately 84 million results. Reddit has a guy. YouTube has a 47-minute video filmed inside someone’s car. There is almost certainly a quiz.
You can read reviews written by people who are furious about circumstances so specific that they raise more questions than they answer.
One star. Did not fit properly in my 1998 Winnebago.
Okay, Gary, but I’m buying a toaster.
And now, of course, we have AI—which I say with great affection as someone who has absolutely asked ChatGPT questions that did not require the computational resources of a large language model.
Sometimes all that information is exactly what you need.
Other times, you cross some invisible line where you now know too much. You started out trying to choose a new desk chair and somehow ended up reading about lumbar-support standards in Scandinavian workplaces. You wanted to know whether one paragraph made sense and have now moved the same sentence back and forth four times. You had a pretty good idea until you researched it.
That last one gets me.
Because there’s a point where the problem isn’t missing information. You’ve just been standing two inches away from the thing for so long that you can see individual pixels.
Time to Bring in Outside Counsel
One of the most useful phrases in the English language has to be:
Can I run something by you?
It requires almost no ceremony. You can show up with an idea you’re excited about, two options that both seem reasonable, something you’ve made and want another set of eyes on, or the beginning of something you haven’t quite figured out yet.
Or, sure, you can arrive carrying a metaphorical banker’s box containing 600 pages of evidence and say, “Okay, here’s the situation.”
I support this.
The beauty of involving another person is that they missed the previous 47 meetings you’ve held with yourself.
They have no idea which parts you stopped questioning two weeks ago or that Option C was formally eliminated in an internal ruling on August 14. They might notice the thing you forgot was unusual. They might ask about something you thought was settled. Or you might get three sentences into explaining the situation and realize you already know what you think.
Annoying.
Could’ve saved a lot of time.
And sometimes there isn’t a problem to solve in the first place. You can run something by someone because the idea is good and you want to play with it, because you made something you like and wonder what else it could do, or because you're considering something that sounds fun, interesting, mildly irresponsible, or all three.
This is also how one idea occasionally becomes three ideas and an entirely new project you had no intention of starting.
I said another person could help.
I did not say they would reduce the number of tabs.
In Retrospect, This Makes a Lot of Sense
I've spent an unreasonable percentage of my adult life responding to some version of “Can I run something by you?”
I have a Ph.D. in how people learn and communicate, years of teaching and research experience, a background in corporate leadership, multiple businesses, and what can only be described as a recreational relationship with research. Somewhere in there, my brain apparently became permanently configured to go:
Ooh. Okay. Hang on.
And for whatever reason, it does not take people very long to start handing me things.
An idea. A question. Something they're working on. A decision they're trying to make. A “Okay, tell me if this is ridiculous...”
I don't know what I'm doing to encourage this, exactly, but I would like to be clear that I am in favor of it.
If I think what you’ve got is great, I’ll tell you it’s great. Then I'll tell you why it's great, which part I especially like, the thing you did that I hope you absolutely do not touch, and probably something else I noticed while I was in there.
And this is where I should probably disclose that I am physically incapable of giving the two-word version of feedback.
If you ask me to “take a quick look,” I understand all four of those words individually. It's when you put them together like that that we run into trouble. “Looks good!” becomes four paragraphs.
I have accepted this about myself.
And none of it comes with judgment attached. Bring me the half-baked version. Bring me the thing you’re not sure makes any sense. Bring me the idea that seemed considerably better before you tried to explain it to another person.
I’ve seen things. We’re good.
And I have absolutely no expectation that you’ll tidy it up before you hand it over. That would rather defeat the purpose.
Which, come to think of it, probably explains why people keep handing me things.
Before You Commission Another Spreadsheet
If you have reached the point where you are zooming in, zooming out, changing it back, reopening things you already closed, or conducting searches that are becoming increasingly difficult to explain, we may need to confiscate your research privileges for a minute.
Nothing permanent. You can have them back.
Probably.
1. Go Do Something You Actually Like
For ten minutes. An hour. Overnight. Whatever gets you far enough away from the thing that you stop seeing its individual molecules.
Read a book. Play a game. Watch something stupid. Go outside. Make an unnecessarily elaborate snack. Put on a song you haven't heard since 1997 and spend four minutes remembering an entire person you forgot existed.
Anything except continuing to work on the thing.
And no, moving from the laptop to your phone and Googling it from the couch does not count as a break. I admire the loophole. Denied.
Sometimes ten minutes is enough to come back and immediately see what was bothering you. Sometimes the draft needs to spend the night alone and think about what it’s done.
Either way: Don’t. Touch. One. More. Tab.
2. Let the Less Reasonable Parts of Your Brain Have a Turn
You have already given logic the floor.
Logic has charts. Logic has evidence. Logic has been recognized by the chair approximately 47 times and would now like to submit an addendum.
Maybe we hear from somebody else.
Pull a tarot card. Journal for five minutes. Flip a coin. Take a shower. Go for a drive. Organize something completely unnecessary. Use whatever slightly less analytical method already works for you.
You are not handing executive authority to the Queen of Wands.
You’re just changing the question from What else can I figure out? to What do I notice when I stop trying so hard to figure it out?
Flip a coin and immediately wish it had landed the other way? Interesting.
Pull a tarot card and instantly begin arguing with it? Also interesting.
Sometimes your reaction gets to the meeting before your reasoning does.
3. Consider the Possibility That It Is Already Fine
I know. Offensive.
But sometimes the 17th pass isn't happening because the thing still needs work. It's happening because you would like to achieve the mythical state known as Just Right, at which point a small bell will ring, woodland creatures will appear, and you will know with absolute certainty that no further improvements could possibly be made.
This has not been my experience.
Sometimes the email is ready. The draft works. The idea is good. The decision is reasonable. You have simply looked at it long enough to become aware of every molecule.
At some point, the best version of the thing may be the one that's finally out there in the world going:
Hi.
Honestly, good for her.
4. Do One Thing That Makes It More Real
Not finish it.
Not make the decision.
Not determine the optimal path forward through Q4.
Just move one tiny piece of it out of your head and into the physical universe.
Print the draft. Send the inquiry. Request the sample. Put the date on the calendar. Open the application. Buy the domain. Text the person. Write the first sentence somewhere other than the document you've been staring at like it owes you money.
Pick something small enough that your brain doesn't have time to convene another subcommittee.
The goal isn't to trick yourself into productivity. It's to give yourself new information—the kind you can only get by doing something instead of continuing to think about doing it.
And sometimes, after ten minutes away, a mildly insubordinate tarot card, permission to let the thing say Hi, and one tiny move into the real world, everything looks different.
Other times you come back, look at it with relatively fresh eyes, and think:
Okay. I still want somebody else to look at this.
Excellent. Now we know what we're dealing with.
So, Run It By Me
The next time you find yourself thinking, I really need to run this by somebody, you can send it to me.
That’s Run It By Me.
It’s a monthly email membership where you can send me whatever you’ve got, and I’ll take a look, ask questions, tell you what I notice, and tell you what I think. And because we’ve already established that “take a quick look” is a phrase I interpret rather loosely, you can keep the conversation going all month.
Fair warning: this may result in clarity, a decision, a better idea, or three entirely new tabs.
I can only do so much.
