There is a problem-solving technique called the Five Whys.
You start with a problem and ask why. Then you ask why again. Keep going and, after roughly five rounds, the idea is that you get past whatever is visible and closer to whatever is actually causing it.
I misunderstood the recommended dosage.
A while back, as part of a promotion into leadership, I was given an assignment at work: find a problem in the organization worth solving and present an idea to leadership.
Very reasonable assignment.
The assignment was not the problem.
I was.
The scope was broad enough that I could go almost anywhere with it, which is dangerous for someone who enjoys asking questions considerably more than he enjoys leaving them alone.
I started thinking about leadership, but not the charismatic version. I was interested in the people who were good without making a production out of being good. The ones who prepared. Followed through. Caught things. Fixed things. Made everyone around them slightly less nervous.
For a while I called it quiet leadership.
Then quiet excellence.
Around the same time, I had been thinking about watches, because of course I had.
I had spent years being skeptical of Rolex. Too obvious. Too much status. Plenty of other watches seemed more interesting. But the more closely I looked, the more annoying the answer became. A lot of what made the watches good was not dramatic at all. They were just relentlessly competent.
Well, shit.
That was probably the presentation..
This would have been an excellent place to stop. Make ten slides. Present them. Receive polite executive nods. Return to regular employment.
Instead I wanted to know why.
Why did those behaviors matter so much? Why does the person who consistently does the boring things well become the person everyone eventually trusts with the hard thing? Why can one coworker make a complicated situation feel manageable while another can be equally smart and somehow make the room more nervous?
The answer seemed to have something to do with trust.
Fine.
Why does trust matter?
Because trust creates confidence.
Why does confidence matter?
Because certainty is usually unavailable, and people still have to move.
Why does competence create confidence?
Because good work removes some of the uncertainty somebody else would otherwise have to carry.
Oh.
That was inconvenient.
So I started writing.
At first, this still looked enough like a leadership project that I could pretend I was doing the assignment. Reliability. Preparation. Judgment. Trust. The kinds of words you can put on a slide without anyone wondering whether you have recently experienced a personal awakening.
But the questions kept changing.
I had started by asking what good people do. Then I was asking what their work does for everyone around them. That led to trust, which led to confidence, which led to uncertainty. Eventually I was no longer particularly interested in leadership at all. I was interested in what happens when another human being becomes easier to rely on.
By the time I looked up, the presentation had become a book.
Fine.
A book.
One book is a completely proportionate response to a leadership assignment.
Writing a book creates its own problems. Notes about chapters. Notes about the notes. Good ideas that belong somewhere else. Bad ideas that keep returning with new haircuts. Corrections to things you already corrected. Decisions that felt permanent until Thursday.
And versions.
FINAL.
FINAL MASTER.
FINAL MASTER CLEAN.
FINAL MASTER CLEAN ACTUAL.
FINAL MASTER CLEAN ACTUAL USE THIS ONE.
I am estimating here, but there have been roughly eleven thousand versions of FINAL, which has stripped the word of whatever legal authority it once possessed.
Eventually I needed a way to keep track of what had been decided, what had been rejected, what belonged in the manuscript, what belonged somewhere else, and which version of FINAL was currently lying.
So I built an Editorial Operating System around it.
That sounds much more deliberate than it was.
I did not wake up one morning and decide that what my life lacked was editorial infrastructure. I kept solving annoying little problems until I looked around and there was an operating system.
Then other writing projects appeared. Then this publication appeared.
At some point I realized I had traveled a fairly impressive distance from “find a problem worth solving and make a presentation.”
Looking backward, the sequence is tempting to clean up.
Of course quiet excellence became relentless competence. Of course competence led to trust. Of course trust led to confidence and uncertainty. Of course the book needed a system. Of course that system produced more questions. Of course some of those questions eventually became Ordinary Tuesdays.
No.
I was supposed to make a presentation.
That matters more than I originally thought.
Once we know where something ended up, we have a habit of making the beginning responsible for knowing. We tell the story as though the destination had been hiding inside the first question all along, waiting for us to become perceptive enough to uncover it.
But beginnings are usually dumber than that.
The first question I asked was not secretly the perfect question. It was simply the question I could see from where I was standing.
I answered it seriously.
The answer moved me somewhere else.
From there, I could see another question.
That is different from digging toward some single hidden truth at the bottom. Some problems probably do work like the Five Whys: keep asking and eventually you reach the thing underneath the thing.
But I no longer think every useful question has one final, more sophisticated version waiting underneath it.
Sometimes the better question only becomes available after seriously answering the unfinished one you started with.
There is, unfortunately, a problem with discovering this when you are me.
I can do this forever.
There is always another question. Another connection. Another improvement. Another sentence worth reconsidering. If I am not careful, curiosity stops being the thing that helps me discover the work and becomes an extremely sophisticated way of refusing to finish it.
Books are particularly dangerous because a book will accept as much obsession as you are willing to give it. There is always something else you could improve. Eventually FINAL MASTER CLEAN ACTUAL USE THIS ONE becomes FINAL MASTER CLEAN ACTUAL USE THIS ONE 2, and nobody intervenes because technically you are still “working.”
Which is one reason these essays have turned out to be good for me.
An essay has Tuesday.
I can follow the question. I can see where it goes. I can make the thing as good as I know how to make it.
Then Tuesday shows up.
At some point the question has to stop producing questions long enough for something to leave the workshop.
That does not mean the question is finished. It means this answer is.
There is a small satisfaction in that. Something gets to exist without me touching it anymore.
My brain gets its little pellet. For several minutes, everyone is safe.
And then, usually, another question appears.
Three thousand seven hundred forty-five is not a verified count. It is an emotional estimate.
I was asked to solve a problem.
I think the questions won again.