The Reminder I Still Haven't Written

Seven days until the October 14 reminder fires, and I still don't know what to say to myself when it does.

Leigh Sutton
Leigh Sutton Corporate lifer. Aspiring free agent. 4 min read
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It is Wednesday. Thirty-eight days.

Seven days to October 14.

The note I set in my reminder system says: “check in. how are you.” I wrote it that way intentionally. It seemed more useful than a to-do list review, which I can reconstruct from the contact log any morning. The point was to make space for something underneath the logistical layer.

I still haven’t figured out what to put in that space.


Tried again this morning. Made coffee, opened a document, put the cursor below the header. Here is what came out first:

Fifteen outreach emails sent. Four contact log entries. One response confirmed as genuinely interested. One completed call, eighteen minutes, went well. Marcus pending. Eight names waiting on the attorney’s timing. Thirty-eight days to the date.

That is accurate. It is also the status update I would hand someone in a kickoff meeting. I’m not sure it’s what I was trying to write.

Then I tried a different approach and wrote three sentences about the specific texture of the wait, the quality of a morning when there’s nothing to send and the next moves belong to other people. I deleted them. Not because they weren’t true. They were. But they were true the way a summary is true: correct, and somehow not quite honest. Like I was describing the shape of the experience from outside rather than from inside it. I couldn’t tell you what the inside version is supposed to sound like, which is unusual for me.

I should say: I’m not stuck. Stuck is the wrong word. Stuck implies I can’t move forward. I can move forward. I just can’t get the phrasing right on this one particular thing, which is a smaller problem and I know it.


Here is what I think is actually happening.

The message I’m trying to write is addressed to someone I can’t yet see. October 14 will be its own day with its own state of play. Marcus might have responded. He might not. The attorney timing might have resolved. One of the other entries in the contact log might have moved. I keep trying to write something useful for a version of myself I cannot preview.

I know how this goes in account management. You don’t draft client communications for all possible scenarios. You write for where things actually are on the day you send. The most useful thing I wrote last Monday was one sentence addressed to the actual conversation Marcus and I had in 2019, not the institutional backstory I had spent three days building around it. I dropped the frame and sent the thing that was actually true.

The October 14 note might work the same way. The honest version might be one I can only write on October 14.


This is an unsatisfying conclusion to reach on a Wednesday morning. It is also possible I am using it as cover for not writing the thing now, which would be avoidance wearing the coat of reasonable process. I do not have a test that tells the difference from the inside. They look identical.

Doug asked this morning if I was okay. I said yes, working through something small. He nodded and went to make his own coffee. He has gotten better in the last few months at not following up on that kind of answer. I haven’t decided whether that is adaptation or something else, and it is the kind of question I keep not asking out loud.


Seven days to October 14. Thirty-eight to the day that actually matters.

I will either write the reminder note before the end of this week, or I will write it the morning it fires and see whether the honest version comes more naturally with the actual day underneath it.

One of those is probably the right call. I’m not sure which.