After the Checkpoint

October 14 had been on my calendar since May. Yesterday it came and went. Today is just Thursday.

Leigh Sutton
Leigh Sutton Corporate lifer. Aspiring free agent. 4 min read
A woman savors a hot drink by a sunlit window in an urban setting.
Photo by Melanie Brumble on Pexels

Wednesday had been on my mind since May.

I don’t mean I was dreading it or counting down to it. I mean it was there. A fixed point I set for myself before I fully understood what I was measuring. When I did the backward map, I put October 14 in the calendar as a check-in and it sat there for five months the way a dentist appointment sits there: noted, occasionally uncomfortable to look at, at least useful once a year.

I passed it. I said what I had to say about it yesterday. And then I closed the laptop and the day ended and I thought: tomorrow it will be October 15.

Now it’s October 15.


The quality of the morning after a self-imposed milestone is something I had no reference for. I spent most of my career working off other people’s calendars. Other people’s fiscal years, sprint cycles, quarterly closes. When a checkpoint passed, the next one was already on the shared calendar. Someone had populated it. The structure renewed itself, and all I had to do was show up to the next thing.

This morning I made coffee and the day had nothing that had to happen.

I mean that literally. Nothing was urgent. Marcus hasn’t written back, which is now four days since the follow-up. The referral name from the four-year-gap call is still just a name in a note I haven’t opened in two weeks. The contact log has four entries.

I sat with that for a while. Then I opened the document and tried to write the thing I’ve been promising.


I told the stranger whose sister is leaving in November that I was working on the fear-of-the-first-month post. That’s accurate. I have been working on it the way you work on something you can’t finish because you’re still inside the material. Four days left in month one. If I don’t write it by then, I’ll be writing it from the wrong side of the line I drew.

I wrote one sentence. It was: The thing I am afraid of is that I did everything right and it didn’t change anything.

I stared at that for a while. It’s not quite right. Closer than I want it to be, which is different from right.

“Did everything right” is too clean. I sent emails when I should have made calls. I have a referral name I haven’t touched in two weeks. I built a contact log and I open it the way I used to open the work dashboard, which is productive-feeling and not the same as taking action. So it’s not that I did everything right.

What I think I mean is: what if I did enough right, and the mechanism is slower than I expected, and I genuinely cannot tell from inside October 15 whether that’s normal or a problem?

That’s the specific shape of it. Not a failure I can name and fix. A wait that’s longer than I have been trained to tolerate, without anyone to send me a note that says you’re on track or here’s what’s next. I was good at my job for twenty-four years. Part of what I was good at was knowing when things were going to close. I have lost that signal. I don’t know yet if I will get it back or if I need to replace it with something different.


I’ve been treating dates as things to pass. October 14. October 19. November 14. I set them, I build toward them, I check them off or I don’t. That worked for most of my career because the dates were mostly about other people’s needs. The contract renewal window. The annual review cycle. Even my own backward map was structured around someone else’s eventual decision, a client who would say yes or not.

But I set October 14 myself. And when it passed, the only person keeping score was me. That’s the thing I’ve been circling without naming: there is no external confirmation available. There is only what I know, and four columns in a Google Doc, and Marcus who hasn’t written.

I looked at the referral name this morning and closed the note without emailing. I can’t tell yet if that’s caution or avoidance. I know the difference between the two most of the time. Not today. Today I am going to find out what Thursday looks like when the calendar has nothing marked, and I’m going to try to be honest about what I find.

The document sentence is still not written. Four days.