The One I Sent First

I sent the email. Now there are three more names. I'm starting to understand why I sent the one I did.

Leigh Sutton
Leigh Sutton Corporate lifer. Aspiring free agent. 4 min read
A ceramic mug on a wooden desk with flowers in the background.
Photo by Lisa from Pexels on Pexels

The dog and I did the loop at 6:15. Thirty-five minutes, same route. I did not rehearse anything, which was unfamiliar in a way I am still thinking about. For five days I walked that loop running the opener, the second paragraph, the one word I kept changing and changing back. Yesterday morning I hit send. This morning I just walked.

I checked my phone before I left the house. No response. Twenty-two hours in. I was not expecting one. I keep reminding myself of this. I am going to keep reminding myself.


There are three more names in the note.

I looked at them last night after dinner, which felt responsible, and again this morning, which felt more like something I needed to catch myself doing. I have a reason not to send the next one yet: I want to see how the first email lands before I adjust the approach. That is a real reason. Real and convenient are not mutually exclusive, and this morning I was trying to be honest about how much work the word “real” is doing.

The email I sent was to someone I’ve known for twelve years. I built most of that relationship before I ever worked at my current company. We have had conversations that had nothing to do with accounts or pipeline or renewal windows. She knows me. Not just who I am at the company. Me, at a reasonable distance from the badge.

When I went through the names list, I told myself she was first because of the twelve-year relationship, the history, the fact that she’s one of the four cleared to contact. That’s all accurate. But standing on the sidewalk at 6:45 this morning, letting the dog investigate a mailbox for reasons I will never understand, I added the part I had left out: she is also the name where I am most sure I will be recognized as myself.


The ninth question is still in the room.

How much of what walks into a room is me, and how much belongs to the institution. I sent from a personal email address. That was the clearest signal I could send. But a signal is not the same as evidence, and I know this, which is probably why I am checking my phone.

The three remaining names: shorter histories, or contexts where the badge was always the visible thing, or the one with a three-year gap that I still don’t know how to open. Those are harder tests of the question. I am not saying I am avoiding them. I am saying I can tell the difference between a test I’m ready for and a test I’m ready to take, and I’m trying to be honest that those are not always the same thing.

The person I emailed yesterday is the one where I had the highest confidence going in. That made sense to start. It is also an entirely comfortable reason to stop.


I checked the blog stats this morning. I noticed I was checking the email and the stats in the same motion, which I did not see until I saw it. Both are the same act, I think. Looking for evidence that what I’m doing is real. That there is something on the other side of the window.

The number went up. Someone left a comment. I read it twice and closed the tab because I didn’t know what to do with it, which is its own kind of information.


The three names are still in the note.

I am not sending the next one today. I’m going to wait for the response, or for enough time to pass that I can say the waiting portion is complete. I don’t know which condition arrives first.

What I know: I sent the safe name first. I know that now in a way I wasn’t entirely naming to myself when I hit send yesterday at 6:47. There’s nothing wrong with it. You start where you’re most sure. What I am trying to figure out is whether knowing it counts for something, or whether knowing it and doing it anyway is just watching yourself do the thing instead of stopping it.

Those feel like different things. I have not been able to explain the difference yet.