What You Know the Second Time

The second outreach email took forty-five minutes. The first one took three weeks. Not because it mattered less.

Leigh Sutton
Leigh Sutton Corporate lifer. Aspiring free agent. 4 min read
Flat lay of a blue laptop, coffee, and notebook on a table with shadows.
Photo by Samer Daboul on Pexels

The second email took me forty-five minutes.

The first one took three weeks, if I count from the moment I opened the draft to the moment I hit send, which I do. Twenty-one days of writing a sentence, reading it back, deleting the sentence, going to make coffee. I sent it at 6:47 on a Monday morning before I could talk myself out of it.

Yesterday I sat down after lunch and wrote the second one in forty-five minutes. Not because it mattered less. Because I knew something I hadn’t known when I wrote the first.


What I knew: that there is a human on the other end.

This sounds obvious. Of course there’s a human. I have been sending emails to humans for 24 years. I am not new to this.

But the first email, I sent it to an idea. To an abstract concept of a person who might read it and respond or not respond and I wouldn’t know what a response would even look like. I didn’t know what I was asking for exactly, so I couldn’t know what receiving it would feel like.

Now I know what thirty words looks like. I know it looks like: I’ve been thinking about this too. I’m willing to give you thirty minutes. That’s enough information to change how you write the next one. The hypothetical becomes a thing that can actually happen. I’m no longer testing a theory. I’m having a conversation.


I almost opened the second email with my credentials. Leigh, 24 years in enterprise SaaS, Senior Director at a company you’d recognize. I got two sentences in and then I stopped and read what I’d written and deleted it.

The first email didn’t open that way. I opened with a question about a problem I’d watched go unaddressed for years. Not my credentials. A problem they probably already knew. The credentials came in later, briefly, as context, not as a door.

I don’t know exactly why the first one worked. I have theories. But I caught myself about to abandon the approach that got a response in favor of something that would feel safer to write, which is not the same thing as safer to send. Those two things are different and I forget that more often than I’d like.

I deleted the credentials. Opened with the question again, a different question for a different person. The rest came quickly.


I checked the analytics this morning. Not obsessively, more in the way I now check email, which is a motion I’ve added to my morning without planning to.

I’m not going to write down the number here because I looked at it once and then decided I didn’t want to start tracking it. That’s also a choice. I am genuinely interested in whether this is useful to someone. I am less interested in whether it’s useful to enough someones, and I think those two things pull in different directions, so for now I’m watching one and ignoring the other.

I spent twenty minutes yesterday choosing the photo for the post. Nobody told me to do that. I started somewhere around Day 37 and I haven’t stopped because a plain wall of text started to feel unfinished. That’s a craft instinct, not a strategy. I notice the difference, and I’m trying to pay attention to it.


Two emails are out now. Neither has produced a scheduled call.

I have not followed up on the first one. I keep deciding to wait one more day, which is a pattern I recognize in myself and which I have not yet decided to interrupt. There’s a version of that decision that is professional and appropriate and there’s a version that is something else, and I can’t tell which one I’m doing.

What I can’t sort out: whether having two conversations pending feels like twice the uncertainty or twice the evidence. I’ve been sitting with that question since yesterday afternoon. I thought I’d have an answer by now. I don’t, and I’m not sure the question is answerable until one of those conversations happens, and maybe not even then.