The Email I Keep Starting

I know how to write a cold outreach email. The problem is I always had a company name to stand behind. Now I have to figure out how to start without that.

Leigh Sutton
Leigh Sutton Corporate lifer. Aspiring free agent. 4 min read
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It is Sunday morning. Forty-one days.

I said I would send the Marcus email in October. It is now October 4. I have opened a draft twice this week and closed it both times without saving anything. I don’t know if that counts as progress. I am going to say it does not.


The thing about the fifteen clean-name emails is that I had a frame for all of them. They knew me as a person with a title, from a particular institution. Even the four-year-gap contact, who hadn’t heard from me since 2022, had something to orient toward: I was the person he remembered from that world, coming from a recognizable room. When he said yes to the call, he said yes to the whole package.

Marcus is different. I know him through a former colleague named Elena, who I worked with from 2014 to 2018. We met twice: at a team dinner in 2016, and at a conference in 2019 where we talked for about twenty-five minutes about the difference between client success metrics and actual client success. He remembered the conversation two years later, which Elena mentioned in passing and which I wrote down at the time for no reason I could name then.

The conversation was good. I think he would take the call.

But I cannot start the email with “as Elena’s former colleague” because I am no longer Elena’s colleague in any institutional sense. And I cannot start with my title, because my title expired September 19. The context I would normally use to orient a cold-ish email is exactly the context that is no longer available.

I am trying to figure out how to introduce myself without the institution behind me.


I have written and deleted variations of the first line for three days. Here is an approximate record of what I have tried:

“We met at the conference in 2019, and I’ve been meaning to reach out…” True. Also sounds like I have been meaning to do this for seven years, which in a literal sense I have.

“Elena mentioned that you’d be worth knowing…” I have not actually asked Elena whether she wants to be invoked here. So this would make me the kind of person who uses someone’s name without asking. I am not that person.

“I’m building a consulting practice around enterprise account retention and I think there’s a conversation worth having…” This is technically accurate. It also sounds like I am pitching him before he has decided whether he wants to read this at all.

In each version I can hear, very clearly, the advice I would give a client. Apologize less. Name the value before the ask. Be direct about the purpose without leading with credentials the other person has no reason to weight yet. I know the advice. I am currently standing on the wrong side of it, which is a different thing entirely.


The other fifteen emails had a context I could stand inside. This one I have to build from scratch, which may be exactly the work I am supposed to be doing right now. Learning to introduce myself without the institutional frame is probably the skill the next two years require. I see that. I would tell someone in my position exactly that.

Seeing something and knowing how to do it are not the same skill. I keep rediscovering this.


I got off the phone with my mother at 10:17. Fourteen minutes. She asked about Zoe’s school visits. I said we had one coming up. She asked if I was eating. I said yes.

She did not ask about October. She did not ask about the blog. She knows November 14 is on the calendar and she is waiting, the way my mother waits for things: quietly, without mentioning it, in a way you can feel through a phone.

I am going to draft the Marcus email today. I said the same thing Thursday and Friday and yesterday, which I recognize. Today I mean it in a slightly different way.

The draft is open. Forty-one days.