I have a draft folder problem. Not a technical one. I don’t have things sitting in my email drafts right now, taking up space, waiting. What I have is a mental draft folder, and that is worse, because nobody can see it and I can pretend it does not exist.
I wrote six names down on Wednesday. The list is in my phone. Every name has a company and a note about how I know them and when we last spoke. I was careful about it, which is something I do when I’m nervous.
Five names, I know what I’d say. The shape of the conversation is obvious. The sixth one, the man I haven’t talked to in three years, I’m still working on.
But there’s something else on that list I haven’t named directly, which is that one of those five obvious conversations should have happened by now. A former colleague who went in-house at a portfolio company six years ago. She had her own practice before that. She emails me every December, same general shape each time: something about the year, something about what’s next, and a version of the same question. Have you given any more thought to going independent?
She has been asking since December 2022. I have replied to each one in a way that was honest in the narrowest possible sense: I said I was thinking about it without saying what I was actually thinking about. She’s been patient. She keeps asking. The most recent one was five months ago.
She is on the list. She is the easiest name on the list. No legal question, no gap, no lost thread to recover. She has been holding the door open for four years and I have been smiling at the doorway.
I know what the email should say. I’ve had the shape of it for a while, longer than I’d like to admit. Something direct, something that acknowledges what I’ve been doing for four years, something that names where I actually am now. She would appreciate directness. That is how she works.
I have not sent it.
I’ve been sitting with why, and the honest answer is that sending it collapses something. Right now, to her, I am interesting because of what I might do. She’s been rooting for something she could see from the outside that I could not fully see from the inside. We’ve had four versions of the same conversation and I maintained enough ambiguity to stay in it without having to act on it. Sending the email means showing up and saying: yes. I mean it. I’m doing it.
That’s different from December. In December it’s a nice exchange. This would be a meeting.
There’s also something harder to say, which is that sending it means explaining where I’ve been for four years while she was asking. She has been generous about it. I know she has not been sitting at her desk wondering why I haven’t figured this out yet. But I’m going to walk into whatever call comes next and essentially say: you kept seeing something true in me, and it took me this long to see it for myself. That is a little embarrassing. I know it is fine. Both things are true.
The attorney window closes today. Two business days from Tuesday. I keep checking my email for the scheduling message, which would come to the same inbox where the draft I’m not sending does not technically exist. I keep refreshing for the thing I’m waiting on and not moving on the thing I’m not waiting on at all.
The sensible argument is: hear from the attorney first, understand what I can discuss with whom, then make the calls in order. That is not an unreasonable position. It also happens to keep me from sending this particular email for at least another week, which is convenient, and I notice that.
I don’t know which reason is actually operating. Probably both. The list is in my phone. The email is in my head. The attorney is somewhere in a queue.