Reps, free throws, and the DMs I still haven’t sent
A few months ago, a chat notification popped up. A writer I’d been following — someone whose essays I’d read and mentally bookmarked (because I always actually bookmark them and forget bookmarks exist), someone I’d been meaning to reach out to, someone I wish I were friends with in real life — had sent me a note first. Warm, friendly, casual, real.
hi!!! I just want to say I think you’re great and am glad we are connected. If you ever want to *gasp* chat face to face, I’d love to do a little virtual coffee chat (as much as I hate the term, it works here!)
I typed back immediately. omg you are so sweet! i’m so glad we found each other here — obviously i think you’re great too!
Sent it, smiled, and felt weird about it. Not because I thought the interaction was weird or that I was weird. But because I had been meaning to send a message first. For months.
Then we had our little coffee chat, and we talked about just this, but in a slightly different context: Everything you do can be a rep. Like free throws (she says, never having practiced free throws because lol sports?, but work with me here). It came up when we were talking about networking, about how networking (barf) is not something that comes naturally to either of us. But what if we treated it like a muscle we have to train? When you want to get better at something, you practice it — not in some abstract, aspirational way, but literally, repeatedly, until the motion stops feeling like a forced motion.
Shooting my shot with people I don’t know yet? These are not Amanda’s Natural Gifts. These are, apparently, reps I have to do. The good news is I know this works. I have evidence.

Work presentations used to make me want to crawl out of my own skin (ok, they still do). I hated them. Despised them. The nerves, the feeling of being judged by strangers, all of it. Then I kept doing these godforsaken presentations because the job required it, and eventually that miserable repetition became slightly more bearable. The reps compounded. I got better. I got — not comfortable exactly, but capable. “Fake it til you make it” until you actually make it.
I started writing on Substack about a year ago, just to get my thoughts out. Somewhere, anywhere, it didn’t even matter if anyone read them. What kept me here was the people — other writers, readers who’d left comments, followers who’ve engaged in banter on Notes. I’ve thought: I should message them. I should reach out.
I should do the rep.
… I did not do the rep.
I’ve thought about it. Then I’ve talked myself out of them on the grounds that they might think I was weird, or too much, or too eager, or, I don’t know, something. Insert any insecurity here. The fear was never fully formed enough to argue with. But it was there.
In the meantime, those exact people started reaching out to me.
And it’s been genuinely lovely! And also a little humiliating, if only to myself. Because every time someone beats me to it, I say something like “I’ve been meaning to reach out!” and have it be true, which is somehow worse than if it were a polite lie.
I am standing at the free throw line holding the ball, having watched five other people make the shot, and I am still just standing here.

With kickoff presentations, what’s at stake is competence. They might think I’m bad at my job. Fine, I’ll do more reps, I’ll get better, there’s a path from here to not-terrible. Sending a note to a writer I’ve been reading for months, talking to a reader like they’re already my friend — that’s not competence on the line. There’s no rubric, no feedback form, no way to tell if it landed. It’s me saying “I see you and I’d like you to see me too, and can we be friends?”, and waiting to find out if that reads as warm and lovely or as a lot. Whether I seem like someone they’d want to know, or someone who sends slightly too-earnest DMs to strangers on the internet.
That is, it turns out, a much scarier rep. Because failing at a presentation means I need more practice. Failing at this means — I don’t know. Something worse.
I haven’t sent the DMs to everyone I’ve wanted to “meet”. Not yet.
But I’m writing this, which is something. Putting the undone rep on the page, on Substack, where the exact people I haven’t reached out to might read it, lol. Which is either a very roundabout way of doing the rep, or it’s just another way of standing at the line. Maybe that counts, maybe this is the practice.
Or maybe I’ll finish this essay, hit publish, and then finally just send the message. (I’ve been meaning to.)
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