First year associate in transactional practice—am I being too inefficient with time when reverting assignments?

I’m a first-year NYC associate in a transactional practice group. We had a pretty late start and didn’t really start getting assignments until after Thanksgiving/early December.

So I have this tendency where I need to quadrupole check things when sending an email to a partner. When it comes to client emails, I check even more. But to give an example, I recently had to send around 10 redlines, not all of which was my work— there’s two partners (one equity and one non-equity partner), and the equity partner wanted to review all of the docs we had been working on since he hadn’t looked at them in a while. All I had to do for this particular thing was generate and then revert those redlines to go up the chain. It took me an hour to do this because I kept checking and rechecking to make sure all of the attachments were correctly labeled, and was the actual redlines they were looking for. Even when I double check and see it’s the correct redline and correctly labeled, I would check multiple times afterwards because I would gaslight myself into thinking I made a mistake and I’m sending the redlines for a different entity or a different version than what they needed.

And I’m genuinely not doing this to run up the time or anything— I had a bunch of other matters I needed to attend to that day, and actually wanted to get this done asap. But at the same time, my biggest fear is sending the wrong redline/document, and the partner judging me that I couldn’t do something as simple as send them the correct redlines. This sort of paralyzes me and I get in this near endless loop of continuously checking to see all the documents are correct before sending.

I feel like a whole hour dedicated to just sending redlines seems excessive. But I’ve also caught onto errors before from this tendency to re-check things multiple times, so this habit has been sort of reinforced. Do I just need to get over it at a certain point and tell myself I’ve checked enough times after doing a single check and then sending? Also, am I being too fearful about my seniors being judgmental in case one of the documents is not the correct one, when in reality they will just forget about that mistake after that day?