At what point did "I should hire someone for this" turn from a thought into an actual hire?

I have caught myself thinking I should hire someone to handle the parts I keep dropping, then talking myself out of it because the business is not big enough yet, or I cannot describe the role cleanly enough to post it. I noticed the thought shows up on the exact days something already slipped, a follow up, a number that was off, never on the calm days. Across a software company, a care home, and a cafe, I have had that thought probably fifty times and only acted on it twice. Curious what actually moved you from thinking about the hire to making it, was it a specific moment, or did the cost of not hiring finally add up somewhere you could see it?