I just had to part way with a contractor. He is a close person to me. I’ve been postponing that decision for months now and what finally triggered it was that he wasn’t taking this job seriously, I was just giving money away without him making an actual effort.

I don’t want to be pushing for someone to be at their prime, you know? That’s something that the person inherently should have.

I don’t want to be teaching them how to think in a “meta” way, you as a productive person, should know what to optimize for, and work towards automating your job completely. What are the steps that you need to perform in your day to day work so that it can be completely automated?

If after months, you are still asking about the most basic stuff, you might not be cut for it. Just try a different thing.