[jcutrell]

Think of your experience and context as “ground floor.” You have a lot of it, which makes your starting point much higher than your colleague’s. Some things you are likely naturally taking for granted, he may have no context for. You can’t fake “taking for granted.”

Your goal should not be to help him do something that is hard. It should be to understand how to make it easy.

So, perhaps guide him towards the path of least resistance. He is likely not wanting to draw the wrong thing either; tell him to treat the first version as a draft and make him promise he will throw this one away.

Maybe draw something out for him and be willing to make mistakes in front of him, so he doesn’t feel self conscious about getting it perfect on the first shot.

Lower the stakes, focus on smaller problems, and find a shared vulnerability.