Curate, connect, and discover
Simon spending all of the first season not trusting people and pushing them away and being actively hostile to anyone who looked semi-suspicious. then he gets people who he can rely on in season 2 and he's able to empathize more with Janet now that he's not in "It's up to ME and no one else, so nothing can stand in my way" mode.
There are still shades of the s1 tunnel-vision and hostility (he did. Kidnap Janet) but the crux of his plan in the cabin is still convincing Janet to come back to the school on her own terms, not just hiding out until the school is empty. Ultimately trusting Janet to stay on the dock and not run off again