Nice work. Keep it up, I bet your body will adapt within a few weeks. Just different muscles, or rhythms for using them.

Now my commute is moderately hilly (<1mi that gains about 300ft), I don't think I would be able to do it SS.

That's not true, I know if I worked hard enough I'd be able to do it. But I'd have a REALLY hard time enjoying it.

I could experiment though, maybe challenge myself by choosing a gear and seeing whether I could make it all the way before bailing out. 39x23? 39x26? I mean, I know I could do it if I just went granny the whole ride (39x34)