Start with a day and see how it goes. If you think it wasn't so bad then try it again another day. If you hate it and it basically reaffirms your decision to stop in the first place, then don't force it. It's not for you.

Seriously, don't over-think it. You can't focus too much on the future. Focus on the present. As they say, one day at a time. One ride at a time.

Prepare to ride to work one day. Get your gear together and lay it out. Pack your stuff the night before and leave it by the door. Pick a route ahead of time. Get up early so you can give yourself plenty of time to get there. See how it goes.