Hi Complicated,
Life has a way of whomping you on the backside of your head just as you're feeling good and going about your merry little way. It makes you afraid to go merrily on your way again and you keep looking back waiting for the whomp to come because this time you don't want it to catch you off guard.
At least that's how I translated what you've written.
In any case, I think I know what you mean. I think it's what they mean by taking baby steps. Take one step forward, look around for the whomp-if the coast is clear then take another step forward.
I wish you well and hope for the best to come for you.