Does that obligate us to spend out days being careful of every little opportunity that we might slip in trying to live perfectly and never go near anything that might temp us?
No, right hand errors are just as dangerous. If we try to be instantly perfect we will burn out, fall, and and up in a worse state than the beginning. Being scrupulous is not the right way.
We should repent each day. Each morning we should spend a few minutes preparing ourselves for the day and asking God's protection. Each night we should spend a few minutes examining our hearts and asking for forgiveness for the ways we have fallen short, which we will mention in confession in due time.
If at all possible we should have a father in confession who sets a rule for us, and guides us around pitfalls of being too lax and pitfalls of being too strict with ourselves, in order to help us to progress, to train us. Like an athlete we must work each day, so that each day we can go a little further on the road to perfection. But we shouldn't look to see how we're doing, we should just focus on working, on weeding out vices and cultivating virtues. What this means practically depends on the person, their stage, their circumstances, their temperament... this is where guidance and obedience come in.
"The way of the Ascetics" by Tito Colliander is a great introduction.