Here are four axioms for your consideration.
1. Misery is not necessarily an indication that you are not doing the will of God.
Sometimes we suffer because we are doing the wrong thing and going in the wrong direction. On the other hand, sometimes suffering is a sign that the devil is displeased and wants to make you hurt: a good thing. Or sometimes suffering is a sign that God is pleased and wants to make you even more alive: a good thing.
2. Misery is not necessarily an indication that you are doing the will of God.
On the other hand, sometimes we suffer because we have done stupid, bad things, and stupid, bad things always end up hurting us. So sometimes you have to just take your punishment and say, Yup, I deserve this. Sometimes it isn’t even a punishment, but just a natural consequence of the stupid, bad thing you’ve done. If you drink fifteen beers and are hung over the next morning, it’s not because God is punishing you or testing you and it’s not a Dark Night Of the Soul. It’s because you are an idiot.
3. Contentment is not necessarily an indication that you are doing the will of God.
Lots of people are content. Saints, I suppose, are perfectly content at least some of the time. Sinners who have gotten very good at ignoring their consciences, I suppose, are perfectly content at least some of the time. Maybe you are content because everything really is going all right. On the other hand, maybe you are content because you have been lulled to sleep, when you should be wakeful.
4. Contentment is not necessarily an indication that you are not doing the will of God.
Skip this one if it makes no sense to you. If, however, you are the sort of person who starts to worry when he starts to feel good — because you’re not quite sure what to do with yourself when you don’t have some terrible agony to offer up — maybe just try being content with being content. Enjoy it while it lasts; maybe the Lord’s giving you a break. You probably need it!
To sum up: feeling are a pretty unreliable way to tell how well you’re doing.
If not feelings, what then?
Prayer, I suppose, charity, a steadfast heart. Love the Lord God with all your heart, soul, mind, and strength, and your neighbor as yourself, and you won’t have to worry about any of this. Or, as Padre Pio said: Pray, hope, and don’t worry.
And it doesn’t hurt to remember: “the will of God” might not be the kind of thing you think it is.