All things work together for our good.

Does God really work in all things for our good if we are his child? What about stupid or bad decisions?

God is in the business of redeeming and using even our poor choices to bring about our ultimate good i.e. our best. So in this sense we can never mess things up. He will always bring about our best no matter what we choose or don't choose, do or don't do.

But the way he brings about good results from bad choices is by allowing us to suffer the consequences of bad choices so we might freely turn from them (repent) and draw near to him. In this way, God always brings about our best through all things, even bad choices. But indirectly, not directly.

Good choices, on the other hand, bring about our best directly. The beauty of being a child of God is He is always working in all things for our good. 

Good choices are preferred because this is a direct pursuit of what is best. When we make good choices -- obey -- we are spared the ¹consequences that result from making a bad choice -- disobedience. But even if or when we unintentionally miss making the right choice (which is always best), he is still working for our ultimate good through these wrong ones i.e. he still uses the wrong choices (all things work for good) to bring about our ²ultimate best. We are just not spared the suffering that comes with the wrong ones. At least not automatically, or as a normal matter of course. 

Of course, this is true for those who love God. If we have no love for God - i.e. are not his child - we only experience the negative consequences of poor choices i.e. our choices are not redeemed and used for our good. This is why this promise is for those "who love God..."

God is not uptight

God doesn't stress over our wrong or bad choices. He is fully in control and uses them to bring about our ultimate good and his ultimate glory. Nothing is bigger than God or can thwart his purpose, even our sin or evil. Our loss (short term) and suffering is real nevertheless. But it is our suffering and loss, not His. He cares about us but looses nothing - He is still as much God after our choices as before them. We are diminished by them (at least short term and not in the ultimate sense) not God.

Job 35:6  If you have sinned, what do you accomplish against him? And if your transgressions are multiplied, what do you do to him? 7  If you are righteous, what do you give to him? Or what does he receive from your hand? 8  Your wickedness concerns a man like yourself, and your righteousness a son of man. 

A free choice is a choice of love

God desires us to turn freely to him, not out of constraint or obligation. God desires we choose obedience freely. If it is not free it is not true obedience and not done out of love. When we freely obey him it is an act of love and not of constraint. 

This is why he allows us to make bad choices. They may be bad but they are ours. Just as good choices are ours. When we learn from our bad choices and make good choices as a result, that is also ours i.e. it is really us, really learning (even Christ learned obedience through the things he suffered. His suffering, however, was never from bad choices but from living in a broken world as a result of our bad choices). 

Aren't we obligated?

We must obey God but not for his acceptance and love (i.e. do it or else you will be rejected) but to draw near to him, and experience all the benefits and joy that comes with those good/obedient choices. It also brings God the greatest glory.

Won't we miss his will if we are disobedient?

Even when you are out (of his direct will) you are still in it (his ultimate overall will) because God uses your being out to bring you further in. To us a modern expression, it's all good. 

To understand this we must understand the different elements of God's will. They are His:

Direct or revealed will: his spoken word/commandments (our direct best from good choices).

Ultimate will: to make us more like his son (our indirect and ultimate best brought about through bad choices or circumstances as well as good ones).

Rom 8:28  And we know that for those who love God all things work together for good (even if they are bad), for those who are called according to his purpose. 29 For (here's the reason why...are you ready?) those whom he foreknew he also predestined to be conformed to the image of his Son, in order that he might be the firstborn among many brothers. 

For a further discussion on how God uses evil for good click here and here. 

For a further discussion on how greater evil might result in greater good click here. 
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¹Though there may be another kind of consequence for obedience i.e. persecution. The difference between this consequence and the consequence of violating our design (disobedience) is we are promised God will directly honor (reward) obedience but not disobedience. Though He uses both, He only rewards the former.

²Our ultimate best is becoming increasingly more like his Son. 

Rom 8:29 For those whom he foreknew he also predestined to be conformed to the image of his Son, in order that he might be the firstborn among many brothers. 

How do our mistakes and failures make us more like Jesus? They humble us. How? By revealing to us 

1. our desperate condition without God 

and 

2. our need for a Savior. 

Ultimately there can be no greater good then for us to discover these 2 things.