The Scripture says that those who through practice and experience have come to be able to discern between good and evil. This means that a mature Christian who has gone on for God for a long time and who has learned through his or her mistakes and successes, has learned by continuing to grow in grace and years of experience to know within themselves what is good and what is evil.
This means that God doesn't have to lead the person around like a dog on a lead when out for a walk. The Scripture says, "Don't be led around like a mule that needs a bit and a bridle to guide them." There are many Christians like that. They need constant guidance, even to the extent of buying a new pair of pants from the shop!
The Scripture says, "Acknowledge the Lord in all your ways, and He will guide your steps." This means that as you seek the kingdom of God, delight in His Word, fellowship with Him in prayer, treat others according to the fruit of the Spirit, God will guide you without you having to ask for it all the time. You will know within yourself by the conviction of the Spirit when you stray from the righteous track.
During the 1970s there was a doctrine of devils came out of Fort Laudedale in Florida called "The Shepherding Discipleship doctrine" which required believers to be subject and obedient to a "discipler" who told them what to do, right down to buying a new pair of pants from the shop. If a believer disagreed with his "discipler" he was accused of being rebellious against God. Believers were forced in public meetings to confess their private shortcomings and failures. and if they had resentment against others in the group, to declare it. This evil doctrine caused much suffering to good people, and drove thousands away from the church and from Christ. This is the dark side of wanting specific guidance over every little thing, instead of trusting God that He will lead you as you do what is obvious and go about your normal daily business.
I believe that God is quite happy for you to do what is in your heart to do. If He wants to prevent you from going somewhere or doing something (like He did with Paul at times), He will let you know for sure. Conviction is like hitting an electric fence. When you start to stray off the path, you get a jolt in your spirit that corrects you and bumps you back to where you should be going.