It is not easy to judge, only God and our Guru can truly know how much we have advanced. However, a simple parameter, which can give us some idea, is to see how much our mind has gotten detached from the world and the extent to which it has gotten attached to God. This is a simple rule of thumb to measure our advancement.
Do a reading of yourself. When you suffer reversals in the world, how upset do you become? If you find that earlier, you would keep brooding when someone insulted you, but now you are able to forget it in an hour's time, then you can conclude that you are progressing; your mind is becoming detached from the world, and your spiritual power is increasing; hence, you are able to remain normal in any circumstances.
Again, analyze how much does your mind yearn for a spiritual association. If earlier, whenever you had free time, you wished to spend it in seeing movies, but now you seek opportunities to sing devotional kirtans, it is a sure sign that you are progressing and that your mind is getting attached to the spiritual realm.