As usual, there are many different authentic Jewish perspectives on this issue. I only know the sources for the more chasidic/kabbalistic approaches to this question, as I think thy are the only ones who really have a satisfactory answer, however I am aware of other positions that appeal to other people more , and they feel that the other approach is the only satisfactory answer. I apologize if I don't do the other positions justice.
In no particular order: (just the order I remember them in)
Nikudah HaBachira (Point of free will): This view of free will states that we only have free will in very few and limited instances. For most people, most things are truly not an option. Killing someone is not something we will do, so when the opportunity comes for us to kill someone, we can't really say we used our freewill to abstain from it. (we hope) Some things are just too far from us to ever imagine doing. On the opposite spectrum, there are some things which we always do, and we don't really have free will to abstain from doing them. For example, scratching an itch. As we progress in life, our "point of free will" shifts on various issues. It is in these points that we are truly human and our own person, every other time we are either acting as an animal does, or as an angel does. (Doing Gd's will for either good or bad) At no point in our life, do we ever lose this single point of free will no matter how close to Hashem's will we make our own.
Divine Spark: This view argues that enclosed in our overly animal body, we have a spark of the Divine and the infinite within us. Our soul, as your question implies is always aiming to attach itself to this divine spark and become part of Gd's infinite nature. Our free will is a mechanism which either pushes our soul towards the animal parts of our nature, or towards our divine nature, and the goal in life is to become "one with Hashem", and have His will be our will, and our will be His will. If all goes well, we lose our free will and just become part of Gd's.
Everything is free will, but the greats get divine intervention: This position argues that Gd's will only exists on a very Macro level of existence. Gd's will and plans are only interested in nations and species. We have complete free will to act as we like, and they will have no affect on Gd's plans nor will they help them or hurt them. The mitzvot are for our own benefit to become close to Hashem and understand the divine intellect. If we are able to achieve this lofty closeness to Hashem, then we will be worthy to be involved in the Divine plan, and miracles and divine intervention will happen for us. But those people are few and far between.
There is no true free will: There is a line in the Talmud which states that there is no free will, everything is predetermined except for one point, Our awe of Hashem. Gd is in control of everything and the only question is if we attach ourselves to Hashem or we do not. Some understand this gemora to be saying that the only thing in life we have control over is our attitude and reaction to the events around us.
Law of Attraction: Every person has complete free will, and the Truth is that Hashem would like to make His will our will. A person will have the life they think of for themselves, and the things that they need and know truly that they need, without doubt, will be given those things by Gd. As long as we keep the mitzvot as we understand them and attach ourselves to our Father in Heaven, Gd will move mountains and stars to get our will fulfilled, but if there is the slightest doubt in our minds, then the strong opinions and thoughts of others will override our own.
Free will only exists for reward and punishment: Nothing we can do will affect or change the divine plan. Free will only exists so that we may rewarded or punished for the things we do. When it comes to Gd's will, we can only do the mitzvot we know and hope that we act correctly. Other than following mitzvot and avoiding sin, we should not worry ourselves with Gd's will or larger plans.
Partner in creation: Gd wants us to follow his Mizvot to help bring creation closer to it's final goal. We have complete free will in this matter. If we do not do the miztvot and do not repair the defects in the world, then they will not be repaired, and Gd's plan will be done by another generation, if they so choose to do so. Our free will exists on the larger scale of perhaps we will help Hashem and His creation, or we will not help and be greedy people with no gratitude and no future. In order to be a true partner in creation, we need complete independence of thought of action and to be made "in the image of Gd". When we make our will Gd's will, then we are just acting as ourselves to be a partner in the creation and Gd's plan, but we are still our own individuals. The fact that we choose to partner with Hashem rather than be an adversary is what defines us.
I know I'm missing some other points of view, but that's all I have time for for now, and can't remember what I'm missing. Hopefully you will notice that many of these ideas complement each other and overlap each other. (If anyone can give me sources for each of those points of view, I would be indebted to you.)
