Yah gave us consciences to assist in this process, and I am mighty grateful that He did, because rarely is a decision opportunity presented to us in a 1-dimensional fashion. Almost always, in fact, decisions involve conundrums that have 3, 4, 5, perhaps infinite numbers of variables, all of which are not correlated. More often than not, our decisions include having to maximize the Glory of Yah in one respect while compromising His Glory in another. Seeking perfection in all matters can lead to paralysis, which translates into doing nothing to implement surrender to His Will. Our consciences, if nurtured and listened to closely, will give us great predictive insight into what paths to take, because just the contemplation of what will follow any given choice -- if our mind is open to His Will -- will paint the picture for us of what is most edifying. Deliberating on a choice interminably leads to paralysis, as does attempting to take too many factors into consideration; these orientations (brooding or overdeliberation) also increase the likelihood of inspiring two different snares: brain fog produced by attempting to juggle too much for too long; or cognitive dissonance, which our minds react to by forcing our thoughts into a mold that is already comfortable for us, and this outcome occurs through partial self-delusion.
When someone who has wisdom and experience says, "Listen to your heart," s/he doesn't mean, "Just go with your feelings." She's talking instead about being present to your conscience; it is that part of a human being that is made in the image of our Creator. Neither think too long nor too impulsively, but listen to your 'heart,' to the part of you that knows the difference between right and wrong -- and then make a decision.
What is often lost in that process is that we are equipped by our Creator with something else of relevance: the ability to make course corrections. Make the decision, take the action, then be rigorous about paying attention to how it's playing out; if your prognostications weren't entirely correct, make a change. Be willing to be wrong in the short term in order to maximize your ability to be right in the long term.
There is also this: in a sense, everything we do is His Will. We are imperfect beings being made perfect by Him over time. Everything in our lives is either a joy or a lesson; we are truly blessed when we experience things such that they are both. We are meant to be learning what we will ultimately need to know, and much of that process will involve trial and error. Listen to your heart, take action, keep listening, and make changes, being willing to repent if the path led too far astray. And then make some more changes.