As Hume said, reason is a slave to the passions. Reason is procedural, linear, discursive, and deleterious -- a process of truth retention. It cannot give you goals, it can only show you how to accomplish them. When you're thinking about possibilities, you're being imaginative, creative, not rational. As Aristotle pointed out, the conclusions of reason are either necessary, or contradictory, but facts are logically contingent, and cannot be deduced, they're inferred, inductively, and imagined abductively.
The Buddha said that when we know what we should do, we shouldn't think about the difficulties of accomplishing it, or the troubles of doing what we know that we should. This is because to do so is to just create possible images, pre-conceptions, and expectations which may have absolutely no basis in reality.
We are creatures driven by narrative, our conscious memories are exclusively an autobiographical narrative. Photo graphic memories aren't actually a thing, people that have the best memories in the world, and can memorize large amounts of information quickly, use mnemonic devices, creating narratives, or stories that incorporate the information that they wish to memorize.
This is not to say that narratives aren't true, but it is to say that they most definitely don't have to be true. Narratives also high-jack the reward and punishment system of the brain, allowing us to override natural instincts in favor of the emotional, passionate force of a narrative. So be sure to take control of the kinds of things you tell yourself, and understand what is sometimes thought obvious reasonable predictions about the future are just guess work. Que sera sera.
So, when making decisions, I would put little to no emotional weight in imagined futures. Decide what you want right now, and take steps right now to achieve them. The psychological future never arrives, and the actual future is constantly upon us.