The softness which I have in mind, and which is yet another kind of self-relinquishment, is what you can observe in people who get used too much to warm and sunny, pleasant weather: they grow hesitant, after a while, to do things that would expose them to a harsh and cold wind, rain and darkness. (Obviously, not everybody who lives in favorable climates gets soft in this sense, there's no necessary causal connection between weather conditions and strength of character. But you know the kind of personal development, or rather personal decline, I'm here referring to, don't you?)
Just as an aversion to bad weather can be what makes you soft, it could be any other sort of disagreeable external as well: if you have a fear of conflict, a dread of poverty, a secret thirst of social standing with a corresponding need for recognition — each of these might lure you gradually into a habit of avoiding things. You're getting used to the pain-free zone so much that you become unable to thrive elsewhere, you shy away from anything outside the range of comfort, and finally wind up avoiding everything else just for your convenience, delaying initiatives towards goals that once were important in your live, finding yourself taking actions against your better judgment, developing self-deceptive views and self-defeating feelings.
Why is softness a form of self-relinquishment? Because it is dependence: it makes you dependent on externals, makes you rate externals higher than they should be rated, and so any accidental lack in externals could lead you away from what you should be doing to doing something to deal with that lack. Only if you gain independence from externals can you fully be yourself. (And in consequence, be free.) If inconvenience or unpleasantness, conflict or bad luck, unfortunate material or social circumstances can keep you from doing the right thing, then you aren't making progress on your path (that is: your path); and you don't live your own life quite as fully as you could. Softness is a way of losing sight of this, a form of giving up the focus on what matters most: how you live your life, and who you are — you, as a person.
There is nothing wrong with being sensitive to other people's feelings, and caring — that's not necessarily softness of the kind we're looking at. Softness means to be untrue to yourself, and you're not untrue to yourself if you care about other people. On the contrary, being kind and comforting can be the exactly right thing to do in a given situation; you're rather giving in to softness the moment you put on a cold face because a bully has just entered the room and you don't want to risk looking weak. That's softness. (However, being nice and smooth also can be a form of softness, if your main motivation for it is to avoid a conflict that you should be rather facing head-on.) The rule that tells if something's softness can't be simply found in descriptions of overt behavior; the fundamental indicator that you're getting soft is that you sacrifice your personal integrity for something that's external: you're relinquishing courage, kindness, honesty, or any sensible behavior in tune with good character in exchange for gains in money or in reputation, pleasure or convenience. Softness is an expression of valuing something external higher than the integral qualities of your person.
It is also self-perpetuating: you are getting soft and softer progressively, and you're gradually putting more and more priority on comfort or convenience, thus tacitly valuing them higher than doing the right thing, working on your character, living a good life (which all bring with them hardship, inconvenience, roughness, disappointment, danger, maybe even death). You'll get more likely to give in to resistance; you'll grow incapable of changing what goes on around you; fears and foolish hopes will get the better of you more and more. All that softness gains you will be more of it. But the flip-side of that process is a loss of what makes you into yourself. No convenience in the world is worth that. Take care.