Draw of the day: striving

I'm doing Wyntercraft's 30-Day Tarot Challenge, with the Tarot of Vanessa Ives.

Definitely a weird one today. For Day 5 of the challenge, the draw question is "Is there something I should be striving for?" I drew the Five of Cups, which is generally the "loss and disappointment" card. Obviously I don't think I should be deliberately striving for loss and disappointment. So this is possibly just telling me I'm currently setting myself up for disappointment for something I am or should be striving for? I'm unsure. A closer look at the Louis text does point out that this card advises salvaging something from a bad situation and cutting necessary ties, so perhaps I should be striving to learn something from some kind of bad situation or personal baggage and let it go. A quick skim of Biddy Tarot also shows a lot of discussion about letting things go, healing from a loss or hurt of some kind, and generally moving on in life. So my best guess about what this card means as an answer to the draw question is either a) I am striving for the wrong thing, due to some sort of personal baggage that I should get over or b) I am holding myself back from something that I should indeed be striving for, out of some sort of fear/hurt/learned helplessness/other maladaptive coping mechanism. I am, possibly relatedly, suddenly remembering all my dad's lectures about Not Being Afraid of Success, from way back when I was wee and the economy hadn't crashed yet. But I suppose it doesn't have to mean material success. What it does mean, then, I will have to think about. I'm sure there are multiple candidates for what this could be indicating.