According to The Pictorial Key to the Tarot by A.E. Waite, the Eight of Cups is described as the following:
A man of dejected aspect is deserting the cups of his felicity, enterprise, undertaking or previous concern.
Divinatory Meanings: The card speaks for itself on the surface, but other readings are entirely antithetical--giving joy, mildness, timidity, honour, modesty. In practice, it is usually found that the card shews the decline of a matter, or that a matter which has been thought to be important is really of slight consequence--either for good or evil.
Reversed: Great joy, happiness, feasting.
Do you ever feel like dropping everything and heading off in search of adventure? The Eight of Cups is your role model, and also your cautionary tale.
The scene shows a man leaving his current life behind and hiking off into the wilderness, and the moon overhead tells us this escape is happening under cover of darkness. His possessions are few, and he doesn’t look back as he begins the climb toward the mountains in the background. It’s clear that despite the romance of it, this is not an easy path, and it may not be as appealing as it initially seems.
When this feeling strikes you, you should first determine why. What situations in your current life have reached a point where you are ready to close the book on them? Have things reached a natural ending point (perhaps the end of a semester, fiscal year, or major project) or does it simply feel like it’s time to cut and run?
Most commenters on this card read a lot into the body language of the man in the scene. Some describe him as world weary or resigned to the situation, while others see a resolute man seeking something better than what he has currently. For our purposes here, the message here seems to be that you must make your own luck.
So it's time for a little introspection. Is there some aspect of your life that you’ve put on hold? Perhaps you’ve left it all to chance, or are waiting for your luck to change. This is particularly common in creative endeavors, where it usually feels like some fickle Muse has more to do with our progress than our own initiative. To discover what area of your life you’ve left to fate, it may help to make a list, or perhaps to write stream-of-consciousness in your journal for a few minutes.
Don’t give in to inertia, or let a difficult path forward daunt you. Once you’ve identified the problem, then this card indicates that you must, indeed, make your own luck. Whatever project you’ve put off, come hell or high water, now is the time to embark. It won’t be easy, but it will be worthwhile—much worthier than simply surrendering to circumstances.
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