So I pulled the five of cups to the question: “Have I finally overcome the obstacle I need to overcome?”
I’m pretty indecisive on the meaning of this card regarding this question. Any suggestions?
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So, disclaimer that 1. I am by no means an authority on anything and 2. Tarot is very open to interpretation, I’d say no as the answer to your question, just thinking of the Rider-Waite illustration of the card. If you don’t mind, can you clarify which deck you’re using?
In the Rider-Waite deck, the 5 of Cups is a cloaked figure essentially crying over spilt milk and ignoring the upright cups right behind him. I think one of the main interpretations of that would be that you’re directing your energy in the wrong place, hiding the reality and abundance right under your nose.
If you are riding with the Rider-Waite interpretations (hehe), then yeah, I’d ask another question along the lines of “HOW do I continue to overcome this obstacle?” or “What am I missing?”
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it’s a simple Mondays Tarot deck I picked up at the bookstore. I appreciate your reply.
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Of course! I’m not familiar with that deck and any particular conflicting imagery so I’d just stick to my guns in my original answer. Remember though, despite the negative response, there are two cups right beside you… you just need to shift your focus. 
Good luck!
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I pulled another card relating to what I need to do and I got strength. What i’m getting is I need to stand up to a beast in my life, though I don’t know what that is yet.
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Strength is a card I associate with myself actually, interestingly enough! Personally I always am inclined to see Strength as taming an internal beast rather than an external (though of course, depending on surrounding cards, this is open to interpretation). The 5 of Cups is another isolated card in which the fault is on one’s self (I swear I’m not trying to roast you, I’m just not sure how to word it). I’d see it a lot more like the cards trying to tell you to buck up and grin and bear it to get to the reality you hope to achieve, you need to be strong, hold something back (internal doubt?).
Just reiterating, the 5 of Cups just feels very much like a self sabotage kind of card to me. If it was the 7 of Swords I’d think differently, maybe, but the 5 of Cups in particular is just really giving off a vibe of “there IS a happy ending even if you aren’t seeing it, so be strong and get yourself there without doubting it”.
Personally, when I get a read like that, I try my best to stop using my cards and create an amount of “self sufficiency” in my choices and trust I’m doing the right thing and going the right way. Could be an option for you, but absolutely get your clarity before putting them up.
Also: if you do come to a conclusion on another outside force you could be strong-arming to better your situation, that could equally be it! I’m just trying to interpret with what I see.
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When you pull a tarot, you have to go off the feeling you get from it, even if it’s upright it can have a negative sensation to it and vice versa, and then align it with it’s meanings and the question.
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So what do the actual cards represent?
Without the answer, what’s the point?
Al.
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Cups = Emotion
Is the obstacle emotional? A poisonous emotional?
In this case I am seeing you acknowledging that you have revealed the true nature of your obstacle and are looking back in reflection having just overcome it. Contemplating what happened. The 2 cups ahead are another obstacle, but nothing you cannot overcome easily because you are wiser and more prepared.
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Try and familiarize yourself with each card in the deck and the general meaning of each card for Tarot in general. I’m still not great at it, so I keep the guide for my vikings Tarot handy as it does a quick description of the overall image and the corresponding meanings of the card.
You can also try doing a full spread. I have had some good results with this one originally built for runes. Square of Nine
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The cards represent energies. That’s it - energies! This is why you can use them actively (ie; talisman) but very few do. Took me more fucking years to learn that then I care to mention and here I am just giving that knowledge away.
Al.
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I sometimes use my tarot cards in manifestations, be it “curses” or “blessings” or manifesting one or more of the meanings a card represents.
Use a different deck to the one you use in divination because working actively will give the cards energies and these energised cards will keep popping up in readings - “Here I am - again!”
Place energised cards between cheap, two glass piece picture ‘frames’ (sealed with metal clamps) or use a 100% natural materials picture frame with glass - no plastics! This ‘frame’ can be reused all the time.
Al.
Not quite, I cleanse my deck after every reading and every working with them.
I would interpret that as a no…It is showing that there is still some emotional conflict somewhere that needs to be addressed. You aren’t quite out of the woods just yet…even if the situation is over…your thoughts, emotions, and feelings about it are still not settled.
Take some time to really assess (especially with a journal) how you are feeling about the situation. Are you still going over it again and again in your head? Are you still angry about it? Are you refusing to let go and move on? Etc…etc…
I’d need to get a new journal for that.
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Do so then. Or you can make mental notes…I just suggest a journal because it is easier to keep track of everything and not forget certain things as time goes by.