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5 of Cups Tarot Card Meaning: Career and money.

Posted on 02/01/2026 Phoenix Vale By Phoenix Vale

Man, the “5 of Cups.” When I first pulled that thing, I just kinda stared at it, you know? Like, “Really? You gotta rub it in?” It was during one of those stretches where everything just felt… off. My job felt like a dead end, the money was tight, and I was just plain sick of it all.

I remember it so clearly. I was sitting there, feeling like I’d messed up so many chances. I’d seen a couple of opportunities pass me by in my career, hesitated on a big decision that, looking back, could’ve really changed my financial game. I just kept dwelling on those “what ifs.” What if I’d taken that other job offer? What if I’d stuck it out with that one project that eventually blew up for someone else? My head was just a loop of regret, playing over and over again, draining me dry.

I felt stuck in this mud of my own making. Every morning, I’d wake up, and that feeling of disappointment would just hit me right in the gut. I saw all the doors that had closed, all the potential earnings I’d missed. It was like I was looking at a table full of spilled drinks, just focusing on the mess, the waste. I practically drowned myself in that kind of thinking for weeks, maybe even months. My energy for anything new in my career was just… gone. And money? Forget about it. I was just trying to keep my head above water, thinking about how I could’ve been in such a better spot.

Hitting Rock Bottom (Figuratively, Anyway)

It got to a point where even my friends were like, “Dude, you gotta snap out of it.” I wasn’t doing anything productive. I was just moping around, lamenting my past choices. My finances were stagnant, my career was stagnant, and my mood was definitely stagnant. One evening, after another particularly gruesome day of staring at my bank account and then at my job board, I looked at that 5 of Cups again.

This time, though, something clicked. Instead of just seeing the spilled cups, I actually noticed the two that were still standing upright. It was like, “Hold on a sec, it’s not all gone.” That was a weird jolt, you know? Like a tiny flicker of light in a really dark room.

I started to think, okay, I messed up some things. Yeah. I lost some opportunities. Yeah. But what do I still have? It sounds simple, but it was a revelation for me. I still had my skills. I still had my experience, even if it wasn’t in the exact direction I wanted. I still had my network, even if I hadn’t tapped into it for a while. And I still had a roof over my head and food in the fridge, even if it wasn’t fancy.

The Shift: From Regret to Rebuilding

That realization was the kickoff. It wasn’t about suddenly becoming optimistic. It was more about getting mad at myself for wasting so much time wallowing. I decided right then and there I was done with the pity party. I told myself, “Alright, you got two cups left. What are you gonna do with ’em?”

Here’s what I started doing, step by step:

  • First, I stopped looking back. Seriously, I made a conscious effort to shut down those “what if” thoughts whenever they popped up.
  • Then, I actually assessed what I had. Not what I lost, but what was left. I listed out all my skills, even the ones I thought were minor. I looked at any past projects that actually went well, however small.
  • I started reaching out. I reconnected with old colleagues, just for a casual chat. Not asking for a job, just saying hi. You’d be surprised how much just talking to people can open your mind up.
  • I picked up a new skill. Something I always thought about but kept putting off. It wasn’t a huge commitment, maybe an hour or two a day, but it made me feel like I was building something, not just patching holes.
  • For money, I got real tight. I cut down on all the extra stuff. No more impulse buys. Tracked every single penny. It was painful at first, but seeing the numbers start to stack up, even slowly, was a huge motivator.
  • I started applying for things. Not necessarily dream jobs, but jobs that were a step up from where I was, or at least sideways into a healthier environment. I practiced interviews, updated my resume like crazy.

It wasn’t a quick fix, not by a long shot. There were still days where I’d feel that old familiar pang of regret. But seeing those two standing cups on that card, and then applying that same mindset to my own life, it truly got me off my butt. I had to acknowledge the losses, yeah, but then I had to turn my head and look at what was still there, ready to be picked up and used.

Tarot Insights

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