Dear Oracle,
I’m in a “What am I doing with my life?” spiral. For the past eight years, I’ve worked freelance in a “cool” job that I’m starting to hate and feel burned out by. I live in my hometown that I love but it’s changing for the worse with tech bros, and my social circle is shrinking as people move away.—Wandering and lost
Cards for right now: Nine of Swords (reversed), Ace of Pentacles (reversed), Judgment
Cards for what to consider: Three of Pentacles (reversed), Three of Cups
Cards to move forward: Three of Wands (reversed), Two of Wands
Dear WAL, I’m filing this column on Oct. 31, known as Samhain in the witch world, and is considered to be the “witch’s new year.”
It might seem strange to have the new year in late fall, just before winter starts, but one reason I like it is that the year starts with a pause. Samhain is a time of death and endings. The birth comes on the winter solstice when the sun is reborn. The six weeks between are essentially what Buddhists call the Bardo state. It’s the journey between death and birth, a time to work through what needs to be worked so that you can arrive at your birth ready for a new life.
We often get stuck in situations that we know we should get out of because we don’t have a backup plan. The Nine of Swords is certainly a card that evokes feelings of being haunted by our past and anxious about the path to take forward. But, it’s also a card of transformation—and that transformation comes whether we’re ready or not. I think you’re very much feeling that push to break out now, even if there’s no backup plan.
While you mentioned quite a few things in your question, I do think your job is something that’s weighing on you the most. With the Ace of Pentacles and Judgment, I think your current job has served you well, and while it may have seemed like it at the time, it’s not actually your true calling. Judgment is actually a depiction of the Rapture, of souls rising to join each other in the great by-and-by. It’s a card of rebirth and resolution, of shaking off the isolating chains and joining the collective.
Send your questions to oracle@cltampa.com or DM @theyboracle on Instagram
Freelance work is, by its nature, an individual affair. (You’re an “independent contractor,” after all.) While you can briefly be part of something larger, you are on your own for the most part. While that can afford a lot of freedom, it does come at a cost. I do wonder if what you’re looking for in your work is to be a part of something bigger—especially as an equal collaborator.
With what to consider, we have both the Three of Pentacles and the Three of Cups. The Three of Pentacles is a harmonious collaboration, especially one involving actual work. It’s when everyone is in the right groove and together you’re able to produce something larger than the sum of your parts. Think of it like a band hitting their stride when recording, or actors in a play building off each other. It’s both grounding and generative.
This is coupled with the Three of Cups, traditionally the card of friendships. This could be you working closely with friends to make something, or it could be finding a group of like-minded people who will become friends through your work. However, with the emotional undercurrent of the cups, what you truly need is for your work to feel meaningful. This might be a creative collaboration (join a band) or a political one (join organizers in your community) or a social one (start a commune), but whatever it is, it has to strike that emotional cord in you. It can’t just be intellectually stimulating or good money. It’s something that you’ll gladly give your heart to.
The final cards of the Three of Wands and Two of Wands, which is both looking back at your past and looking forward to your future. The Three of Wands is a practice of acknowledging everything that brought you to this current moment, the good and the bad. It can be a time to make peace with what didn’t work out and express gratitude for what did. The Two of Wands, meanwhile, is a card of pure hope and ambition. It’s looking at the horizon with excitement and moving forward with that hope in your heart.
Both cards are actually perfect for the time. Samhain (and the six weeks that follow) is a time known as the “parting of the veil”. It’s believed this time is when the voices of our past can come to us—and the voices of the future. Over the next six weeks, try to spend more time in silence and meditation, reflecting on your past and how far you’ve come and what you’re hopeful for in the future.
Perhaps you’ll hear a message—from your gut, your ancestors, your divine watcher—about what step you should take on your path of life. Perhaps you’ll be visited by a spirit of inspiration. Whatever it is, take these next six weeks as a time to reflect. What inspires hope in you? What do you think would feed your heart? How can you fit into a collective? What do you want to be waiting for you on the horizon?
This isn’t the time for making moves. You don’t have to quit your job, disappear from your family and start life anew. It’s a time to pause and think. But eventually, that feeling of transformation will become too big to ignore. You’ll be driven to change and to avoid feeling like you’re just doing the same shit over and over again. Give yourself the gift of honest wonder. What could be different in your life? What would you like to be different?
These questions aren’t easy ones to answer, but I hope when the answer comes, it feels as natural as drawing a breath.
See more of Caroline and learn about her services via carolinedebruhl.com.
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This article appears in Oct. 30 – Nov. 5, 2025.