The Vicious Cycle of Late-Night Regret
Man, let’s talk about that feeling, you know? The one that hits you at 3 AM when you’re staring at the ceiling, replaying that one huge decision you made three years ago. You just bought the damn farm, figuratively speaking, and now you can’t stop calculating whether you should have just stuck with the safe corporate desk job. That’s where I was stuck, totally jammed up, after I finally pulled the trigger on selling my old software company. Massive payout, massive freedom, massive anxiety.
I swear, for six months straight, I would wake up and immediately start auditing my own life choices. Did I sell too cheap? Should I have waited for the next round? Was that whole pivot to digital nomad life a stupid, mid-life crisis move? I needed to shut that voice up, and traditional self-help garbage just wasn’t cutting it. I didn’t need advice; I needed a reckoning. I needed to drag myself into court and get a definitive ruling.
Dragging Out the Judgement Card
I’ve been reading cards for years, but usually for prediction, right? Asking about the future. But this time, I decided to flip the script. I wasn’t looking forward; I was looking at the rearview mirror, but through the lens of one specific card: Judgement (XX). Forget the traditional definition of being judged by God or whatever. For this practice, I decided Judgement was simply about answering your own damn roll call.
The whole point of Judgement, when you strip away the robes and the trumpets, is resurrection. It’s about being called up from the dead and deciding, “Yep, that was my life, and I stand by it.” My practice started simple. I didn’t use a spread. I just pulled that card out of the deck, set it on my desk, and stared at it for an hour straight. I forced myself to sit with the big decision—the sale, the move, the whole shebang.
The Reflection Process: Answering the Call
The practice wasn’t meditation; it was active interrogation. I grabbed a notepad and started mapping out the timeline. I wasn’t allowed to write down regrets, only actions. I made myself list every single step that led to my current situation:
- I felt miserable in the old environment for 18 months.
- I hired a broker in May 2021.
- I signed the NDA in July 2021, knowing it was final.
- I packed three suitcases and sold the rest of my stuff in December 2021.
- I booked the flight and moved across the globe.
After I laid out the facts, I introduced the Judgement card into the conversation. The card wasn’t asking, “Was the outcome perfect?” It was asking, “Did you answer the call when it came?” The key realization I unlocked was that every single action I took was based on the information and desire I had at that moment. It was an authentic response to a terrible feeling of stagnation. I pulled the trigger because I had to, not because I was guaranteed success.
Stopping the Perpetual Audit
Here’s the thing about doubt: it’s a time sink. It’s constantly trying to apply today’s knowledge to yesterday’s choices. That’s not wisdom; that’s just self-sabotage dressed up as introspection. The Judgement practice finally drilled this simple truth into my thick skull: the time for analysis was before the decision; the time for action is now.
The major breakthrough came when I decided to define failure differently. Failure isn’t making a bad choice; failure is getting stuck in the judgment cycle forever. I realized the only actual failure would be spending the rest of my life re-litigating a case that was already closed. The Judgement card isn’t about re-doing the past; it’s about accepting that your past choices were necessary steps to get you here, right now, ready for the next thing.
I packed the card away, not because the practice was over, but because the need for the card was over. I had called myself up, asked the hard questions, and realized that my choices, however messy they looked in hindsight, were mine. And that was enough. If you’re stuck, stop trying to predict the perfect future and start owning the messy present. Pull out Judgement and let it remind you: the only person who needs to validate your life choices is you.
