Timing questions are the bane of every reader’s existence, you’re definitely not alone in this struggle. There’s a great guide for it, but there’s still a reason why a lot of readers just won’t bother. I’ve been reading professionally for years and I still hedge my bets on “when”. The cards show energy patterns and probability flows, but humans have this annoying habit of exercising free will that throws off the most careful predictions.
People who don’t understand the Tarot want to be told guarantees and 100% promises, but if they don’t take the time to really understand how the Tarot works, they’ll never get anything from it. I turn away clients all the time when it’s clear they just don’t understand. They’re wasting their money and my time.
For what it’s worth, I’ve had the best luck with the seasonal method. Pentacles for winter months, Cups for summer, that sort of thing. But even then, I tell clients we’re looking at windows of opportunity, not appointments set in stone. The smart ones take a lot from that and can make big positive and wonderful changes in their life. The daft ones stare at me like they’re waiting for a card to drop out and say “10th of October at 2:37 PM”.
The self-reading thing though… that’s actually backed by psychology. There’s something called the subject-object paradox, where you literally can’t observe yourself objectively because you’re inside your own head. Your emotional investment clouds everything. I finally gave up and just get readings from other readers for anything important in my own life. We have a whole thread for that, doing readings for each other because it works out much better that way.