Humor aside, this is like my worst nightmare. In order to do A, I must do B, which means I should do C, but not until I do D… and on and on. Some have affectionately called this process Yak Shaving. I call it the cost of a high maintenance lifestyle. And I think it is avoidable.
It's avoidable through being honest about wants vs needs. It's avoidable by choosing simplicity over complexity. Through buying experiences instead of things... and when you have to buy things, buying quality over quantity.
If you're interested in a simpler, easier, high-happiness, low-maintenance kind of lifestyle like the one I'm describing, here are a few places to start: