I have always been the kind of person who worries a lot about money, to the point where it's a preoccupation. Sure, a lot of this is because I've always had a job that comes along with significant uncertainty - I never know what the next year (or even the next month) of my life will look like, financially speaking - but still: for years and years (until pretty recently, actually), I made my life far more stressful than it had to be by putting off the decision to come up with an actual plan.
When things are going well - money's coming in, no major unexpected expenses are popping up - it's easy to sail along in a happy bubble of obliviousness; I know this first-hand, because I've spent a lot of time hanging out in that bubble. But then - inevitably - the bubble pops. And you find yourself in a world of pain.
As an example, I thought I'd tell a story I'm not sure I've ever touched upon here, even though I've certainly been asked about it plenty over the years. (Spoiler: it's about my dog. But stay with me; I'm going somewhere with this.)