I *strongly* encourage you to pick a budgeting program and stick with it. I say this as someone who comes from perhaps more meager means than most in this thread and I now am in a similar position as you.

I use YNAB but I'm sure any will do. Essentially, I give every dollar a "job", whether that is to be the next car insurance payment 6 months from now or for our vacation fund. I know what money I have and where it's going. I have tracked every single dollar I've spent for about the last 10 years, less some petty cash.

I still have financial insecurity worries that likely stem from my childhood and I doubt they'll ever fully go away (see: people who grew up during the Great Depression), but I can allow myself to spend now and do so confidently.