As someone who grew up poor, one of the best things I've ever done to get past that real hesitancy around spending money is to use envelope budgeting (I use YNAB but the tool isn't important).
My old habits had me tracking after the fact and I found that I either obsessed over minutiae, failed to plan for the future, or worried too little about bigger purchases.
But now, I put my money in a virtual envelope the moment it comes in, and I have to start thinking about how I'm using it: if I empty out the "restaurant" fund, I have the freedom to reallocate, but I'm forced to decide to reallocate – I don't just swipe a card and figure it out later.
This also shows me without any question what my current baseline is: I can look month over month and know how much of my spending is discretionary, how much is saving, and what the bare minimum is that I need to survive.
My old habits had me tracking after the fact and I found that I either obsessed over minutiae, failed to plan for the future, or worried too little about bigger purchases.
But now, I put my money in a virtual envelope the moment it comes in, and I have to start thinking about how I'm using it: if I empty out the "restaurant" fund, I have the freedom to reallocate, but I'm forced to decide to reallocate – I don't just swipe a card and figure it out later.
This also shows me without any question what my current baseline is: I can look month over month and know how much of my spending is discretionary, how much is saving, and what the bare minimum is that I need to survive.