I used to have this habit of spending all my money once it left the note form. What I mean by this is that if I have say a $100 note, I’d spend it all if I spent as little 50cents from this $100. The rest is just change lol.
With money, I would like to believe like anything else, experience is the best way to learn how to spend(or not to spend). Like you said, the old fashioned way. Or the hard way if you’ll say it my terms haha.
Well I think if everything you're spending on is totally worth it, then there's absolutely no cause for alarm. Provided you're achieving things with it and it's beneficial to some certain extent. Frugality doesn't take one anywhere and there's no joy in frugality. Sometimes terrible experiences in the past is why people choose to be frugal.